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Horton on the Go: Mount Vernon Fall Wine Festival

Horton Vineyards at the Mount Vernon Fall Wine Festival.

Blue Ridge Mountain Maze - Columbus Day Monday Opening

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).

Game Night

Game night at 92 Acres Winery.

Music Bingo

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

Trivia w/ Olivia

Monday trivia with Olivia at Three Notch'd Charlottesville, 7-9 PM. Free to play.

Food Truck: PotLucky Cville

Trivia Night

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

Wine Down Wednesday with The Unsuitables

Run, Walk, Crawl Club

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

Twilight Raven Paint Party @ Patch Brewing Co.

Twilight Raven Paint Party @ Patch Brewing Co. at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

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.

Bingo & Bourbon!

Bingo and Bourbon event at 92 Acres Winery.

Porch Nights: Michael Clem ✨

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.

Cornhole Night OCPR

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

Cutting Board Paint Night Workshop

Mahjong with Mountain Mahj

Beginner-friendly Mahjong lessons with Mountain Mahj: learn the rules, strategies, and traditions of the game in easy-to-follow steps while hanging out with friends. Lesson is 2.5 hours. Ticketed event (mountainmahjczt.com/classes).

Trail Run Club

Fresh Pour Thursday

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

Trivia Night

Next Stop Comedy

Next Stop Comedy at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

The Front Porch Presents: Songwriter's Open Mic

Spark Studio Permanent Jewelry Pop-Up

Twisted Oak BBQ Food Truck

Live Music: Chris Hammock

Friday Night Out with John Kelly

Friday Sundowner's Music featuring Bailey Hayes

Live Music: Tidewater Valley

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

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

Zuzu's Hot 5 with SwingCville Live

Friday Cheers with Creek Mill Grass

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

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

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.

Live Music with Brian Franke: Classic Rock Favorites

Live Music: Barbara Martin/Liz Barnes Band

Live Music: South River Strings Band

Music Bingo

An evening of music and bingo at Grace Estate Winery.

Sunset Soirée - Chickenhead Blues with Twisted Provisions

Friday Sunset Soirée live music with Chickenhead Blues, food by Twisted Provisions.

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.

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.

Ciders & Screams Movie Night: Ghostbusters

Scuffletown Duo!

The Greenhorns @ Pro Re Nata

Live music at Pro Re Nata Farm Brewery.

FIRESIDE COLLECTIVE

Lecture: Fall Color at Grelen (Free)

A free class highlighting trees and shrubs with vibrant autumn color available now at the Grelen Nursery, which thrive locally, and how to choose the best ones for your landscape. RSVP requested.

Pumpkin Decorating Workshop

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.

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).

Fall Foliage Fest

Grilled Cheese & Beer Pairing

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

Harvest Party Oyster Roast

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.

Horton on the Go: Town Point Virginia Fall Wine Festival

Horton Vineyards at the Town Point Virginia Fall Wine Festival.

Meetin on the Mountain: British Car Show

The Shenandoah Valley British Car Club brings classic British cars to Afton Mountain Vineyards, with food trucks and vineyard views. Tasting room open 11am–7:30pm.

Live Music: Heidi Riddell

Come see Heidi Riddell! Heidi will be playing from 12:30-3:30PM.

Live Music – Soul Shakers

An Afternoon with Sue Harlow

Live Music with Rebecca Romano

Talented local artist Rebecca Romano performs for an afternoon of music with award-winning Valley Road Vineyards wine. Bring a picnic or grab a pizza, baguette and cheese.

Live Music: The Inclinators

Live Music: The Peacemakers

Live music featuring The Peacemakers at Woodbrook Farm Vineyard. Sip Woodbrook wines and take in the views; Barry Long will be serving BBQ.

Music in the Mountains with Pat Anderson

Live Music: Bluzonia

Live Music: The Crybabies

The Crybabies perform live at Afton Mountain Vineyards, with food trucks on site. Tasting room open 11am–7:30pm.

Sunset Music Series: Zuzu's Hot 5 + Crozet Seafood

Free sunset live music with Zuzu's Hot 5, plus the Crozet Seafood food truck. No reservations on music nights; bring a chair or blanket. Wines by the glass and bottle, Potter's hard cider by the can.

