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The Shacktones
Glass HouseJoin us in welcoming The Shacktones, making their first appearance with us here in our slice of Free Union Paradise! The Shacktones are a talented trio bringing a soulful mix of blues and blues-rock to the stage.
More InfoBloom Girls Flower Pop Up
The Market at GrelenBuy a fresh bouquet for Mom! The Bloom Girls bring beautiful fresh flowers for Mother's Day weekend.
More InfoThe Art of Growing Peonies
The Market at GrelenFree Grelen Gardening Education Series class — learn the art of growing peonies. Free but please RSVP. Saturdays at 9am.
More InfoRose All Day Event
Afton Mountain VineyardsAll-day wine tasting event featuring rosé wines. Tasting House Open 11-7:30PM.
More InfoGoat's Milk Soap-Making Workshop hosted by Hand the Light
Merrie Mill Farm & VineyardCreate custom nourishing goat's milk soaps choosing from soft florals, calming lavender, fresh citrus, and botanical-inspired blends. Perfect for beginners and experienced makers. Tickets: $35 (single bar) or $42 (two bars).
More InfoSpring Fling
Southwest Mountains VineyardsThe second annual spring celebration featuring the release of their 2025 Cuvée Rosé wine.
More InfoPop-Up Art Market at Blenheim Vineyards
Blenheim VineyardsOn Saturday, May 9 from 11am-4pm, we're hosting a pop-up art market featuring local artists and makers under the tent. Enjoy a glass while you explore and shop!
More InfoMother's Day Brunch - Mimosas are Better with Mom!
Woodbrook Farm VineyardCelebrate Mom with brunch and bubbles at Woodbrook Farm Vineyard. Brunch by Forked on Main, 2 mimosas included, 15% off all wine purchases, and bonus coupons for Forked on Main. Spots are limited!
More InfoWildManDan Beer & Grilled Cheese Pairing (May 9)
WildManDan BreweryEach month WildManDan features a different beer paired with just the right grilled cheese. Only 12 seats available. Saturdays at 11:30 AM (before the brewery opens to the public). May pairing: Cotted Sow Pale Wheat Ale with house-made whole milk mozzarella, spicy roasted red pepper foraged pesto spread, and arugula on Batard. $24.79/person.
More InfoSpring Fling Wine Tasting Experience
Southwest Mountains VineyardsGuided tasting featuring a curated selection of seasonal wines — bright, floral whites, crisp rosés, and light-bodied reds.
More InfoLive Music – Josh Davidson
Keswick VineyardsJoin us for live music with Josh Davidson, a local artist who plays a variety of genres.
More InfoMother's Day Craft Market at Patch
Patch BreweryMother's Day Craft Market at Patch Brewing Co. — shop local makers and celebrate Mom.
More InfoSpring Fête
Michael Shaps WineworksCelebrate spring at Michael Shaps Wineworks with live music, wine tastings, and seasonal fare. A festive outdoor event welcoming the new season.
More InfoLive Music Saturday at James River Brewery
James River BreweryWeekly live music every Saturday. Check the 2026 Music Lineup for specific artists.
More InfoLive Music with Jim Theobald
Valley Road VineyardsJoin us for an afternoon of live music with Jim Theobald at Valley Road Vineyards.
More InfoChelle's Shack Homemade Goods Pop-Up
Fallen Tree VineyardChelle's Shack Homemade Goods from Charlottesville hosts a special pop-up at Fallen Tree Vineyard.
More InfoSecond Saturday Music In The Mountains with Ron Gentry
DucardJoin us as we open the 2026 Second Saturday season at DuCard with live music by Ron Gentry! Influenced by the sounds of Motown, The Beatles, CCR, The Stones, Hendrix, and many other artists, Ron is back in the area doing what he enjoys most playing a variety of great music.
More InfoTy Burkhardt, an Accomplished Finger-Style Guitarist
Fallen Tree VineyardTy Burkhardt performs masterful finger-style guitar from 2:30-5:30 PM at Fallen Tree Vineyard.
More InfoLive Music: Caravan of Fools
Afton Mountain VineyardsLive music at Afton Mountain Vineyards. Tasting House Open 11-7:30PM.
More InfoLUA Project
Knights Gambit VineyardLive music by LUA Project, 5-8pm. Seating is first come first serve — bring a chair or blanket! Wines by the glass and bottle + Potter's hard cider available.
More InfoThe Inclinators Live at Potter's Craft
Potter's Craft CiderGet ready to dance! The Inclinators bring live music to Potter's Craft Cider.
More InfoDon't Look Up
Bald Top Brewing Co.Rhythm and blues from Staunton's Don't Look Up. DLU brings energy and musicality to the Bald Top stage with favorite R&B tunes.
More InfoJosh Davidson Live at Patch Brewing
Patch BreweryJosh Davidson performs live at Patch Brewing Co.
More InfoEarly Mountain x Crimson Lane Winemaker Dinner
Early Mountain VineyardsJoin us for an evening that brings together Early Mountain and Crimson Lane, shaped by a shared commitment to quality and Virginia wine. A Winemaker Dinner Series — Two evenings. Two estates. One shared table. Winemaker Maya Hood-White and Dominick Fioresi will guide the evening, sharing the vineyards, vintages, and decisions that shape each bottle. Space is limited.
More InfoLive Music in the Orchard: Her Checkered Past
Albemarle CiderworksLive music in the orchard at Albemarle Ciderworks.
More InfoCrown Club Saturday: Vineyard Walk
Chiswell Farm & WineryClub members are invited to an exclusive behind-the-scenes walk through the vineyard. RSVP in advance!
More InfoJeremy's Ten: The Pearl Jam Tribute
Pro Re Nata BrewpubThe nation's most authentic tribute to Pearl Jam. GA tickets: $18 (Presale); $25 (Door).
More InfoJeremy's Ten: The Pearl Jam Tribute @ Pro Re Nata
Pro Re Nata BrewpubThe nation's most authentic tribute to Pearl Jam, delivering an unforgettable experience.
More InfoMother's Day Special Brunch
The Market at GrelenMother's Day special brunch menu with rose discounts at The Market at Grelen.
