Thursday Night Rendezvous @ Chisholm Vineyards
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
Thursday Music Series feat Music Bingo 6-8PM
Thursday, October 30 | 5:30–7:00 PM
Commerce Street Books at The Doyle Hotel, Charlottesville
Join us for Read Between the Wines, a new event series pairing Virginia authors and stories with wines from the Monticello Wine Trail.
Our October gathering features Dearest by Jacquie Walters, a richly layered novel exploring love, memory, and belonging, beautifully complemented by the expressive Mourvèdre from Stinson Vineyards.
Co-hosted by Samantha Jones and presented in partnership with The Monticello Wine Trail, this evening invites readers and wine lovers alike to slow down, sip, and share in conversation that connects page to place.
The event is free and open to the public, with wines available for purchase by the glass and bottle (21+).
10/31 Halloween Party 6-9pm
Vinyl DJ Ryan Wood of Kendall Street Company will spin Halloween themed tunes.
Two Brothers Southwestern Grill food truck
Costume contest (adults, children, dogs), activities and treats
Open 12-9pm so come early!
Virginia Wine & Oyster Celebration with Salty Bottom Blue Oysters 5-8PM
Live Music feat Zuzu's Hot 5 5-8PM
Live Music feat Sue Harlow 12:30-3:30PM
Eastwood After Dark feat Live Music by The Near Passerines 5-8PM
Gather your friends and family and join us on Saturday nights for live music that you’ll want to dance to!
Live Music feat Sue Harlow 12:30-3:30PM
Eastwood After Dark feat Live Music by The Near Passerines 5-8PM
Gather your friends and family and join us on Saturday nights for live music that you’ll want to dance to!
Holiday Soiree
Date: Thursday, November 6, 2025
Time: 4:00 PM – 8:00 PM
Location: 101 S Main St, Gordonsville, VA 22942 - Verdant by Monica Garrett Interiors
RSVP: https://partiful.com/e/FA4SoBTUzAjT9IFLMf4N
Join us for an evening of holiday celebration and private shopping! This festive event will feature:
Verdant by Monica Garrett - First dibs on Christmas & everyday decor
Horton Vineyards - Award-winning wine for purchase and tasting
Tess & Co Jewelers - Custom creations trunk show
Westwind Flowers - Holiday florals & more
Discover the perfect holiday gifts while enjoying wine and shopping with local artisans and vendors. RSVP required
Thursday Music Series feat Haywood Giles 5-8PM
Live Music feat Matthew O'Donnell 5-8PM
Shrimp Boil 4-7:30PM
Inspired by the renowned Game Fairs of the UK, the East End Fair brings the spirit of country tradition and Virginia wine country to life. Hosted at the East End Farm in Louisa, this unique celebration features tastings from 11 of Virginia’s favorite wineries, plus craft beer, cider, and spirits. Enjoy live music, field sport demos, and hands-on activities like archery and axe throwing with Boar’s Head Outfitters.
Savor delicious bites from local food trucks, shop outdoor lifestyle and heritage brands, and experience the best of Virginia’s land, wine, and tradition—all in one unforgettable day.
General admission tickets are available, but be sure to check out all the exclusive perks of our VIP tickets for an elevated East End Fair experience
https://www.smvwines.com/east-end-fair
Live Music feat Porch Dogs 12:30-3:30PM
Eastwood After Dark feat Live Music by The Near Passerines 5-8PM
Gather your friends and family and join us on Saturday nights for live music that you’ll want to dance to!
Service Dogs of Virginia Pop-Up 12-3PM
Music Bingo 2-4PM
Before the rush of Thanksgiving, we’re taking a moment to celebrate something we’re truly grateful for… Cabernet Franc.
Join us for Francsgiving — a cozy pre-holiday wine experience featuring a special flight of Cabernet Franc expressions paired with seasonal bites and great company. From bright and aromatic Franc Blanc to Raisin Red, this lineup tells the story of Virginia terroir in the most delicious way.
 Featured Flight Includes:
*Blanc de Franc 2019
*Franc Blanc 2020
*Cabernet Franc 2022
*Meritage 2021
*Raisin Red NV
Whether you’re stocking your table for Thanksgiving or just love discovering exceptional wines, this tasting is a perfect seasonal escape.