Library Wine Deep Dive

Live Music: Greg Ward

Matthew O’Donnell Music

Live music from Matthew O’Donnell in the Hark Vineyards tasting room, with estate-grown, Governor's Cup gold medal wines.

The Wavelength 🎺 | Eastwood After Dark

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!

LUA Project Live

An Evening with Frank Morgan: Virginia & French Wines Tasting

Frank Morgan guides a comparative tasting of Pollak and French wines exploring Virginia wine's Old World inspiration.

Harvest Party at King Family Vineyards

Hogfish Live at Patch

Hogfish Live at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

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).

Valerie Smith and Liberty Pike

Live music featuring Valerie Smith and Liberty Pike

Stage Fright! An Improv Comedy Show

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.

Four Thirty Four (434)

Autumn Plein Air at Grelen

Autumn plein air painting at The Market at Grelen. Registration is closed. (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).

Bloody Mary & NFL Sunday

Enjoy Bloody Marys and watch NFL games at 92 Acres Winery.

Chen's Kitchen - Guest Food Truck

Chen's Kitchen - Guest Food Truck at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Fall Family Day & Harvest Party Market

Family Field Day

Gina Sobel Live Music

Live Music with Rachael Karpo

Live Music: Brian Franke

Come see Brian Franke! Brian will be playing from 1-4PM.

Live Music: Forde Upshur

Session Sunday with Robert Jospé Band

Session Sundays continue at Stinson Vineyards with live music on the patio performed by the Robert Jospé Band. Weather permitting; please leave outside alcohol at home.

Sunday Jazz and Blues featuring Whiskey Django

Sunday Session - The Trio

Sunday Session live music with The Trio.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Alex Caton & Friends: Trad Irish Music

Alex Caton & Friends: Trad Irish Music at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

An Lar Traditional Irish Band

Armchair Expedition - Sparkling Wine

Cider & Strings: An Afternoon with Acoustic Union Live

Live Music: Andy Tichenor

Live Music: Joel Streeter

Mulvaney Music on the Deck

Game Night

Game night at 92 Acres Winery.

Music Bingo

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

Fletcher Daniel

Spooky Halloween Trivia

Halloween-themed Monday trivia at Three Notch'd Charlottesville, 7-9 PM. Free to play.

Food Truck: PotLucky Cville

Trivia Night

Steal the Glass

The third Wednesday of every month, take home a souvenir glass with a draft purchase! Check Blue Mountain's social media for this month's glass.

Andrew Beverly Live Music

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

Wine Down Wednesday – South Canal Street Band

An Evening of Hope

Evening of Hope: A Community Celebration & Fundraiser October 21, 2026 | 6:00–9:00 PM Eastwood Farm and Winery Join us for Reclaimed Hope’s annual community celebration and fundraiser, where friends, families, and supporters come together for a memorable evening with purpose.

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.

Vinyl Share

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

Porch Nights: Ty Burkhardt ✨

Come see Ty Burkhardt 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.

Paint + Sip at the Virginia Wine Collective

Come paint with us, no experience necessary, all materials included! Your ticket includes a canvas, specialty paint, and all supplies. Each class is taught by a professional artist who will guide you through the design step by step at a comfortable pace. Ticketed event.

Trail Run Club

Voodoo Doll Workshop

Trivia Night with Mike & Miranda

Fresh Pour Thursday

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

Trivia Night

Karen's Line Dancing (Free, Ages 16+)

Karen's Line Dancing (Free, Ages 16+) at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Live Music: Sue Harlow

Friday Night Out with Mirabelle & Matty

Live Music: Wavelength

OCTOBER BACHATA

Sunset Salsa Bachata night at Hazy Mountain Vineyards.

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

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

Fall Wine Dinner w/Chef Rachel Pennington

A ticketed fall wine dinner at Hark Vineyards prepared by Chef Rachel Pennington and paired with Hark's estate wines. Tickets via Ticket Tailor.

Friday Cheers with Jacob Paul Allen

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

Friday Sundowner's Music featuring Mercy Creek

Friday Sunset Soirée - Big Fun with Sweet Jane's Kitchen

Friday Sunset Soirée live music with Big Fun, food by Sweet Jane's Kitchen.

Harvest Nights at the Collective

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.

Live Music: Chickenhead Blues Band

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.

