Vintner’s Harvest Wine Pour @ Woodbrook Farm Vineyard
October 7, 2025 – 6 – 9 PM – Vintner’s Harvest Wine Pour
October 7, 2025 – 6 – 9 PM – Vintner’s Harvest Wine Pour
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
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
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
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.
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
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.
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
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
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+
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
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
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.
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
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.
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
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
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
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!
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.
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!
When: Saturday, October 25, 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.)
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.
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
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
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!
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
Session Sundays continue! This Sunday, October 5th, we'll have Cville Jazz
Congregation performing live on the patio from 1-4 PM. Spend your afternoon in the vineyard
with a glass of wine and great music. A friendly reminder that Session Sundays may be
canceled due to inclement weather. Keep an eye on our social media for the latest information.
6:00PM
Join us for an intimate alfresco four-course wine dinner in collaboration with The Local at the historic Hall's Tavern on our East End Farm. Alongside this exquisite dinner, we are teaming up with The Louisa Co. Historical Society and Transcend Paranormal to offer fascinating history about the property, intimate tours of the haunted tavern, and readings with a medium over nightcap cocktails! A portion of the proceeds will support the historical society's efforts to preserve stunning structures like Hall's Tavern. Ticketed event.
East End Farm
245 Nolting Rd.
Lousia, VA 23093
Saturday Night Special - 6pm - 9pm
10/4 Little Walter and the Convictions
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
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
Thursday Night Rendezvous 4-8pm
October 2, 9, 16, 23, 30
Huge news for Session Sundays! We made the cut for 180's reunion tour. Join
us on September 28th for an afternoon to remember and don't forget your dancing shoes. Live
music is from 1-4 PM. 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
Oktoberfest Food Truck 12-4:30PM
Live Music feat Brian Franke 1-4PM
We’re thrilled to invite you to a truly special experience:
Harvest Luncheon & Winery Tour with Michael Shaps
Sunday, September 28th | 11:00 AM | Limited to 20 guests
Join Michael for a rare, behind-the-scenes look at our 2025 harvest in action. This exclusive guided tour of our winery offers an insider’s view of the winemaking process—with tastings directly from the production floor.
After the tour, enjoy a beautifully crafted 3-course family-style lunch by Chef Aaron Gardner, served al fresco (weather permitting) or in our charming Loft Room. Each course will be expertly paired with wines hand-selected by Michael.
Tour Location: Michael Shaps Production Facility
1781 Harris Creek Way, Charlottesville, VA
Lunch Location: Michael Shaps Wineworks
1650 Harris Creek Road, just down the drive
Tickets: $225 per person
RSVP Now – Only 20 seats available, https://www.virginiawineworks.com/product/harvest-tour-luncheon
**Please note: Cancellations within 48 hours of the event are non-refundable unless we can fill your seat**
Saturday Night Special (6-9pm)
9/27 South River Strings
�� James Tamelcoff is Back! ��
Join us Saturday, August 27 | 2–5 PM at Woodbrook Farm Vineyard for a relaxing afternoon of:
✨ Live music from James Tamelcoff
�� Amazing wines to sip and enjoy
�� Tasty eats from Pepper’s on the Go food truck
This event will be held outside on the patio (weather permitting) — so bring your lawn chairs and blankets and get comfy!
Great music, great wine, and great company — the perfect way to spend a Saturday!
Oktoberfest Food Truck 12-7:30PM
Live Music feat John Kelly 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!
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
Thursday Music Series feat John Benjamin 5-8PM
Thursday Night Rendezvous- Vertical Tastings (4-8pm)
9/4 Cabernet Franc
9/11 Cabernet Sauvignon
9/18 Petit Verdot plus Vinyl DJ Ryan Wood (5-8pm)
9/25 Farmer's Reserve
Wine Club discounts apply to vertical tastings.
20% off 3+ bottles of featured wine (any offered vintage)
Paint & Sip - Ticketed Event, Reserve Your Spot 6-8PM
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
Looking for the perfect Sunday afternoon? Session Sundays continue this
Sunday, September 21st, from 1-4 PM. We'll have live music from Perennial Collection
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.
Oktoberfest Food Truck 12-4:30PM
Oktoberfest Market 12-5PM
Saturday, September 20th
11:00AM – 5:30PM
Kick off the season with a full day of wine country fun—grape stomping, hayrides, a savory pig roast, local food truck fare, and plenty of lawn games to enjoy. The day’s soundtrack features Jon Spear opening and the Chamomile & Whiskey Duo headlining, filling the vineyard with incredible live music from start to finish.
Celebrate the beauty of harvest time in the Monticello AVA!
Here is a link to sign up for the FREE grape stomp
https://www.eventbrite.com/e/harvest-fest-tickets-1680268190389?aff=ebdssbdestsearch
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 CSharp 5-8PM
Corks & Karaoke at Woodbrook Farm Vineyard
Kick off your weekend early on Thursday, September 18 with Corks & Karaoke at
Woodbrook! We’re open special hours this day from 12:30–8:30pm, with karaoke
featuring Rachael Karpo from 5:30–8:30pm.
This event is held outside on the lawn unless otherwise announced on social media
or our website—so plan accordingly!
Bring chairs & blankets—seating is limited
Outside food welcome—pack a picnic!
Grab your friends, sip some wine, and enjoy
Thursday Music Series feat Ron Gentry 5-8PM
Thursday Night Rendezvous- Vertical Tastings (4-8pm)
9/4 Cabernet Franc
9/11 Cabernet Sauvignon
9/18 Petit Verdot plus Vinyl DJ Ryan Wood (5-8pm)
9/25 Farmer's Reserve
Wine Club discounts apply to vertical tastings.
20% off 3+ bottles of featured wine (any offered vintage)
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, September 14th! Join us
from 1-4 PM for live music on the patio with Robert Jospé Band. 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.