This is an annual calendar of events taking place on and around the Chesapeake Bay that are water related or related to the Bay's cultural, ecological, or maritime culture. The calendar includes a wide variety of events including festivals, boat races, boat shows, fishing tournaments, exhibitions, seminars and workshops. Chesapeake Bay EventsApril
April 3 - Blessing of the Fleet, 5:30pm to 9:30pm, Cape Charles Harbor. Commercial fishing boats from all over the Chesapeake Bay will converge at Cape Charles Harbor for the blessing of a safe season and good harvest for local fishermen. Share the bounty of the Bay, the freshest seafood brought to the dock by local watermen. The celebration includes beer and award-winning Eastern Shore wine. Cape Charles, VA. April 18. Privateer Day and Pyrate Invasion. A pirate themed celebration at Fell's Point will include tall ships, pirate re-enactors, live music, strolling entertainers, games, storytelling, costume contests for kids and adults, food, pirate gear and nautical arts and crafts. A Pyrate Invasion at many bars and restaurants will begin at 6:00pm. 11:00am to 6:00pm. Fells Point, Baltimore, MD. More Information. April 18. Boatyard Bar & Grill Spring Fishing Tournament. Annual catch and release tournament to benefit the Chesapeake Bay Foundation, Coastal Conservation Association, and the Annapolis Police Department's fishing camp. An outline of the winning fish will be painted on the rafters at the Boatyard, which will host the after tournament party. Annapolis, MD. More Information. April 18. Bay Day. The Chesapeake Bay Maritime Museum host this annual Bay themed version of Earth Day. There will be demonstrations, food, lectures, and more. 10:00 to 5:00pm. St. Michaels, MD. More Information. April 18 -19. Portsmouth Power in the Park. The Virginia Boat Racing Association will hold its annual State Championship races in the waters off Portsmouth City Park. Noon to 6:00pm. Portsmouth City Park, Portsmouth, VA. More Information. April 23- 26 - Bay Bridge Boat Show. Bay Bridge Marina, Stevensville, 10 a.m.-6 p.m. Thursday, 10-a.m.-7 p.m. Friday-Saturday, 10 am to 6 pm Sunday. More Information. Kent Island, MD. April 25 - Low Country Shrimp Boil. An annual small town shindig following the Garden Week Tour. Feast on the Eastern Shore's version of a delicious Low Country Shrimp Boil on the grounds of the Cape Charles History Museum. Explore the latest display and enjoy a silent auction. Local Blue Grass Music. Opens at 5:00pm. Cape Charles, VA. April 25 -- Bull and Oyster Roast. Join the crew of the Martha Lewis in Hutchins Park for a celebration to kick off the summer cruise season. Doors open at 6:00 pm. More info. Havre de Grace, MD. April 25 -- Annual Oxford Day. All of the organizations and businesses in town have been working hard to prepare for this all-day family event. So invite your friends and family to visit, plan on staying home, put aside the yard work and errands. Just relax, walk around our wonderful town and enjoy all the activities. Oxford, MD.
MayMay 1 -3 -- Rod 'N Reel Pro-Am Tournament. Annual fishing tournament features over $30,000 in prizes. Rod 'N Reel Marina, Chesapeake Beach, MD. More Information. Chesapeake Beach, MD. May 1 - 3 -- Annual Decoy and Wildlife Art Festival. Havre de Grace Middle & High Schools and the Havre de Grace Decoy Museum. Premier carvers & wildlife artists, live and silent auctions, carving competitions, retriever demonstrations. Free shuttle buses. Fri. 6-9:00pm; Sat. 9am - 5pm; Sun. 10am - 4pm. Havre de Grace, MD. May 2 - Solomons Maritime Festival. 10 a.m. to 5 p.m. Free. Come and celebrate Southern Maryland traditions! This family event offers something for every member of your family. The Antique Boat and Marine Engine Show, home crafts and cooking demonstrations, children's games, music, and boat rides for all. Calvert Marine Museum. Solomons, MD. May 2 - 3 -- Re-Enactment of the Attack on Havre de Grace - War of 1812. The British will attach on the Lock House Grounds. Visit the encampments, musket firing displays, marching and drill, and more. Havre de Grace Lock House Museum. Havre de Grace, MD. May 3 -- Blessing of the Fleet. Local clergy lead a blessing of the commercial and recreational fleet as the fishing season begins. Chanty singers, bagpipers. 5:00 pm at Omega Protein Plant off Fleeton Road. Come by land or by boat on Cockrell’s Creek. Reedville, VA. May 9 -- Virginia Wine Festival. Wine tastings, gourmet food, live entertainment, and new releases from Virginia wineries at Town Point Park on the Norfolk waterfront. More Information. Norfolk, VA. May 9 -- Art on the Half Shell. The Middlesex Art Guild presents this annual art festival featuring over 80 artists’ displays, performing arts, a children’s art center, food, entertainment and many cash prizes. 