There’s little else that says “fall on the Chesapeake Bay” than fresh oysters. In October and early November, several waterfront communities celebrate the opening of oyster season by organizing festivals dedicated to the quintessential bivalve.
Pick a weekend, and boat or drive to one (or more) of these oyster extravaganzas. Expect a myriad of prepared oysters, local craft beers, live music, shucking competitions, and much more.
World Is Your Oyster Fest, Baltimore: October 2
With the world’s largest human-made oyster reef soon-to-be completed and the tripling of the Maryland oyster population, the staff at the Oyster Recover Partnership (ORP) have cause to celebrate.
ORP hosts the World is your Oyster Fest at the B&O Railroad Museum in Baltimore, where attendees will try local oysters, sip craft cocktails, and cheer on the pros in the Tito’s Handmade Vodka shucking competition. The winner will have the opportunity to compete at the 2025 U.S. National Oyster Championship Contest in St. Mary's County.
Organizers urge attendees to buy tickets early as they always sell out. It is a 21-plus event.
Yorktown Wine and Oyster Festival: October 4,5
Shell-abrate life’s great moments with a glass of wine and a plate of oysters at the two-day Yorktown Wine and Oyster Festival! Enjoy spectacular views of the York River and delicacies from the sea and local vineyards. The event pairs the finest Virginia wines with the freshest local seafood—including succulent oysters served raw, roasted, and steamed. Sip and stroll along the scenic waterfront while enjoying live music, gourmet food trucks, and artisan vendors. With the river breeze, a glass of wine in hand, and the taste of the bay on your plate, this is coastal sophistication at its finest.
Even better? Every sip and slurp supports a good cause—proceeds benefit Sister Cities Yorktown, Yorktown Hospice House, The Fifes and Drums of York Town, the Yorktown Women’s Club, and many other organizations.
This is a closed-ticketed only event. Everyone must purchase a ticket to enter the event area. There will be a limited number of non-drinking tickets available this year. No outside food, drink, tables, tents, or umbrellas. Unopened bottled water and a small folding lawn chair will be permitted. Service pets only. One-day tickets cost $50, two-day tickets cost $85. The free accessible Yorktown Trolley will be running during this event.
Westminster Oyster Stroll: October 11
Shop, slurp, and stroll through historic downtown Westminster! This is an annual festival featuring local oyster farmers, live entertainment, delicious food, and a lot of fun for the whole family. The Oyster Stroll is designed to raise awareness about Chesapeake Bay farm-raised oysters and highlights how Westminster is working to restore wild oysters back into the bay. The event directly supports CCA Maryland's Living Reef Action Campaign.
Shuck It! Solomons: October 11
A brand-new oyster celebration in Solomons is in the works. Enjoy a variety of oyster and seafood dishes, live entertainment, special retail offers, themed boat rides, interactive demonstrations, and more. Don’t forget to pick up your Oyster Passport and explore participating Solomons businesses for a chance to win oyster-themed prizes. The event is still in the planning stages. Follow the Visit Solomons Facebook page for updates.
Poquoson Seafood Festival: October 17-19
Living up to its name, the Poquoson Seafood Festival offers a multitude of dishes including crab cakes, oysters, clams, and soft-shell crabs, along with local specialties like she-crab soup and clam chowder. For non-seafood lovers, the festival also offers BBQ, fried chicken, gator bites, and classic carnival treats such as funnel cakes and corn on the cob. There will be live music on two stages all weekend; a kids’ zone with a petting zoo, rides and exhibits; and crab pot construction and net-making demonstrations, highlighting watermen’s skills and traditions.
The Poquoson Harbor, south of the wide York River entrance, is known for its fantastic fishing and recreational boating. Both York Haven Marina and Whitehouse Cove Marina have transient slips and are close to the festival grounds.
Captain Avery Museum Oyster Festival: October 18
11 a.m. to 5 p.m. on the banks of the West River in Shady Side, MD, at the Captain Avery Museum. Good community company, fine regional music, an array of choice gifts for purchase, a cash raffle, local food and drink, and the best oysters anywhere. This year there will be double the bands, more vendors, and more hours of fun for you to enjoy! Rain date: Sunday, October 19. Tickets cost $10 for members, $20 for non-members, and it's free for children eight and under. Parking is off-site at Shady Side Park (1355 E. West Shady Side Rd.) or Clarks Landing (1442 Ford Rd., Shady Side). A shuttle service will run between the festival and the off-site parking lots.
US Oyster Festival, Leonardtown: October 18,19
Attended by thousands, this beloved two-day festival celebrating culture culminates in the US National Oyster Shucking Championship, where top shuckers from across the nation compete for the title of US National Champion. The winner could represent the U.S. in the World Oyster Opening Championships in Ireland.
As one would expect, there will also be live music, performers, beer, craft vendors, oysters served every way you could imagine, and a national oyster cook-off.
If arriving by boat, there are nearby anchorages in Breton Bay and a 160-foot floating dock pier at the Leonardtown Wharf that holds up to 14 boats. Call (310) 475-9791 about docking.
Chesapeake Bay Maritime Museum’s OysterFest, St. Michaels: October 25
The oyster extravaganza highlights oysters from the Talbot Watermen Association and several local oyster farms, with most bivalves having been harvested just hours prior to the event.
Local vendors serve ham and oyster biscuits, buttermilk fried oysters, oyster stew, and Bloody Mary oyster shooters. Buy an OysterFest mug, and join the judging for the perennial favorite oyster stew competition. Beyond slurping oysters, guests can dive into Chesapeake history through a slate of demonstrations, children’s activities, and more.
Boaters should know that the on-site marina is exclusively for CBMM members. Find docking information at cbmm.org/docking.
For those who want to venture into historic downtown St. Michaels, local restaurants outside of the venue will serve oyster dishes.
Urbanna Oyster Festival: November 7-8
The longest-running festival celebrating the Chesapeake’s oyster harvest is located in the postcard-perfect small town of Urbanna, along the Rappahannock River. Oyster grounds surround this colonial port town and produce some of the finest oysters in Virginia.
This celebration is a town-wide effort, employing hundreds of volunteers to celebrate generations of oystermen and shuckers. Everyone pitches in to cook, shuck, and sauce-up delicacies on the half-shell. Expect oyster-shucking contests, multiple parades, children’s activities, three live music stages, wine tastings, arts and crafts, historic boats, and oyster ecology at the waterfront.
Clark Laster, a local schoolteacher, oversees the waterfront boat exhibits, bringing in vessels such as the Lynx, a working replica of a privateer schooner used during the War of 1812. She and the crew were captured by the British on the Rappahannock River. There will be at least five replica boats on site that attendees can board.
Docking for the event is at URBBY Marina or Urbanna Town Marina. Both are close to the village and the festivities.
By Carrie Gentile