Events in Charlottesville Wine Country

Virginia Sunflower Festival

Demystifying Organics Workshop & Farm Tour

A workshop and farm tour at Radical Roots Community Farm exploring the world of organic farming. Hosted in partnership with Loving Cup Vineyard.

Locals Vinyl Share & $5 Pints

Bring your records for the locals vinyl share, with $5 pints on tap. 21+ only.

Thursday Rendezvous - Vinyl DJ Ryan Wood of Kendall Street Company

Porch Nights: Ron Gentry

Game Night!

Bold Book Club: Bend Her

Bold Rock's book club meets to discuss Bend Her. Join fellow readers for great conversation paired with Bold Rock ciders.

Tailgate Thursday w Scuffletown & OCSF Oysters & Sun Queen Ice Cream

Tailgate Thursdays are back! Live music with Scuffletown, fresh oysters from Oyster Catcher Sea Farms, and ice cream from Sun Queen. Grills fired up — bring your own food to grill, lawn games, and picnic gear.

US History Trivia Month - The 13 Colonies

Test your knowledge of American history with this month's US History Trivia theme — The 13 Colonies. Great prizes and Bold Rock ciders await!

Erin Lunsford Rhinestones Release ft. Sally Rose, Model House

An evening of music and community at Potter's Craft Cider as Erin Lunsford releases her sophomore record, Rhinestones. Presented by 106.1 The Corner and Pandemonium Air with support from Nelson County's Sally Rose and Charlottesville's neo folk act Model House. Outside on the lawn, weather permitting - bring a blanket or lawn chair. Doors at 6, show at 7. Potter's kitchen open until 8pm.

Summer Culinary Series: Pours & Pasta

An intimate al fresco dining experience showcasing seasonal pasta dishes paired with Southwest Mountains wines. A Thursday evening of culinary excellence.

Trivia Night

Weekly trivia at the Tap Barn with craft beer and hot artisanal pizza.

Adult Karaoke Night

Karaoke night for adults at Patch Brewing Co.

Mimosas & Masterpieces

A guided paint-and-sip brunch on the Trump Cidery patio with a professional artist, all painting materials, a welcome mimosa or bellini made with Trump Cider Apple-achian, and curated light brunch fare. Check-in from 9:45 AM.

Happy Hour at Bryant's Cider & Brewery

Happy Hour 3-5PM. Kick off your weekend at Bryant's.

Summer Bouquet Making Workshop with Blooms4Good

Join us on Friday, July 31, from 4:00-5:00 PM for a Summer floral bouquet workshop. Joining hands with Kate & Kira of Blooms4Good — 100% of proceeds go to SARA and International Neighbors. One ticket includes one floral bouquet of your design ($60).

Barry's BBQ

Guest food truck at Patch Brewing Co.

Trump Cidery Summer Concert Series: Lama & the Hound

Free live music on the lawn at Trump Cidery, 3550 Blenheim Road, with estate-crafted sparkling hard cider and vineyard views. Featuring Lama & the Hound, 4-7pm.

Locals Night at Bryant's Cider

Cider specials and a fun time for all.

Live Music: Sean Patrick

Enjoy an evening of live music from Sean Patrick at Jefferson Vineyards. Sip award-winning Virginia wines on the beautiful grounds.

Friday Night Out with The Lonesome Millies & 1/2 Price Wine Flights

Kick off the weekend with live music from The Lonesome Millies — folk, Americana, and light rock. Half price wine flights all evening. Bring a picnic!

Virginia Oyster & Wine Celebration with Live Music: Eli Cook

Final Fridays Concert: Blake Hunter & the Gatherers + Crozet Seafood Supply

Final Fridays Concert at Pollak Vineyards featuring Blake Hunter & the Gatherers with fresh seafood from Crozet Seafood Supply. A perfect Friday night in the vineyard.

Friday Sundowner's Music Series featuring Matt Tyrrell

Kick off the weekend with the Friday Sundowner's Music Series at Merrie Mill Farm & Vineyard featuring Matt Tyrrell. Live music from 5:30-8:30 PM with stunning sunset views.

Friday Cheers with Fretwell

Gina Sobel Duo Live

Smooth grooves, summer evenings, and cider in hand. Gina Sobel is a natural improviser accomplished on flute, sax and voice, radiating energy in live performance and sought after as a soloist with national and international performers. An award-winning songwriter and composer, Sobel brings together funk, jazz and American folk into a fresh and compelling sound.

