Labor Day weekend is here, offering one last chance to soak up summer before school-year routines, earlier sunsets and pumpkin-spice-everything officially take over.
Whether you want to stay close to home or turn the three-day weekend into a New England day trip, there is plenty happening from Friday, September 4 through Monday, September 7, 2026. We gathered some of the most promising festivals, fairs, waterfront celebrations and scenic escapes across Massachusetts—plus a bonus trip over the Maine border.
Feast of the Three Saints
📍 Lawrence
📅 September 4–6
The 103rd Feast of the Three Saints is a Labor Day weekend tradition in Lawrence dating back more than a century.
The celebration honors Saints Alfio, Filadelfo and Cirino while showcasing the area’s Italian-American heritage. Expect processions, live music, entertainment and, perhaps most importantly, plenty of Italian food.
This is a great choice when you want the atmosphere of a big festival without committing to a full-day road trip.
Gloucester Schooner Festival
📍 Gloucester
📅 September 3–6
Cape Ann provides one of the most scenic send-offs to summer during the 42nd Annual Gloucester Schooner Festival.
Gloucester Harbor will fill with historic schooners for several days of sailing, deck tours and waterfront activities. Saturday’s Maritime Heritage Day includes exhibits, demonstrations, food, music and family activities. On Sunday, the Parade of Sail and Mayor’s Cup races provide spectacular views from locations such as Stacey Boulevard and Stage Fort Park.
Public sails may also be available, but advance reservations are a good idea. Even if you prefer to stay on dry land, watching these beautiful ships move through the harbor is worth the trip.
First Fridays at the New Bedford Whaling Museum
📍 New Bedford
📅 Friday, September 4
🕔 Doors open at 5:00 p.m.; music begins at 6:00 p.m.
Kick off the weekend with First Fridays: Brass, Sass and Serious Fun at the New Bedford Whaling Museum.
Guests can explore the museum’s galleries before The Catnip Junkies take over the Harbor View Gallery with lively New Orleans-inspired music, playful pop covers and traditional jazz. A cash bar and complimentary light bites will also be available.
Tickets are $25 for the public and $12.50 for museum members. Afterward, take a walk through the historic waterfront district or stop for dinner downtown.
Spencer Fair
📍 Spencer
📅 September 4–7
The Spencer Fair delivers the full country-fair experience with agricultural exhibits, live animals, carnival rides, tractor and truck pulls, live music, a demolition derby and plenty of fair food.
General admission is $18, with discounted admission available for children, seniors and military members. Children under age seven are admitted free, and parking is free throughout the weekend.
This is an easy pick for families—or anyone who considers fried dough a perfectly reasonable Labor Day meal.
Appleseed Country Fair
📍 Red Apple Farm in Phillipston
📅 September 5–7, from 10:00 a.m. to 6:00 p.m.
If you are ready for just a hint of fall, head to the Appleseed Country Fair at Red Apple Farm.
The weekend includes pick-your-own apples, blueberries, sunflowers and pumpkins, along with hayrides, food trucks, vendors, face painting, live music and sheepdog-herding demonstrations. Adults can also visit the Brew Barn and Cidery, while the ice cream window offers an attraction everyone can agree on.
Admission is $15 per carload, with proceeds benefiting the Athol and Phillipston Fire Association.
Labor Day Weekend Lawn Party
📍 Wachusett Mountain in Princeton
📅 September 4–7
Head to Wachusett Mountain for a free Labor Day Weekend Lawn Party featuring live music, lawn games, food, drinks and outdoor activities.
The party runs from 3:00 to 7:00 p.m. Friday and from 11:00 a.m. to 5:00 p.m. Saturday through Monday. Children can enjoy a free bounce house from noon to 3:00 p.m., and leashed dogs are welcome on the lawn.
For an additional charge, take the Skyride to the summit for a 360-degree view of the surrounding landscape. It is a fun choice for anyone who wants mountain scenery without the actual mountain climbing.
Step Back in Time at Minute Man National Historical Park
📍 Lincoln
📅 Saturday and Sunday
🕚 Programs at 11:00 a.m. and 2:00 p.m.
For a free outing with a little history mixed in, visit Hartwell Tavern at Minute Man National Historical Park.
During The Minute Men: Neighbors in Arms, a park ranger explains what it meant to serve as a minute man in 1775, how these volunteers trained and what motivated them to be ready at a moment’s notice. The approximately 30-minute program may include a musket-firing demonstration.
Pair the program with a walk along the park’s Battle Road Trail for an easy, educational day outdoors.
King Richard’s Faire
📍 Carver
📅 September 5–7, from 10:30 a.m. to 6:00 p.m.
Labor Day weekend marks the opening of the 45th season of King Richard’s Faire.
Travel back to a 16th-century village filled with knights, royalty, artisans, musicians, food and entertainment across 11 stages. The day includes three jousts and more than 100 artisans, so there is enough happening to keep the entire family entertained.
The Faire is held rain or shine. Costumes are optional—but if you have been waiting for an appropriate occasion to wear a cape, your moment has arrived.
Take a Cape Cod Day Trip
📍 South Yarmouth
📅 Labor Day weekend
The 11th Annual Labor Day Weekend Craft Festival in South Yarmouth features more than 75 juried artisans offering American-made art, jewelry, photography, home décor, specialty foods and gifts.
Admission is free, making it easy to combine the festival with a beach walk, seafood lunch or drive along historic Route 6A.
Leave early and allow extra travel time. The Cape has never been known for keeping its Labor Day weekend popularity a secret.
Cross the State Line for Ogunquit, Maine
📍 Ogunquit and Perkins Cove
Looking for a day trip without traveling too far into Maine? Walk the Marginal Way, a 1.25-mile paved coastal path connecting Shore Road with Perkins Cove.
Along the route, you will find rocky coves, ocean views and 39 benches where you can stop and enjoy the scenery. Once you reach Perkins Cove, browse the shops, watch the lobster boats or grab lunch by the water.
Parking can fill quickly on a holiday weekend, so an early start is your friend.
A Few Tips Before You Hit the Road
A little planning can help keep the weekend memorable for the right reasons:
- Check your tires, fuel or battery charge before a longer drive.
- Keep your current vehicle registration and insurance information with you.
- Confirm that roadside assistance is included in your policy or available through another service.
- Secure your home, lock windows and avoid posting that it is empty in real time.
- If you are towing a boat, camper or trailer, make sure your equipment and insurance coverage are appropriate before leaving.
- Never leave valuables visible inside a parked vehicle.
- Designate a sober driver whenever alcohol is part of the plan.
Coverage varies by policy, vehicle and situation. If you have questions about your auto, home, boat, RV or umbrella insurance, the team at Risman Insurance Agencies is happy to help.
Event details can change because of weather or other circumstances, so check the organizer’s website before heading out.
However you spend the weekend—at a festival, on the water, strolling along the coast or happily doing absolutely nothing—we hope you have a safe and enjoyable Labor Day!
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