More InfoMother's Day Spring Pour
King Family VineyardsCelebrate the moms and mother figures in your life with a beautiful day at the vineyard. Open regular hours with special Mother's Day activities.
More InfoMother's Day: Special Brunch Menu & Rose Discounts
The Market at GrelenEnjoy a special brunch menu with discounts on rose to celebrate Mother's Day.
More InfoMother's Day Special Brunch & Rosé Discounts
The Market at GrelenJoin The Market at Grelen for a special Mother's Day brunch menu with rosé discounts. A beautiful way to celebrate mom at this beloved botanical marketplace and nursery.
More InfoLive Music: Sally Rose
Afton Mountain VineyardsLive music featuring Sally Rose on Mother's Day. Tasting Room open 11-5PM.
More InfoMother's Day Bouquet Workshop with Blooms4Good
Merrie Mill Farm & VineyardCelebrate Mother's Day with a floral bouquet workshop hosted by Blooms4Good at Merrie Mill Farm & Vineyard.
More InfoMother's Day Brunch at the Glass House Bed & Breakfast
Glass HouseJoin us for an intimate Mother's Day Brunch at the Glass House Bed & Breakfast! Just 12 guests, one seating, and a four-course menu by Chef Tim. Sunday, May 10 – Noon to 1:30 PM. $80 per person – tax and gratuity included. Seating is limited.
More InfoSunday Session- Mother's Day- Olivarez Trio with Two Brothers Southwestern Grill
Chisholm VineyardsLive music, 100% estate wine and Blue Ridge Mountain view. Based in Charlottesville, Virginia, the Olivarez Trio — Rick Olivarez, Dave Berzonsky and Jeff Cheers — create a vibrant acoustic blend of French Gypsy jazz styles mixed with eastern European folklore, waltzes, early jazz improvisations, with a sampling of everything from Classical and Baroque themes to Beatles melodies. It's a new roots music that only the Olivarez Trio can provide. Two Brothers Southwestern Grill food truck. No outside alcohol by VA ABC Law. Children and dogs welcome but must remain with their group.
More InfoSundays Jazz and Blues featuring Paulien
Merrie Mill Farm & VineyardLive jazz and blues performance by Paulien at Merrie Mill Farm & Vineyard. Part of the Sunday Blues and Jazz series.
More InfoLive Music with Brian Franke — Classic Rock Favorites
Fallen Tree VineyardBrian Franke takes the stage with classic rock favorites from 1:00–4:00 PM at Fallen Tree Vineyard.
More InfoMother's Day Brunch
Cunningham Creek WineryJoin us for this special event with seating options at 1 pm, 2 pm, and 3 pm, and let's honor the remarkable mothers in our lives with a delightful afternoon.
More InfoGootGenuG
Pro Re Nata BrewpubFusion of jazz mixed with funk, R&B, and Latin music.
More InfoRandy Johnston
Glass HouseCelebrate Mother's Day with fantastic music by acclaimed musician Randy Johnston. We are thrilled to welcome Randy back to our tropical space for a solo performance showcasing his incredible artistry and musicianship, rich in jazz and blues.
More InfoGootGenuG @ Pro Re Nata
Pro Re Nata BrewpubGootGenuG explores the improvisational stratosphere with a mix of jazz and funk.
More InfoKing Golden Banshee Live at Patch
Patch BreweryLive music from King Golden Banshee at Patch Brewing Co.
More InfoMusic at the Vineyard – Kenn Herrington
Jefferson VineyardsEnjoy Kenn Herrington performing live while you sip award-winning Jefferson Vineyards wines. Sunday afternoons feature local musicians providing the perfect soundtrack among the vines.
More InfoCider & Strings: Tristan Dougherty and The Heart Pines
Potter's Craft CiderFingerpicking and harmonizing their way into the hearts of serious music lovers. An afternoon of cider and strings at Potter's Craft Cider.
More InfoWine Tasting & Live Music - Sunday
Roslyn Farm & VineyardJoin us for wine tasting and live music every Sunday from 2:00 PM to 6:00 PM at Roslyn Farm & Vineyard.
More InfoMusic on the Deck: Jason Burke
Cardinal Point WineryJoin us for music on the deck from 2-5pm with Jason Burke.
More InfoPaint + Sip
Hazy MountainJoin us for a fun Paint + Sip afternoon at Hazy Mountain Vineyard. Enjoy wine while creating your own masterpiece.
Pressed Flower Workshop
Pippin Hill Farm & VineyardCelebrate mom with a one-of-a-kind experience! Learn how to press and preserve flowers, and create your own framed masterpiece. From $135.23.
More InfoIrish Music: Aaron Olwell & Friends
Albemarle CiderworksMonthly traditional Irish music jam session at Albemarle Ciderworks.
More InfoMug Club Madness
James River BreweryWeekly Mug Club Madness every Monday from 3pm to close at James River Brewery.
More InfoEvening Wine Tasting - Monday
Roslyn Farm & VineyardJoin Roslyn Farm & Vineyard for evening wine tasting every Monday. Open to the public.
More InfoEvening Wine Tasting - Tuesday
Roslyn Farm & VineyardJoin Roslyn Farm & Vineyard for evening wine tasting every Tuesday. Open to the public.
More InfoFirst Club Practice – Roseland Polo Season
King Family VineyardsFirst club practice of the 2026 Roseland Polo Season at King Family Vineyards.
More InfoWine Wednesday
King Family VineyardsBreak up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks.
More InfoCommunity Tap Night
James River BreweryWeekly Community Tap Night every Wednesday at James River Brewery.
More InfoWine Down Wednesday – South Canal Street Band
Keswick VineyardsEnjoy Wednesday evening with Keswick wines, local beers, or canned cocktails. South Canal Street brings a unique blend of sounds to the vineyard.
More InfoRun, Walk, Crawl Wednesday
WildManDan BreweryWeekly Wednesday event at WildManDan Brewery. 21+ only establishment.
More InfoLocals Vinyl & $5 Pints Thursday
WildManDan BreweryWeekly Thursday Locals Vinyl night with $5 pints at WildManDan Brewery. 21+ only establishment.