 Date: Saturday November 15th
 Location: 1650 Harris Creek Rd. Charlottesville VA
 Tickets: $65/$55 Wine Club
 Includes: Flight + small bites + early access to holiday wine bundles
When: Saturday, November 15th, 8:00 - 11:00 pm
Teaser: Marvel at the beauty of the night sky with a glass of organic wine.
Full Description:
A celestial cornucopia! The low moon should give us a chance to see quite a bit: Saturn will be visible by 8 pm, and the Andromeda and Pinwheel Galaxies visible a little later. The Hercules Cluster and the Veil Nebula are high, and maybe we could even see some Orionid meteors as well!
Should be good for the naked eye as well as telescopes. Bring your own telescope or share one of ours.
The tasting room and veranda will be open all night and you can come and go freely to the lower level where the telescopes will be set up.
Event free to attend. All ages ok.
(Facility lights will be kept low to minimize the light pollution.)
The Wine Vault is open, showcasing 30 years of Port wine production by Horton Vineyards!
You must have a ticket to attend. Tickets are limited to 150 attendees.
Event location is in an exclusive area at the winery.
The area is climate controlled for wine. Please dress appropriately.
Light charcuterie provided.
Due to the nature of the event dietary restrictions or allergies cannot be accommodated.
Event hours: 11:30am- 4:00pm.
Tastings are drop-in-Tickets are non-refundable.
Wine price list available at event.
Regular tasting room and tastings are separate but available for purchase.
Please alert us prior to the event of any handicap requirements.
Tickets are non-refundable unless event is cancelled
Event Link for Tickets: https://www.eventbrite.com/e/horton-vineyards-port-wine-tasting-tickets-1496736241389?aff=oddtdtcreator
Event Location: Horton Vineyards 6399 Spotswood Trail Gordonsville, VA 22942
Event Information:
Ticket base price $45
Sunday Sessions (1-4pm)
9/7 Matty & Mirabelle Metcalfe
9/14 Driftwood Radio
9/21 The Trio
9/28 Robert Jospé Trio
10/5 Uncle Pen
10/12 TBD
10/19 The Trio
10/26 Dave's Basement
Mark your calendars for the ultimate Session Sunday finale on Sunday, October
26th, from 1-4 PM! We're thrilled to welcome back Susie and the Pistols to bring the energy to
our patio one last time this year. As a special treat, Oyster Catcher Sea Farms will be joining us
with their incredible fresh oysters. And to make things even more fun, we're hosting a costume
contest! So come dressed in your best, enjoy fantastic music and delicious oysters, and help us
celebrate the end of another wonderful season of Session Sundays! A friendly reminder that
Session Sundays may be canceled due to inclement weather. Keep an eye on our social media
for the latest information.
Oktoberfest Food Truck 12-4:30PM
Paint & Sip 12-2PM - Ticket Event, Reserve Your Spot!
Live Music feat Anthony Semiao 2-5PM
Saturday Oct 25 7:30pm – 9:30pm
Venture into the vineyard after dark for a haunting journey of wine and fright. Your $25 ticket (plus tax) includes four spooky wine drink stops along a haunted path winding through the property. Be warned—this isn’t just a casual stroll!
Title: Virginia: Then & Now — Library Tasting (Virginia Wine Month)
Date: Saturday, October 25, 2025
Time: 1:30-3:30 PM
Location: Michael Shaps Wineworks — 1650 Harris Creek Rd. Charlottesville
Capacity: 30 seats (seated, guided)
Price: $75 General | $65 Club
Overview
Celebrate Virginia Wine Month with a guided, seated tasting that pairs library vintages with current releases across five varietals—10 pours total. Taste how time, vintage, and terroir shape Virginia wines, with light seasonal bites to complement the flight.
Oktoberfest Food Truck 12-7:30PM
Live Music feat Heidi Riddell 12:30-3:30PM
Eastwood After Dark feat Live Music by LockJaw 5-8PM
Gather your friends and family and join us on Saturday nights for live music that you’ll want to dance to!
