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Labor Day Weekend 2025 in Boston: Festivals, Fairs and More Things To Do with Kids

Feel like royalty this Labor Day Weekend 2025 in Boston! Photo courtesy of King Richard's Faire

8/27/25 - By N Ferreira

Looking for the best things to do this Labor Day Weekend in Boston? Here are some family-friendly events and activities to add to your list for this weekend.

Summer is winding down, but Labor Day Weekend in Boston sends it off in style. Festivals across New England keep the fun going, from King Richard's Faire’s medieval adventures to the Gloucester Schooner Festival’s full-sail activities. The weekend ends with the inaugural Boston’s First Labor Day Parade, a historic march honoring the city’s labor legacy. With parades, fairs, and hands-on fun around every corner, there’s no shortage of ways to celebrate the end of summer with kids in Boston.

For more fall fun for Boston families, check out our guide to 15 fall day trips from Boston. Don't forget–it's also time to visit the best places to go apple picking near Boston. And be sure to explore our Fall Fun guide for more great ideas for activities!

More Things To Do in Boston this Week with Kids: