10(+) Things to Do Around Tewksbury, Labor Day Edition

Fill your Labor Day Weekend with fun and activities as summer draws to a close!

Labor Day weekend marks the unofficial end of summer—see it off in style. From parades to farm fun, there’s no shortage of ways to enjoy the long weekend. Whether you’re into history, music, food, or just good old-fashioned apple picking, here’s your guide to the best things to do this Labor Day weekend

41st Annual Bread and Roses Heritage Festival

Held each Labor Day Monday in Lawrence, this free, open-air festival honors labor history and the 1912 Bread and Roses strike with a full day of live music, dance, kids’ activities, theater, spoken word, food, walking tours, and social justice exhibits.

Marlborough Labor Day Festival & Parade

Marlborough’s festival kicks off this Sunday from 12 PM–5 PM on Main Street. Expect food trucks, live music, vendors, and kids’ activities—great for families. Their parade is held on Labor Day Monday, starting at 12 PM, featuring marching bands, floats, performers, and community groups.

King Richard’s Faire

Starting Labor Day weekend and running through Fall, this Renaissance faire brings medieval magic to life! Expect jousting, comedy acts, artisan vendors, and costumed merriment— convenient to Tewksbury and perfect for a whimsical weekend adventure.

Lexington Arts & Crafts Festival

On Labor Day Monday through September 3rd, shop unique, handcrafted goods and meet local artisans in charming Lexington. This festival showcases dozens of local photographers, painters, jewelry makers, and more.

Hopkinton State Fair

Rides, livestock shows, food, and fun—this classic fair has something for everyone. Running now through Labor Day, it’s a go-to destination for families seeking the full fair experience.

Institute of Contemporary Art (ICA) – Free Admission Labor Day Monday

Take in five cutting-edge exhibits at the ICA’s scenic waterfront location in the Seaport—for free! A fantastic option for art lovers and curious minds alike.

SoWa Open Market – Boston

This Sunday, SoWa’s vibrant open-air market features local artists, food trucks, live music, and vintage finds. A great way to take a final summer stroll in the city.

Local Vibes: Live Music at TJ Callahan’s Pub

Catch Ignition, a rock band from Billerica, live at TJ Callahan’s in Tewksbury, Saturday night. Keep the weekend energy going with a cold drink and some live tunes!

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Apple Picking & Farm Fun at These Local Orchards!

Labor Day weekend is the perfect time to usher in the fall season with a trip to one of Massachusetts’ charming orchards. Whether you’re looking to pick your own apples, enjoy live music, or simply soak in the festive farm atmosphere, there are plenty of great options to choose from.

Smolak Farms in North Andover is going all out this weekend with its End of Summer Luau. In addition to its popular pick-your-own apple offerings, the farm will feature live music, fresh cider donuts, seasonal drinks, and daily kids’ activities—including face painting, spin art frisbee, cow train rides, hayrides, and feeding the animals (note: the cow train is available on Saturday only). With a farm stand open daily from 7 AM–6 PM and concessions and bar service from 11 AM–3 PM, it’s a festive way to send off summer in luau style.

Parlee Farms will also be open for apple picking and hayrides throughout the weekend, offering fresh farm stand treats and a classic New England farm experience—perfect for families looking to enjoy a scenic and tasty outing on Labor Day.

Open all weekend, Shelburne Farm‘s fall experience offers not just apple and pumpkin picking, but also hayrides, cider donuts, farm animals, a kids’ playground, and a lively cider barn with live music and food trucks. It’s an ideal destination for families, couples, or anyone eager to get a jumpstart on fall festivities.

Wherever you go, be sure to bring your appetite—and maybe a few empty baskets!

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No matter your vibe—city lights, small-town charm, or farm-side fun—there’s something for everyone this Labor Day weekend. Get out, make memories, and celebrate the final days of summer in style!