We reviewed 9,000+ Boston-area events and found 7 festivals & street fairs in the Boston area between October 27 and November 2. Last updated October 27, 2026.
Trunk or Treat in Chelsea Square offers trick-or-treating, entertainment, and activities with free candy, open to all ages.
Treats, crafts, and costumes at Connolly Branch precede a Centre Street parade ending at Mozart Park with games and additional treats for all ages.
Costume contest, arts & crafts, face painting, selfie center, games, raffles, and pizza for purchase fill the Salemwood School Fieldhouse.
Free games, music, crafts, and treats fill Mozart Park for the Hyde Square Task Force Halloween Fall Fiesta, all ages.
Park-9 Dog Bar hosts a Halloween party with duck bobbing, treat bar, basket decorating, movies, costume contests, DJ, tarot readings, specialty cocktails and spooky décor, all ages, free.
Waltham Common hosts Marketplace Day with music and vendors offering crafts, clothing, jewelry, food, home goods, beauty products, and more; Classic Groove and Gerry Beaudoin Trio perform.
Hayride, carnival games, Trunk or Treat, live music, food, beer, and pony rides fill Pierce Park’s Fall Fest; tickets $16, all ages.
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