Events › Barboursville, Orange, Madison & Greene

Winery Events in Barboursville, Orange, Madison & Greene

North on Rt 29 & Rt 33 · 25–50 min from Charlottesville

The rolling country north of Charlottesville — Barboursville, Gordonsville, Orange, Madison, and Greene County's foothills around Ruckersville — is home to some of Virginia's most storied vineyards, including estates on land the founding fathers once farmed, plus mountain-view wineries and breweries up Route 29.

This weekend in Barboursville & the North Oct 30–Nov 1

Upcoming events in Barboursville, Orange, Madison & Greene

Special Screening: We the Wine People at Royal Cinemas at Ducard
Other

Special Screening: We the Wine People at Royal Cinemas

Tue, Oct 27, 2026
7:00 PM – 9:00 PM

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

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Trivia Night at Bald Top Brewing Co.
Trivia

Trivia Night

Thu, Oct 29, 2026
6:30 PM – 8:30 PM

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

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Friday Night Out with Kirsten Haze at Ducard
Music

Friday Night Out with Kirsten Haze

Fri, Oct 30, 2026
5:00 PM – 8:00 PM

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.

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Kubota Tour - Fall Color Around The Nursery at The Market at Grelen
Tour

Kubota Tour - Fall Color Around The Nursery

Sat, Oct 31, 2026
During tasting room hours

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.)

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Halloween and Music in the Mountains with The Wavelength at Ducard
Music

Halloween and Music in the Mountains with The Wavelength

Sat, Oct 31, 2026
2:00 PM – 5:00 PM

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.

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Wide Margin at Bald Top Brewing Co.
Music

Wide Margin

Sat, Oct 31, 2026
6:00 PM – 9:00 PM

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.

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Music in the Mountains with John Kelly at Ducard
Music

Music in the Mountains with John Kelly

Sun, Nov 1, 2026
2:00 PM – 5:00 PM

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.

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Trivia Night at Bald Top Brewing Co.
Trivia

Trivia Night

Thu, Nov 5, 2026
6:30 PM – 8:30 PM

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

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Outdoor Movie Night: Kelly's Heroes at Horton Vineyards
Family

Outdoor Movie Night: Kelly's Heroes

Fri, Nov 6, 2026
5:30 PM – 8:30 PM

An evening under the stars at Horton Vineyards with a screening of the classic film Kelly's Heroes. Bring a blanket or lawn chair and settle in for a relaxed night among the vines. Popcorn and milkshakes available for purchase. Starts 5:30 PM. Free admission.

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Salute & Sip: A Military K9 Tribute at Horton Vineyards
Benefit

Salute & Sip: A Military K9 Tribute

Sat, Nov 7, 2026
11:00 AM – 4:30 PM

In celebration of Veterans Day weekend, a free, family-friendly event supporting the Military Working Dog Team Support Association (MWDTSA). Sip Horton wine on the grounds while learning about the bond between military working dogs and their handlers, with K9 trainer Austin Bodine and retired military working dog Bali Y499. 10% of all sales that day go to MWDTSA. Free admission, no tickets required. 11 AM - 4:30 PM.

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Norton Showcase – Presented by Norton Network – Grand Norton Tasting at Ducard
Tasting

