Saturday & Sunday, Nov. 8 and 9, 2025
Join the wineries of the Chesapeake Bay Wine Trail for our 2025 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 check with participating wineries to learn more about their events, including hours and safety guidelines.
(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. 8 from 12-4pm and Sunday, Nov. 9 from 11am-3pm
Description: Fried Oysters with Vidalia Onion Hush Puppies. Oyster Stew.
Reservations: Reservations are not required but 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. 8 from and Sunday, Nov. 9 (please contact winery for event hours)
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. Be sure to join us on Sunday, November 9, for a special event with Matheson Oyster Co. and Sarah Matheson-Harris, Owner & CMO, featuring wine, oysters, and stories from the Bay.
Good Luck Cellars
1025 Good Luck Rd
Kilmarnock, VA 22482
804-435-1416
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Dates: Saturday, Nov. 8 from 11am-6pm & Sunday, Nov. 9 from 12-5pm
Description: Salty Bob’s Oyster & Seafood Co. 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 Troy Breslow. 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: Sangria will not be served on Sunday. Please note: (a) glass/bottle sales only; flights are not offered during busy events so staff can serve guests in a timely manner. (b) Sangria will not be served on 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. 8 & Sunday, Nov. 9 from 12-4pm both days
Description: Featuring raw, fried and grilled oysters prepared on-site by Denson’s Chesapeake Bay Farm to Table, plus crab cakes and other seafood. Non-seafood items will also be available. Live music from 1-4pm both days (Saturday: Faron Hamblin; Sunday: Hard to Tell). Creekside Farm Brewery will be onsite as a guest brewery both days. 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 Friday and Saturday.
Dates: Start off the Oyster Crawl weekend early on Friday, Nov. 7 from 12-9pm. Then join us on Saturday Nov. 8 from 12-9 pm.
Description: Oysters will be available in a variety of styles, including, Raw, Roasted “à la Jacey” and Oyster Shooters. Other items from the menu will be available. Live music on Friday by CrossRoads, including an Open Mic section from 5-9pm. Live music by Brett Baboorian on Saturday.
Reservations: First come, first served, though we will try to accommodate parties of 6 or more with reservations.
Rivah Vineyards at the Grove
671 Kinsale Bridge Road
Kinsale, VA 22488
804-599-8552
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Dates: Saturday, Nov. 8 & Sunday, Nov. 9 from 12-4pm
Description: Featuring oysters by Arnest Seafood (menu TBA). Live music both days (Emily Woodhull from 1-4pm on Saturday; JD Roberts from 1-4pm on Sunday). Several local vendors will also be onsite.
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)