More InfoThursday Rendezvous - Vinyl DJ Ryan Wood of Kendall Street Company
Chisholm VineyardsEnjoy a vinyl DJ set by Ryan Wood alongside the Kendall Street Company.
Paint + Sip: "Sunset Bridge" at Pro Re Nata Crozet
Pro Re Nata BrewpubLearn how to paint this design in a step by step format, no experience necessary.
More InfoPaint + Sip: 'Sunset Bridge' at Pro Re Nata
Pro Re Nata BrewpubCome paint with us, no experience necessary. All materials and first drink included!
More InfoTrivia Night – Bald Top Brewing (May 14)
Bald Top Brewing Co.Grab your buddies for a fun night of trivia, delicious beers, and hot artisanal pizza. Hosted by Daniel every Thursday 6:30–8:30 PM.
More InfoThe Devils Backbone Lumberjack Classic
Devils BackboneJoin us for the return of the Lumberjack Classic!
More InfoEarly Closing: 5:30pm
Valley Road VineyardsValley Road Vineyards will close at 5:30pm for a private event. Last call for on-premise consumption at 5:00pm and 5:15 for bottle sales.
More InfoCousins Maine Lobster Food Truck at Fallen Tree
Fallen Tree VineyardCousins Maine Lobster Truck serving classic Maine and Connecticut lobster rolls, lobster tacos, quesadillas, lobster tots, chowder and more.
More InfoCousins Maine Lobster Food Truck
Fallen Tree VineyardJoin us for a delicious night with Cousins Maine Lobster Truck rolling in! They'll be serving up their famous Maine lobster dishes like classic chilled Maine and buttery Connecticut lobster rolls, lobster tacos, quesadillas, lobster tots, chowder and more straight from the food truck. Paired with live entertainment, this is a night everyone will want to attend. Come hungry, stay awhile, and enjoy great food and vibes with friends!
More InfoGina Sobel & Matt Draper Music Trio (May)
Fallen Tree VineyardGina Sobel and Matt Draper perform across multiple instruments at Fallen Tree Vineyard.
More InfoMusic at the Vineyard – Chris Hammock
Jefferson VineyardsEnjoy Chris Hammock performing live while you sip award-winning Jefferson Vineyards wines. Friday evenings feature local musicians providing the perfect soundtrack among the vines.
More InfoSunset Music Series
Knights Gambit VineyardFree sunset music series every Friday from 5-8pm. Bring a chair or blanket! No reservations needed (unless renting The Cabana). Wines by the glass and bottle + Potter's hard cider available. Food truck or snacks from the Tasting Room.
More InfoNightfall of Diamonds: Grateful Dead Jams Live
Potter's Craft CiderLet there be songs to fill the air... Nightfall of Diamonds brings Grateful Dead jams to Potter's Craft Cider.
More InfoFriday Sun Downers Music Series featuring Bailey Hayes
Merrie Mill Farm & VineyardLive music by Bailey Hayes as part of the Friday Sundowners Series at Merrie Mill Farm & Vineyard. Every Friday 5:30–8:30 PM through October.
More InfoHorton on the Go: Mount Vernon Spring Wine Festival
Horton VineyardsKen Farmer & The Authenticators
Glass HouseJoin us in the tropics of Free Union for a priceless night of rocking good fun featuring KEN FARMER & THE AUTHENTICATORS!
More InfoArtist Reception
Cunningham Creek WineryCelebrating Creation in Paint, showcasing artwork.
More InfoThe Greenhorns @ Pro Re Nata
Pro Re Nata BrewpubThe Greenhorns blend New Orleans funk, jump blues, R&B and a little jazz.
More InfoLocal Open Mic Night
Albemarle CiderworksOpen mic night at Albemarle Ciderworks.
More InfoGrelen's Annual Spring Plant Bar
The Market at GrelenShop Grelen's curated selection of annual plants at the Spring Plant Bar. A beloved seasonal event at The Market at Grelen nursery.
More InfoAnnual Plant Bar
The Market at GrelenJoin us for our annual plant bar event at The Market at Grelen.
More InfoThe Art of Container Gardening
The Market at GrelenLearn how to create stunning container gardens. Free event at The Market at Grelen.
More InfoThe Art of Container Gardening
The Market at GrelenLearn how to create beautiful container gardens.
More InfoWildManDan Beer & Grilled Cheese Pairing (May 16)
WildManDan BreweryEach month WildManDan features a different beer paired with just the right grilled cheese. Only 12 seats available. Saturdays at 11:30 AM (before the brewery opens to the public). May pairing: Cotted Sow Pale Wheat Ale with house-made whole milk mozzarella, spicy roasted red pepper foraged pesto spread, and arugula on Batard. $24.79/person.
More InfoJoin us for an Intimate L. Scott Vertical Tasting
Michael Shaps WineworksTwo days and two opportunities to experience six vintages of L. Scott in a guided vertical tasting that highlights the depth and evolution of this flagship wine. A portion of proceeds from this tasting will support ALS research through the Hummingbird Fund.
More InfoLive Music Saturday at James River Brewery
James River BreweryWeekly live music every Saturday. Check the 2026 Music Lineup for specific artists.
More InfoLive Music with Tristan Adams
Valley Road VineyardsEnjoy live music with Tristan Adams at Valley Road Vineyards.
More InfoPaxton Henderson — Modern Bluegrass & Singer-Songwriter
Fallen Tree VineyardPaxton Henderson performs modern bluegrass and singer-songwriter music from 2:30–5:30 PM.
More InfoLive Music in the Orchard - Ben Reade
Albemarle CiderworksBen Reade is a seasoned singer/songwriter whose roots are planted in the blue ridge mountains giving him a unique style where Americana collides with improvisational jam rock.
More InfoPaxton Henderson Live Music
Fallen Tree VineyardEnjoy an afternoon with Paxton Henderson from 2:30–5:30 PM, featuring modern bluegrass and singer-songwriter selections.
More InfoKaraoke - Cassette Tape Classics: 80's Pop Rewind
Woodbrook Farm VineyardGet ready to rewind time and belt out your favorite 80s hits! Hosted by Rachael Karpo. Channel your inner rockstar with Madonna, Journey, or Whitney.