Norton Showcase – Presented by Norton Network – Grand Norton Tasting

Sat, Nov 7, 2026
11:00 AM – 5:00 PM

The Norton Showcase – Presented by Norton Network Date: November 7, 2026 | Time: 11:00 AM – 5:00 PM Celebrate Norton, Virginia’s native grape, at the Norton Showcase, presented by Norton Network! This exclusive event brings together Virginia’s premier Norton producers for a day of exceptional wines, great food, live music, and friendly competition. Whether you’re a longtime Norton fan or discovering the varietal for the first time, you’ll enjoy sampling a wide range of Norton wines, meeting the winemakers behind them, and experiencing the passion that makes Virginia’s native grape so special. Grand Norton Tasting Tickets CLICK TO PURCHASE YOUR TICKETS HERE Your Grand Norton Tasting Ticket includes tasting samples from each of the participating wineries. $30 when purchased in advance $40 when purchased at the gate on the day of the event Guests must be 21 years of age or older with a valid government-issued photo ID to purchase or redeem a Grand Norton Tasting Ticket. All IDs will be checked before participating in wine tastings or purchasing wine by the bottle or glass. Event Highlights Grand Norton Tasting featuring Virginia’s top Norton producers Fred Reno Norton Challenge Cup wine competition will be held and the winner announced during the event Meet the winemakers Live music Local food trucks and artisan vendors CLICK TO PURCHASE YOUR TICKETS HERE Please Note No pets allowed. This is an outdoor event. Please dress for the weather. Join us for a day of great wine, delicious food, live entertainment, and a celebration of Virginia’s signature grape! Cost: $30

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Music in the Mountains by Mike Proffitt at Ducard
Music

Music in the Mountains by Mike Proffitt

Sat, Nov 7, 2026
2:00 PM – 5:00 PM

Come on out and join us on this beautiful fall afternoon! We’ll have great live music by Mike Proffitt Choose your favorite DuCard wine and sit back while you listen to music. Lite noshing menu of local fare available or bring your own picnic.

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Music In The Mountains with Acoustic Aubrey at Ducard
Music

Music In The Mountains with Acoustic Aubrey

Sun, Nov 8, 2026
2:00 PM – 5:00 PM

Join us for Music in the Mountains from “Acoustic” Aubrey. Aubrey plays venues all over Virginia, DC, Maryland, and North Carolina and is best known for covers of classic R&B, jazz, acoustic rock, and more. Always a great time at DuCard to sit, relax, and enjoy a fantastic afternoon of music with some great wine. Lite noshing menu is available or bring your own snacks. No cover. Reservations are recommended. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

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Trivia Night at Bald Top Brewing Co.
Trivia

Trivia Night

Thu, Nov 12, 2026
6:30 PM – 8:30 PM

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

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Music in the Mountains by Scuffletown at Ducard
Music

Music in the Mountains by Scuffletown

Sat, Nov 14, 2026
2:00 PM – 5:00 PM

Come out and join us Saturday afternoon for the rollicking live music by Scuffletown! Your favorite wine is available for pairing with the yummy eats from our lite noshing menu. Sit back and enjoy it all while you listen to Marc’s smooth-as-the-cab-franc voice and Johnny’s multi-instrumental accompaniments. There’s something for everyone, so come join the fun! 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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Truffle Feast at Barboursville Vineyards
Dinner

Truffle Feast

Sat, Nov 14, 2026
7:00 PM

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.

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Truffle Lunch at Barboursville Vineyards
Dinner

Truffle Lunch

Sun, Nov 15, 2026
12:00 PM

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.

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Armchair Expedition Viognier 2pm at Ducard
Tasting

Armchair Expedition Viognier 2pm

Sun, Nov 15, 2026
2:00 PM – 4:00 PM

Often called Virginia’s signature white grape, Viognier is deeply rooted in Virginia soil. But where did it come from? How do different terroirs and vinification practices affect its aromas and flavors? Join us to discover the answers. An aromatic beauty, Viognier is the only grape permitted in the Northern Rhône application of Condrieu. Viognier is also the most-planted white Rhone varietal in the US and produces a full bodied wine with intense aromatics of peach, apricot, honeysuckle and rose. In this class, we will taste old and new world examples and see how terroir influences what ends up in our glasses. This 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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Trivia Night at Bald Top Brewing Co.
Trivia

Trivia Night

Thu, Nov 19, 2026
6:30 PM – 8:30 PM

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

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Library Wine Deep Dive at Ducard
Tasting

Library Wine Deep Dive

Fri, Nov 20, 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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Music In The Mountains with Bomar & Ritter at Ducard
Music

Music In The Mountains with Bomar & Ritter

Sat, Nov 21, 2026
2:00 PM – 5:00 PM

Join us for an afternoon of good wine and music with the duo of Mary Bomar and Bob Ritter. Bomar & Ritter are excellent singers, songwriters, and guitarists that play original folk/pop. Grab a glass or bottle of your favorite wine and relax while listening to these two amazing artists. Plus the view couldn’t be better! No cover. Reservations are recommended. Make yours here. Add this event to your Google calendar, or any other calendar (iPhone, Outlook, etc.) by using the buttons below.

