Charlottesville Wine CountryWhat's on this weekend

Food Truck: PotLucky Cville

Cider Dinner

Beer & Board Games

Trivia Night

Special Screening: We the Wine People at Royal Cinemas

Join us at the historic Royal Cinemas in Front Royal for a special private showing of a film about Virginia Wine on October 27, 2026 at 7:00 pm. Purchase your tickets HERE WE THE WINE PEOPLE is a feature documentary about Virginia wine and the people turning a complex region into one of America’s most compelling wine stories. Moving from Blue Ridge vineyards to coastal farms, blind tastings, harvest celebrations, barrel rooms, and tasting rooms, the film follows the growers, winemakers, educators, organizers, and advocates who are building a regional identity together. More than a wine film, it is a story about land, belonging, resilience, hospitality, and the belief that a rising tide lifts all boats. Directed and produced by Greek-born filmmaker and wine storyteller Chrisa Giorgi, the film travels through vineyards, barrel rooms, tasting rooms, blind tastings, and harvest gatherings to reveal Virginia as a state that is made up of regions where winemaking is defined by collaboration, resilience, history, and place. DuCard Vineyards is sponsoring this screening and DuCard wine will be available for purchase by the bottle or glass. The price is $20. Purchase your tickets now for this special film. A share of the proceeds go to fund filmmaker’s post-production costs. Purchase your tickets HERE Cost: $20

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

How Might We Wednesdays

Bring the thing that's bugging you. Every Wednesday from 5 to 7 PM, write your problem on a card at the bar and pin it to the board; the room picks one and spends two hours working on it together. Not a talk and not a demo, an actual go at something a neighbor is stuck on. Hosted by The Smithy.

Run, Walk, Crawl Club

Weekly Run, Walk, Crawl Club every Wednesday at 6 PM at WildManDan Brewery (21+ only).

Trivia Night at Patch

Trivia Night at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Karaoke Night

Join us for karaoke night at the Virginia Wine Collective in the loft! Grab a drink, bring your friends, and take the mic for a night of fun, music, and great vibes. Karaoke is hosted 7-9PM, the Collective will be open 5-10PM! 21+.

Vinyl Share

Vinyl Share every Thursday 4-7 PM at WildManDan Brewery (21+ only). Bring a record to spin.

Bold Book Club: Lights Out

Trail Run Club

Trivia Night

Ready to test your knowledge and have some fun? 92 Acres is hosting Trivia Night with Tag Team Entertainment!

Trivia Night

Trivia every Thursday 6:30-8:30 PM. Grab your buddies for a fun night of trivia, delicious beers, and hot, artisanal pizza.

Fresh Pour Thursday

A new beer is tapped at 6:30 PM every Thursday at Three Notch'd Charlottesville, with a free taste.

Adult Karaoke Night

Adult Karaoke Night at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Live Music: Bob & Kenn

Rum Punch Jamaican Cuisine - Guest Food Truck

Rum Punch Jamaican Cuisine - Guest Food Truck at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Live Music: Starfire

Friday Night Out with Kirsten Haze

Come on over to the winery and enjoy 1/2 price wine flights (after 4pm) and the music of Kirsten Haze. Kirsten plays a variety of folk, alt-country, roots-rock, country-blues, and a hint of jazz and swing. Order a snack from our noshing menu or bring your own. We’ve got the wine if you’ve got the time, so make sure to be here to enjoy it with us! 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.

Virginia Oyster & Wine Celebration with Live Music: Lenny Burridge

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 by Lenny Burridge, 5-8PM.

Lost in the Supermarket (Clash Tribute Band) Live

Final Fridays Concert: Blake Hunter & the Gatherers

Final outdoor concert of the year with Blake Hunter and the Gatherers plus Crozet Seafood Supply food truck.

Edible Insight: All Hallows' Eve

Friday Sundowner's Music featuring Wavelength

Friday Sundowner's Music Series featuring Wavelength (last of the season!) at Merrie Mill Farm & Vineyard, 5:30 PM to 8:30 PM.

Friday Cheers with Jason "Tater" Tomlin

Live music 5:30-8 and fried seafood specials at Blue Mountain Barrel House.

A Haunted Supper at Hall's Tavern

Alfresco four-course wine dinner, haunted house tours, and a medium reading over nightcap cocktails - don't miss the fun! Held at Hall's Tavern at East End Farm, 245 Nolting Rd, Louisa, VA. Ticketed event: https://www.exploretock.com/southwestmountainsvineyards/event/622540/a-haunted-supper-at-halls-tavern

Dara James and the Soul Disciples

Dara James and the Soul Disciples return to Free Union with Blues, R&B, and a whole lot of SOUL! Featuring Dara James on guitar and vocals, Eric Franzen on organ, and Jeff Louderback on drums. Friday, October 30th, 6 to 8:30pm. Open to all. No cover. Canelos Burritos 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.