Hawaiian Luau Secret Supper

Paint + Sip: Tropical Paradise

Sunset Soirée - Little Walter & the Convictions with Sweet Jane's Kitchen

Summer Culinary Series: Pours & Pasta

An intimate al fresco dining experience showcasing seasonal pasta dishes paired with Southwest Mountains wines. A Friday evening of culinary excellence.

Steve Lanza Jr. and Friends Live at Patch

Weekly Friday live music with Steve Lanza Jr. and Friends.

Friday Night Jam Session

JRB's open Friday Night Jam Session at 6:30 PM. Join in and possibly get in the lineup for a paid gig.

Don't Look Up

Live music from Don't Look Up at Glass House Winery. An evening of great music paired with Glass House wines.

Grill Cheese & Beer Pairing

Ticketed grilled cheese and beer pairing - only 12 seats available. Current pairing features hot honey goat cheese with fresh peach-mango chutney on ciabatta, paired with a Honey Blonde, Honey Thyme, or Hop Honey brew.

Trump Grand Tasting

A one-hour guided tasting of six estate-grown wines in the new Meritage Barrel Room, led by a wine educator, including a souvenir Trump Winery glass. Small groups up to 16 guests; advance reservations required.

Live Music | Matt Johnson

Farmer's Market

Saturday farmers market at Patch Brewing Co.

Music in the Mountains with Bailey Hayes

Enjoy the afternoon at DuCard with singer/songwriter Bailey Hayes — country, classic rock, pop/soul, folk, and original music. Sit by the stream and sip.

Chris & Jane + Brick City Kitchen

Live Music In The Orchard: Melissa Hansen

Enjoy a relaxing Sunday afternoon of live music with Melissa Hansen in the beautiful orchard setting at Albemarle CiderWorks. Hard ciders and soft drinks available.

An Afternoon with Sue Harlow

Sue Harlow brings a roots-inspired sound shaped by heartfelt lyrics and classic influences.

Bordeaux Library Tasting: Petit Verdot | Malbec

Rick Hollowell Music

Enjoy live music from Rick Hollowell at Hark Vineyards. A great afternoon of wine and acoustic performance.

Rum Punch Jamaican Cuisine

Guest food truck at Patch Brewing Co.

Live Music: Timeless

Live Music: Michael Clem

Free sunset live music series at Knights Gambit Vineyard, 5-8pm. Wines by the glass and bottle plus Potter's hard cider by the can; bring a picnic, chair or blanket. Seating is first come, first served and no reservations are taken on live music nights.

Live Music: Lama And The Hound

Danny Kensey

Bald Top welcomes decorated country singer/songwriter Danny Kensey to the BT stage for the first time. Having opened for the likes of Rascal Flatts and Brad Paisley, Danny's edgy but traditional sound is exactly what country music fans of today are craving, playing both originals and favorite country hits.

Hogfish Live at Patch

Live music from Hogfish at Patch Brewing Co.

Abrams Bridge: Springsteen Tribute @ Pro Re Nata

Abrams Bridge performs a Springsteen Tribute at Pro Re Nata Farm Brewery. Born to Run music, Virginia craft beer. Don't miss it.

Royce Campbell and Friends

An evening of live jazz and acoustic music from Royce Campbell and Friends at Glass House Winery.

Sunday Jazz and Blues featuring Wavelength

Spend a relaxing Sunday afternoon at Merrie Mill Farm & Vineyard with jazz and blues from Wavelength. 1:00-4:00 PM.

Sunday Session - Jacob Paul Allen

WTJU Vinyl Takeover

Sunday Funday with your favorite WTJU Radio DJs back at the tasting room. Five full hours of vinyl to keep you grooving and relaxing all day long. Grab a cider, kick back, and relax to the music. DJ schedule TBA.

Music in the Mountains with Hokie Joe

Keep the weekend going at DuCard with Hokie Joe — blues, classic rock, old country, and originals from this talented guitarist.

Wine & Cheese Pairing Experience

Explore the art of pairing fine Virginia wines with expertly selected cheeses in this guided experience.

Jo and Ray Enke

Enjoy a Sunday afternoon of live music from Jo and Ray Enke at Glass House Winery.

Live Music: Mojo Pie

Enjoy an afternoon of live music from Mojo Pie at Jefferson Vineyards. Sip award-winning Virginia wines on the beautiful grounds.

Don't Look Up @ Pro Re Nata

Don't Look Up performs live at Pro Re Nata Farm Brewery. An afternoon of great music and Virginia craft beer.