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Music in the Mountains with Pat Anderson at Ducard
Music

Music in the Mountains with Pat Anderson

Sun, Nov 22, 2026
2:00 PM – 5:00 PM

The mountains are calling and so is the music by Pat Anderson – an Oklahoma-born, Virginia-raised singer-songwriter. 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 snacks 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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Special Private Screening: Immigrant Grapes: Odyssey of Forbidden Wines by Lucie Morton at Ducard
Other

Special Private Screening: Immigrant Grapes: Odyssey of Forbidden Wines by Lucie Morton

Sun, Nov 22, 2026
5:30 PM – 7:00 PM

Join us at 5:30 PM on Sunday, November 22 for a special private screening of Immigrant Grapes: Odyssey of Forbidden Wines, a new film by viticulturist, author and now filmmaker Lucie Morton. The film follows her personal quest to bring the Cunningham grape back to its ancestral home on her family’s farm in Tidewater Virginia. This fascinating journey includes grapevine science, politics, intrigue and romance. Her odyssey took her across the US and across the Atlantic to the Azores, Madeira Island, the Cevennes Mountains of France, and southern Brazil. As Lucy ultimately becomes successful in repatriating Cunningham to Virginia, it will join Norton, which we have planted at DuCard and use for our Norton varietal wine, our C’est Trop port-style wine and the fun and funky Dorothy’s Slippers rosé, as the only other surviving Virginia native grape. And yes, DuCard Norton will be available to sip while enjoying the film. Tickets are $10 and can be paid at the door. Space is limited so please make your reservations by emailing Beth at beth@ducardvineyards.com Cost: $10

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Thanksgiving Celebration Lunch at Barboursville Vineyards
Dinner

Thanksgiving Celebration Lunch

Thu, Nov 26, 2026
1:00 PM

A four-course feast prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $105 per person for the meal. $140 per person for the meal with wine pairings (+9.3% tax & 22% service charge).

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Black Friday Music In The Mountains with South Canal Street at Ducard
Music

Black Friday Music In The Mountains with South Canal Street

Fri, Nov 27, 2026
2:00 PM – 5:00 PM

Bring your Thanksgiving guests and your dancing shoes and come out to DuCard for the fun and fabulous music of South Canal Street! They bring their repertoire of your favorites including songs by The Beatles, Chicago, Motown, Eagles and top hits from the golden era of music, late 1950’s to the 1970’s! Grab your favorite DuCard wine and have some fun! Hungry? We’ve got a great noshing menu to select from or bring your own snacks. 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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Music In The Mountains with Grass Fed at Ducard
Music

Music In The Mountains with Grass Fed

Sat, Nov 28, 2026
2:00 PM – 5:00 PM

Come out to the foothills of the Blue Ridge and spend your afternoon at DuCard Vineyards listening to live music from Grass Fed. This amazing group plays a mix of funk, rock and roll, and reggae. Choose your favorite bottle of DuCard wine, add a snack from our lite noshing menu and enjoy the beautiful mountain scenery to complete the day! 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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Vinyl Day at the Vineyard at Ducard
Music

Vinyl Day at the Vineyard

Sun, Nov 29, 2026
2:00 PM – 5:00 PM

We’re dusting off the turntable and bringing in our favorite LP’s for Vinyl Day at DuCard Vineyards. Dig out the old record albums and bring them along for an afternoon of listening, sharing, and reminiscing. We can’t wait to hear all of your favorites while we share ours. There will be wine, of course and our light noshing menu is available while you sit and enjoy. No better way to spend the afternoon. Catch you on the flip side! Reservations recommended. No cover.

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Port Tasting at Horton Vineyards at Horton Vineyards
Tasting

Port Tasting at Horton Vineyards

Sat, Dec 5, 2026
11:30 AM – 4:00 PM

The Wine Vault is open! Celebrate 30 years of Port at Horton Vineyards with a drop-in tasting in the climate-controlled Wine Vault: vintage Ports spanning 1995-2020 alongside Courage Port, plus Port-style dessert wines Pear Dessert, Bone Orchard, and About Face. Light charcuterie provided. 11:30 AM - 4:00 PM. Ticketed event (limited to 150, ages 21+, non-refundable unless cancelled). Dress warmly. Regular tasting room service is separate.

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Music in the Mountains with Pat Anderson at Ducard
Music

Music in the Mountains with Pat Anderson

Sat, Dec 5, 2026
2:00 PM – 5:00 PM

The mountains are calling and so is the music by Pat Anderson – an Oklahoma-born, Virginia-raised singer-songwriter. Pat’s a roots rocker with a strong affinity for Dylan, Springsteen, and Petty and possessed of 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 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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Private Showing of We the Wine People – a feature documentary at Ducard
Other

Private Showing of We the Wine People – a feature documentary

Sat, Dec 5, 2026
5:30 PM – 8:00 PM

Join us at DuCard Vineyards for a special private showing of a film about Virginia Wine on December 5, 2026 at 5:30pm. 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. Wine will be available for purchase by the bottle or glass. The price is $25 and space is limited to 100 so purchase your tickets now. A share of the proceeds go to fund filmmaker’s post-production costs. Purchase your tickets HERE Sorry, no wine club member discounts for this event. Cost: $25

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The Octagon Dinner at Barboursville Vineyards
Dinner

The Octagon Dinner

Sat, Dec 5, 2026
7:00 PM

A four-course wine paired feast featuring older, rare vintages of Octagon. Prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

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The Octagon Lunch at Barboursville Vineyards
Dinner

The Octagon Lunch

Sun, Dec 6, 2026
12:00 PM

A four-course wine paired feast featuring older, rare vintages of Octagon. Prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $270 per person, all-inclusive.

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Library Wine Deep Dive at Ducard
Tasting

Library Wine Deep Dive

Fri, Dec 11, 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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Music in the Mountains with Jimmy O at Ducard
Music

Music in the Mountains with Jimmy O

Sat, Dec 12, 2026
2:00 PM – 5:00 PM

Spend a beautiful winter afternoon relaxing at the winery and listening to the music of Jimmy O. He is an amazing guitarist with an unique style of classic rock, oldies, and a rockin’ country mix that’s sure to please everyone! Just add a bottle of wine, some great Virginia views, and you’ve set your weekend off to a great start! A light noshing menu is available to accompany your wine. 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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Live Music: Jimmy O at The Barn at 678
Music

Live Music: Jimmy O

Sat, Dec 12, 2026
2:00 PM – 5:00 PM

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

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Music in the Mountains with Acoustic Aubrey at Ducard
Music

Music in the Mountains with Acoustic Aubrey

Sat, Dec 19, 2026
2:00 PM – 5:00 PM

Join us in the foothills for Music in the Mountains from “Acoustic” Aubrey. Aubrey plays venues all over Virginia, DC, Maryland, and North Carolina and is best known for covers of classic R&B, jazz, acoustic rock, and more. Always a great time at DuCard to sit, relax, and enjoy a fantastic afternoon of music with terrific views and great wine. Our lite noshing menu is available, too. No cover. Reservations are recommended.

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Christmas Celebration Lunch at Barboursville Vineyards
Dinner

Christmas Celebration Lunch

Sun, Dec 20, 2026
12:00 PM

A four-course feast prepared by Executive Chef Michael Clough. For reservations, please email or call 540-832-7848. Price: $105 per person for the meal, $140 per person for the meal with wine pairings (+9.3% tax & 22% service charge).