Sunset Soirée - Richelle Claiborne & Friends with Two Brothers Southwestern Grill

Friday Sunset Soirée live music with Richelle Claiborne & Friends, food by Two Brothers Southwestern Grill.

Harvest Nights at the Collective + Winemaker Pop-Up: Josh Cataldo

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 Josh Cataldo — free samples and a facility tour with one of the Collective's independent winemakers.

Bent Theater Comedy Night

Get ready to laugh with Bent Theatre, Charlottesville’s live improv comedy troupe! Every scene is created on the spot using suggestions from the audience, so no two shows are ever the same. Grab a glass of wine, settle in, and enjoy a completely unpredictable night of comedy.

Steve Lanza Jr. and Friends Live at Patch

Steve Lanza Jr. and Friends Live at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

JRB's Friday Night Jam Session

Weekly Friday night jam session at James River Brewery. Join in and possibly get in the lineup for a paid gig.

Big City Band @ Pro Re Nata

Free show. Big City Band is a 6-piece rockin' country band formed in 2017, known for gritty lead vocals and family harmonies inspired by traditional country and southern rock, mixing covers and original songs.

Kai Crowe-Getty Songwriter Spotlight

Ciders & Screams Movie Night: The Craft

Grave Rave

THE GOLDEN AGE OF BASS MUSIC HAS RISEN FROM THE DEAD. October 30th, MOLDVTE and Faux Shaux are bringing back the sound of an era when festival trap and dubstep ruled the speakers. Welcome to GRAVE RAVE — a night of filthy bass, massive drops, throwback anthems, Halloween costumes, and the kind of energy that made the early-to-mid 2010s unforgettable. *Costumes Encouraged - But Not Required Tickets: $24 per person 8:30 PM Doors 9 - 10 PM: Faux Shaux 10 - 12: MOLDVTE Genre: Electronic Ticketed event at The Foundry at Basic City Beer Co., Waynesboro.

Kubota Tour - Fall Color Around The Nursery

Fall Colors at Grelen Kubota Tour with Plant Manager Darren Marsh: a behind-the-scenes Holding Yard tour plus a 45-minute Kubota ride across the 1,000-acre nursery. Limited to three guests (16+). SOLD OUT. (No time listed on Grelen's website.)

Blue Ridge Mountain Maze Corn Maze & Fall Festival

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).

Grilled Cheese & Beer Pairing

Saturday grilled cheese and beer pairing at WildManDan Brewery. Only 12 seats available; tickets required (21+ only).

Halloween at Brewing Tree

Captain Marrrrta's Halloween Extravaganza!

Live Music – Rixeyville Revival

Come out and rock with the Rixeyville Revival Band — bringing the best hits from the ’70s through today! From classic rock to modern chart-toppers, we’ve got the groove to get you moving. Don’t miss a night of unforgettable music and high-energy fun!

Halloween at Eastwood 🎃

Celebrate Halloween at Eastwood with a fun afternoon for the whole family! Join us on Saturday, October 31 from 12–4 PM for live music, Halloween treats, kids’ activities, and plenty of festive fun. Kids are invited to come dressed in their favorite costumes for our costume parade and prizes, while parents can enjoy a glass of wine, cider, or beer and a bite to eat.

Live Music: Sean Stringer

Halloween and Music in the Mountains with The Wavelength

Join us at DuCard this Halloween to enjoy the sounds of local band, The Wavelength. The Wavelength is a consortium of Charlottesville’s finest musicians. Led by vocalist/harmonica Waverly Milor, Larry Bisgaier on guitar/vocals, and Andre LaVelle on bass bringing you vintage rock and jazzy bluesy vibrations. Don’t be surprised if special guests join in the fun on vocals, drums, and more. Our lite noshing menu is available, or bring your own picnic! No cover. Reservations are recommended.

Live Music: South Canal Street

Live music from South Canal Street from 2-5pm at The Barn at 678. Enjoy wine, flights, beer, cider and mead on the porch. No outside beverages.

Raw Beets Classic Rock with Strings

Raw Beets puts a fresh spin on classic rock by reworking familiar favorites through a string-driven sound. Featuring banjos, guitars, and plenty of personality, their set feels both nostalgic and totally unexpected. It’s classic rock you know—just flipped on its head

Live Music in the Orchard: Her Checkered Past

Come share a cider with friends. Enjoy live music by Her Checkered Past with Anne O'Brien and Frank Bechter in the orchard.

Sunset Music Series: Buzzard Hollow Boys

Free Halloween-night sunset live music with the Buzzard Hollow Boys. No reservations on music nights; bring a chair or blanket or a picnic. Wines by the glass and bottle, Potter's hard cider by the can.

