5 Unforgettable Ways to Celebrate Labor Day Weekend in Massachusetts

Labor Day weekend in Massachusetts is the ultimate bittersweet holiday. It’s our final bow to sun-soaked beach days, long patio nights, and classic New England summer traditions—but it’s also the gateway to cozy autumn vibes, crisp air, and early foliage.

If you’re looking to squeeze every last drop out of summer while welcoming the upcoming fall season, here are 5 of the best things to do across the Bay State this long weekend.

1. Catch the Final Summer Waves

Before packing away the swimsuit, head down to Cape Cod or the Islands for one last epic beach day. Hit Coastguard Beach in Eastham or Crane Beach in Ipswich for prime ocean views and crisp late-August surf. Pair your sunbathing with a stop at a local seafood shack for a final, authentic hot lobster roll.

2. Step back in time at King Richard’s Faire

Nothing says "transitioning to autumn" quite like Carver’s legendary Renaissance Faire. Opening right over Labor Day weekend, King Richard’s Faire offers giant turkey legs, medieval jousting, and handcrafted goods nestled in an 80-acre pine forest. It’s an iconic New England late-summer tradition with big fall energy.

3. Stroll Open Newbury Street in Boston

If you prefer city views over forest walks, head into the hub for Open Newbury Street. Boston closes down the famous street to vehicular traffic, turning it into a pedestrian-only paradise of patio dining, outdoor shopping, and street performers. Grab an iced latte, shop end-of-summer sales, and soak in the urban sunshine.

4. Road Trip to an Agricultural Fair

Nothing bridges summer and fall better than a historic New England country fair. Head out to Western Mass for the historic Three County Fair in Northampton—the oldest operating fair in the country—or check out the Spencer Fair. Expect carnival rides, livestock exhibits, local food vendors, and demolition derbies.

5. Start Early Apple Picking in the Berkshires or Central Mass

While peak foliage is still a few weeks away, early-season apple varieties like Paula Red and Ginger Gold are ready to harvest! Orchards across Central and Western Mass open their doors over Labor Day weekend. Grab your first batch of cider donuts of the season and toast to the coming autumn. Mmmmm!

How are you spending your long weekend?