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Music in the Mountains with Shane Click at Ducard
Music

Music in the Mountains with Shane Click

Sun, Dec 20, 2026
2:00 PM – 5:00 PM

Born and raised in the Shenandoah Valley, Shane’s early musical influences ranged from Exile and Alabama all the way to Motown greats like the Temptations, Marvin Gaye and many more. With over 20 years experience and hundreds of shows under his belt, it’s no wonder his cover band was voted “Best in the Valley” by the Daily News Record readers poll. He brings a professional experience and provides a great time to its patrons with a huge variety of music and fun. Add some DuCard wine, terrific mountain views, family and friends, and you’re all set! Reservations are recommended. No cover.

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View all 52 upcoming events in Barboursville, Orange, Madison & Greene ❧

Venues in Barboursville, Orange, Madison & Greene

BreweryNext: Thu, Oct 29 · 5 eventsBald Top Brewing Co. logo

Bald Top Brewing Co.

1830 Thrift Road, Madison, VA 22727
Monday: Closed Tuesday: Closed Wednesday: Closed Thursday: 5pm-9pm Friday: 4pm-10pm Saturday: 12pm-10pm Sunday: 12pm-7pm

Bald Top Brewing Co. is billed as Virginia's first historic farm brewery, located at 1830 Thrift Road in Madison, Virginia. The taproom pours 20 taps of house-brewed Bald Top beer alongside wine and cider, and its made-from-scratch Scratch Kitchen serves pizza, BBQ, and other fare. Set on a farm with sweeping views from the lawn to the surrounding mountains, the brewery offers a relaxed setting for food and drink. Visitors can enjoy live music, and the property includes event spaces available for private bookings. An interactive virtual tour lets guests preview the taproom, kitchen, and grounds before stopping by.

DogsOutdoor Seating

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WineryNext: Sun, Nov 1 · 8 eventsBarboursville Vineyards logo

Barboursville Vineyards

17655 Winery Road, Barboursville, VA 22923

Barboursville Vineyards is a historic estate winery in Barboursville, Virginia, in the Monticello wine region, known as one of the state's most celebrated producers. Its flagship wine is Octagon, a Bordeaux-style red blend that has earned recognition including a Gold medal at the Virginia Governor's Cup and repeated appearances on national best-of lists, and the estate draws on Italian winemaking heritage with bottlings such as its long-running Nebbiolo. Visitors can take part in tastings and tours, dine at the on-site Palladio Restaurant, and stay overnight at the estate's Inn and cottages. The property also hosts private parties and weddings, and grounds include the historic ruins of the Barboursville mansion. With its focus on sustainability and acclaimed wines, the estate offers a full destination experience for visitors to central Virginia wine country.

WeddingsB&B

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WineryChestnut Oak Vineyard logo

Chestnut Oak Vineyard

5050 Stony Point Road, Barboursville, VA 22923
Monday: Closed Tuesday: Closed Wednesday: Closed Thursday: Closed Friday: 12pm-5pm Saturday: 12pm-5pm Sunday: 12pm-5pm

Chestnut Oak Vineyard is a winery on the Monticello Wine Trail, located in Barboursville, Virginia within the Monticello AVA and about 20 minutes north of Charlottesville. Visitors can enjoy flight tastings, wine by the glass, or bottles to share in the tasting room or outdoors with views of the surrounding mountains, with curbside pickup also available. The vineyard produces a range of wines from light to robust, including Cabernet Sauvignon, Merlot, Petit Verdot, Nebbiolo, Viognier, Chardonnay, Petit Manseng, and Tannat, and counts Virginia Governor's Cup medal winners among its bottlings. A free wine club offers members a 20 percent discount along with quarterly releases in March, June, September, and December that can be shipped or picked up. The tasting room is open Friday through Monday, making it a relaxed stop among the many wineries near Charlottesville.

