77 events · This Weekend · Fri, Oct 16 – Sun, Oct 18
Spark Studio Permanent Jewelry Pop-Up at Fallen Tree Vineyard
Special Event

Spark Studio Permanent Jewelry Pop-Up

Fri, Oct 16, 2026
4:00 PM – 7:00 PM

Join us as we welcome Spark Studio to Fallen Tree Vineyard for a permanent jewelry pop-up. Spark Studio specializes in custom-fitted, clasp-free jewelry, including bracelets, anklets, rings, and necklaces, available in options like sterling silver, gold-filled, and 14k solid gold.

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Twisted Oak BBQ Food Truck at Fallen Tree Vineyard
Food Truck

Twisted Oak BBQ Food Truck

Fri, Oct 16, 2026
4:00 PM – 7:00 PM

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!

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Friday Night Out with John Kelly at Ducard
Music

Friday Night Out with John Kelly

Fri, Oct 16, 2026
5:00 PM – 8:00 PM

Wind down at DuCard with a wine flight, and entertainment after the long work week with the music of John Kelly. He is a long-time local musician, writer, and producer who has worked with many other artists from the area, as well as various national artists. He brings along his rock-solid guitar playing and singing, rooted in traditional and country styles. We’ll have wine flights for 1/2 price beginning at 4pm. Grab a snack from our noshing menu or bring your own picnic and settle in for a relaxing great time! No cover. Reservations are recommended. Make yours here today.

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Library Wine Deep Dive at Ducard
Tasting

Library Wine Deep Dive

Fri, Oct 16, 2026
5:00 PM – 7:00 PM

Join us for a special Library Deep Dive tasting as we open the cellar and revisit some of our favorite older vintages. This is a unique opportunity to taste wines from our library, discover how they’ve evolved with age, and enjoy a few bottles that rarely make an appearance. We will focus each session on a single wine. Seating is limited, and advance reservations are required. A limited number of bottles will be available for purchase after the tasting. Cost is $ 32 per person – pay at the event. Make your reservation today! Come sip, savor, and take a little journey through the years with us! Cost: $32

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Virginia Oyster & Wine Celebration with Live Music: Matthew O’Donnell at Eastwood Farm and Winery
Food

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

Fri, Oct 16, 2026
5:00 PM – 8:00 PM

Kick off the weekend with us! Just 5 miles from the Downtown Mall, join us for a celebration of Virginia oysters and wine every Friday night this season. Pair your oysters with a glass of sparkling Blanc de Blancs or enjoy our many other food options paired with a variety of gold medal winning wines. We also offer juice flights and cheese boards for the kids. There is something for the whole family at Eastwood. Live Music September 4: FarAway | 5-8PM September 11: John Kelly | 5-8PM September 18: Matthew O’Donnell | 5-8PM September 25: Sue Harlow | 5-8PM October 2: Eli Cook | 5-8PM October 9: John Kelly | 5-8PM October 16: Matthew O’Donnell | 5-8PM October 23: Matthew O’Donnell | 5-8PM

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Barbara Martin/Liz Barnes Band with Carrie's Soul Food Truck at Glass House
Music

Barbara Martin/Liz Barnes Band with Carrie's Soul Food Truck

Fri, Oct 16, 2026
6:00 PM – 8:30 PM

Jazz/blues music by the Barbara Martin/Liz Barnes Band (Liz Barnes – piano, Barbara Martin – vocals, Tom Harbeck – bass, Jim Howe – drums), performing live inside the tropical glass conservatory. Friday, October 16th, 6 to 8:30pm. Open to all. No cover. Carrie's Soul Food food truck will be onsite with service beginning at 5:30pm. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

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Harvest Nights at the Collective + Winemaker Pop-Up: Joy Ting at Virginia Wine Collective
Tasting

Harvest Nights at the Collective + Winemaker Pop-Up: Joy Ting

Fri, Oct 16, 2026
6:00 PM – 8:00 PM

Experience Virginia wine country during its most exciting season. Join us on Friday evenings throughout harvest for a behind-the-scenes look at what happens when grapes begin their journey to becoming wine. Also tonight: Winemaker Pop-Up with Joy Ting — free samples and a facility tour with one of the Collective's independent winemakers.