Weekly Wine Tasting

Weekly wine tasting at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Sip a variety of their finest wines in a picturesque farm setting with staff guiding you through each blend.

Paint + Sip: Lemon Vista

Music on Deck: John Kelly

Granny Hobby Club

Each week explores a different hobby at Bryant's Farm and Cidery. Learn something new, or share your tips and tricks to something old.

Little Birdies @ Patch Brewing Company

Family-friendly Little Birdies session at Patch Brewing Company.

Long Live the Jam!

Field Day - Susie & The Pistols

Special Free Screening of the documentary film Shenandoah

Free screening of Virginia Public Media's stunning documentary Shenandoah at The Barn at Stony Brook in Madison County. DuCard wine and PopPop's famous kettle corn available.

Mug Club Madness

Every Monday from 3 PM to close: $2 off 20 oz mug fills for Mug Club members.

Music Bingo

Weekly Monday music bingo at Patch Brewing Co.

Food Truck: PotLucky Cville

King Trivia With Clayton

Community Tap Night

JRB's Community Tap Night, Wednesdays 3 PM to close. Local non-profits partner with the brewery for a fundraiser and earn 20% of the day's sales.

Wine Wednesday

King Family Vineyards' popular Wine Wednesday series featuring live music, food trucks, and wine specials. A midweek escape to wine country.

Wine Down Wednesday - Big Gavel Classic

Run, Walk, Crawl

Weekly Wednesday evening run/walk followed by beers at the brewery. 21+ only.

Trivia Night at Patch

Weekly Wednesday trivia night at Patch Brewing Co.

Virginia Sunflower Festival

Locals Vinyl Share & $5 Pints

Bring your records for the locals vinyl share, with $5 pints on tap. 21+ only.

Game Night!

Open Mic Night

Open Mic Night at Cunningham Creek Winery! Bring your talent or just your ears for an evening of live, local performances. Wine and beer available.

Mingle Mahj: A FUNdraiser for The Haven

Come play for a cause - 100% of your suggested donation goes directly to The Haven. Join the Friends of The Haven for an evening of Mahjong, cider, food, prizes, and good company. Whether you're just learning the ropes or ready for the cruise ships, there's a table for you. This is Mahjong for fun, not competition. $25 suggested donation (cash, check, CC or Venmo). Come a little early at 5 PM to grab a drink and dinner; games kick off at 5:30. Bring your 2025 & 2026 NML cards if you have them.

Tailgate Thursday w Jimmy O & OCSF Oysters

Tailgate Thursdays continue! Live music with Jimmy O, fresh oysters from Oyster Catcher Sea Farms. Grills fired up — bring your own food to grill, lawn games, and picnic blankets.

Board Games and Cards Night in The Lounge

Board games and cards night in the Lounge at Patch Brewing Co.

Trivia Night

Weekly trivia at the Tap Barn with craft beer and hot artisanal pizza.

Happy Hour at Bryant's Cider & Brewery

Happy Hour 3-5PM. Kick off your weekend at Bryant's.

Locals Night at Bryant's Cider

Cider specials and a fun time for all.

Hughes Fish Fry

Guest food truck at Patch Brewing Co.: Hughes Fish Fry.

Trump Cidery Summer Concert Series: Slate River Band

Free live music on the lawn at Trump Cidery, 3550 Blenheim Road, with estate-crafted sparkling hard cider and vineyard views. Featuring Slate River Band, 4-7pm.

Spark Studio Permanent Jewelry Pop-Up

Spark Studio brings a permanent jewelry pop-up to Fallen Tree Vineyard, specializing in custom-fitted, clasp-free bracelets, anklets, rings, and necklaces in sterling silver, gold-filled, and 14k solid gold. Come sip, shop, and create a little forever sparkle.

Friday Night Out with Dave Goodrich & 1/2 Price Wine Flights

Welcome in the weekend with half price DuCard wine flights and live music with Dave Goodrich — blues, rock, pop, Motown, and originals.

Late Friday + Live Music with Travis Elliott

A Charlottesville-based singer, songwriter, and guitarist with roots in Richmond. His sound blends alternative pop hooks, punk energy, and Americana grit. Enjoy extended evening hours at Valley Road Vineyards.

Summer Send-Off with Koda Kerl

Say goodbye to summer in style at King Family Vineyards with live music from Koda Kerl. An evening of great music, wine, and the beauty of the Blue Ridge Mountains.

Live Music: Nicholas Darden

Enjoy an evening of live music from Nicholas Darden at Jefferson Vineyards. Sip award-winning Virginia wines on the beautiful grounds.