Outdoor SeatingDogs

WineryNext: Tue, Oct 27 · 22 eventsDucard logo

Ducard

40 Gibson Hollow Ln, Etlan, Virginia 22719
Open Daily, Year-round Monday – Thursday: 12-5 PM Friday: Summer (April – October) 12-9pm with live music starting at 5:30 Friday: Winter (Nov – March) 12-6pm Saturday: 12-6pm with live music starting at 2:30 Sunday: 12-6 PM

DuCard Vineyards is an authentic farm winery in Etlan, Madison County, Virginia, set against the eastern slope of Shenandoah National Park near Old Rag Mountain. Its wines are handmade on site using traditional methods from estate grapes grown at three local Madison County vineyard sites, an approach that has earned the winery gold medals and 90-plus point ratings along with recognition as a top-rated Central Virginia winery and a leader in environmental sustainability. Visitors can settle in for full-service wine flights of reds and whites served in crystal glassware at their table, or enjoy current-release and library wines by the bottle. The setting offers comfortable seating at mountain-view tables on the back lawn, a stream-side deck, a pavilion, and an air-conditioned event room, all surrounded by scenic Blue Ridge views. DuCard is family-friendly, dog-friendly, and picnic-friendly, with live music on weekends and a calendar of special events, plus optional reservations and space for private gatherings.

DogsFamily FriendlyOutdoor Seating

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WineryNext: Fri, Oct 30 · 2 eventsEarly Mountain Vineyards logo

Early Mountain Vineyards

6109 Wolftown-Hood Road, Madison VA 22727
Monday: 11 am - 5:30 pm Tuesday: Closed (Retail wine sales, 10 am - 4 pm) Wednesday: Closed (Retail wine sales, 10 am - 4 pm) Thursday: 11 am - 5:30 pm Friday: 11 am - 8:00 pm Saturday: 11 am - 5:30 pm Sunday: 11 am - 5:30 pm

Early Mountain Vineyards is a Virginia winery in Madison, in the heart of the state's wine country, founded in 2012 by Jean and Steve Case with the belief that Virginia can produce wines that stand alongside the finest in the world. Guided by winemaker Maya Hood White and her team, the winery emphasizes a strong commitment to the vineyard and an expression of place, crafting high-quality wines that have helped lead Virginia's rise as a respected wine region; its 2023 Petit Manseng was recently named "a benchmark for the state" by Decanter. Visitors come to the award-winning tasting room to enjoy curated wine flights, a tasting bar, and the in-depth Elevation tasting featuring library and exclusive wines, all led by knowledgeable educators. The experience is paired with a renowned culinary program, where Chef Tim Moore and his team turn seasonal produce from local farms into dishes designed to complement the wines. Beyond tastings, Early Mountain offers a wine club, on-site stays, special events and wine dinners, and serves as a premier venue for weddings and private gatherings amid its scenic mountain surroundings.

Outdoor SeatingWeddings

WineryNext: Fri, Nov 6 · 3 eventsHorton Vineyards logo

Horton Vineyards

6399 Spotswood Trail, Gordonsville, VA 22942
Monday: 10:00 am - 5:00 pm Tuesday: 10:00 am - 5:00 pm Wednesday: 10:00 am - 5:00 pm Thursday: 10:00 am - 5:00 pm Friday: 10:00 am - 5:00 pm Saturday: 10:00 am - 5:00 pm Sunday: 10:00 am - 5:00 pm

Horton Vineyards is a pioneering, family-run Virginia winery set in the scenic countryside of Orange County at 6399 Spotswood Trail in Gordonsville. Now a three-generational operation led by remarkable women, founder Sharon Horton still oversees the vineyard she began decades ago, second-generation Shannon Horton bridges vineyard and winery, and winemaker Caitlin Horton crafts the vintages from grapes her grandmother nurtured. The winery is known as one of the East Coast's most unique vineyards, blending tradition with innovation and continually exploring new varietals and techniques, with a signature Viognier among its many award-winning bottlings. The tasting room offers a self-guided experience drawn from a lineup of more than 40 wines spanning whites, reds, rosés, and distinctive fruit and dessert wines, with knowledgeable staff on hand to help guests choose. Horton is open daily year round from 10am to 5pm (closed Thanksgiving and Christmas Day), and visitors can also join its Monthly or Fill the Cellar wine clubs.