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Music Bingo at Grace Estate Winery
Music

Music Bingo

Fri, Oct 16, 2026
6:00 PM – 8:00 PM

Now starting at 6 PM! Music Bingo Night with Tag Team Entertainment (the crew behind Wine Down Trivia Nights and Friday Night Karaoke) — the perfect blend of music, games, and wine, set against a gorgeous sunset. Bring your friends and grab a glass.

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The Greenhorns @ Pro Re Nata at Pro Re Nata Brewpub
Music

The Greenhorns @ Pro Re Nata

Fri, Oct 16, 2026
7:00 PM – 10:00 PM

Free show. The Greenhorns, a 7-piece Charlottesville band, bring a blend of New Orleans funk, jump blues, R&B and jazz to Pro Re Nata Brewpub & Music Hall in Crozet. Drinks and dinner available from the Taproom Table.

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Fireside Collective at Basic City Beer Co.
Music

Fireside Collective

Fri, Oct 16, 2026
8:00 PM – 11:59 PM

Fireside Collective returns to The Foundry at Basic City Beer Co. on Friday, October 16th, bringing their high-energy blend of bluegrass, Americana, folk, and roots music back to Waynesboro for an unforgettable night. Known for their electrifying live performances, tight musicianship, and fearless improvisation, Fireside Collective seamlessly weaves traditional bluegrass with modern influences, creating a sound that is both deeply rooted and refreshingly original. Expect soaring harmonies, blazing instrumentals, and a show packed with energy from start to finish!! Doors: 6:30 PM Show: 8:00 PM All Ages (under 18 must be accompanied by an adult) Genre: Jamgrass Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

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Pumpkin Decorating Workshop at The Market at Grelen
Workshop

Pumpkin Decorating Workshop

Sat, Oct 17, 2026
9:00 AM

Potting-bar style pumpkin decorating workshop: pick a pumpkin, choose succulents, cacti or terrarium plants, and Grelen's plant experts guide you step by step. $10 ticket includes instruction, soil, moss and dried flowers; pumpkin and plants priced a la carte. Limited to 12 people.

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Harvest Party Oyster Roast at Eastwood Farm and Winery
Food

Harvest Party Oyster Roast

Sat, Oct 17, 2026
12:00 PM – 3:00 PM

Raise a glass of award-winning Eastwood wine to harvest season! Join us at Eastwood Farm and Winery on Saturday, October 17, for our Harvest Party Oyster Roast, part of a celebration of Virginia wine across the Commonwealth. Gather your friends, sip your favorite Eastwood wines, and enjoy a special menu by Salty Bottom Blue, featuring oysters Rockefeller, crab cakes, grilled oysters, and oysters raw on the half shell. Eastwood’s full menu will also be available all day, from 12–7:30 PM. Make a day of it with live music by Heidi Riddell from 12:30–3:30 PM and The Wavelength from 5–8 PM! It’s a day to celebrate the season and the people, places, and flavors that make Virginia wine special.

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Horton on the Go: Town Point Virginia Fall Wine Festival at Horton Vineyards
Festival

Horton on the Go: Town Point Virginia Fall Wine Festival

Sat, Oct 17 – Sun, Oct 18, 2026
12:00 PM

Horton on the Go: find Horton Vineyards at the 38th Annual Town Point Virginia Fall Wine Festival, Saturday & Sunday, October 17-18, 2026, at Town Point Park on the Downtown Norfolk Waterfront (113 Waterside Drive, Norfolk). More than 25 of the Commonwealth's top wineries pour over 200 wines. Off-site event; all-day listing on Horton's calendar.

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Live Music – Soul Shakers at Keswick Vineyards
Music

Live Music – Soul Shakers

Sat, Oct 17, 2026
1:00 PM – 4:00 PM

This Southern Soul Horn Band brings the perfect blend of smooth rhythms and electrifying horns that will have you grooving all day long. Whether you’re a fan of classic soul or funky beats, The Soul Shakers are here to deliver an unforgettable experience. Come hungry Barrel and Board will be open serving charcuterie, sandwiches and much more!