10 a.m.–5 p.m. More information. Urbanna, VA. May 15 - 17 - Black Drum World Championship Fishing Tournament. Enjoy world-class black drum fishing for cash prizes. Captains meeting Friday night, fishing Saturday and Sunday. More information. Cape Charles, VA. May 16 - Chesapeake Bay Blues Festival. This year's charities are Special Olympics, Camp Face and WE Care. Musical guests include Jonny Lang, Los Lonely Boys, Ana Popovic, Big Bad Voodoo Daddy, and Shemekia Copeland. Many more will follow. One concert stage with Jumbtron, large crafter village, a wide variety of food and drink, Beer and Wine, beach, playgrounds, lawn seating (General Admission only). Sandy Point State Park. More Info. Annapolis, MD. May 17 -- Bay Hundred Ladies Rockfish Tournament. The Bay Hundred Chapter of Ducks Unlimited sponsors this annual ladies fishing tournament. Men are allowed to participate as captains, mates, and guests at the after party. Harrison's Chesapeake House, Tilghman Island, MD. More Info. Tilghman Island, MD. May 22 - 24 -- Chestertown Tea Party. Come downtown to commemorate the local merchants' revolt against the British tea tax. A reenactment, parade, concessions, and crafts highlight the day on Saturday. Raft race on Sunday. More Information. Chestertown, MD. May 23 -- Elizabeth River Run. A 10k race attracting up to 1,000 participants, who run along the Elizabeth River, the race's namesake. Includes a post-race party at the NTELOS Pavilion. A benefit for the Portsmouth Museums Foundation. 8 a.m. More Information. Portsmouth, VA. May 24 -- Soft Shell Spring Fair. 12 noon - 5 pm at the City Dock, fresh local seafood, arts and crafts, Hall of Fame Awards, Entertainment and plenty of great seafood. More Information. Crisfield, MD. May 30 - 31 -- Chesapeake Bay Wine Festival. Enjoy local wines, food, and entertainment on the shores of the Chesapeake Bay. Noon to 6:00pm both days. Terrapin Nature Park, Stevensville, MD. More Information. Kent Island, MD.
JuneJune 5 - Upper Chesapeake Health Foundation's Annual Harford Hospice Regatta. Come to the Concord Point Lighthouse to enjoy a sailboat Regatta, steak & chicken dinner by Outback Steakhouse, unlimited beer & soda, live band, gaming wheels, and a silent auction. $75 per person. email. Havre de Grace, MD. June 5 - 7 -- Blackbeard Festival. Pirates take over the downtown waterfront in this family festival. More Information. Hampton, VA. June 12 - 13 -- Reedville Bluefish Derby. Celebrating its 25th anniversary, this tournament will offer 30 cash prizes including prizes for largest bluefish, rock fish, and croaker. Buzzard's Point Marina, Reedville, VA More Information. Reedville, VA. June 12 - 14 -- Annual Rockfish Tournament. Catch the fun and excitement of this big money tournament. Join the fleet or just watch as contestants weigh-in daily at the Rock Hall bulkhead. Sponsored by the Maryland Waterman’s Association. More information. Rock Hall, MD. June 14 -- Great Chesapeake Bay Swim. 4.4 mile swim and 1 mile Bay Challenge. Sandy Point State Park to Kent Island. Charitable events benefits the March of Dimes. More information. Annapolis, MD. June 19 - 21 -- 17th Annual Antique & Classic Boat Festival - Annual event featuring more than a hundred antique and classic boats, as well as wooden boat building demonstrations, maritime craft vendors, live music and food. Fri 11 AM - 5 PM, Sat 9 AM - 5 PM, Sun 9 AM - 2 PM. Ches. Bay Maritime Museum. St. Michaels, MD. June 19 - 20 -- Cock Island Race. Called the " Best Sailing Event on the East Coast." by landlubbers and sailors alike, this waterfront classic features Friday & Saturday night live entertainment. More Information. Portsmouth, VA. June 26 - 28-- Hampton Jazz Festival. Annual jazz music festival featuring top national blues, soul, and pop performers. Hampton Coliseum. More Information. Hampton, VA. June 27 -- Tilghman Island Summer Seafood Festival. Spend the day enjoying live music, local seafood, crafts, Little Miss Tilghman contests and the fireman's parade. Benefit the Tilghman Island Volunteer Fire Company. Kronsberg Park. More Information. Tilghman Island, MD. June 27 -- Oxford Cardboard Boat Race. A summertime tradition on the Tred Avon River in Oxford. Starts at 9:00am on the Strand. Oxford, MD. June 28 -- Canal Day. A day of music, food, drinks and fun along the streets of historic South Chesapeake City, MD. Chesapeake City, MD. More Information.
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