Halloween is almost here, and towns throughout the Patriots’ Trail are getting ready with plenty of ways to celebrate. From downtown trick-or-treating and costume parades to trunk-or-treats, skating and community festivals, there are lots of opportunities to get into the Halloween spirit with the whole family.
Whether you’re looking for a favorite annual tradition or something new to try this year, here are some of the Halloween events happening across our local communities in 2026.
Acton – Spooktacular Halloween Party (Saturday, October 24th). The Acton-Boxborough Family Network (ABFN) is hosting its annual family Halloween celebration at Raymond J. Grey Junior High from 10am-12:30pm. Come dressed in your best family costume and enjoy a magician, costume contest and activities from local preschools and businesses. The first half hour is designed to be more sensory-friendly. The event is free for ABFN members and $15 per non-member family (advance registration required for non-members). Donations for the Acton-Boxborough Food Pantry are also encouraged.
Bedford – Annual Trunk or Treat (Friday, October 30th). Local businesses will be filling the Whole Foods parking lot with decorated trunks and treats from 3-5pm. This popular Bedford Chamber event is free for families.
Boxborough – Skating Spooktacular (Saturday, October 24th). Head to Nashoba Valley Olympia Rink for a Halloween evening on and off the ice. Free Trunk or Treating takes place in the back parking lot from 5-6pm, followed by Halloween ice skating from 6:15-7:15pm. Skating fees apply and skate rentals are available.
Burlington – Halloween Party at Wayside (Tuesday, October 27th). Wayside Shopping Center is hosting a free afternoon of family Halloween fun from 3-5pm, including live entertainment from Bubbles McGee, a Halloween photo BOOth, face painting, pumpkin crafts, treats and a DJ. Costumes are encouraged.
Carlisle – Halloween Spook Trail & Trunk or Treat (Saturday, October 31st). Bring the family to Center Park in Carlisle for an afternoon of Halloween fun, including the popular Spook Trail and Trunk or Treat. Costumes are encouraged, with plenty of tricks, treats and spooky fun along the way. Be sure to say hi to the Barrett Sotheby’s International Realty team while you’re there!
Concord – Annual Trunk or Treat (Sunday, October 25th). Join Concord Recreation and the Beede Swim & Fitness Center from 2-3pm for this free annual event. Families can make their way from trunk to trunk collecting treats while residents and local organizations show off their Halloween decorating skills.
Lexington – Downtown Trick or Treat (Friday, October 30th). Get your costume on and head to Lexington Center from 2-5pm, when participating local stores and businesses will be welcoming trick-or-treaters. Stop by Barrett Sotheby’s International Realty for a treat while you’re downtown!
Lincoln – Fall Fest and Trunk or Treat (Sunday, November 1st). Keep the Halloween fun going into November at Lincoln’s annual Fall Fest at Pierce Park from 12-3pm. Enjoy hayrides, carnival games, live music, food, pony rides and more, with Trunk or Treat taking place from 12-1pm in the Pierce House parking lot. Tickets are available in advance.
Littleton – Trunk or Treat and Halloween Parade (Saturday, October 24th). Head to Alumni Field for this free family event featuring a costume parade beginning at 6pm, followed by Trunk or Treating from approximately 6:15-8pm. No registration is required for trick-or-treaters.
Melrose – Trick or Treat on Main Street (Friday, October 30th). Downtown Melrose stores and other participating local businesses will welcome costumed trick-or-treaters from 3:30-5pm. It’s an easy way to enjoy Halloween while exploring local shops and businesses.
Stoneham – 16th Annual Halloween Stroll (Saturday, October 24th). Head to Stoneham Square from 1-3pm for an afternoon of Halloween fun. Hosted by the Stoneham Chamber of Commerce in partnership with Stoneham Recreation and Stoneham TV, the annual celebration includes trick-or-treating at local businesses (including the Barrett Sotheby’s International Realty office!), pumpkin carving, crafts, inflatables and other family activities.
Westford – Monster Mash on Main Street (Saturday, October 24th). Monster Mash returns to Main Street beginning at 1pm with food trucks and family festivities at Roudenbush Community Center. A costume parade begins at 2pm and heads to Town Hall for Trunk or Treat before returning to Roudenbush for Touch-a-Truck.
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Winchester – FAN and Win Rec's Halloween Bash (Saturday, October 24th). Join FAN and Winchester Recreation & Community Education for a morning of Halloween fun from 10am-12:30pm. Downtown Trick or Treat runs from 10-11:30am, while the Trunk or Treat at the Jenks Center parking lot runs from 10:30am-12:30pm with characters, crafts and more. The Trunk or Treat is free for FAN members and $10 per non-member family.
Woburn – Woburn Host Lions Halloween Parade (Sunday, October 25th). One of the area’s biggest Halloween traditions returns for its 72nd year. The parade steps off at 1pm and travels from the Showcase Cinema area along Main Street toward Horn Pond, with floats, marching bands and plenty of costumes along the route. This year’s theme celebrates America’s 250th Anniversary.
Halloween is always a fun time to get out and enjoy the communities we call home. These local traditions are just a few of the things that make fall such a special season throughout the Patriots’ Trail.
Looking for more ways to enjoy the area? Ask our agents. From local events and favorite restaurants to trails, shops and hidden gems, our team’s in-depth knowledge of the communities we serve goes well beyond real estate. We live and work throughout the towns north and west of Boston, and we’re always happy to share our local favorites.