Family Friendly

WineryMontifalco Vineyard logo

Montifalco Vineyard

1800 Fray Road, Ruckersville, VA 22968
Monday: Closed Tuesday: Closed Wednesday: Closed Thursday: Closed Friday: 2pm-6pm Saturday: 12pm-5pm Sunday: 12pm-5pm

Montifalco Vineyard is a small, family-run farm winery established in 2016 in Ruckersville, Virginia, within the Monticello American Viticultural Area. Owner and winemaker Justin Falco crafts the wines from grapes grown on site, and the name plays on both the family's "Falco" heritage, meaning hawk or falcon, and the nearby Monticello region. Guests are welcomed Saturdays and Sundays from noon to 5pm for award-winning traditional wine tastings offered in the winery's Cave and Curiosities Gallery by reservation or walk-in. The setting is intentionally relaxed and contemplative, with an emphasis on appreciating the craft of grape growing and winemaking, and the property is also a haven for raptors and birdwatching, from peregrine falcons and red-tailed hawks to its popular goldfinch feeders. A member of the Monticello Wine Trail and several Virginia and international wine associations, Montifalco is an adults-only working farm winery that welcomes outside food outdoors and limits groups to six guests for an unhurried experience.

Outside FoodOutdoor Seating

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Moss Vineyards

849 Moss Vineyards LN, Dyke, VA 22935
Monday: Closed Tuesday: Closed Wednesday: Closed Thursday: Closed Friday: 12pm-5pm Saturday: 12pm-5pm Sunday: 12pm-5pm

Moss Vineyards is a family winery near Nortonsville, Virginia, set on a mountaintop at the doorstep of the Blue Ridge Mountains in the Monticello wine region. The vineyard produces Old World, dry-style wines, including hand-crafted Bordeaux-style blends made from grapes such as Viognier, Cabernet Franc, Cabernet Sauvignon, Merlot, and Petit Verdot, along with a newer gold-medal dry cider. Visitors can take in sweeping mountain views from indoor and outdoor seating areas, available on a first-come basis, and are welcome to bring their own food and seating, though no outside alcohol is permitted. The winery is open Friday through Sunday from noon to 5 and some holiday Mondays, and is dog- and family-friendly with leashed pets and supervised children welcome. A vacation cottage on the property is also available for overnight stays through Airbnb.

DogsFamily FriendlyOutdoor Seating

WineryStone Mountain Vineyards logo

Stone Mountain Vineyards

1376 Wyatt Mountain Road, Dyke, VA 22935
Monday: Closed Tuesday: Closed Wednesday: Closed Thursday: Closed Friday: Closed Saturday: 12pm-5pm Sunday: 12pm-5pm

Stone Mountain Vineyards is a family-run winery perched at over 1,700 feet of elevation in Dyke, Virginia, offering some of the most expansive mountain views of any vineyard in the state. Visitors can relax on the property's decks and enjoy wine by the flight, glass, or bottle, with current releases ranging from oak-aged Reserve Chardonnay and crisp stainless-steel Chardonnay to the sweet, refreshing Bacon Hollow Revenuer's Select. The winery welcomes walk-ins without reservations, though parties of eight or more are asked to call ahead. Guests can also arrange tours of the wine processing area and a 120-foot wine cave. Stone Mountain hosts weddings and private events and offers a wine club along with military and wine-industry discounts. Outside food and leashed pets are welcome, making it a relaxed destination for a day in the mountains.

Outdoor SeatingDogsOutside Food

WineryNext: Sat, Oct 31 · 6 eventsThe Barn at 678 logo

The Barn at 678

6045 Governor Barbour St, Barboursville, VA 22923
Monday: Closed Tuesday: Closed Wednesday: Closed Thursday: 11am-5pm Friday: 11am-7pm Saturday: 11am-6pm Sunday: 11am-5pm

The Barn at 678 is a small, family-run winery in Barboursville, Virginia, just off Route 33 in Orange County and minutes from the heart of the Monticello wine region. Opened in 2022 by co-founders Ricky and Lorrie Bryant, who turned decades of experience in farming and land management to growing grapes, the vineyard reflects the agricultural and adventurous spirit of its owners. Guests can relax with a glass on the porch and choose from estate wines, tasting flights, and a rotating selection of beer, cider, and mead. The Barn hosts live music on weekend afternoons through the season, along with special celebrations such as a New Year's Eve party. Outside beverages are not permitted.