Live Music: Mojo Parker

Mojo Parker performs live at Afton Mountain Vineyards on Halloween, with food trucks on site. Tasting room open 11am–7:30pm.

Eastwood After Dark: Halloween Edition 👻

Halloween is taking over Eastwood! Put on your best costume and join us for an evening of swing dancing, live music, wine, and Halloween fun. Swing Cville will kick things off with a swing dance lesson at 4 PM, followed by live music from Zuzu’s Hot 5 from 5–8 PM. Costumes are highly encouraged! Show off your Halloween spirit in our costume contest, with prizes for the best looks.

NOCTURNE II HALLOWEEN BALL

NOCTURNE II HALLOWEEN BALL at Merrie Mill Farm & Vineyard, 5 PM to 11 PM. Tickets required; see event page.

Halloween Party with music by Doctor Rhythm featuring King Gypsy and Jones Catering

Halloween fun – put on your costumes (if you so choose) and groove to the funky beats of Doctor Rhythm featuring King Gypsy. R&B, Blues, Soul, and Reggae tunes in the spooky tropical oasis. Saturday, October 31st, 5 to 8pm. No cover. Open to all. Jones Catering will be onsite with burgers, dogs, wings, fries and more, service beginning by 5:00pm. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

Halloween Party with The Falsies

Wide Margin

Halloween live music 6-9 PM. Wide Margin will be your guide through this All Hallows Eve, with classic rock, Americana, pop, blues and beyond, along with your favorite cold brews.

Music in the Mountains at the Corn Maze

Live music every Saturday night 6-9 PM at the Blue Ridge Mountain Maze at Blue Toad Hard Cider (included with maze ticket).

Virginia Green Band Live at Patch

Virginia Green Band Live at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Halloween Karaoke Night!

Basicween with The Wahookies, SoulCry & XOAP

BASICWEEN: A HALLOWEEN NIGHT AT THE FOUNDRY Something wicked is brewing in Basic City. This Halloween, the lights go down, the volume goes up, and The Foundry opens its doors for BASICWEEN — a full night of live music, costumes, cold beer and whatever else crawls out after dark. On Saturday, October 31st, three bands descend on The Foundry stage: The WaHookies, SOULCRY and XOAP. BASICWEEN COSTUME CONTEST: stick around after SOULCRY's set for the official costume contest, with winners in three categories (Scariest, Most Seductive, Funniest). Each winner takes home a Basic City Beer Co. gift card. Doors: 6:30 PM Show: 8 PM – Late All Ages | Guests under 18 must be accompanied by an adult Genre: Rock

Blue Ridge Mountain Maze Corn Maze & Fall Festival

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).

Bloody Mary & NFL Sunday

Bloody Marys every Sunday with NFL games streaming at 92 Acres!

Autumn Vertical Tasting Guided by Winemaker Luca Paschina

A seated tasting consisting of 7 wines to include older, rare vintages. Food accompaniments by Executive Chef Michael Clough include an appetizer and pasta dish for each guest. For reservations, email or call 540-832-7848. Price: $130 per person (+9.3% tax and 22% service charge).

Silent Book Club

Sip cider and read in quiet camaraderie. No assigned reading, no obligations. Bring your own book of choice. A free social event hosted in the Orchard Room, now the first Sunday of each month.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Long Live the Jam!

Live Music: Chris Hammock

Paint & Sip with Blue Ridge Brushes

Come paint with Blue Ridge Brushes at Hazy Mountain Vineyards! Design: "Autumn Morning". Instructor: Catelyn. Your ticket includes all painting materials and an 11x14 canvas. Step-by-step instruction from a professional artist, no experience necessary. Ticketed event.

Music in the Mountains with John Kelly

Wrap up the weekend at DuCard Vineyards with some contemporary rock and classic tunes by local singer/songwriter John Kelly. You don’t want to miss this talented artist! Grab a bottle of your favorite DuCard wine, enjoy the beautiful mountain scenery, and relax! What could be better than that? A lite noshing menu is available or bring your own snacks. No cover. Reservations are recommended.

Live Music: John Shenk

Balloon Glow

Sunday, November 1st | Beginning at 6 PM $25 per vehicle (tickets required) Join us for a spectacular evening as four hot air balloons from Monticello Ballooning take to the sky above our polo field. Enjoy the glow from the field with food trucks, King Family wines, and an unforgettable evening under the night sky. Tickets are $25 per vehicle, so gather your friends and family, bring a lawn chair or blanket, and settle in for an evening of food, wine, and the magic of Balloon Glow at King Family Vineyards.

'Whispers' An Immersive Art Experience

Game Night

Game Night every Monday at 92 Acres – bring your own game or play one of ours!

Music Bingo

Music Bingo at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.