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As summer inevitably slips away, don’t let it fall through the cracks like an expired policy—make this Labor Day Weekend in Massachusetts one to remember! From family-friendly fairs and fireworks to arts, crafts, and waterfront festivals, the Bay State has something for everyone.

Whether you’re looking for Labor Day events near Boston, things to do on Cape Cod Labor Day weekend, or family-friendly festivals in Massachusetts, here are some highlights:


🎶 Bread and Roses Heritage Festival – Lawrence

One of the top Labor Day festivals in Massachusetts, this free event celebrates labor history with live performances, food, cultural activities, and guided tours. Perfect for history buffs and families alike.


🎨 Labor Day Weekend Arts & Craft Festival – Yarmouth

Looking for things to do on Cape Cod Labor Day weekend? This popular Yarmouth festival features over 75 booths filled with local art, jewelry, home goods, and gourmet treats. A can’t-miss stop for shoppers and beachgoers.


🐄 Three County Fair – Northampton

The Three County Fair in Northampton is one of America’s oldest agricultural fairs. Enjoy livestock shows, rides, and classic fair food—an authentic New England Labor Day fair experience.


🎡 Spencer Fair – Spencer

The Spencer Fair has it all: midway rides, ox pulls, poultry shows, and outdoor entertainment. If you’re searching for a family Labor Day event in Central Massachusetts, this fair is a perfect pick.


Gloucester Schooner Festival – Gloucester

One of the most iconic Labor Day weekend events on the North Shore, the Gloucester Schooner Festival showcases majestic ships, parades, and waterfront activities. Ideal for anyone looking to combine history, sailing, and scenic views.


🎆 Boston Harbor Fireworks

Celebrate the holiday with Labor Day fireworks in Boston Harbor. Free music and a fireworks show light up the skyline—one of the most popular Labor Day activities in Boston.


🤍 Boston “White Party” Cruise – Boston

If nightlife is more your style, sail away on this all-white themed Labor Day cruise in Boston with DJs, cocktails, and stunning city views.


Risman Holiday Hours & Helpful Links

Our office will close Friday, August 29th at 2:30 p.m. and reopen on Tuesday, September 2nd at 8:30 a.m.

While we’re away, here are quick links to help you:


No matter where your Labor Day weekend adventures take you—Cape Cod, Boston, or beyond—rest easy knowing Risman Insurance has your coverage in place. While you enjoy fairs, fireworks, and festivals, we’ll be here to help protect what matters most.

From all of us at Risman Insurance Agencies—have a safe and happy Labor Day!