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The Chesapeake Bay stretches 200 miles from Maryland’s northeastern border down to Virginia’s entrance to the Atlantic presenting scenic landscapes and charming waterfront towns. The summer boating season is prime time to check out the region’s traditions from cultural celebrations and music festivals to regattas and maritime events. Catch the following festivities hosted along the Bay from July to September.
Rock Hall, MD July 7
Set sail to Rock Hall this July for a special celebration that honors working watermen of the maritime industry. A day full of family-friendly activities takes place at the Rock Hall Bulkhead where boaters can anchor along the harbor. Enjoy a variety of vendors and the popular boat-docking contest.
Where to Dock: Rock Hall Bulkhead
Leonardtown & Coltons Point, MD July 12 – 14
This musical event boasts delicious seafood, performances and jazz cruises along Breton Bay. The weekend kicks off with a free concert at the College of Southern Maryland in Leonardtown, then the main event on Saturday at the St. Clements Island Museum in Coltons Point. Head back to Leonardtown on Sunday to close out the festival with brunch, shopping and live music at Port of Leonardtown Winery.
Where to Dock: Combs Creek Marina or Coltons Point Marina
Norfolk, VA July 20 – 21
Downtown Norfolk’s Town Point Park hosts two days of free events along the waterfront. Feast on authentic cuisine, enjoy live music and learn to salsa dance at the Latino Music Festival on Saturday. On Sunday, the Virginia Symphony Orchestra performs a concert featuring national recording artists.
Where to Dock: Tidewater Yacht Marina
Chincoteague, VA July 24
This barrier island splits Assateague Island, MD, with Chincoteague Island, VA, straddling the Chesapeake Bay to the west and Atlantic Ocean to the east. The beachy nature preserve is famous for wild ponies that roam the state park. Each summer, spectators flock to watch about 50 of these beauties swim from Assateague to Chincoteague and back. The Chincoteague Fireman’s Carnival is also open each night with rides, games, food and raffles.
Where to Dock: Snug Harbor Marina
Ocean City, MD August 5 – 9
Located on a barrier island between the Bay and the Atlantic, Ocean City, annually hosts what is known as the “world’s largest and richest billfish tournament.” Fishing enthusiasts from across the nation cruise to this beachfront town for a chance to compete for substantial jackpots. Last year’s event awarded more than $10.5 million in prize money.
Where to Dock: White Marlin Marina, Sunset Marina or Bahia Marina
Cape Charles, VA August 10 – 11
Celebrating its 21st year, this two-day event is part of the Southern Bay Distance Racing Series. After a race across the Bay to Cape Charles, head to the social event with food, music and awards at Oyster Farm Marina at King’s Creek. Vessels race back to Buckroe Beach on Sunday. The daily raffles and auctions offer chances to win prizes!
Where to Dock: Oyster Farm Marina
Ocean City, MD August 15 – 17
This annual ladies-only billfish release tournament benefits breast cancer research with a weekend of raffles, fun events and friendly competition. Kick-off with the Pink Party at Bahia Marina and the Battle for the Bras Competition on Friday, followed by daily weigh-ins, fishing and winners announced on Saturday. Close out with the Captain, Crew & Anglers luncheon and awards banquet at the Ocean City Convention Center on Sunday.
Where to Dock: Bahia Marina
Norfolk, VA August 16 – 17
The area’s longest running outdoor jazz fest returns to downtown Norfolk with a two-day star-studded lineup. Escape in smooth saxophone sounds and dance to groovy tunes from renowned musicians at Town Point Park’s waterfront venue. Headliners include Norman Brown, Rebecca Kade and Four80East with Jeff Kashiwa.
Where to Dock: Morningstar Marinas at Little Creek
Deal Island, MD September 7
Peddle along Deal Island’s backroads, marshes and scenic forested wetlands of a wildlife refuge on this 15-, 30- or 60-mile bike ride. The tour begins at Deal Island Harbor and covers beautiful trails along the water. Proceeds benefit the Deal Island Chance Volunteer Fire Company.
Where to Dock: Scotts Cove Marina
Eastport, MD September 21
The Seafarers Yacht Club, a community-based organization promoting seamanship and youth education, teams up with the Eastport Yacht Club to host this charitable event. Located just south of downtown Annapolis in the Eastport neighborhood, the regatta celebrates with a Shore Party and a day full of cruising. Net proceeds benefit the Seafarers Foundation’s mission to support underserved Maryland communities.
Where to Dock: Eastport Yacht Center
Hampton, VA September 21 – 22
The East Coast’s premier inboard hydroplane race returns to Hampton’s waterfront for an adrenaline-pumping weekend. Spectators can watch boats crank from 80 to 170 mph across the Bay. View from the Mercury Boulevard bridge that leads to Fort Monroe and the grassy areas on Stilwell Drive.
Where to Dock: Old Point Comfort Marina
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Baltimore, MD September 24 – 28
Head to Baltimore’s upscale Harbor East neighborhood for this annual boat show on the Patapsco River. Peruse the intimate in-water selection of new and used powerboats, attend educational seminars and network with fellow cruisers. Just steps away, feast on fabulous fine dining at an Atlas Restaurant establishment such as Loch Bar at the Four Seasons Hotel or the recently opened prime steakhouse, The Ruxton.
Where to Dock: Harbor East Marina
Cruise to St. Michaels, MD, to catch the following summer events at the museum:
• Big Band Night, July 6
• Watermen’s Appreciation Day, August 11
• Charity Boat Auction, August 31
• Boating Party Fundraising Gala, September 7
• Log Canoe Cruise Charters: MRYC Governor’s Cup Series, July 27, MRYC Labor Day Series, September 7 and Higgins, Commodore & Bartlett Cups, September 14
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