Paint + Sip "Stack o' Pumpkins"

Paint and sip event featuring a pumpkin stack at Hazy Mountain.

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.

The Winemaker's Journey Part 2

Continue the winemaker's journey at Hazy Mountain Vineyards.

Ciders & Screams Movie Night: Scooby-Doo

The Four Horsemen & Vulgar Display of Pantera

Planning and Planting the Home Orchard

Workshop on planning and planting a home orchard at Albemarle CiderWorks

Pumpkin Decorating Workshop

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.

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).

Hallowine

Nelson Days

Grilled Cheese & Beer Pairing

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

Chelle's Shack Homemade Goods Pop-Up

Fall Festival

Halloween Scavenger Hunt

Hark's annual Halloween scavenger hunt in the vineyard, Oct 24–25. Follow clues through the vines to uncover spooky items hidden across the property. Wine for 21+, goodie bags for the kids. Costumes encouraged!

Live Music | Danny Jams

Live Music: FarAway

Come see FarAway! FarAway will be playing from 12:30-3:30PM on the stage in The Barn.

Live Music: Jon Spear Band

Clark Shifflett & Marc MacGlashan Live

Clark Shifflett and Marc MacGlashan come in from Nashville to perform in the Woodbrook tasting room. CubaMex will be serving homemade food.

Live Music: Matty & Mirabelle

Music in the Mountains with Jimmy O

The Wavelength Trio

4th Annual Chili Cook Off

James River Brewery's 4th Annual Chili Cook Off. Live music from Old Hank and the 10-4 Good Buddies, Mr. Z's BBQ food truck, raffles and guest prizes. $5 event tickets.

Five Old Gentlemen (FOG) Live

Classic rock live music at Blenheim Vineyards, free event.

Live Music: Danny Goodson Band

The Danny Goodson Band performs live at Afton Mountain Vineyards, with food trucks on site. Tasting room open 11am–7:30pm.

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.

Wine & Design at Horton Vineyards

Wine and design event at Horton Vineyards.

Sunset Music Series: Ken Farmer & Authenticators

Free sunset live music with Ken Farmer & Authenticators. 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.

The Norms Music

Live music from The Norms at Hark Vineyards, with estate-grown wines and mountain views.

Classic Road 🎺 | Eastwood After Dark

Come see Classic Road! They will be playing from 5-8PM. 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.

Live Music: Patrick Dimeo

SKANK Live

Mojo Parker Express

Live music featuring Mojo Parker Express

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).

The Cows Live at Patch

The Cows Live at Patch at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

The Pollocks

Hallowine's Spooky Wine Walk

Glam'r Kiti Live

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).

Fall Sound Bath

A restorative one-hour Fall Sound Bath in the Center at Oakencroft with light stretching and meditation. $34 per ticket.

Guided Farm & Vineyard Walk

A leisurely guided stroll through Oakencroft's vineyards, orchard and pastures: scenic views, farm animals and the sustainable practices behind the wines, followed by a complimentary glass of wine or seasonal sangria. $22 per ticket.

Heart of Virginia Artisans AUTUMN MARKET

Autumn artisan market at Hazy Mountain Vineyards.

Bloody Mary & NFL Sunday

Enjoy Bloody Marys and watch NFL games at 92 Acres Winery.

Family Field Day

Live Music with Pat Anderson

Paint & Sip “Garden Ghost”

Come paint with us, no experience necessary, all materials included! Instructor: Catelyn With your ticket, you get all painting materials, an 11×14 canvas, and a fun time with friends! Join us to learn how to paint this design in a step by step format. Each class is taught by a professional artist that will guide you through various techniques at a comfortable pace. Ticketed event.

Live Music: Mike McCray

Mike McCray performs acoustic guitar music at Afton Mountain Vineyards, with food trucks on site. Tasting room open 11am–5pm.

POLOWEEN – Halloween Sunday Polo

Session Sunday

Session Sundays run every Sunday through October at Stinson Vineyards: relax on the patio with live music from 1-4 PM. Check Stinson's social media for performer and weather updates.

Sunday Jazz and Blues featuring John D'earth

Sunday Session - The Michael Elswick Gathering

Sunday Session live music with The Michael Elswick Gathering.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Witches' Day Out

Allie Kelly – Artist Meet & Show

Meet local artist Allie Kelly and view her work at Blenheim Vineyards.