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Music in the Mountains with Pat Anderson at Ducard
Music

Music in the Mountains with Pat Anderson

Sat, Oct 17, 2026
2:00 PM – 5:00 PM

The mountains are calling and so is the music by singer-songwriter Pat Anderson. Pat’s a roots rocker with a strong affinity for Dylan, Springsteen, and Petty and possessed with the tough-minded country-rock sensibility of Todd Snider. We are thrilled to have him share his talents with us here at DuCard Vineyards. Bring along a picnic or select eats from our lite noshing menu while you take in the rhythm and views! No cover. Reservations are recommended and can be made here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

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The Inclinators at Glass House
Music

The Inclinators

Sat, Oct 17, 2026
5:00 PM – 8:00 PM

The Inclinators make their Glass House Winery & Brewery debut on the conservatory stage. This high-energy quartet is known for a "danceable, soulful sound that blends a timeless spirit of the past with modern twist echoing the warmth of vinyl." Saturday, October 17th, 5 to 8pm. Open to all. No cover. Drew Lambert – Lead Vocals, Chris Yung – Guitar/Vocals, James Grimm – Bass/Vocals, Paul McDaniel – Drums. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

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The Wavelength 🎺 | Eastwood After Dark at Eastwood Farm and Winery
Music

The Wavelength 🎺 | Eastwood After Dark

Sat, Oct 17, 2026
5:00 PM – 8:00 PM

Join us for upbeat & fun bands every Saturday night. Gather your friends and family and join us for live music that you’ll want to dance to! Plus sit back and enjoy your favorite beverage and delicious food. Saturday Night Music Lineup: September 5: Transatlantic Invasion | 5-8PM September 12: LockJaw | 5-8PM September 19: The Wavelength | 5-8PM September 26: Kat & The Travelers | 5-8PM October 3: The Unsuitables | 5-8PM October 10: Jason Burke: Bunch O’Mugs | 5-8PM October 17: The Wavelength | 5-8PM October 24: Classic Road | 5-8PM Check back for more dates this fall!

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Valerie Smith and Liberty Pike at Bald Top Brewing Co.
Music

Valerie Smith and Liberty Pike

Sat, Oct 17, 2026
6:00 PM – 9:00 PM

Live music 6-9 PM. It's fall in the Blue Ridge and there's nothing better on the stage than some real Appalachian bluegrass. Liberty Pike has a long history on the bluegrass circuit and they really are the total package: whimsical and upbeat.

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Stage Fright! An Improv Comedy Show at Goat Rodeo Comedy Co.
Comedy/Improv

Stage Fright! An Improv Comedy Show

Sat, Oct 17, 2026
7:00 PM

Celebrate spooky season with a night of completely unscripted comedy inspired by audience suggestions at Vinegar Hill Theatre (Lighthouse Studio, 220 W Market St). Featuring members of Goat Rodeo's improv teams Big Head Fight and Billionaire Robot Dogs. $10 advance, $15 at the door.

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Four Thirty Four (434) with 21 Gunz & Savage Theory at Basic City Beer Co.
Music

Four Thirty Four (434) with 21 Gunz & Savage Theory

Sat, Oct 17, 2026
8:00 PM – 11:00 PM

FOUR THIRTY FOUR (434) RETURNS TO THE FOUNDRY with 21 Gunz & Savage Theory Saturday, October 17th, 2026 Doors: 6:30 PM | Show: 8:00 PM We’re excited to welcome back our good friends Four Thirty Four (434) to The Foundry at Basic City Beer Co. for another huge night of live rock! If you’ve caught 434 at The Foundry before, you already know what they bring — a high-energy show, heavy guitars, big vocals, and the kind of performance that feels right at home on our stage. Joining them for the night are 21 Gunz and Savage Theory, rounding out a three-band lineup built for fans who like their rock loud and live. Come early, grab a beer, and get ready for a loud one. Genre: Hard Rock Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

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Heirloom Apple Tasting at Albemarle Ciderworks
Tasting

Heirloom Apple Tasting

Sun, Oct 18, 2026
11:00 AM – 12:00 PM

Of course, you've heard of Granny Smith and Red Delicious, but what about Esopus Spitzenburg and Belle de Boskoop? At Albemarle CiderWorks, we cultivate over 250 unique apple varieties. Join us for a guided heirloom apple tasting.