Live Music: PBJ Acoustic
Afton Mountain VineyardsLive music with PBJ Acoustic. Tasting House Open 11-7:30PM.
More InfoPerennial Collection
Glass HousePerennial Collection returns! Featuring female-led vocal covers of R&B, Soul, Hip-Hop, and Jazz with dynamic vocal harmonies and jazz-infused arrangements. Saturday, May 16th, from 5 to 8pm. Open to all. No cover.
More InfoScuffletown
Knights Gambit VineyardLive music by Scuffletown, 5-8pm. Seating is first come first serve — bring a chair or blanket! Wines by the glass and bottle + Potter's hard cider available.
More InfoBlue Healer Live at Potter's Craft
Potter's Craft CiderHits and deep cuts from the classic rock and blues canons. Blue Healer Live at Potter's Craft Cider.
More InfoDara James and Soul Disciples
Bald Top Brewing Co.With roots in blues and rock, expect power and precision with the Soul Disciples' thick, bluesy sound reminiscent of SRV.
More InfoStrange Desire: An Electric INXS Experience @ Pro Re Nata
Pro Re Nata BrewpubStrange Desire brings the hits of INXS to life with high-voltage energy.
More InfoGuided Farm & Vineyard Walk
Oakencroft Farm & WineryGuided farm and vineyard walks at Oakencroft Farm - experience the farm in every season. Explore their approach to sustainability and soil health, then unwind with a glass in the Tasting Room. Held every third Sunday.
More InfoSundays Blues and Jazz featuring Wavelength
Merrie Mill Farm & VineyardLive blues and jazz by Wavelength at Merrie Mill Farm & Vineyard. Part of the Sunday Blues and Jazz series.
More InfoAromas of Wine & Perfume: A Sensory Experience of Scent & Terroir
Early Mountain VineyardsAn Unforgettable Afternoon of Sensory Discovery. Guests learn perfume composition, select from three distinctive fragrance bases, and blend up to 10 additional fragrance notes, crafting a personalized 20mL signature scent to take home. Then enjoy a revelatory wine experience led by Early Mountain's Sommelier Peggy Kearns Dean exploring 5 carefully selected wines with seasonal culinary bites. $145 General Public | $125 Members. Limited seating available.
More InfoUVA Planetarium Constellation Tours
Albemarle CiderworksCome learn about the stars and planets from the Dark Skies, Bright Kids (DSBK) portable planetarium! We will be giving constellation tours, traveling to the center of the universe and doing more amazing science.
More InfoGina Sobel and Matt Draper
Glass HouseA fabulous Sunday Fun Day with the brilliant multi-instrumentalist duo Gina Sobel and Matt Draper performing Americana and Bluesy tunes. Sunday, May 17th, from 2 to 5pm. No cover. Open to all.
More InfoJohn Shenk @ Pro Re Nata
Pro Re Nata BrewpubJohn Shenk's love of music is profound...and it shows.
More InfoAcoustic Union Live at Potter's Craft
Potter's Craft CiderA mixture of Americana, singer/songwriter and improvisational jam music. Acoustic Union Live at Potter's Craft Cider.
More InfoMusic on the Deck: Kevin Kehrberg
Cardinal Point WineryJoin us for music on the deck from 2-5pm with Kevin Kehrberg.
More InfoYoga in The Vines (May)
Hazy MountainSantosha Yoga all-levels class in the Solarium with mountain views. Free for Wine Club members.
More InfoMusic at the Vineyard – Sue Harlow
Jefferson VineyardsEnjoy Sue Harlow performing live while you sip award-winning Jefferson Vineyards wines. Sunday afternoons feature local musicians providing the perfect soundtrack among the vines.
More InfoWine Tasting & Live Music - Sunday
Roslyn Farm & VineyardJoin us for wine tasting and live music every Sunday from 2:00 PM to 6:00 PM at Roslyn Farm & Vineyard.
More InfoSteal the Glass
Blue MountainThe third Wednesday of every month, take home a souvenir glass with a draft purchase! Check out our social media for this month's glass.
More InfoWine Wednesday
King Family VineyardsBreak up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks.
More InfoRun, Walk, Crawl Wednesday
WildManDan BreweryWeekly Wednesday event at WildManDan Brewery. 21+ only establishment.
More InfoCooking Class: Flavors of the Turkish Black Sea
Pippin Hill Farm & VineyardDiscover the distinctive cuisine of Turkey's Black Sea coast in this immersive cooking class. $193.92 per person.
More InfoLocals Vinyl & $5 Pints Thursday
WildManDan BreweryWeekly Thursday Locals Vinyl night with $5 pints at WildManDan Brewery. 21+ only establishment.
More InfoKaraoke Night with Rachael Karpo
Chiswell Farm & WineryOn the third Thursday of each month, Rachael Karpo hosts karaoke night at Chiswell Farm & Winery — free to attend!
More InfoTailgate Thursday Kickoff w Perennial Collection & OCSF Oysters
Stinson VineyardsTailgate Thursdays are back! Kicking off the season with live music from The Perennial Collection, fresh eats with on-site shucking by Oyster Catcher Sea Farms, and grills fired up and ready. Pack dancing shoes, favorite grill-ables, lawn games, picnic blankets, and family.
More InfoKickin' Country Line Dancin' at Pro Re Nata
Pro Re Nata BrewpubGet ready for an energetic night of Kickin' Country Line Dancin' featuring lessons and open dancing all evening long.
More InfoKickin' Country Line Dancin'
Pro Re Nata BrewpubEnergetic night of Kickin' Country Line Dancin' featuring lessons and open dancing.
More InfoTrivia Night – Bald Top Brewing (May 21)
Bald Top Brewing Co.Grab your buddies for a fun night of trivia, delicious beers, and hot artisanal pizza. Hosted by Daniel every Thursday 6:30–8:30 PM.
More InfoThe Front Porch Presents: Songwriter's Open Mic
Potter's Craft CiderCalling all songwriters! The Front Porch presents a Songwriter's Open Mic at Potter's Craft Cider.
More InfoJohn Goslin Live Music
Fallen Tree VineyardJohn Goslin brings an easygoing local music vibe to the vineyard, known for performing around Central Virginia wineries and breweries. A laid-back live music atmosphere perfect for sipping wine and relaxing with friends.