Live Music: Alex Arbaugh

Live Music: Greg Ward

Music Bingo

Everyone loves singing along with their favorite songs and who doesn’t love a competitive game of Bingo? Music Bingo brings together the best of both worlds for a high energy game that is fun for everyone. Simply listen to your favorite music, match the songs to the titles on your music bingo cards, and win great prizes!

Music in the Mountains by Gina Sobel

Old Time String Band Jam

Old Time String Band Jam at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Early Mountain X Barboursville Vineyards

Homecoming: An Evening with Mariana Bell

Game Night

Game night at 92 Acres Winery.

Music Bingo

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

Trivia w/ Olivia

Monday trivia with Olivia at Three Notch'd Charlottesville, 7-9 PM. Free to play.

Food Truck: PotLucky Cville

Cider Dinner

Beer & Board Games

Special Screening: We the Wine People at Royal Cinemas

Trivia Night

Wine Wednesday – Extended Tasting Room Hours & Food Trucks

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

Trivia night at 92 Acres Winery.

Fresh Pour Thursday

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

Trivia Night

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.

Friday Night Out with Kirsten Haze

Live Music: Starfire

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.

Edible Insight: All Hallows' Eve

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.

Friday Cheers with Jason "Tater" Tomlin

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

Friday Sundowner's Music featuring Wavelength

Lost in the Supermarket (Clash Tribute Band) Live

A Haunted Supper at Hall's Tavern

Bent Theater Comedy Night

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.

Live Music: Dara James and the Soul Disciples

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.

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.

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.

Big City Band @ Pro Re Nata

Live music at Pro Re Nata Farm Brewery.

Ciders & Screams Movie Night: The Craft

Kai Crowe-Getty Songwriter Spotlight

GRAVE RAVE

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).

Captain Marrrrta's Halloween Extravaganza!

Halloween at Brewing Tree

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 – Rixeyville Revival

Live Music: Sean Stringer

Halloween and Music in the Mountains with The Wavelength

Halloween Party with Doctor Rhythm

Raw Beets Classic Rock with Strings

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.

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.

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.

NOCTURNE II HALLOWEEN BALL

Halloween Party with The Falsies

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.

Wide Margin

Live music featuring Wide Margin

Halloween Karaoke Night!

BASICWEEN with The Wahookies

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).

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).

Bloody Mary & NFL Sunday

Enjoy Bloody Marys and watch NFL games at 92 Acres Winery.

Vinyasa Yoga

Sunday vinyasa yoga at Chisholm Vineyards. Tickets required.

Live Music: Chris Hammock

Long Live the Jam!

Live Music: John Shenk

An Immersive Creative Experience for the Curious Spirit

Music Bingo

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

Food Truck: PotLucky Cville

Trivia Night

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.

Vinyl Share

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

Cider Bingo

Comedy Uncorked

Get ready for a night of big laughs and great wine! Comedy Uncorked is coming to Eastwood Farm and Winery for an evening of live stand-up comedy in the vineyard.

Trail Run Club

Bent Theatre Improv

Bent Theatre Improv at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Live Music: Gina Sobel

Virginia Oyster & Wine Celebration with Live Music: John Kelly

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 John Kelly, 5-8PM.

Friday Sunset Soirée - The Inclinators with Two Brothers Southwestern Grill

Friday Sunset Soirée live music with The Inclinators, food by Two Brothers Southwestern Grill.

Live Music: South River Strings Band

Matt Palmieri Country Music

Member Mingle at Evening Star

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.

NOVEMBER trivia WITH TAG TEAM ENTERTAINMENT

November Trivia night with Tag Team Entertainment at Hazy Mountain.

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.

Outdoor Movie Night: Kelly's Heroes

Outdoor movie night screening Kelly's Heroes at Horton Vineyards.

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).

Sip & Savor Express Train Ride

Scenic round-trip train ride from Louisa station with guided tasting of four estate wines and artisan charcuterie board.

Grilled Cheese & Beer Pairing

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

Joyful Bauble Co. Pop-Up

Live Music: Jim Richardson

Come see Jim Richardson! Jim will be playing from 12:30-3:30PM.