Friday Sundowner's Music Series featuring Bailey Hayes

The Friday Sundowner's Music Series at Merrie Mill featuring Bailey Hayes. Extended live music from 5-9 PM with beautiful sunset views and excellent wine.

Bachata Night

Virginia Oyster & Wine Celebration with Live Music: John Kelly

LUA Project Live

A new style of traditional music inspired by the sounds and sones of Mexico, Appalachia, and the Atlantic Basin. Kick off your weekend with LUA Project, a cultural pollinator bridging musical styles from different continents and centuries - drawing on Mexican and Appalachian song forms, Eastern European tonalities, baroque melodic ideas and narrative storytelling.

Sunset Soirée - Brandon Wayne and His Lonesome Drifters with Oyster Catcher Sea Farms

Summer Sundown

Summer Culinary Series: Corks & Coals

Fire up the summer with an evening of grilled culinary creations paired with Southwest Mountains wines. A perfect evening under the stars.

Friday Night Jam Session

JRB's open Friday Night Jam Session at 6:30 PM. Join in and possibly get in the lineup for a paid gig.

Steve Lanza Jr. and Friends Live at Patch

Weekly Friday live music with Steve Lanza Jr. and Friends.

Baby Jo's Boogie Band @ Pro Re Nata

Baby Jo's Boogie Band brings the funk to Pro Re Nata Farm Brewery. An evening of high-energy music and Virginia craft beer.

Summer Supper Somm Tomato Celebration Dinner (Sold Out)

A four-course wine paired feast featuring heirloom tomatoes from Village Garden Farm in Hanover, VA. Prepared by Executive Chef Michael Clough. $185 per person, all-inclusive. Currently sold out.

Crozet Seafood (All-Day) & Vincent Zorn Music (4:00-7:00 p.m.)

Fresh seafood from Crozet Seafood all day paired with Hark Vineyards wines, plus live music from Vincent Zorn from 4-7pm. A perfect Saturday combination.

Crab Feast

Grill Cheese & Beer Pairing

Ticketed grilled cheese and beer pairing - only 12 seats available. Current pairing features hot honey goat cheese with fresh peach-mango chutney on ciabatta, paired with a Honey Blonde, Honey Thyme, or Hop Honey brew.

Farmer's Market

Saturday farmers market at Patch Brewing Co.

Trump Grand Tasting

A one-hour guided tasting of six estate-grown wines in the new Meritage Barrel Room, led by a wine educator, including a souvenir Trump Winery glass. Small groups up to 16 guests; advance reservations required.

Honey Tasting

Live Music | Josh Davidson

Saturday Live Music with Bob & Kenn

Enjoy an afternoon of live music at Cunningham Creek Winery with Bob & Kenn. Great wines, good vibes.

Austin Boggs + Uncle Bob & Sweet T's BBQ

Live Music in the Orchard: The Pollocks

Spend a Saturday afternoon with The Pollocks performing live in the orchard at Albemarle CiderWorks. Hard ciders and soft drinks available.

Gina Sobel & Matt Draper Music Trio

Join us for the distinctive sounds of Gina Sobel and Matt Draper as they perform across multiple instruments, weaving together classic, folk, and modern selections.

Artist Reception: Juliette Swenson

Meet the artist Juliette Swenson at Loving Cup Vineyard during this special afternoon reception. View her paintings, enjoy wine, and celebrate local art.

Live Music: The Cry Babies

Rum Punch Jamaican Cuisine

Guest food truck at Patch Brewing Co.

Live Music: Mirabelle and Matty

Free sunset live music series at Knights Gambit Vineyard, 5-8pm. Wines by the glass and bottle plus Potter's hard cider by the can; bring a picnic, chair or blanket. Seating is first come, first served.

Live Music: The Loya Brothers

Press Play Music Series: Adam's Plastic Pond Live

Southern lap steel and folk ballads to bright, breezy guitar pop. Potter's Craft Cider presents the Press Play Music Series, a year-round lineup of top notch local bands on select Saturday evenings focused on good vibes, upbeat music, and dancing the night away. Featuring Adam's Plastic Pond, a collective of seasoned Charlottesville musicians bringing movement and soul to the songwriting of Adam Long. Bring a blanket, grab a cider, and catch the groove as the sun sets. Music starts at 5:30 PM on the lower lawn.

Don't Look Up

Quickly becoming a regular staple at Bald Top, Staunton's own blues outfit returns to the Tap Barn. Specializing in blues and blues/rock, they are known for high energy shows filled with familiar blues tunes.