More InfoLate Friday + Live Music with Shane Click
Valley Road VineyardsLive music at Valley Road Vineyards featuring Shane Click.
More InfoMusic at the Vineyard – Melissa Hansen
Jefferson VineyardsEnjoy Melissa Hansen performing live while you sip award-winning Jefferson Vineyards wines. Friday evenings feature local musicians providing the perfect soundtrack among the vines.
More InfoSunset Music Series
Knights Gambit VineyardFree sunset music series every Friday from 5-8pm. Bring a chair or blanket! No reservations needed (unless renting The Cabana). Wines by the glass and bottle + Potter's hard cider available. Food truck or snacks from the Tasting Room.
More InfoMatthew O'Donnell Live at Potter's Craft
Potter's Craft CiderA modern energy to traditional drinking songs, sea shanties, Irish jigs & reels, timeless folk favorites and original songs.
More InfoFriday Sunset Soirée- 180 Band with Twisted Provisions
Chisholm VineyardsLIVE MUSIC
Midnight Buzz with Sweet Jane's Kitchen Crab Cakes
Glass HouseMidnight Buzz brings their eclectic blend of acoustic and electric classic rock covering the Allman Brothers, Tom Petty, Steve Miller, Joni Mitchell, Fleetwood Mac, Linda Ronstadt, and more. Friday, May 22nd, from 6 to 8:30pm. Open to all. No cover. Sweet Jane's Kitchen on-site with Maryland style Crab Cake Sandwiches from 5:30pm.
More InfoMidnight Buzz
Glass HouseMidnight Buzz returns to our tropical paradise here in Free Union! They'll be bringing their eclectic blend of acoustic and electric classic rock tunes covering the Allman Brothers, Tom Petty, and more.
More InfoCompletely Unchained: The #1 Van Halen Tribute Band @ Pro Re Nata
Pro Re Nata BrewpubCompletely Unchained brings the Van Halen experience to the stage.
More InfoCelebration of the Chesapeake Seafood Dinner
Barboursville VineyardsA four-course wine paired feast showcasing nature's bounty from the Chesapeake Bay, prepared by Executive Chef Michael Clough at Barboursville Vineyards. $185 per person (all-inclusive). Reservations required; contact 540-832-7848.
More InfoCompletely Unchained: The #1 Van Halen Tribute Band
Pro Re Nata BrewpubThe quintessential Van Halen tribute band. GA tickets $20 (Advance); $25 (Door).
More InfoThe Wavelength Trio with Special Guest Lisa Carter
Glass HouseJoin us in the tropics for The Wavelength trio with special guest, Lisa Carter! Expect the unexpected...surprising rock cover songs, blues and classics.
More InfoGrelen's Annual Spring Plant Bar
The Market at GrelenShop Grelen's curated selection of annual plants at the Spring Plant Bar. A beloved seasonal event at The Market at Grelen nursery.
More InfoChelle's Shack Homemade Goods Pop-Up (May 23)
Fallen Tree VineyardFallen Tree is hosting Chelle's Shack Homemade Goods from Charlottesville for a special pop-up. They specialize in homemade baked goods, fresh breads, desserts, sweet treats, plus unique handmade décor and custom canvas tote bags. Come grab a glass of wine and browse while everything is fresh.
More InfoThe Art of Growing Culinary Herbs
The Market at GrelenLearn how to grow culinary herbs at home. Free event at The Market at Grelen.
More InfoWaves of Flavor — Memorial Day Seafood Weekend at Keswick
Keswick VineyardsTry Fabulous Foods is back at Keswick Vineyard for two days only — Saturday May 23rd and Sunday May 24th. An incredible seafood event paired with Keswick wines.
More InfoWildManDan Beer & Grilled Cheese Pairing (May 23)
WildManDan BreweryEach month WildManDan features a different beer paired with just the right grilled cheese. Only 12 seats available. Saturdays at 11:30 AM (before the brewery opens to the public). May pairing: Cotted Sow Pale Wheat Ale with house-made whole milk mozzarella, spicy roasted red pepper foraged pesto spread, and arugula on Batard. $24.79/person.
More InfoLive Music | Danny Jams
Keswick VineyardsDanny Jams is an indie-electronic loop artist based in Richmond, VA. His music combines jam-focused improvisation with layered electronic production.
More InfoGuest Star Hike Experience
Southwest Mountains VineyardsJoin Jeremy, our Assistant Winemaker, for a one-of-a-kind hiking experience. Enjoy the outdoors while getting an inside look at the craft behind our wines, guided by one of the brilliant minds shaping our program. Come explore, learn, and have some fun along the way.
More InfoLive Music Saturday at James River Brewery
James River BreweryWeekly live music every Saturday. Check the 2026 Music Lineup for specific artists.
More InfoLive Music: Cason Spencer with Food Truck CubaMex
Woodbrook Farm VineyardJoin us for a great afternoon of music, wine and food! Cason Spencer will be back in the Tasting Room. Food truck: CubaMex.
Stillhouse Crossing Live Music
Fallen Tree VineyardStillhouse Crossing takes the stage from 2:30–5:30 PM, bringing big sound, tight harmonies, and classic rock favorites that keep the afternoon buzzing.
More InfoStillhouse Crossing — Five-Piece Classic Rock Band
Fallen Tree VineyardStillhouse Crossing brings big sound, tight harmonies, and classic rock from 2:30–5:30 PM.
More InfoLive Music: Danny Goodson Band
Afton Mountain VineyardsLive music with Danny Goodson Band. Tasting House Open 11-7:30PM.
More InfoThe Wavelength Trio with Special Guest Lisa Carter
Glass HouseThe Wavelength trio with special guest Lisa Carter — soulful vocals with surprising rock covers, blues and classics. Backing her up: Larry Bisgaier (guitar/vocals), Andre LaVelle (bass) & Waverly Milor (harmonica/vocals). Saturday, May 23rd, from 5 to 8pm. Open to all. No cover.
More InfoDara James & The Soul Disciples
Knights Gambit VineyardLive music by Dara James & The Soul Disciples, 5-8pm. Arepas on Wheels food truck on site. Seating is first come first serve — bring a chair or blanket!