Saturday, Oct 25
Join us for a festive day of fall fun at SMV! We will have face painting, bounce house, pumpkin florals with Blooms 4 Good, apple bobbing, trick-or-treating, pumpkin painting and a spooky trail walk during extended hours. Fuel up with Arepas on Wheels and Sweet Jane’s Kitchen and stick around for live music & evening DJ throughout the day!
Movies Begins about 7:30PM
Join us for an evening beneath the stars and lights as we extend our hours to feature a fun seasonal movie on our outdoor screen! Reservations are best, make yours today! Join us for an evening beneath the stars and lights as we extend our hours to feature a fun seasonal movie on our outdoor screen! Reservations are best, make yours today!
Sept 26: The Breakfast Club
Oct 10: You’ve Got Mail
Oct24th: Practical Magic
Friday Night Sunset Soirée (6-9pm)
9/5 80's Dance Party with Signature DJ & Twisted Provisions food truck
9/12 Mr. Space Cat with Raclette Man food truck
9/19 Chickenhead Blues with Twisted Provisions food truck
9/26 Brandon Wayne & His Lonesome Drifters with Two Brothers Southwestern Grill
10/3 90's Dance Party with Signature DJ and Twisted Provisions food truck
10/10 Crewe d'Bayou/ Chickenhead Blues Mashup with Raclette Man Food Truck
10/17Chickenhead Blues with Raclette Man Food Truck
10/24 The Boomerangs with Twisted Provisions Food Truck
10/31 TBD
Virginia Wine & Oyster Celebration with Salty Bottom Blue Oysters 5-8PM
Live Music feat FarAway 5-8PM
Thursday Music Series feat Jim Richardson 5-8PM
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
Looking for the perfect Sunday afternoon? Session Sundays continue this Sunday,
October 19th, from 1-4 PM. We'll have live music from Gallatin Canyon on the patio—the perfect
backdrop for enjoying your favorite Stinson wine. A friendly reminder that Session Sundays may
be canceled due to inclement weather. Keep an eye on our social media for the latest
information.
Sunday Sessions (1-4pm)
9/7 Matty & Mirabelle Metcalfe
9/14 Driftwood Radio
9/21 The Trio
9/28 Robert Jospé Trio
10/5 Uncle Pen
10/12 TBD
10/19 The Trio
10/26 Dave's Basement
OktoOktoberfest Food Truck 12-4:30PM
Harvest Party Artisan Market 12-5PM
Live Music feat John Kelly 1-4PM
Join us on Saturday, October 18th from 2–5 PM for an afternoon with A.P. Project! Enjoy their
great tunes on the patio (weather permitting) while sipping your favorite Woodbrook wines. Don’t
forget your lawn chairs and blankets for a cozy vineyard afternoon.
Small Town Saturday Night Series
6:00pm – 9:00pm Extended Hours RSVP
Come enjoy a Fall sunset with us! Enjoy local food trucks and live music with extended tasting room hours.
Oct 4 - Street Dog & Rixeyville Revival
Oct 11 - Fat Tyler's Meats & Such & The Blue Guitar
Oct 18 - Crozet Seafood Truck & The Jason Burke Band
Oktoberfest Food Truck 12-7:30PM
Live Music feat Meisha Herron 12:30-3:30PM
Eastwood After Dark feat Live Music by The Wavelength 5-8PM
Gather your friends and family and join us on Saturday nights for live music that you’ll want to dance to!
Celebrate Virginia's bounty with a feast of Virginia-grown wine and food.
Virginia Harvest Party 10/18/25
Gather your friends.
Select Virginia wine (Chisholm Vineyards!).
Plan your feast. Design a menu with Virginia-grown foods to pair with selected wines.
Place an order online (by 10/13/25 to secure your order) with Chisholm Vineyards for a picnic.
Peck Board box (cheese, dried fruits & nuts)
Firehook Crackers
Terra di Siena Proscuitto & Salami
Other items available in store including locally grown flowers from Leap Frog Flower Farm.
Celebrate & Toast to Virginia!
