Saturday & Sunday, Nov. 14 and 15, 2026
Join the wineries of the Chesapeake Bay Wine Trail for our 2026 Fall Oyster Crawl! Virginia is quickly becoming known as the “Oyster Capital of the East Coast.” A great way to enjoy the experience is with local wines & oyster pairings along the Chesapeake Bay Wine Trail. Each participating winery will be offering one or more delicious oyster dishes to pair with its wines. Several wineries will also feature live music.
Tickets are not required for this event. Normal wine tasting fees will apply at each winery and oysters will be available for purchase at market rates. We encourage you to visit participating winery websites to learn more about their menu & offerings.
(Please note: This event takes place at individual wineries throughout the Trail. Event hours may vary by winery.)
The following wineries are confirmed to be participating:
Ditchley Cider Works
1571 Ditchley Road
Kilmarnock, VA 22482
(757) 710-2890
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Dates: Saturday, Nov. 14 from 12-4pm & Sunday, Nov. 15 from 11am-3pm
Description: Featuring Fried Oysters and Oyster Stew. Oysters sourced from Kellum Seafood.
Reservations: Reservations are suggested but not required. Reservations can be made by submitting an email to info@ditchleyciderworks.com.
The Dog and Oyster Micro-Vineyard
Located at the Hope & Glory Inn
65 Tavern Rd
Irvington, VA 22480
804-438-6053
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Dates: Saturday, Nov. 14 from 12-6pm and Sunday, Nov. 15 from 12-5pm
Description: Enjoy raw, fried, or roasted oysters paired with award-winning Virginia wine — a combination The Dog and Oyster has been perfecting for over fifteen years. New this year – “The Dog and Oyster”: Nathan’s Colossal Hot Dog topped with Apple Butter-Dijon Sauce and Fried Oysters topped with Chesapeake Remoulade.
Good Luck Cellars
1025 Good Luck Rd
Kilmarnock, VA 22482
804-435-1416
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Dates: Saturday, Nov. 14 from 11am-6pm & Sunday, Nov. 15 from 12-5pm
Description: Two fish Bistro will be on site both days, serving up locally sourced oysters. Live music on Saturday from 1-4pm by The Windbags and Sunday from 1-4pm by Mike Reed. The Tidewater Oyster Gardeners Association (TOGA) will host an informational booth both days, and there will be a handful of local artisans as well. Please note: Glass and bottle sales only; no tastings/flights this weekend. This is to ensure our guests are attended to in a timely manner. Sangria will not be made/offered on this Sunday for the same reason.
Reservations: Reservations are not required. There will be plenty of indoor, porch, and greenspace to spread out. Feel free to bring portable chairs.
Ingleside Vineyards
5872 Leedstown Rd
Oak Grove, VA 22443
804-224-8687
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Dates: Saturday, Nov. 14 & Sunday, Nov. 15 from 12-4pm both days
Description: Featuring a variety of oysters prepared on-site by Nomini Bay Oyster Ranch. Live music from 1-4pm both days (Saturday: Sally & Brian; Sunday: High & Dry). Indoor and outdoor seating available.
Reservations: Reservations are requested for groups of 6 or more. Other seating will be first-come, first-serve on day of event.
Jacey Vineyards
619 Train Lane
Wicomico Church, VA 22579
804-580-4053
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Please note: Jacey will participate on Saturday, Nov. 14th only.
Dates: Saturday, Nov. 14 from 12-5pm
Description: Featuring Oysters on the Half Shell, Oysters à la Jacey and Crab Cakes.
Rivah Vineyards at the Grove
671 Kinsale Bridge Road
Kinsale, VA 22488
804-599-8552
Visit website
Dates: Saturday, Nov.14 & Sunday, Nov. 15 from 12-4pm both days
Description: Menu TBA. Live music both days.
Learn More
– Like us on Facebook for updates
– View some sample itineraries and lodging options here
– Visit our Homepage for an interactive map of our Wine Trail
– View our Press Mentions
– Learn more about Virginia oysters on the Virginia Oyster Trail
(Photo credits: Vineyards and Oysters by Ingleside Vineyards. Bottles by Stephanie Campbell)