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Charlottesville Wine Country

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43 events · Next 7 Days · Mon, Oct 12 – Sun, Oct 18
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Blue Ridge Mountain Maze - Columbus Day Monday Opening at Blue Toad Hard Cider
FestivalPast

Blue Ridge Mountain Maze - Columbus Day Monday Opening

Blue Toad Hard Cider
Mon, Oct 12, 2026
10:00 AM – 6:00 PM

Our only Monday opening of the season! Blue Toad Hard Cider presents the Blue Ridge Mountain Maze fall festival: 5-acre corn maze ('A-Maze-ing Catch'), giant mountain slides, farm animals, pumpkins, apple sling shot, night maze, food trucks and Blue Toad cider on tap. Admission $16 ($15 age 12 & under).

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Porch Nights: Michael Clem ✨ at Eastwood Farm and Winery
Music

Porch Nights: Michael Clem ✨

Eastwood Farm and Winery
Thu, Oct 15, 2026
5:00 PM – 8:00 PM

Come see Michael Clem from 5-8PM! Porch Nights at Eastwood ✨ There’s something about a porch at golden hour that makes the world slow down in the best possible way. At Eastwood Farm and Winery, we’re leaning into that feeling all season long with Porch Nights — our weekly Thursday gathering featuring outdoor live music and an easygoing atmosphere. Grab a seat on our covered veranda or at one of our many picnic tables, relax with the sparkly lights overhead, fireflies in the fields, and a glass of porch-sipping wine in hand – join us for your new favorite Thursday tradition.

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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

Eastwood Farm and Winery
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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Harvest Party Oyster Roast at Eastwood Farm and Winery
Food

Harvest Party Oyster Roast

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

The Wavelength 🎺 | Eastwood After Dark

Eastwood Farm and Winery
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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