Read Between the Wines: Dearest x Stinson Vineyards Mourvèdre - Doyle Hotel
Oct
30
5:30 PM17:30

Read Between the Wines: Dearest x Stinson Vineyards Mourvèdre - Doyle Hotel

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+).

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Holiday Soiree with Horton Vineyards @ Verdant
Nov
6
4:00 PM16:00

Holiday Soiree with Horton Vineyards @ Verdant

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 

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East End Fair @ Southwest Mountain Vineyards
Nov
8
12:00 PM12:00

East End Fair @ Southwest Mountain Vineyards

  • Southwest Mountain Vineyards (map)
  • Google Calendar ICS

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

 

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Francsgiving- A Celebration of Cabernet Franc @ Michael Shaps Winery
Nov
15
1:30 PM13:30

Francsgiving- A Celebration of Cabernet Franc @ Michael Shaps Winery

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

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Nov
15
8:00 PM20:00

Stargazing at Loving Cup: Evening Event Series

  • Loving Cup Vinyard & Winery (map)
  • Google Calendar ICS

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.)

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Horton Vineyards - Port Wine Tasting December 6th 11:30AM - 4PM
Dec
6
11:30 AM11:30

Horton Vineyards - Port Wine Tasting December 6th 11:30AM - 4PM

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

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Sunday Sessions @ Stinson Vineyards
Oct
26
1:00 PM13:00

Sunday Sessions @ Stinson Vineyards

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.

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Oct
25
1:30 PM13:30

Virginia: Then & Now — Library Tasting @ Michael Shaps Winery

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 

Reserve Here

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.

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Oct
25
11:00 AM11:00

Hallowine @ Southwest Mountain Vineyards

  • Southwest Mountain Vineyards (map)
  • Google Calendar ICS

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!

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Oct
24
7:30 PM19:30

Dinner & A Movie @ Southwest Mountain Vineyards

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

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Oct
24
6:00 PM18:00

Friday Night Sunset Series @ Chisholm Vineyards

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

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Sunday Sessions @ Stinson Vineyards
Oct
19
1:00 PM13:00

Sunday Sessions @ Stinson Vineyards

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.

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Oct
18
6:00 PM18:00

Small Town Saturday Night Series @ Southwest Mountain Vineyards

  • Southwest Mountain Vineyards (map)
  • Google Calendar ICS

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

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Oct
18
12:00 PM12:00

Harvest Party @ Chisholm Vineyards

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:

https://chisholmvineyards.orderport.net/wines/Events

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Oct
17
6:00 PM18:00

Friday Night Sunset Series @ Chisholm Vineyards

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

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Red Wine Showcase @ Eastwood Farm & Winery
Oct
17
1:30 PM13:30

Red Wine Showcase @ Eastwood Farm & Winery

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+

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Sunday Sessions @ Stinson Vineyards
Oct
12
1:00 PM13:00

Sunday Sessions @ Stinson Vineyards

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.

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Oct
11
6:00 PM18:00

Small Town Saturday Night Series @ Southwest Mountain Vineyards

  • Southwest Mountain Vineyards (map)
  • Google Calendar ICS

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

View Event →

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