More InfoReckless Brigade
Bald Top Brewing Co.Fredericksburg's own bluegrass band for Memorial Day weekend. Playing bluegrass standards and modern hits — perfect Appalachian entertainment.
More InfoLive Music in the Orchard: LUA Project
Albemarle CiderworksMusical group bridging styles across continents and centuries.
More InfoShiny Metal Boxes: The Music of The Police & Sting
Pro Re Nata BrewpubA FREE SHOW featuring the iconic sound and vibe of The Police.
More InfoShiny Metal Boxes: The Music of The Police & Sting @ Pro Re Nata
Pro Re Nata BrewpubEnjoy a night of high-energy nostalgia as Shiny Metal Boxes – The Police Tribute takes the stage at PRN.
More InfoBasketweaving Workshop (May)
The Market at GrelenBasketweaving workshop at The Market at Grelen.
More InfoBasketweaving Workshop
The Market at GrelenJoin us for a fun basket weaving workshop at The Market at Grelen.
More InfoFarmhouse Four-Day Retreat
Veritas Vineyard and WineryAn all-inclusive wine lover's retreat amidst 120 acres of Veritas Vineyard and Winery. Enjoy yoga, Blue Ridge Mountain hikes, farm-to-table meals, exclusive winery tours, and exceptional wine. Pricing starts at $2,500 per room (double occupancy). Includes breakfast, lunch, dinner, wine, yoga, hiking, cooking classes and more.
More InfoLive Music – Henley & Lou
Keswick VineyardsExperience music that lifts your spirits, fills your heart, and gets your feet moving with Henley & Lou.
More InfoSilent Book Club 5/24/2026
Albemarle CiderworksSip cider and read in quiet camaraderie. No assigned reading, no obligations. Bring your own book of choice. This is a free social event hosted in our Orchard Room.
More InfoChiswell Book Club May Meeting
Chiswell Farm & WineryEvery other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
More InfoBonus Session Sunday w Robert Jospe Trio
Stinson VineyardsA special Bonus Session Sunday with the Robert Jospe Trio bringing the rhythm from 1:00 PM - 4:00 PM. Whether relaxing with a glass of wine or enjoying world-class percussion, a perfect Sunday afternoon escape. Grills fired up and ready for use.
More InfoSunday Blues and Jazz featuring John D'earth
Merrie Mill Farm & VineyardLive blues and jazz by John D'earth at Merrie Mill Farm & Vineyard. Part of the Sunday Blues and Jazz series.
More InfoBasket Weaving Workshop
The Market at GrelenCultivating Creativity & Community — a hands-on basket weaving artisan workshop at The Market at Grelen. Registration required.
More InfoHurricane Party
Knights Gambit VineyardHurricane Party, 2-6pm. Ticketed event.
More InfoMusic on the Deck: Michael Joseph
Cardinal Point WineryJoin us for music on the deck from 2-5pm with Michael Joseph.
More InfoMusic at the Vineyard – Chris Hammock
Jefferson VineyardsEnjoy Chris Hammock performing live while you sip award-winning Jefferson Vineyards wines. Sunday afternoons feature local musicians providing the perfect soundtrack among the vines.
More InfoSunday Polo at Roseland
King Family VineyardsFree public polo match at the Roseland Polo Club. Gates open at 10:00 AM, match begins at 12:00 PM. General admission on a first-come, first-served basis. Reserved tailgate spaces available. Field and weather conditions permitting.
More InfoWine Tasting & Live Music - Sunday
Roslyn Farm & VineyardJoin us for wine tasting and live music every Sunday from 2:00 PM to 6:00 PM at Roslyn Farm & Vineyard.
More InfoBRIMS Ceol agus Ceili: Irish Session & Social Dance
Potter's Craft CiderGet ready to dance! BRIMS presents an Irish music session and social dance at Potter's Craft Cider.
More InfoSippin' Monday: Memorial Day
Chiswell Farm & WinerySpend the Memorial Day holiday enjoying wine and live music at Chiswell Farm & Winery. Local acoustic musicians perform from 1-4 PM.
More InfoWine Wednesday
King Family VineyardsBreak up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks.
More InfoWine Wednesday
King Family VineyardsBreak up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks.
More InfoWine Down Wednesday with Pat Anderson
Keswick VineyardsJoin us for a fantastic evening of live music with Pat Anderson, an Oklahoma-born Virginia-raised musician.
More InfoRun, Walk, Crawl Wednesday
WildManDan BreweryWeekly Wednesday event at WildManDan Brewery. 21+ only establishment.
More InfoWine Line with Andrew Hodson
Veritas Vineyard and WineryJoin Owner Andrew Hodson for an engaging, educational vertical tasting featuring Veritas wines. Veritas Wine Club Members attend free; public may join waitlist for $25 per person. Email wineclub@veritaswines.com.
More InfoTailgate Thursday w Inclinators
Stinson VineyardsTailgate Thursday featuring live music from Inclinators. Pack your dancing shoes, favorite grill-ables, lawn games, picnic blankets, and family.
More InfoTrivia Night with Mike & Miranda at Potter's Craft
Potter's Craft CiderIt's Trivia time! Join Mike & Miranda for a fun trivia night at Potter's Craft Cider.
More InfoTrivia Night – Bald Top Brewing (May 28)
Bald Top Brewing Co.Grab your buddies for a fun night of trivia, delicious beers, and hot artisanal pizza. Hosted by Daniel every Thursday 6:30–8:30 PM.
More InfoSunset Music Series
Knights Gambit VineyardFree sunset music series every Friday from 5-8pm. Bring a chair or blanket! No reservations needed (unless renting The Cabana). Wines by the glass and bottle + Potter's hard cider available. Food truck or snacks from the Tasting Room.
More InfoMusic at the Vineyard – Gina Sobel
Jefferson VineyardsEnjoy Gina Sobel performing live while you sip award-winning Jefferson Vineyards wines. Friday evenings feature local musicians providing the perfect soundtrack among the vines.
More InfoHumberto Sales + Matt Wyatt Live
Potter's Craft CiderVocal and instrumental music rooted in Brazilian and Latin repertoire. Live at Potter's Craft Cider.
