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.)

Trail wineries are confirmed to be participating:

The Dog and Oyster Micro-Vineyard Located at the Hope & Glory Inn, 65 Tavern Rd, Irvington, VA 22480. 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. Two Fish Bistro will be onsite 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.

Ingleside Vineyards 5872 Leedstown Rd, Oak Grove, VA 22443.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.

Rivah Vineyards at the Grove 671 Kinsale Bridge Road, Kinsale, VA 22488. 12-6pm. Menu TBD. Live music.