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Things to Do in Charlottesville This Weekend
48 events at wineries, breweries & cideries around Charlottesville, Oct 16–18.What's on today ❧
This weekend at a glance
This weekend in Charlottesville (Oct 16–18, 2026): 48 events at area wineries, breweries and cideries.
Friday: 16 events, including Spark Studio Permanent Jewelry Pop-Up at Fallen Tree Vineyard (12 PM); Twisted Oak BBQ Food Truck at Fallen Tree Vineyard (12 PM); Mah Jongg Fridays at Cunningham Creek Winery (1 PM); plus 13 more.
Saturday: 18 events, including Fluvanna Artist's Tour at Cunningham Creek Winery (10 AM); Annual Harvest Fest at Cunningham Creek Winery (11 AM); Fall Foliage Fest at Bold Rock (11 AM); plus 15 more.
Sunday: 14 events, including Fluvanna Artist's Tour (Day 2) at Cunningham Creek Winery (10 AM); Annual Harvest Fest (Day 2) at Cunningham Creek Winery (11 AM); Bloody Mary & NFL Sunday at 92 Acres (12 PM); plus 11 more.
Also this weekend: 31 live music shows, 4 festivals or markets, 12 dog-friendly venues with events.
Listings last updated Oct 12, 6:00 AM ET from venue calendars.
Friday Fri, Oct 16
- 12pmSpark Studio Permanent Jewelry Pop-Up
- 12pmTwisted Oak BBQ Food Truck
- 1pmMah Jongg Fridays
- 4pmLive Music: Chris Hammock
- 5pmFriday Night Out with John Kelly
- 5pmFriday Sundowner's Music featuring Bailey Hayes
- 5pmLive Music: Tidewater Valley
- 5pmZuzu's Hot 5 with SwingCville Live
- 6pmLive Music with Brian Franke: Classic Rock Favorites
- 6pmLive Music: Barbara Martin/Liz Barnes Band
- 6pmLive Music: South River Strings Band
- 6pmMusic Bingo
- 7pmCiders & Screams Movie Night: Ghostbusters
- 7pmScuffletown Duo!
- 7pmThe Greenhorns @ Pro Re Nata
- 8pmFIRESIDE COLLECTIVE
Saturday Sat, Oct 17
- 10amFluvanna Artist's Tour
- 11amAnnual Harvest Fest
- 11amFall Foliage Fest
- 12pmFood Truck: Simply Trending Catering
- 12pmHorton on the Go: Town Point Virginia Fall Wine Festival
- 1pmLive Music – Soul Shakers
- 2pmAn Afternoon with Sue Harlow
- 2pmLive Music: Rivanna Roadshow
- 2pmLive Music: The Inclinators
- 2pmMusic in the Mountains with Pat Anderson
- 3pmLive Music: Bluzonia
- 5pmLibrary Wine Deep Dive
- 5pmLive Music: Greg Ward
- 5:30pmLUA Project Live
- 6pmAn Evening with Frank Morgan: Virginia & French Wines Tasting
- 6pmHarvest Party at King Family Vineyards
- 6pmValerie Smith and Liberty Pike
- 8pmFour Thirty Four (434)
Sunday Sun, Oct 18
- 10amFluvanna Artist's Tour (Day 2)
- 11amAnnual Harvest Fest (Day 2)
- 12pmBloody Mary & NFL Sunday
- 12pmFamily Field Day
- 12pmGina Sobel Live Music
- 12pmLive Music with Rachael Karpo
- 1pmLive Music: Forde Upshur
- 1pmSunday Jazz and Blues featuring Whiskey Django
- 2pmAn Lar Traditional Irish Band
- 2pmArmchair Expedition - Sparkling Wine
- 2pmCider & Strings: An Afternoon with Acoustic Union Live
- 2pmLive Music: Andy Tichenor
- 2pmLive Music: Joel Streeter
- 2pmMulvaney Music on the Deck
Free this weekend
Nothing listed for this weekend yet. See all upcoming.
