Spring Events along the Chesapeake Bay

As flowers bloom across the Mid-Atlantic and coax new life into picturesque scenery, Chesapeake boaters gear up for coastal cruising. The Bay offers a variety of springtime events from music festivals to historic-themed festivities and patriotic celebrations. Check out the following activities in Maryland and Virginia from May to June.

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MAY

Ocean City Jeep Week

Ocean City, MD, May 9 – 12

Jeep enthusiasts gather annually in this popular beach town to celebrate with a week of events such as Jeep Jam and the Jeep Beach Crawl, taking off from the Ocean City Inlet traveling north to 29^th Street. 

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Black-Eyed Susan Day & Preakness

Baltimore, MD, May 17 – 18 

Part of the world-famous Triple Crown, Pimlico Race Course hosts Black-Eyed Susan Day on Friday, then the official 149^th Preakness Stakes on Saturday accompanied by a huge party at the infield and live performance from Jack Harlow.  

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Cambridge Classic Powerboat Regatta

Cambridge, MD, May 18 – 19 

Dorchester County celebrates one of the oldest powerboat races in the country on Maryland’s historic Eastern Shore. About 70 boats will race along Hambrooks Bay off the Choptank River. Spectators can watch on land from Gerry Boyle Park at Great Marsh or anchor along the Bay with plenty of open waterfront views from your vessel.

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Blue Angels Air Show

Annapolis, MD, May 22 

Head to Maryland’s state capital to witness the U.S. Navy Blue Angels perform an exciting flyover that is sure to rattle your engines and ears. Explore shopping and dining as you watch from the downtown Annapolis waterfront.

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Patriotic Festival Country Weekend

Norfolk, VA, May 23 – 26 

Celebrate Memorial Day weekend with an all-American festival at downtown Norfolk’s Scope Arena Complex. Catch a star-studded country music lineup featuring Zac Brown Band, Warren Zeiders, Bailey Zimmerman and Hardy. 

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Smith Island Fishing Tournament 

Ewell, Smith Island, MD, May 24 – 26 

This third-annual tournament celebrates the culture of this iconic Chesapeake Bay island community. Proceeds benefit the Smith Island Fire Department and its first responders. 

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Chestertown Tea Party Festival

Chestertown, MD, May 25 – 26

Join the revolution this Memorial Day weekend at historic Chestertown’s 18th century-themed festival. Browse artisan booths and street parties, watch the military marching band parade and Tea Party reenactment, then close out the festival with Beerfest on Sunday. 

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JUNE

Clean the Bay Day

Virginia, June 1

Give back to our beloved Bay and join the Chesapeake Bay Foundation’s annual three-hour spring clean-up event. This Virginia tradition hosts clean-ups throughout various waterfront cities from state parks to transient marinas. Use CBF’s event locator map to find a city near you.

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Blackbeard Pirate Festival

Hampton, VA, June 1 – 2 

Travel back in time to when 18^th-century Hampton was overrun by pirates and witness live historical reenactments led by the infamous Blackbeard himself. Join family-friendly attractions such as the Grand Pirate Bash at the Virginia Air & Space Center. 

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Bands in the Sand

Annapolis, MD, June 8

Enjoy live music, local vendors, fresh oysters and waterfront views at Chesapeake Bay Foundation’s ultimate fundraising party of the year. Tickets sell out fast!

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Chesapeake Bay Motoring Festival

Kent Island, MD, June 8 – 9 

Head to Kent Island Yacht Club to peruse the Eastern Shore’s finest collection of classic yachts, motorcars and antique speed boats. Enjoy events such as Cars & Coffee in the morning and cocktail parties in the afternoon. 

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Antique & Classic Boat Festival & Coastal Arts Fair

St. Michaels, MD, June 14 – 16 

Celebrate Father’s Day weekend on the Miles River at the Chesapeake Bay Maritime Museum’s annual festivities. Browse wooden and fiberglass classics and vintage racers, plus free boat rides!

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Maryland Fleet Week & Flyover

Baltimore, MD, June 12 – 18 

Tour U.S. Navy and Coast Guard vessels, witness amazing flyovers and enjoy celebrations with live music, exhibitors and military displays. Festivals take place at the Inner Harbor, Fells Point and Martin State Airport. 

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Hampton Jazz Festival

Hampton, VA, June 28 – 30 

This festival has graced the city with renowned jazz, blues, soul and R&B performances for 50 years. Snag your ticket to Hampton Coliseum’s entertainment venue for three days of grooving.