Back 40 East Live at Patch

Live music from Back 40 East at Patch Brewing Co.

Slate River Band @ Pro Re Nata

The Slate River Band performs live at Pro Re Nata Farm Brewery. A great evening of music and craft beer in Crozet.

Crown Club Saturday: Summer Bounty Celebration

Sound Bath with Anya

Begin with 10-15 minutes of gentle, guided movement to settle into your body before transitioning into stillness. Anya then guides a restorative sound bath designed to encourage reflection and relaxation as summer softens toward fall. Held in the light-filled Oakencroft Center, running about one hour. A seasonal spritz in the tasting room is included with each ticket.

Food Truck Sunday: Crozet Seafood Supply

Crozet Seafood Supply returns with lobster rolls, crab cakes, and other seafood favorites. No reservations required - just great food, great wine, and beautiful vineyard views. Truck open 11:30 AM to 4:00 PM.

Mercy Creek

Live Music | Andy Tichenor

Sunday Jazz and Blues featuring Paulien

Spend a relaxing Sunday afternoon at Merrie Mill Farm & Vineyard with jazz and blues from Paulien. 1:00-4:00 PM.

Sunday Session - Dave's Basement with Catch the Chef

Unlabeled: A Blind Wine Tasting

Blind tasting hosted by Michael Shaps: twelve pours from the Michael Shaps portfolio tasted side-by-side with counterparts from France's most storied regions. Four flights - Rose (France vs. Virginia), Chardonnay (Virginia vs. Burgundy), Pinot Noir (three Burgundy sites) and Petit Verdot (three Virginia sites) - with a guided reveal and discussion after each. $65 per person / $55 members, includes cheese plate and gratuity. Seated format.

Live Music: Gina Sobel

Enjoy an afternoon of live music from Gina Sobel at Jefferson Vineyards. Sip award-winning Virginia wines on the beautiful grounds.

Granny Hobby Club

Each week explores a different hobby at Bryant's Farm and Cidery. Learn something new, or share your tips and tricks to something old.

King Golden Banshee

Live music from King Golden Banshee at Patch Brewing Co.

Music on Deck: Brian Franke

Weekly Wine Tasting

Weekly wine tasting at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Sip a variety of their finest wines in a picturesque farm setting with staff guiding you through each blend.

Irish Music: Aaron Olwell & Friends

Enjoy a Sunday afternoon of traditional Irish music with Aaron Olwell & Friends in the orchard at Albemarle CiderWorks. Hard ciders and soft drinks available.

August Trivia

Mug Club Madness

Every Monday from 3 PM to close: $2 off 20 oz mug fills for Mug Club members.

Food Truck: PotLucky Cville

Trivia Night

Community Tap Night

JRB's Community Tap Night, Wednesdays 3 PM to close. Local non-profits partner with the brewery for a fundraiser and earn 20% of the day's sales.

Wine Wednesday

King Family Vineyards' popular Wine Wednesday series featuring live music, food trucks, and wine specials. A midweek escape to wine country.

Wine Down Wednesday - The Inclinators

Run, Walk, Crawl

Weekly Wednesday evening run/walk followed by beers at the brewery. 21+ only.

Jamaica vs. Roseland International Cup

Watch world-class polo at King Family Vineyards as the Jamaica team faces Roseland in the International Cup. High-goal polo action on beautiful grounds with wine available.

Locals Vinyl Share & $5 Pints

Bring your records for the locals vinyl share, with $5 pints on tap. 21+ only.

Game Night!

Tailgate Thursday w Small Town Rodeo & Crozet Seafood

Tailgate Thursdays continue! Live music with Small Town Rodeo, seafood from Crozet Seafood. Grills fired up — bring your own food to grill, lawn games, and picnic blankets.

Live Music: The Go-Tos (Grass on the Other Side)

Trivia Night

Weekly trivia at the Tap Barn with craft beer and hot artisanal pizza.

Caldwell Farms Pop-Up

Happy Hour at Bryant's Cider & Brewery

Happy Hour 3-5PM. Kick off your weekend at Bryant's.

Locals Night at Bryant's Cider

Cider specials and a fun time for all.

Summer Rooftop Mingle with Winemaker Maya Hood White

Join winemaker Maya Hood White for a casual evening mingle on the rooftop at Early Mountain Vineyards.