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[Food Truck] Rum Punch at Albemarle Ciderworks
Food Truck

[Food Truck] Rum Punch

Sun, Oct 18, 2026
12:00 PM – 5:00 PM

Originally from Jamaica, Chef Racquel White has become an integral part of the Charlottesville community, introducing locals to authentic Jamaican cuisine. Rum Punch food truck on site at Albemarle CiderWorks.

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Exclusive DuCard Vineyards & Estate at Meander Gold Medal Experience at Ducard
Dinner

Exclusive DuCard Vineyards & Estate at Meander Gold Medal Experience

Sun, Oct 18, 2026
12:00 PM – 4:00 PM

Join DuCard Vineyards and The Estate at Meander for an intimate autumn experience celebrating award-winning Virginia wine, seasonal farm-to-table dining, and historic countryside hospitality. Your Journey begins at 12:00 PM at DuCard Vineyards, bordering Shenandoah National Park at the western edge of Madison County. Personally hosted by the Owner, enjoy DuCard’s Gold Medal Wine Flights & Vineyard Tour with special pours of its gold medal winning wines presented in crystal glassware and accompanied by light bites and conversation. Walk the vineyard rows to discover the care and techniques behind DuCard’s wines, then explore the winery and barrel room. A seated tasting offers a special opportunity to sample wines still aging in oak and learn how they develop before bottling. A second tasting session will feature sparkling wines, with samples both from DuCard and around the world. Following the experience, make the approximately 30-minute drive to The Estate at Meander. Settle into your suite or cottage if staying overnight, then gather for our signature four-course Table Experience dinner in the historic Manor House. Your $299-per-person experience includes: DuCard’s private wine tastings Vineyard and winery tour A bottle of The Reverend wine – a special Bordeaux-style blend crafted in ode to Meander’s original builder – awaiting in your room or presented at Meander to take home The Estate at Meander’s signature four-course Table Experience dinner at the Harvest & Hearth Bistro Complimentary Estate breakfast for overnight guests Space is limited. Advance reservations are required BOOK YOUR EXPERIENCE HERE Overnight accommodations are available at an additional cost. Participants meet at DuCard and travel onward to Meander; transprotation is not included BOOK YOUR STAY ONLINE or call The Estate at Meander at 540-672-4912. Cost: $299

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Live Music with Rachael Karpo at Keswick Vineyards
Music

Live Music with Rachael Karpo

Sun, Oct 18, 2026
12:00 PM – 4:00 PM

Rachael is a New Jersey Native and an Air Force Veteran is a soloist who pours her heart into every note she sings. From 80’s and 90’s to Classic Rock and Country, Rachael’s unique blend of music adds to her artistry performances. Barrel and Board will be serving sandwiches, salad, charcuterie and much more!

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Armchair Expedition - Sparkling Wine at Ducard
Tasting

Armchair Expedition - Sparkling Wine

Sun, Oct 18, 2026
2:00 PM – 4:00 PM

Sparkling wine is not just for special occasions, it can be an everyday drink of choice. There are several methods to make sparking wine across history which are well known or may have just come back in fashion. Now is a time to discover a’ Pet Nat’ or understand what the ‘traditional method’ really means. Is this regional or local? Join us to sip and discuss with sparkling wines from around the world. The session will be at 2pm. Small bites will accompany the wines, and wines will be available for purchase at the end of the session. Session price: $49 per person (Wine Club discounts apply, Email Beth for WC reservations), advance reservation required, and space is limited. Purchase tickets by clicking HERE. Check out an article about these world of wine events here Cost: $49

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