Live music this weekend
- Live Music: Chris Hammock · Jefferson Vineyards · Fri 4pm
- Friday Night Out with John Kelly · Ducard · Fri 5pm
- Friday Sundowner's Music featuring Bailey Hayes · Merrie Mill Farm & Vineyard · Fri 5pm
- Live Music: Tidewater Valley · Brewing Tree Beer Company · Fri 5pm
- Zuzu's Hot 5 with SwingCville Live · Potter's Craft Cider · Fri 5pm
- Live Music with Brian Franke: Classic Rock Favorites · Fallen Tree Vineyard · Fri 6pm
- Live Music: Barbara Martin/Liz Barnes Band · Glass House · Fri 6pm
- Live Music: South River Strings Band · Starr Hill Brewery - Crozet · Fri 6pm
- Music Bingo · Grace Estate Winery · Fri 6pm
- Scuffletown Duo! · The Batesville Market · Fri 7pm
- The Greenhorns @ Pro Re Nata · Pro Re Nata Brewpub · Fri 7pm
- FIRESIDE COLLECTIVE · Basic City Beer Co. · Fri 8pm
Festivals & markets
- Annual Harvest Fest · Cunningham Creek Winery · Sat 11am
- Fall Foliage Fest · Bold Rock · Sat 11am
- Horton on the Go: Town Point Virginia Fall Wine Festival · Horton Vineyards · Sat 12pm
- Annual Harvest Fest (Day 2) · Cunningham Creek Winery · Sun 11am
Family-friendly
- Spark Studio Permanent Jewelry Pop-Up · Fallen Tree Vineyard · Fri 12pm
- Twisted Oak BBQ Food Truck · Fallen Tree Vineyard · Fri 12pm
- Mah Jongg Fridays · Cunningham Creek Winery · Fri 1pm
- Live Music: Chris Hammock · Jefferson Vineyards · Fri 4pm
- Friday Night Out with John Kelly · Ducard · Fri 5pm
- Zuzu's Hot 5 with SwingCville Live · Potter's Craft Cider · Fri 5pm
- Live Music with Brian Franke: Classic Rock Favorites · Fallen Tree Vineyard · Fri 6pm
- Live Music: South River Strings Band · Starr Hill Brewery - Crozet · Fri 6pm
- The Greenhorns @ Pro Re Nata · Pro Re Nata Brewpub · Fri 7pm
- FIRESIDE COLLECTIVE · Basic City Beer Co. · Fri 8pm
- Fluvanna Artist's Tour · Cunningham Creek Winery · Sat 10am
- Annual Harvest Fest · Cunningham Creek Winery · Sat 11am
Dog-friendly wineries
- Cunningham Creek Winery · 7 events this weekend
- Ducard · 4 events this weekend
- Potter's Craft Cider · 3 events this weekend
- Starr Hill Brewery - Crozet · 3 events this weekend
- Basic City Beer Co. · 2 events this weekend
- Bold Rock · 2 events this weekend
- Glass House · 2 events this weekend
- Jefferson Vineyards · 2 events this weekend
- Keswick Vineyards · 2 events this weekend
- Bald Top Brewing Co. · 1 event this weekend
- Pippin Hill Farm & Vineyard · 1 event this weekend
- Pro Re Nata Brewpub · 1 event this weekend
FAQ
What's happening in Charlottesville this weekend?
48 events are listed at Charlottesville-area wineries, breweries and cideries this weekend (Oct 16–18), including Spark Studio Permanent Jewelry Pop-Up at Fallen Tree Vineyard (Fri 12 PM); Twisted Oak BBQ Food Truck at Fallen Tree Vineyard (Fri 12 PM); Mah Jongg Fridays at Cunningham Creek Winery (Fri 1 PM); Live Music: Chris Hammock at Jefferson Vineyards (Fri 4 PM); plus 44 more.
Which wineries have live music this weekend?
31 live music shows this weekend: Live Music: Chris Hammock at Jefferson Vineyards (Fri 4 PM); Friday Night Out with John Kelly at Ducard (Fri 5 PM); Friday Sundowner's Music featuring Bailey Hayes at Merrie Mill Farm & Vineyard (Fri 5 PM); Live Music: Tidewater Valley at Brewing Tree Beer Company (Fri 5 PM); Zuzu's Hot 5 with SwingCville Live at Potter's Craft Cider (Fri 5 PM); Live Music with Brian Franke: Classic Rock Favorites at Fallen Tree Vineyard (Fri 6 PM); plus 25 more.
Free things to do in Charlottesville this weekend
No events marked free are listed for this weekend yet. Many winery and brewery music sets have no cover — check each listing's pricing.