Food Truck: Farmacy

Late Friday + Live Music with Tristan Adams

Relatively new to the live music scene, Tristan recently moved to Nelson County. He's delighted to be back at Valley Road for an encore performance. Enjoy extended evening hours.

Live Music: Gina Sobel

Enjoy an evening of live music from Gina Sobel at Jefferson Vineyards. Sip award-winning Virginia wines on the beautiful grounds.

Virginia Oyster & Wine Celebration with Live Music: Matthew O'Donnell

Friday Sundowner's Music Series featuring Mercy Creek

The Friday Sundowner's Music Series at Merrie Mill featuring Mercy Creek. Live music from 5:30-8:30 PM with stunning sunset views and excellent wine.

Sunset Soirée - The Inclinators with Crozet Seafood Supply

Beekeepers Table Secret Supper

Music Bingo

Test your music knowledge at Music Bingo at Cunningham Creek! Identify songs and artists for a chance to win great prizes. Wine and beer available.

Friday Night Jam Session

JRB's open Friday Night Jam Session at 6:30 PM. Join in and possibly get in the lineup for a paid gig.

Isaac Hadden w/ Dara James & The Soul Disciples @ Pro Re Nata

Isaac Hadden with Dara James & The Soul Disciples perform at Pro Re Nata Farm Brewery. Soul, R&B, and craft beer.

Cousins Maine Lobster

The fan-favorite Cousins Maine Lobster food truck comes to Hark Vineyards for a full day of delicious lobster rolls, lobster bisque, and more paired with great wine.

Grill Cheese & Beer Pairing

Ticketed grilled cheese and beer pairing - only 12 seats available.

Live Music – Rixeyville Revival

Trump Grand Tasting

A one-hour guided tasting of six estate-grown wines in the new Meritage Barrel Room, led by a wine educator, including a souvenir Trump Winery glass. Small groups up to 16 guests; advance reservations required.

Simply Trending Catering BBQ

Enjoy delicious BBQ from Simply Trending Catering paired with Cunningham Creek wines and beers. A perfect Saturday afternoon feast.

Joyful Bauble Co. Pop-Up

Joyful Bauble Co., a Charlottesville-based handmade jewelry brand created by Katherine, features whimsical, unique pieces made with polymer clay and brass. Stop by to sip, shop, and find a little joy while enjoying wine, food, and mountain views.

Saturday Live Music with Sh'Boom

Live music with the high-energy Sh'Boom at Cunningham Creek Winery. An eclectic variety of songs you know and love including folk, rock, and acoustic blues.

Midnight Buzz Duo Acoustic Electric

Midnight Buzz Duo blends acoustic warmth with electric edge, creating a sound that feels both familiar and unexpected, bringing classic rock to life.

Live Music: Loya Brothers

Live Music: Gina Sobel Duo + Crozet Seafood

Free sunset live music with the Gina Sobel Duo, 5-8pm, with Crozet Seafood on site as the food truck. Wines by the glass and bottle plus Potter's hard cider by the can.

Live Music: Don't Look Up

Mojo Parker Express

All aboard the Mojo Parker Express! One of the area's most accomplished and unique bands brings its mix of funk, jazz, rock, and blues back to Bald Top.

Dueling Piano Dinner Party

An electrifying evening of dueling pianos paired with an exquisite dinner at Southwest Mountains Vineyards. Come ready to sing, laugh, and celebrate!

Sunday Jazz and Blues featuring John D'earth

Spend a relaxing Sunday afternoon at Merrie Mill Farm & Vineyard with jazz and blues from legendary John D'earth. 1:00-4:00 PM.

Sunday Session - The Trio

Live Music: Forde Upshur

Live Music: Paxton Henderson

Enjoy an afternoon of live music from Paxton Henderson at Jefferson Vineyards.

Granny Hobby Club

Each week explores a different hobby at Bryant's Farm and Cidery. Learn something new, or share your tips and tricks to something old.

Weekly Wine Tasting

Weekly wine tasting at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Sip a variety of their finest wines in a picturesque farm setting with staff guiding you through each blend.

Music on Deck: Charlie & Ian

Quests & Cabernet at Horton Vineyards

Mug Club Madness

Every Monday from 3 PM to close: $2 off 20 oz mug fills for Mug Club members.

Food Truck: PotLucky Cville

Trivia Night

Gina Sobel

Community Tap Night

JRB's Community Tap Night, Wednesdays 3 PM to close. Local non-profits partner with the brewery for a fundraiser and earn 20% of the day's sales.

Wine Wednesday

King Family Vineyards' popular Wine Wednesday series featuring live music, food trucks, and wine specials.