More InfoFinal Friday: John D'earth Quintet
Pollak VineyardsFinal Fridays concert series at Pollak Vineyards featuring John D'earth Quintet.
More InfoPaint + Sip
Hazy MountainWrap up May with an evening Paint + Sip event at Hazy Mountain Vineyard. Wine, creativity, and good company.
Friday Night Soirée- Ken Farmer & the Authenticators with Two Brother's Southwestern Grill
Chisholm VineyardsLIVE MUSIC
Veritas Supper Series - French Bistro
Veritas Vineyard and WineryThe fourth annual Veritas Supper Series kicks off with French flavors, Veritas wines, and a cozy evening at the vineyard. Family-style dinner spotlighting seasonal and regional foods. $100 per person including wine pairings and service. Wine Club Members receive 20% off first two tickets.
More InfoBoots & Brims SMV Social
Southwest Mountains VineyardsReserve your door fee in advance and pick up your heels at our Vineyard Boots & Brims Social at Southwest Mountains Vineyards! Pre-order your custom cowboy hat if you want one.
More InfoBOSTYX - The Ultimate Boston & Styx Tribute @ Pro Re Nata
Pro Re Nata BrewpubJoin us for an electrifying night with BOSTYX, the Ultimate Tribute Band honoring the iconic sounds of Boston & Styx.
More InfoBOSTYX - The Ultimate Boston & Styx Tribute
Pro Re Nata BrewpubGet Ready for BOSTYX - The Ultimate Boston & STYX Tribute. GA tickets $20 (Presale); $25 (Door).
More InfoBehind the Scenes Nursery Tour at Grelen
The Market at GrelenA rare behind-the-scenes experience at Grelen combining a Holding Yard Tour with a Kubota ride across the property with Darren Marsh. Limited to 3 spaces per date.
More InfoBehind the Scenes at Grelen Nursery Tour
The Market at GrelenTake a behind-the-scenes tour of Grelen Nursery. Limited seats available.
More InfoRockfish River Rodeo
Blue Toad Hard CiderA professional rodeo featuring bull riders, barrel racing, mutton bustin', and bucking broncos at Blue Toad Hard Cider. Pre-party begins at 11 AM with live music, food trucks, and cider farm access. Gates open at 4 PM; Grand Entry and National Anthem at 5:30 PM. Main event runs approximately 3 hours.
More InfoWildManDan Beer & Grilled Cheese Pairing (May 30)
WildManDan BreweryEach month WildManDan features a different beer paired with just the right grilled cheese. Only 12 seats available. Saturdays at 11:30 AM (before the brewery opens to the public). May pairing: Cotted Sow Pale Wheat Ale with house-made whole milk mozzarella, spicy roasted red pepper foraged pesto spread, and arugula on Batard. $24.79/person.
More InfoLive Music Saturday at James River Brewery
James River BreweryWeekly live music every Saturday. Check the 2026 Music Lineup for specific artists.
More InfoPancho Live Music
Fallen Tree VineyardPancho brings a full, boots-on-the-ground country sound—big hooks, big heart, and plenty of twang.
More InfoLive Music: Honest Labor
Afton Mountain VineyardsLive music featuring Honest Labor. Tasting House Open 11-7:30PM.
More InfoHorton on the Go: Bull Run Wine Festival Spring 2026
Horton VineyardsMichael Clem + Crozet Seafood
Knights Gambit VineyardLive music by Michael Clem, 5-8pm. Crozet Seafood on site. Seating is first come first serve — bring a chair or blanket! Wines by the glass and bottle + Potter's hard cider available.
More InfoMighty Fine Company Live at Potter's Craft
Potter's Craft CiderSaturday nights are better with live music. Mighty Fine Company Live at Potter's Craft Cider.
More InfoThe Rivanna Band
Bald Top Brewing Co.Rivanna is back at Bald Top with their own blend of originals, country, and rock — covering a lot of ground and sure to play many favorite tunes.
More InfoAn Evening for ALS Research
Michael Shaps WineworksJoin us for an intimate, open-air dining experience at Michael Shaps Winery in collaboration with Public Fish & Oyster House and The Hummingbird Fund. This special evening brings together food, wine, and community in support of ALS research. Guests will enjoy a thoughtfully curated multi-course menu paired with Michael Shaps wines, alongside live music by Baby Jo's. Tickets: $200 per guest. Limited seating | Advance reservations required.
More InfoLive Music in the Orchard: ZUZU's Hot 5
Albemarle CiderworksSwing ensemble performance at Albemarle Ciderworks.
More InfoHorton on the Go: Uncorking Norton
Horton VineyardsJoin Horton Vineyards at the Uncorking Norton event celebrating Virginia's native Norton grape.
More InfoSmoke & The Poet
Pro Re Nata BrewpubHigh energy and exuberance, leading audiences into a musical experience.
More InfoSmoke & The Poet @ Pro Re Nata
Pro Re Nata BrewpubSmoke & the Poet is a young country band enjoying rising success.
More InfoSeed to Bloom - Cut Flower Gardening 101
Oakencroft Farm & WineryFrom Seed to Bloom is a two-part floral journey that unfolds with the season, inviting guests to slow down and engage with the beauty of growth over time. Hosted by Hope Henderson of FLORA.
More InfoSeed to Bloom - Floral Arranging with FLORA
Oakencroft Farm & WineryPart II of the Seed to Bloom floral journey hosted by Hope Henderson of FLORA. A two-part seasonal class exploring the beauty of growth over time, culminating in floral arranging. Join both sessions with the Seed to Bloom Seasonal Class Bundle.
More InfoSunday Blues and Jazz featuring Sharif
Merrie Mill Farm & VineyardLive blues and jazz by Sharif at Merrie Mill Farm & Vineyard. Part of the Sunday Blues and Jazz series.
More InfoGina Sobel Duo Live at Potter's Craft
Potter's Craft CiderSunday vibes with the Gina Sobel Duo Live at Potter's Craft Cider.
More InfoMusic on the Deck: Matt Cole
Cardinal Point WineryJoin us for music on the deck from 2-5pm with Matt Cole.
