Labor Day Weekend Events


As we cruise through summer at what feels like high-speed, it’s time to plan trips and events to close out the season. 

Traditionally, Labor Day weekend is when boaters in northern regions soak up the last bit of sun and outdoor fun. From music and boating festivals to races, fundraisers, parades and fireworks, Marinalife has your holiday planning covered. The following events take place across New England, the mid-Atlantic and the Great Lakes.


Schooner sailing in Gloucester Harbor, MA. | Wangkun Jia on Shutterstock

39th Annual Gloucester Schooner Festival

Gloucester, MA, August 31 – September 3

Every year, schooners from across the globe flock to Gloucester Harbor to race and celebrate the beauty of sailing. Enjoy this four-day festival hosted by Maritime Gloucester featuring the main schooner race on Sunday.

Camden Windjammer Festival

Camden, ME, September 1 – 2 

Cruise to Camden Harbor Park to attend shows including the Schooner Talent Show and Nautical Dog Show, performances from Bay Winds North Wind Ensemble, and races such as First Fish Relay Race and Lobster Crate Race. 

Rhythm & Roots Festival

Charlestown, RI, September 1 – 3 

Enjoy a wide range of genres from blues and country to Cajun and Zydeco at this groovy music festival. Located at Ninigret Park, guests can purchase a day pass or pitch a tent for the weekend at onsite campgrounds. Headliners include Trombone Shorty & Orleans Avenue and Greensky Bluegrass. 

Labor Day Fireworks Cruise on Northern Lights

Boston, MA, September 1 – 4 

Watch fireworks illuminate the Boston Harbor skyline aboard the beautiful 1920s-style commuter yacht, Northern Lights. One complimentary drink is included with admission, and cheese boards, flatbreads, sandwiches and additional snacks are available for purchase onboard. 

Labor Day Parade of Lights

Port Henry, NY, September 2

Head to Bridgeview Harbour Marina to watch a spectacular lighted boat display cruise down Lake Champlain. The route travels north to an anchorage just south of Port Henry Pier where the annual Labor Day fireworks show is launched.


Basket of Crabs | David Kay on Shutterstock

76th National Hard Crab Derby

Crisfield, MD, September 1 – 3 

This annual crab-themed event is a southern Maryland tradition with live entertainment, cooking, crafts, beauty pageants, crab races and crab-picking contests. Enjoy a parade and fireworks and grab seats to the Crisfield Boat Docking event on Sunday. 

19th Annual DC JazzFest at The Wharf

Washington, DC, September 2 – 3 

Both international acts and local talent grace The Wharf’s outdoor stages for two days of jazz music at this signature DC event. Dock at The Wharf Marina and walk the strip of newly developed shops, dining and attractions. 


Rehoboth, DE, September 2 – 3 

This beach town closes out the summer season with a huge party at one of Delaware’s most popular events. The fundraiser supports CAMP Rehoboth’s essential health, wellness, arts and advocacy programs and hosts a live auction, comedy and drag shows, and nationally recognized DJs that transform the Rehoboth Beach Convention Center into a giant dance party.

Labor Day Weekend Cruise & Crab Feast at Clayton’s

Cambridge, MD, September 3

Come by land or sea to this 25th annual crab feast at one of the oldest crab companies on the Chesapeake Bay — the J.M. Clayton Company. Hosted by Eastport Yacht Club in Annapolis, MD, the event rallies a cruise to Cambridge to gather with fellow sailors for a BYOB happy hour, potluck and crab-picking. 

Deal Island Skipjack Races & Festival

Deal Island, MD, September 3 – 4

Witness skipjacks along Deal Island Harbor while enjoying live music, vendors arts and crafts, kids’ activities, an antique car show and a parade. Catch the fishing tournament, silent auction, Blessing of the Fleet and the 64th Annual Skipjack Race on Labor Day.


Chicago Jazz Festival

Chicago, IL, August 31 – September 3

Programmed by the acclaimed Chicago Jazz Institute, this Labor Day weekend tradition showcases local talent and international artists to raise awareness of the arts. Concerts are held throughout neighborhoods citywide. 

Air Show Parties at the Great Lakes Science Center

Cleveland, OH, September 1 – 3 

Witness the U.S. Air Force Thunderbirds amazing air show from the deck of steamship William G. Mather or from the Science Center’s terrace overlooking North Coast Harbor. Enjoy family-friendly games, activities and a lunch buffet. Dock at Oasis Marinas at North Coast Harbor.

Oktoberfest | credit franky242

Cleveland Oktoberfest

Middleburg Heights, OH, September 1 – 4 

Head to the Cuyahoga County Fairgrounds for two weekends celebrating the popular German tradition. Sample cultural food and drinks, enjoy live entertainment and check out the Bier Garten and VIP Jägermeister tent. The festival returns September 8 – 9. 

Annual Labor Day Mackinac Bridge Walk: Cross the Mighty Mac

Mackinac Island, MI, September 4

The unique town of Mackinac hosts this annual tradition drawing thousands to cross the beloved Mackinac Bridge. Participants walk hundreds of feet above where Lake Michigan and Lake Huron meet and traverse the midpoint from Mackinaw City and St. Ignace, then walk back.


Madison, WI, September 4

Of all the activities through Labor Day weekend, this event is an ode to the holiday’s true meaning: to honor those who made sacrifices for worker protection and benefits. The Milwaukee Area Labor Council union members celebrate with a day of children’s entertainment, science and magic shows, and live music along the lakefront.

Related Articles
No items found.

Want to Stay In the Loop?

Stay up to date with the latest articles, news and all things boating with a FREE subscription to Marinalife Magazine!

Thanks for subscribing!
Oops! Something went wrong while submitting the form.
Marinalife articles