wkndFri Oct 16 2026, 7 to 8pm$25Gore PlaceGore Place offers a spooky evening tour of its 1806 Federal mansion in Waltham on Friday, October 16. Guides tell tales of lady pirates, escapees and drownings from the estate's history as visitors see the mansion in a new, slightly creepy light. The one-hour tour runs 7 to 8 PM. Tickets are $25, $20 for members and $15 for Card to Culture holders.
Fri Oct 16 2026, 4 to 8pmFreeFrog Pond on Boston CommonThe city's annual free Halloween party for kids at the Frog Pond on Boston Common. Come in costume for a haunted maze, trackless train rides, pumpkin bowling, crafts, field games, music, and treats.
Mon Oct 12 2026, 10am to 10pm$20TopsfieldAmerica's oldest continuously operating county fair, running since 1818. Eleven days of carnival rides, livestock and agricultural exhibits, the New England Giant Pumpkin Weigh-Off, pig races, lumberjack shows, a championship rodeo, grandstand concerts, and classic fair food.
Sun Oct 11 2026, 12 to 8pmFreeSomervilleThree days of free outdoor street music as 35 activist brass bands from across the country take over Davis Square and surrounding Somerville neighborhoods. Friday and Saturday bring street concerts and dancing; Sunday closes with a brass parade down Mass Avenue to Harvard Square, arriving in time for Oktoberfest.
Sun Oct 11 2026, 11am to 6pmFreeHarvard Square (Kiosk Main Stage)Free all-day street festival with world food stalls, artisan crafts, four beer gardens, chalk art, and 20-plus HONK! brass bands marching down Mass Ave. Includes the fifth annual Filipino American Festival.
Sun Oct 11 2026, 11am to 5pm$40HinghamThe South Shore Conservatory hosts its 12th annual rock festival honoring the late Dave Jodka, raising funds for the Dave Jodka Scholarship for Future Rockers. The one-day lineup includes Vundabar, the Aldous Collins Band, My Mom Is Here, Kate Loraine and the Mad Love student band, plus food trucks and a kids zone. Tickets $40 adults, $20 students, $10 kids, under 2 free. Rain or shine.
Sun Oct 11 2026, 11am to 5pmSoWa Power StationA weekend market of independent makers at the SoWa Power Station: handmade jewelry, home decor, art, fashion, and food from small businesses, with DIY stations, a free tote for early shoppers, and free entry for kids under 12.
Sun Oct 11 2026, 10am to 4pmMarket SquareDowntown Newburyport's annual fall celebration of arts and culture, presented by the Greater Newburyport Chamber of Commerce. Live local music, food and drinks from area vendors, and handcrafted goods from local artists and makers, plus scarecrows from local businesses around town.
Sat Oct 10 2026, 12pmFreeSamuel Adams Boston BrewerySam Adams teams up with Wellfleet Shellfish Company for a fall oyster celebration at the Jamaica Plain brewery. Pop-up raw bars in the beer garden, live music, and oyster-paired beer releases including the return of Oyster Stout. Entry is free; oysters sold separately.
Sat Oct 10 2026, 1 to 5pm$43.92Art Complex MuseumDuxbury Oyster Company and the Art Complex Museum host the 2026 Shuckfest, a one-day celebration of Duxbury oysters with raw bars, local chefs, craft beverages, live music and an art market. A kids corner runs all afternoon with free admission for children under 10. Tickets are $43.92 including fees. The event was moved from late September to October 10 because of the September nor'easter.
Sat Oct 10 2026, 10:30am to 12pmFreeDerby WharfAnnual parade of costumed pets along the Salem waterfront. Dogs, cats, lizards, bunnies, and more compete for prizes in creative categories while spectators cheer. Registration starts at 10:30 am; the parade steps off around 11:00 am.
Sun Oct 4 2026, 11am to 6pmFraminghamFramingham's lager brewery celebrates German beer culture with a fall Oktoberfest weekend on Clinton Street. The weekend opens with a free cask-tapping kickoff party on Friday night, followed by an open-air street festival Saturday and Sunday with polka bands, stein-hoisting contests, carnival games, German food and kid-friendly activities. Saturday and Sunday are ticketed (general admission about $13 to $18); the Friday kickoff is free.
Sun Oct 4 2026, 10am to 6pmFreeSalemWeekend street fair on historic Salem Common that kicks off October in the Witch City. More than 80 vendors sell handmade jewelry, art, apparel, crafts, and Halloween decor. Free to browse.
Sun Oct 4 2026, 12 to 5pmFreeScituateThe Town of Scituate's free waterfront festival honoring local fishermen, moved from September 27 to October 4 because of the nor'easter. The town pier fills with seafood vendors, live music, kids activities and marine exhibits. Free admission.
Sat Oct 3 2026, 12 to 6pmFreeQuincyThe city's ninth annual street festival takes over Coddington Street with more than 30 food and dessert trucks, live music on multiple stages, kids entertainment and axe throwing. Free admission.
Sat Oct 3 2026, 11am to 6pmFreeBostonA fall harvest festival built around bold, spicy flavors on City Hall Plaza. More than 30 food vendors, farmers, and hot sauce makers plus a chef demo stage, a hot sauce challenge, photo booth, and live entertainment. Free to attend; ticketed VIP tasting bar on site.
Sat Oct 3 2026, 12 to 4pmFreeBostonOne of the only apple festivals held in Boston proper, celebrating the Roxbury Russet apple that has grown in the neighborhood since the 1600s. Free cider pressing, farm animals, wool spinning, crafts, live music, and fall treats on the grounds of the historic Shirley-Eustis House.
Sat Oct 3 2026, 11am to 3pmFreeFraminghamThe city's second annual celebration of its people, cultures and businesses returns to Framingham Centre Common after drawing more than 5,000 attendees in 2025. Expect four hours of live multicultural entertainment, local food trucks, artisan and retail vendors, nonprofits, interactive art and a dedicated children's area with games and storytelling. Free admission. Rain date is Sunday, October 4, 1 to 5 PM.
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