Memorial Day Weekend Festivals & Events 2025

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By
Alexa
Zizzi

As Memorial Day weekend approaches, boaters plan for one of the busiest days on the water with the usual cookouts, rendezvous and aquatic activities. If you’re cruising the coast and want to mix things up with something different, waterfront cities from New England to Florida offer tons of fun activities to kick off the season.

Featuring everything from music and arts festivals to cruises and traditional patriotic tributes, check out the following events happening this holiday weekend. 

NEW ENGLAND

 

Fan Pier Marina | Photo by ©JimRaycroft, Courtesy of Ocean Havens

Boston Calling

Boston, MA, May 23 – 25

Located at the Harvard Athletic Complex, this music festival hosts a star-studded lineup featuring Luke Combs, Sheryl Crow, Fall Out Boy, Cage the Elephant, Vampire Weekend, Dave Matthews Band and more. 

Where to Dock Nearby: Boston Yacht Haven Inn & Marina, Fan Pier Marina

 

Downeast Spring Birding Festival

Trescott, ME, May 23 – 26

Cobscook Institute hosts four days of guided hikes, boat tours and presentations led by local guides. Bask in Maine’s natural beauty and embark on a birdwatching experience during primetime spring migration and breeding season.

Where to Dock Nearby: Town of Lubec Marina on Johnson Street (daily 2-hour tie up or moorings), Eastport Breakwater/City Dock (seasonal/daily dockage)

 

Battle of Chelsea Creek 250th Anniversary Celebrations

Chelsea, MA, May 24

Explore the SSV Ernestina-Morrissey schooner and the Governor Bellingham-Cary House Museum open house or take a 90-minute guided boat tour with Boston Harbor Now through Mill Creek and Boston Bay.

Where to Dock Nearby: Boston Yacht Haven Inn & Marina

 

Memorial Day Open House

Boston, MA, May 26

The Museum of Fine Arts, Boston, hosts an open house this Memorial Day with special exhibitions, music, artmaking and more. Free admission offered to Massachusetts residents!

Where to Dock Nearby: Boston Yacht Haven Inn & Marina, Fan Pier Marina

 

CHESAPEAKE BAY

 

Chestertown Tea Party Festival

Chestertown, MD, May 23 – 25

The revolutionary event kicks off with a Block Party at Wilmer Park on Friday, followed by a weekend of events, entertainment, education and family fun all across historic Chestertown.

Where to Dock Nearby: Chestertown Marina

 

Courtesy of Haven Harbour Marina

Memorial Day Weekend Cruise to Rock Hall

Rock Hall, MD, May 23 – 26

Join Herrington Bay Yacht Club for a beautiful Chesapeake Bay cruise to Rock Hall Landing to dock, dine and explore the local area with fellow cruisers. Stay overnight at the marina or at Mariner’s Motel.

Where to Dock Nearby: Rock Hall Landing Marina, Haven Harbour Marina Resorts

 

George W. Owings, III Stars & Stripes Festival

Chesapeake Beach, MD, May 24

Honor the fallen with local officials and guest speakers with this annual ceremony at Veterans Memorial Park.

Where to Dock Nearby: Rod ‘N’ Reel Resort

 

Artscape

Baltimore, MD, May 24 – 25

Baltimore’s beloved art festival moves to Memorial Day weekend this year, lining the city with vendors and immersive public art. Support local artisans, artists, vendors and live performances.

Where to Dock Nearby: Inner Harbor Marina

 

DC & VIRGINIA

 

Rolling to Remember

Washington, DC, May 23 – 25

This 37th annual parade of patriotic motorcyclists takes place in the heart of the nation’s capital. Activities kick off with “The Blessing of the Bikes” on Friday, followed by a weekend of events and the final “Ride Day” on Sunday.

Where to Dock Nearby: The Wharf Marina, The Yards Marina

 

Patriotic Festival Country Weekend

Norfolk, VA, May 23 – 25

Head to Norfolk Scope Arena complex for a country weekend featuring performances from Old Dominion, Riley Green and Jordan Davis.

Where to Dock Nearby: Tidewater Yacht Marina

 

Memorial Day Weekend Salute to Summer

Virginia Beach, VA, May 23 – 25

Enjoy free concerts from local bands at 17th, 24th and 31st Street Parks and join the Heroes’ Walk beginning at 16th Street.

Where to Dock Nearby: The Marina at Marina Shores

 

Courtesy of The Wharf Marina, Washington, DC.

National Memorial Day Parade

Washington, DC, May 26

Join the nation’s ultimate Memorial Day celebration happening in the heart of all the action along Constitution Avenue in Washington, DC. Music performances start at 1:00 p.m., followed by the parade at 2:00 p.m.

Where to Dock Nearby: The Wharf Marina, The Yards Marina

 

THE SOUTH

 

Gulf Coast Masters

Orange Beach, AL, May 21 – 25

Mobile Big Game Fishing Club’s annual tournament takes place at Orange Beach Marina along Alabama’s Gulf Shores.

Where to Dock Nearby: Orange Beach Marina, The Wharf Marina Alabama

 

Orange Street ArtsFest

Wilmington, NC, May 24 – 25

The Thalian Association Community Arts Theatre presents this 29th annual arts festival with exhibitions and events held at the Hannah Block Historic USO/Community Arts Center.

Where to Dock Nearby: Wilmington Marine Center

 

Memorial Day Concert

Charleston, SC, May 26

The Charleston Concert Band and Columbia Community Band will grace the stage on Memorial Day for a free patriotic concert at Hampton Park.

Where to Dock Nearby: Safe Harbor Charleston City

 

Taps at Twilight

St. Simons Island, GA, May 26

The St. Simons Rotary Club hosts this traditional observance and tribute at Neptune Park on Memorial Day featuring patriotic music from St. Simons Casino bandstand.

Where to Dock Nearby: Brunswick Landing Marina, Morningstar Marinas Golden Isles

 

FLORIDA

 

Courtesy of Windward Sadler Point Marina

Jacksonville Jazz Festival

Jacksonville, FL, May 22 – 25

Head to Tailgaters Parking in the heart of Jacksonville’s Sports & Entertainment District for this completely free music festival featuring performances from award-winning jazz artists.

Where to Dock Nearby: Windward Sadler Point Marina

 

Blue Crab Festival

Palatka, FL, May 23 – 25

Just west of St. Augustine, head to Palatka’s downtown waterfront for a weekend of carnival rides, live music, arts and crafts and events including a seafood cook-off and military tributes.

Where to Dock Nearby: Boathouse Marina

 

Memorial 4-Day Weekend at Sunset Walk

Kissimmee, FL, May 23 – 26

The Promenade at Sunset Walk hosts four days of fun featuring bands, DJs, street performers and vendors, plus a car show and artisan market.

Where to Dock Nearby: Big Toho Marina

 

Memorial Day Weekend Craft Festival

Delray Beach, FL, May 24

Explore the Delray Beach artist community at this 27th annual craft fair taking place on NE 4th Avenue. Shop artisan works, handmade wares and a Green Market. The show starts in the heart of downtown and extends two blocks north to NE 2nd Street.

Where to Dock Nearby: City Marina

 

Hyundai Air & Sea Show

Miami, FL, May 24 – 25

Witness two days of amazing air shows above the gorgeous shores of Miami Beach between 11th and 15th Streets. Check out military displays, demonstrations and performances, plus concessions, exhibitions and a Kids Zone with a bounce house and rock-climbing walls.

Where to Dock Nearby: Sunset Harbour Yacht Club, Miami Beach Marina

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