Wine Down Wednesday – South Canal Street Band

Run, Walk, Crawl

Weekly Wednesday evening run/walk followed by beers at the brewery. 21+ only.

Wine Dinner at Keswick Hall

Locals Vinyl Share & $5 Pints

Bring your records for the locals vinyl share, with $5 pints on tap. 21+ only.

Game Night!

Tailgate Thursday w Perennial Collection & OCSF Oysters

Tailgate Thursdays continue! Live music with Perennial Collection, fresh oysters from Oyster Catcher Sea Farms. Grills fired up — bring your own food to grill, lawn games, and picnic blankets.

Team Trivia

Grab your friends and test your knowledge at Team Trivia at Cunningham Creek Winery. Wine, beer, and prizes await the winners!

Trivia Night

Weekly trivia at the Tap Barn with craft beer and hot artisanal pizza.

Happy Hour at Bryant's Cider & Brewery

Happy Hour 3-5PM. Kick off your weekend at Bryant's.

Locals Night at Bryant's Cider

Cider specials and a fun time for all.

Kooking with Kam

A sweet afternoon with Kooking with Kam, a local Charlottesville-area baker known for homemade specialty cookies and creative baked goods. Kam will be on site with a selection of cookies available for purchase, perfect to enjoy with a glass of wine.

Live Music: Virginia Scenic Railway

Twisted Oak BBQ

Twisted Oak Barbecue, Charlottesville's premier craft BBQ trailer known for its Texas-style smoked brisket, ribs, pulled pork, savory sides, and house-made banana pudding, is rolling into Fallen Tree Vineyard.

Food Truck: Farmacy

The Music of John Kelly

John Kelly takes the stage performing an acoustic set that weaves together multiple musical genres.

Live Music: Bob & Kenn

Enjoy an evening of live music from Bob & Kenn at Jefferson Vineyards.

Virginia Oyster & Wine Celebration with Live Music: FarAway

Friday Sundowner's Music Series featuring Brisk!

The Friday Sundowner's Music Series at Merrie Mill featuring Brisk! Live music from 5:30-8:30 PM with stunning sunset views and excellent wine.

Sunset Soirée - Chickenhead Blues with Arepas on Wheels

Supper Series: Mid-Atlantic Blue Crab Dinner

An intimate farm-to-table dinner celebrating the region's beloved blue crab seafood tradition. Veritas partners with skilled chefs for collaborative culinary experiences. $100 per person, includes wine pairings and service.

Friday Night Jam Session

JRB's open Friday Night Jam Session at 6:30 PM. Join in and possibly get in the lineup for a paid gig.

Funky Bone @ Pro Re Nata

Funky Bone gets the groove going at Pro Re Nata Farm Brewery. Funk, soul, and Virginia craft beer.

Grill Cheese & Beer Pairing

Ticketed grilled cheese and beer pairing - only 12 seats available.

Live Music – Henley & Lou

Trump Grand Tasting

A one-hour guided tasting of six estate-grown wines in the new Meritage Barrel Room, led by a wine educator, including a souvenir Trump Winery glass. Small groups up to 16 guests; advance reservations required.

Happy Little Rectangles

Fallen Tree welcomes Happy Little Rectangles as part of its ongoing effort to support local artists, makers, and small businesses. Stop by, sip some wine, and browse their thoughtful cards, perfect for birthdays, thank-yous, and gifts from the heart.

Saturday Live Music with Matty & Mirabel

Enjoy an afternoon of live music at Cunningham Creek Winery with Matty & Mirabel. Great wines, good vibes.

The Wavelength Trio

The Wavelength Trio takes the stage with a groove-driven blend of vintage rock, blues, original music, and more.

Live Music: Bill & John

Live Music: Barbara Martin and Liz Barnes Trio

Free sunset live music series at Knights Gambit Vineyard, 5-8pm. Wines by the glass and bottle plus Potter's hard cider by the can; bring a picnic, chair or blanket.

Starry Nights

Starry Nights returns to Veritas Vineyards for one night only! Relax under the stars with favorite wines and dance the night away to music from Hipshack. Bring a picnic and lawn chairs, or enjoy stationed or plated meals from Veritas chefs.

Saturday Night Special - The Shacktones with Sweet Jane's Kitchen

The Reckless Brigade

Bluegrass on an August evening in the Blue Ridge. The Reckless Brigade will be pickin' on the Bald Top stage - perfect for a night out on the lawn draped by the backdrop of Appalachia.

