Fall events in Boston
Fall in Boston: festivals, fairs, Halloween events and harvest weekends across Greater Boston.
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Sunday, October 11
Mad Love Music Festival11am to 5pm$40One Conservatory Drive, Hingham, MA 02043The 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.
Friday, October 16
Head of the Charles Regatta 20268am to 4:30pm, day 1 of 3, Oct 16 to 18FreeCharles River, Boston and Cambridge, MAOne of the world's largest rowing regattas takes over the Charles River for three days. Crews from around the country race a three-mile course against the clock while spectators line the banks from Boston University to Cambridge. A riverside expo, food vendors, and fall foliage along the course make it a full autumn outing.
Fall-o-Ween Children's Festival 20264 to 8pmFreeCorner of Charles and Beacon Streets, Boston, MA 02108The 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.
Salem Night Faire 20265 to 10pm, day 1 of 2, Oct 16 to 17$2098 West Avenue, Salem, MA 01970A dark-arts night market among the pines of historic Pioneer Village, presented by The Black Veil. More than 50 artists and vendors sell clothing, jewelry, art, and oddities, alongside live performances, fireside ghost stories, a Biergarten, food trucks, and hot cider. Proceeds benefit Pioneer Village.
Things that Go Bump in the Night at Gore Place7 to 8pm$2552 Gore Street, Waltham, MA 02453Gore 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.
Saturday, October 17
Boston Book Festival 202610am to 6pmFreeCopley Square, Boston, MA 02116A free day celebrating books in Copley Square. More than 200 authors take part in panels and talks at venues around the square including the Boston Public Library, alongside a street fair with 60-plus exhibitors, a kids' zone, and a coffee tent. The day opens with a kids' costume parade.
Witch Hats on the Wharf11am to 12pmFree160 Derby Street, Salem, MA 01970A one-of-a-kind community gathering and world record attempt on Salem's historic waterfront for the city's 400th anniversary. Wear a witch hat and join hundreds of others for a drone photo. Special-edition Salem 400 hats will be sold by the city to benefit HAWC.
Rockport Harvest Fest 202611am to 5pmFreeHarvey Park, Rockport, MA 01966Seaside fall celebration in downtown Rockport hosted by the Greater Cape Ann Chamber of Commerce. An apple pie bake-off, live music, artisan vendors, a beer tent, kids' activities, face painting, a live animal exhibit, and a scarecrow photo booth, with free shuttle service from Blue Gate Meadow.
Maudslay is Haunted1:30 to 4pm, day 1 of 2, Oct 17 to 18$10Maudslay State Park, Newburyport, MA 01950Theater in the Open's annual haunting of Maudslay State Park. A woodland trail walk dotted with spooky-but-silly theatrical vignettes for all ages, more mischievous than scary. Admission $10, children under 4 free; $5 parking. Rain date Oct 24.
Sweater Weather Fest: Where Fall Meets Film2 to 11pmFree1 City Hall Square, Boston, MA 02201Boston's film industry opens up to the public on City Hall Plaza. The free all-ages day includes panels with working filmmakers, a vertical film contest, fall vendors, food, a beer garden, and a feature film projected onto City Hall after dark.
Thursday, October 22
Affordable Art Fair Boston 20265 to 9pm, day 1 of 2, Oct 22 to 23550 Harrison Ave, Boston, MA 02118Thousands of original contemporary artworks from dozens of galleries, all priced between $100 and $12,000. The second Boston edition opens with a ticketed first-look night, an art-after-dark Friday, and family programming on Sunday at the SoWa Power Station.
Boston Public Market Harvest Party 20265:30 to 7:30pm100 Hanover Street, Boston, MA 02108The Boston Public Market's annual fundraiser: an evening of unlimited tastings from market vendors, local beer, wine and spirits, live entertainment, and a silent auction. Proceeds support the market's nonprofit work with New England farmers and food producers.
Saturday, October 24
41st Annual Essex ClamFest and Arts & Crafts Festival11am to 4pmFree24 Martin Street, Essex, MA 01929Cape Ann's annual celebration of its clam-shucking heritage, free to the community at Shepard Memorial Park. Highlights include a clam chowder competition with local restaurants, live music, food trucks, a beer truck, a K-9 demonstration, face painting, and more than 40 craft and nonprofit vendors.
Doggone Halloween Pet Parade 202612 to 3pmFree9 Summer Street, Boston, MA 02110Boston's biggest Halloween dog costume parade in Downtown Crossing. Costumed pups compete for prizes across categories like best costume and best dog-and-human duo, with a photo booth, face painting, and free treats for all.
Saturday, October 31
Spooky Tales at Hale and Candlelight Tour of the Ancient Burial Ground8 to 10:30pm$1039 Hale Street, Beverly, MA 01915Halloween-night double feature from Historic Beverly. First, spooky storytelling inside the atmospheric Hale Farm, then a candlelit walking tour through Beverly's Ancient Burial Ground among weathered headstones and winding paths.
Saturday, November 7
New England Harvest Feast5:30 to 7pm, every Saturday137 Warren Avenue, Plymouth, MA 02360A dinner-theater evening at Plimoth Patuxet Museums built around historic New England foodways. Guests share a family-style meal of 17th-century dishes (roast turkey, stewed pumpkin, pork chine, ricotta cheesecake) while costumed performers bring the past to life with music and storytelling. Each feast ticket includes two days of admission to the museum's historic sites. Advance ticket purchase is required; tickets are non-refundable.
Friday, November 20
SoWa Christmas Market 20264 to 9pm, day 1 of 3, Nov 20 to 22$10550 Harrison Ave, Boston, MA 02118The 11th annual SoWa holiday market fills the Power Station with more than 100 makers, artists, designers, and specialty food vendors. Shop handmade gifts, sip winter cocktails, and catch live music including dueling pianos. Admission $10; kids 12 and under free.
Saturday, November 21
America's Hometown Thanksgiving Parade10am to 12pmFreeHistoric Plymouth Waterfront, Water Street, Plymouth, MA 02360America's Hometown Thanksgiving Celebration brings its annual parade back to the Plymouth waterfront for 2026, during the nation's 250th anniversary year. More than 100 entries, floats, marching bands and military units step off at 10 AM from Plymouth Rock and march through the waterfront to Court Street in historically chronological order. Free to watch along the route.
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