Outdoor Seating

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WineryNext: Sat, Oct 31 · 2 eventsThe Market at Grelen logo

The Market at Grelen

15091 Yager Rd Somerset, VA 22972
Wednesday: 10am-4pm (Cafe 11am-3:30pm) Thursday: 10am-4pm (Cafe 11am-3:30pm) Friday: 10am-4pm (Cafe 11am-3:30pm) Saturday: 10am-4pm (Cafe 11am-3:30pm) Sunday: 10am-4pm (Cafe 11am-3:30pm) Monday: Closed Tuesday: Closed Closed January and February

The Market at Grelen is a European-style garden shop, café, and nationally recognized garden wedding venue set on a 1,000-acre tree nursery in Somerset, Virginia. The garden center offers seasonal plants, shrubs, trees, garden accessories, and gifts, while the café serves farm-to-table fare, small-batch ice cream, and Virginia beer, cider, and wine with outdoor and greenhouse seating. Beyond shopping and dining, visitors can explore six miles of hiking trails, pick their own fruit, and pose at the Virginia Living LOVE sign amid the display gardens. The property hosts weddings and events for groups of all sizes across spaces including the Market, Boxwood Villa, Spotswood Lodge, and The Depot, several of which offer overnight lodging. Seasonal offerings round out the experience, from Christmas trees, handmade wreaths, and holiday workshops in winter to an on-site landscape nursery supplying plants and landscaping services.

DogsOutdoor SeatingWeddings

DistilleryVirginia Foothills Distillery & Co logo

Virginia Foothills Distillery & Co

5361 Spotswood Trail, Barboursville, VA 22923
Monday: Closed Tuesday: Closed Wednesday: 11am-8pm Thursday: 11am-8pm Friday: 12pm-8pm Saturday: 12pm-8pm Sunday: 12pm-7pm

Virginia Foothills Distillery & Co is a craft distillery located at 5361 Spotswood Trail in Barboursville, in the foothills near Orange, Virginia. Inspired by local ingredients, the distillery produces small-batch spirits including bourbon whiskey, brandy, and rum, reviving a distilling tradition that traces back to the early history of Virginia, often called the birthplace of American distilled spirits. Visitors can stop in to taste and learn about the spirits, with the tasting room open Wednesday through Sunday and closed on Mondays and Tuesdays. The distillery also offers merchandise and online ordering through its store. Set in the scenic central Virginia countryside, it makes for a relaxed stop for those exploring the region's wineries and craft beverage makers.

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Woodbrook Farm Vineyard

11461 Spicers Mill Road Orange, Virginia 22960
Monday: Closed Tuesday: Closed Wednesday: Closed Thursday: 12pm-5pm Friday: 11am-7pm Saturday: 11am-7pm Sunday: 1pm-6pm

Woodbrook Farm Vineyard is a family-owned and operated vineyard and winery located at 11461 Spicers Mill Road in Orange, Virginia, in the rolling countryside of the state's Piedmont. The owners take pride in sharing the rich history of their working farm with guests who stop in to taste and buy their wines. The tasting room is open Thursday through Sunday, with extended Friday and Saturday hours, offering a relaxed, welcoming setting to enjoy a glass or pick up bottles to take home. The vineyard is dog-friendly, welcoming leashed pets both indoors and out, and visitors are encouraged to bring their own food. Wines can also be purchased online and shipped within Virginia, making it easy to enjoy Woodbrook Farm's offerings at home.

DogsOutside Food

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Charlottesville · North Garden · Scottsville · Crozet & Western Albemarle · Afton & Nelson County · Keswick & Eastern Albemarle