Andrew Hill

Taste of Nelson: In the Corn Maze

Sip and stroll the corn maze with unlimited tastings from cideries, breweries and wineries along Nelson 151, plus two live bands, food trucks and a souvenir glass. VIP entry at 1 PM; general admission 2-6 PM. Early bird GA $44, VIP $79.

Wings Over Wine Country

Live Music: Kiz Carter (Trio)

The Sounds of Erynn McLeod

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.

Salute & Sip: A Military K9 Tribute

Salute and Sip event honoring military K9s at Horton Vineyards.

Live Music: Don't Look Up

Lockjaw Classic Rock 🎺 | Eastwood After Dark

Come see Lockjaw! They will be playing from 5-8PM. About Lockjaw: Crowd-pleasing classic rock and blues. 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.

Sarah White & The New Band

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).

Smuggler Sunday

Wine club members only specialty flight of library or special release wines.

Chen's Kitchen - Guest Food Truck

Chen's Kitchen - Guest Food Truck at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Mercy Creek Live Music

Live Music: Brian Franke

Come see Brian Franke! Brian will be playing from 1-4PM.

Live Music: Melissa Hansen

Live Music: Scuffletown

Music: King Golden Banshee

Music: King Golden Banshee at Patch Brewing Co. in Gordonsville. Listed on Patch's events calendar.

Second Sunday Bluegrass Jam

Food Truck: PotLucky Cville

Trivia Night

Run, Walk, Crawl Club

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

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.

Craft Door Mats Workshop

Live Music: The Go-Tos

Trail Run Club

Open Mic Night

Live Music: Paxton Henderson

Live Music: Sue Harlow

Come see Sue Harlow! Sue will be playing from 5-8PM.

An Evening with Dave McIntyre

Don't Look Up

Silver Starlight Opportunity Ball

Come enjoy a memorable night for a great cause at Afton Mountain Vineyards. All-day listing; see event page for details and tickets.

Sip & Savor Express Train Ride

Scenic round-trip train ride from Louisa station with guided tasting of four estate wines and artisan charcuterie board.

Grilled Cheese & Beer Pairing

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

East End Fair

Live Music: Porch Dogs

Come see the Porch Dogs! They will be playing from 12:30-3:30PM. About Porch Dogs Porch Dogs Keith and Everette have been entertaining Central and Southwest Virginia for over seven years with a variety of music from mellow to rocking. Pop, Rock, Americana, Soul, Country and Oldies. These dogs do it all!

Live Music with Brian Franke

Live Music: Dara James

The Art of Wine

An artistic wine experience at Grace Estate Winery.

Live Music: The Loya Brothers

The Wavelength 🎺 | Eastwood After Dark

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.

Crown Club Saturday: Murder Mystery Party

Wine Dinner

NCCF Silver Starlight Ball

An elegant evening benefiting the National Children's Cancer Foundation. Tickets from $250.

Mama Tried

Truffle Feast

A four-course wine paired feast prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

Paint Your Pet Autumn Workshop

Local artist Anissa Frantz sketches your pet on an 11x14 canvas from a photo you send two weeks ahead, then teaches you to paint the portrait. All materials provided; $60/ticket.

Truffle Lunch

A four-course wine paired feast prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

Live Music: Forde Upshur

An Lar Traditional Irish Band

Live Music: Alex Arbaugh

Live Music: Matty & Mirabelle

Music Bingo

Everyone loves singing along with their favorite songs and who doesn’t love a competitive game of Bingo? Music Bingo brings together the best of both worlds for a high energy game that is fun for everyone. Simply listen to your favorite music, match the songs to the titles on your music bingo cards, and win great prizes!

Artist Reception: Ellen Copeland

Meet the artist! Ellen Copeland will be in the Loving Cup Tasting Room Gallery to discuss the large-format abstract oils in her exhibit "Color and Comfort in Hang Time" (on view Oct 2 – Dec 13). Sip a glass of certified-organic wine and enjoy a Sunday afternoon with art.

Fletcher Daniel

Food Truck: PotLucky Cville

Trivia Night

Willie De Live Music

Mahjong with Mountain Mahj

Beginner-friendly Mahjong lessons with Mountain Mahj: learn the rules, strategies, and traditions of the game in easy-to-follow steps while hanging out with friends. Lesson is 2.5 hours. Ticketed event (mountainmahjczt.com/classes).

Trail Run Club