Calendar of Events

This is a calendar of events taking place on and around the Chesapeake Bay for the months of July, August, and September. This includes events for Maryland’s Eastern Shore, Eastern Shore of Virginia, Southern Maryland, and Virginia’s Northern Neck, Middle Peninsula, and Hampton Roads. The calendar includes a wide variety of events including festivals, boat races, boat shows, fishing tournaments, exhibitions, seminars, and workshops.

Return to the Calendar index page to select different months.

July – September 2025

July 2, 2025 – Queen Anne’s County 2025 Independence Day Celebration – Family activities, entertainment, and fireworks at the Chesapeake Heritage and Visitors Center.

July 4, 2025 – 4th of July Great American Picnic & Fireworks – Fourth of July event serving up food, live entertainment from military bands, and a big fireworks show over the Elizabeth River. Town Point Park. Norfolk, VA.

July 26, 2025 – Wheels on the Waterfront Cruise-in – Charity cruise-in event. Participating cars line up in the downtown Crisfield area. Crisfield, MD.

August 1, 2025 – Annapolis Rotary Crab Feast – The 79th annual all-you-can-eat crab feast featuring crabs, corn, BBQ, and hot dogs, plus beer from the keg and sodas & water. Held at Navy-Marine Corps Memorial Stadium. Annapolis, MD

August 2 & 3, 2025 – 5th Annual Crab Slam – The 5th Annual Crab Slam features a boat docking competition, parade, live music, skiff races, and oyster eating contest. Saturday is open to the public, but Sunday will be ticketed at $25 per person (kids 5 & under free). Cape Charles, VA

August 11 – 16, 2025 – Queen Anne’s County Fair – Exhibits, 4H competitions, amusement rides and more. Queen Anne’s County 4-H Park, Centreville, MD.

August 10th – Watermen’s Appreciation Day – Hosted by the Chesapeake Bay Maritime Museum in partnership with the Talbot Watermen Association. Festivities include a workboat docking competition, live music, a locally harvested crab feast, with plenty of additional options to eat and drink. St. Michaels, Maryland.

August 16, 2025 – 7th Annual Crab Crackin’ at Ker Place – All-you-can-eat feast with steamed crabs; steamed clams; sweet corn; barbecue; coleslaw; beer and wine (limited quantity of beer and wine included, with additional available for purchase) held on the lawn of Ker Place historic house museum in downtown Onancock. Onancock, VA.

August 23 & 24, 2025 – 53rd Annual Seawall Art Show – The Seawall Art Show features works for sale by 85+ artists, a student art show, live entertainment and food. High Street, between Crawford and Court Streets. Free admission. Portsmouth, Virginia.

August 30, 2025 – Chesapeake Bay Maritime Museum Annual Charity Boat Auction – Bid on donated vessels of all shapes and sizes. Proceeds support the Chesapeake Bay Maritime Museum. St. Michaels, Maryland.

Labor Day Weekend – National Hard Crab Derby – A full weekend of events including the famous Crab Derby races, crab picking contests, boat docking contests, live entertainment, and more. Held at Crisfield’s Somers Cove Marina. Crisfield, MD.

September 5 & 6, 2025 – Mathews Market Days – Annual festival held in downtown Mathews, VA on the first Friday and Saturday after Labor Day. Arts & crafts, food, and informational vendors. Live music. Mathews, VA.

September 13, 2025 – Classic Boat Show – Classic boats on display at the Reedville Fishermen’s Museum. Visitors can also enjoy, live music, a beer garden, Oyster Po’ Boys Brats and Hot Dogs, Cruises on the Fannie, a 50/50 raffle, vendors, and Nautical Flea Market. Reedville, Virginia.

September 13 – 14, 2025 – Crabtown Seafood Festival – Held along the downtown waterfront from Mill Point Park to the downtown docks, this festival features seafood vendors, exhibits, games, activities, and live entertainment. Hampton, VA.

September 13 & 14, 2025 – Maryland Seafood Festival – The Maryland Seafood Festival returns to Sandy Pointe State Park in Anne Arundel County (on the Annapolis side of the Chesapeake Bay Bridge) for 2025. Hotels near the Maryland Seafood Festival.

September 27, 2025 – 4th Annual Crisfield Heritage Festival – Kid’s activities, live entertainment, food, arts and craft vendors and live demonstrations – all showcasing the Chesapeake Bay culture of Crisfield.  Crisfield, MD.

September 27 & 28, 2025 – Hampton Cup Regatta – North America’s oldest continuously-run hydroplane boat race. This event features high-speed hydroplane boat racing. Hampton, VA.