Improv with Big Blue Door

Leroy Burks & The Voodoo Whiskey Band @ Pro Re Nata

Leroy Burks & The Voodoo Whiskey Band bring the heat to Pro Re Nata Farm Brewery. Blues, rock, and Virginia craft beer.

Guided Farm Walk

Join a guided walk through Oakencroft's vineyards, orchard, and pastures, enjoying scenic views, meeting the farm animals, and learning about the sustainable practices that shape the wines. Afterward, unwind in the Tasting Room with a complimentary glass of Oakencroft wine or seasonal sangria.

Sangria Summer Market

Willie De

Live Music with Rachael Karpo

Sunday Session - The Michael Elswick Gathering

Cabernet Franc Reserve Feast

A four-course wine paired feast featuring older, rare vintages of Cabernet Franc Reserve. Prepared by Executive Chef Michael Clough. $185 per person, all-inclusive. For reservations, email or call 540-832-7848.

Live Music: Jerry Cappa

Enjoy an afternoon of live music from Jerry Cappa at Jefferson Vineyards.

Music on Deck: Jimmy O

Granny Hobby Club

Each week explores a different hobby at Bryant's Farm and Cidery. Learn something new, or share your tips and tricks to something old.

Weekly Wine Tasting

Weekly wine tasting at Roslyn Farm & Vineyard, 100 Roslyn Heights Rd. Sip a variety of their finest wines in a picturesque farm setting with staff guiding you through each blend.

Mug Club Madness

Every Monday from 3 PM to close: $2 off 20 oz mug fills for Mug Club members.

Food Truck: PotLucky Cville

Trivia Night

Community Tap Night

JRB's Community Tap Night, Wednesdays 3 PM to close. Local non-profits partner with the brewery for a fundraiser and earn 20% of the day's sales.

Wine Wednesday

King Family Vineyards' popular Wine Wednesday series featuring live music, food trucks, and wine specials.

Wine Down Wednesday with Scuffletown

Run, Walk, Crawl

Weekly Wednesday evening run/walk followed by beers at the brewery. 21+ only.

Locals Vinyl Share & $5 Pints

Bring your records for the locals vinyl share, with $5 pints on tap. 21+ only.

Game Night!

Tailgate Thursday w Midnight Buzz & Crozet Seafood

Tailgate Thursdays continue! Live music with Midnight Buzz, seafood from Crozet Seafood. Grills fired up — bring your own food to grill, lawn games, and picnic blankets.

Music in the Park at Taylor Park Orange

Music Trivia Night with Rachael Karpo

Trivia Night

Weekly trivia at the Tap Barn with craft beer and hot artisanal pizza.

Happy Hour at Bryant's Cider & Brewery

Happy Hour 3-5PM. Kick off your weekend at Bryant's.

Locals Night at Bryant's Cider

Cider specials and a fun time for all.

Trump Cidery Summer Concert Series: Mercy Trail

Free live music on the lawn at Trump Cidery, 3550 Blenheim Road, with estate-crafted sparkling hard cider and vineyard views. Featuring Mercy Trail, 4-7pm.

Food Truck: Farmacy

Live Music: Chris Hammock

Enjoy an evening of live music from Chris Hammock at Jefferson Vineyards.

Late Friday + Live Music with Ron Gentry

Don't miss VRV favorite Ron Gentry. A great way to celebrate a Friday night — his music is a delight and the perfect accompaniment to Valley Road wine.

End-Of-Summer Wine Fest: Live Music - Acoustic Soul featuring Tucker Rogers & Richelle Claiborne

Friday Sundowner's Music Series featuring Wavelength

The Friday Sundowner's Music Series at Merrie Mill featuring Wavelength. Live music from 5:30-8:30 PM with stunning sunset views and excellent wine.

DJ - 70's & 80's Dance Party with Twisted Provisions

Music Bingo

Test your music knowledge at Music Bingo at Cunningham Creek! Identify songs and artists for a chance to win great prizes. Wine and beer available.

Summer Culinary Series: Toasts & Tacos

Celebrate the flavors of summer with a festive taco dinner paired with Southwest Mountains wines. A perfect late-summer evening.

Friday Night Jam Session

JRB's open Friday Night Jam Session at 6:30 PM. Join in and possibly get in the lineup for a paid gig.

Gone Country @ Pro Re Nata

Gone Country brings country hits to Pro Re Nata Farm Brewery. A great evening of country music and Virginia craft beer.

Paint + Sip: Sunset Silhouette