Order link:
Friday Night Sunset Soirée (6-9pm)
9/5 80's Dance Party with Signature DJ & Twisted Provisions food truck
9/12 Mr. Space Cat with Raclette Man food truck
9/19 Chickenhead Blues with Twisted Provisions food truck
9/26 Brandon Wayne & His Lonesome Drifters with Two Brothers Southwestern Grill
10/3 90's Dance Party with Signature DJ and Twisted Provisions food truck
10/10 Crewe d'Bayou/ Chickenhead Blues Mashup with Raclette Man Food Truck
10/17Chickenhead Blues with Raclette Man Food Truck
10/24 The Boomerangs with Twisted Provisions Food Truck
10/31 TBD
Raise a glass to Virginia Wine Month with an unforgettable celebration of exquisite Virginia wines at the Red Wine Showcase. Set against the picturesque backdrop of Eastwood Farm and Winery, this exclusive event brings together 18 esteemed wineries from the Monticello Wine Trail for an unforgettable celebration of red wine.
Two ticket types are available.
The VIP Experience begins at 5:30 PM with limited availability, expanded time with our featured wineries, additional wines not included with the General Admission ticket, and a reserved parking area for your convenience.
The General Admission experience begins at 6:30 PM with the event concluding at 8:30 PM.
Event Highlights:
Venue: Nestled amidst the scenic beauty of Eastwood Farm and Winery, this charming venue provides the perfect setting for an evening of wine tasting. Immerse yourself in the tranquility of the countryside as you explore the diverse offerings of Monticello’s finest wineries.
Red Wine Showcase: As part of Virginia Wine Month, this event serves as a showcase of the exceptional wines and wineries that define the Monticello Wine Trail. Discover the exquisite and robust flavors of red wines as you sample a curated selection from renowned wineries along the Monticello Wine Trail. From fruit-forward Merlots to earthy Cabernet Francs and full-bodied Meritage blends, each wine offers a unique expression of the region’s terroir and winemaking craftsmanship.
Gourmet Pairings: Elevate your tasting experience with gourmet pairings specially crafted to complement the red wines on offer. From artisanal cheeses to hearty hors d’oeuvres & comforting delicacies, each bite is thoughtfully curated to enhance the nuances of the wines and delight your palate.
Ticket holders must be 21+
Thursday Music Series feat John Benjamin 5-8PM
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
Paint & Sip 6-8PM - Ticket Events, Reserve Your Spot!
Sunday Sessions (1-4pm)
9/7 Matty & Mirabelle Metcalfe
9/14 Driftwood Radio
9/21 The Trio
9/28 Robert Jospé Trio
10/5 Uncle Pen
10/12 TBD
10/19 The Trio
10/26 Dave's Basement
Our Session Sundays series continues this Sunday, October 12th! Join us from 1-4
PM for live music on the patio with Liz Barnes / Barbara Martin Quintet. Come relax in the
vineyard with your favorite flight, glass, or bottle of wine. A friendly reminder that Session
Sundays may be canceled due to inclement weather. Keep an eye on our social media for the
latest information.
Enjoy 4 wines (1 oz. each) paired with 4 muffins by Butter & Crumb Bakery.
2022 Sparkling Brut | Honey Butter
2022 Gigi Red Blend | Pumpkin Maple
2022 Cabernet Sauvignon | Cranberry Orange
2018 Tannat | Dark Chocolate Raspberry
$20pp
Oktoberfest Food Truck 12-4:30PM
Music Bingo 2-4PM
Small Town Saturday Night Series
6:00pm – 9:00pm Extended Hours RSVP
Come enjoy a Fall sunset with us! Enjoy local food trucks and live music with extended tasting room hours.
Oct 4 - Street Dog & Rixeyville Revival
Oct 11 - Fat Tyler's Meats & Such & The Blue Guitar
Oct 18 - Crozet Seafood Truck & The Jason Burke Band
We’re excited to welcome Austin Boggs back to the vineyard on Saturday, October
11th from 2–5 PM! He’ll be performing on the patio (weather permitting), so grab your lawn chairs
and blankets for an amazing afternoon of music, wine, and good company.