More InfoSunday Polo at Roseland
King Family VineyardsFree public polo match at the Roseland Polo Club. Gates open at 10:00 AM, match begins at 12:00 PM. General admission on a first-come, first-served basis. Reserved tailgate spaces available. Field and weather conditions permitting.
More InfoWine Tasting & Live Music - Sunday
Roslyn Farm & VineyardJoin Roslyn Farm & Vineyard for wine tasting and live music every Sunday afternoon. Open to the public.
More InfoMusic at the Vineyard – Melissa Hansen
Jefferson VineyardsEnjoy Melissa Hansen performing live while you sip award-winning Jefferson Vineyards wines. Sunday afternoons feature local musicians providing the perfect soundtrack among the vines.
More InfoSeed to Bloom – Floral Arranging (Part II)
Oakencroft Farm & WineryLearn to gather, condition, and compose flowers into a natural arrangement at Oakencroft Farm. Guests take home their creations.
More InfoFarmhouse Retreat
Veritas Vineyard and WineryMulti-day immersive retreat experience at Veritas Vineyard.
More InfoWine Wednesday
King Family VineyardsBreak up the midweek monotony and join us as we keep the tasting room open until 8:30pm every Wednesday! Unwind with a rotating lineup of local food trucks.
More InfoCooking Class: Flavors of Punjab, India
Pippin Hill Farm & VineyardA vibrant culinary journey through the flavors of Punjab, India at Pippin Hill Farm & Vineyard. $193.92 per person.
More InfoTailgate Thursday w Midnight Buzz & OCSF Oysters
Stinson VineyardsTailgate Thursday with Live Music from Midnight Buzz, fresh eats from on-site shucking by Oyster Catcher Sea Farms, and grills fired up and ready. Pack dancing shoes, favorite grill-ables, lawn games, and picnic blankets.
More InfoLive Music at Jefferson Vineyards: Gina Sobel
Jefferson VineyardsLive music from local musicians on Friday evenings at Jefferson Vineyards. Nestled among the rolling hills and sun-drenched vines, Music at Jefferson Vineyards brings together the finest in live music and the art of winemaking. Friday evenings 5-7pm.
More InfoSunset Soirée- Speidel, Goodrich & Friends with Arepas on Wheels
Chisholm VineyardsLIVE MUSIC
Summer Sundown (June)
Chiswell Farm & WineryLocal musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6-8:30 PM.
More InfoTrivia Night
Hazy MountainTrivia Night at Hazy Mountain mezzanine. Sip wine, test your knowledge, and win prizes!
More InfoInnerspeaker
Pro Re Nata BrewpubA FREE SHOW featuring a setlist of 21st century jams.
More InfoAnnual Plant Bar (June)
The Market at GrelenJoin us for another Annual Plant Bar event at The Market at Grelen.
More InfoGrelen's Annual Spring Plant Bar
The Market at GrelenShop Grelen's curated selection of annual plants at the Spring Plant Bar. A beloved seasonal event at The Market at Grelen nursery.
More InfoThe Art of Growing Culinary Herbs (June)
The Market at GrelenAnother chance to learn how to grow culinary herbs at home. Free event at The Market at Grelen.
More InfoSip & Thrift hosted by Horton Vineyards in Collaboration with Good Samaritan Inc.
Horton VineyardsDay of I Do's
Albemarle CiderworksLooking for a wedding (or vow renewal) that feels meaningful, beautiful, and a little whimsical, without the overwhelm of endless decisions? On June 6th, we're hosting a special Day of I Do's event.
More InfoSip Into Summer Wine Festival
Woodbrook Farm Vineyard1st Annual Sip Into Summer Wine Festival at Woodbrook Farm Vineyard! Featuring incredible Virginia wineries, live music, and a food truck. Meet winemakers and owners while discovering new wines. $45 advance / $60 day-of (taxes & service fees not included).
More InfoLive Music Saturday at James River Brewery
James River BreweryWeekly live music every Saturday. Check the 2026 Music Lineup for specific artists.
More InfoField Day at Blenheim Vineyards: Jay Pun & Friends
Blenheim VineyardsJoin us for Field Day at Blenheim Vineyards and enjoy an easygoing afternoon of live music, vineyard views, and time well spent together. Jay Pun & Friends will be playing live from 3-5 PM under the tent overlooking the vineyard.
More InfoHorton on the Go: Sip Into Summer Wine Festival
Horton VineyardsHorton Vineyards participates in the Sip Into Summer Wine Festival.
More InfoLive Music in the Orchard: The Wavelength
Albemarle CiderworksVintage rock and blues featuring vocalist and harmonica player.
More InfoWidely Grown
Pro Re Nata BrewpubRoots rock band with a sound shaped by years of Traveling, Hitchhiking, and Storytelling.
More InfoHive to Honey
Oakencroft Farm & WineryJoin us for a Hive to Honey Discovery Session with beekeeper Allison Wickham and learn the basics of beekeeping and why pollinators matter!
More InfoBasket Weaving Workshop (June)
The Market at GrelenBasket weaving workshop at The Market at Grelen.
More InfoHive to Honey Discovery Session
Oakencroft Farm & WineryLearn the basics of beekeeping and why pollinators matter with beekeeper Allison Wickham. After the workshop, join in the Tasting Room for a Honey and Elderflower wine spritz or N/A beverage.
More InfoBasket Weaving Workshop
The Market at GrelenA workshop focused on basket weaving techniques.
More InfoSunday Session - Dave's Basement
Chisholm VineyardsCome enjoy live music from Dave's Basement at our Sunday Session.
Sunday Polo at Roseland
King Family VineyardsFree public polo match at the Roseland Polo Club. Gates open at 10:00 AM, match begins at 12:00 PM. General admission on a first-come, first-served basis. Reserved tailgate spaces available. Field and weather conditions permitting.
More InfoMusic on the Deck: Jason Burke
Cardinal Point WineryJoin us for music on the deck from 2-5pm with Jason Burke.
More InfoHive to Honey Discovery Session
Oakencroft Farm & WineryLed by beekeeper Allison Wickham — covers beekeeping basics and pollinator importance, followed by beverages in the Tasting Room.
More InfoFeatured Venues
Wineries, breweries & distilleries near Charlottesville
