Guide to Halloween in the Neighborhood 2026

Spooky Season in Eastie is here!! Here is a roundup of all the Halloween Happenings in the neighborhood! This list will be updated, so check back!
Fall-o-Ween Children’s Festival
Mayor Michelle Wu and the Boston Parks and Recreation Department will host the fourth annual Fall-o-Ween Children’s Festival on the Boston Common Parade Ground at the corner of Beacon and Charles Streets on Thursday, October 22, from 5 p.m. to 8 p.m. Get all the details here!
The Tall Ship Boo Bash
The Tall Ship in East Boston is hosting its 5th Annual Boo Bash on Sunday, October 25th, from 12–4pm. Bring the whole family for an afternoon of pony rides, inflatables, a petting zoo, face painting, games, and plenty of Halloween fun. Food and drink specials will also be available. The event is free and open to the public, even if advance RSVPs are sold out. Weather permitting. Get all the details here.
Halloween Parade on the Greenway
Celebrate Halloween with a Parade of Wheels on the Mary Ellen Welch Greenway on Saturday, October 31st, from 10am–12pm. The festivities kick off at the East Boston Branch Library at 365 Bremen Street. Decorate your bikes, scooters, strollers, or wheelchairs and join the parade in costume. Enjoy pumpkin decorating, treats, and free giveaways from Tadpole Shop. A fun way to celebrate Halloween with the whole family. Learn more from the Mary Ellen Welch Greenway.
Tombstone Tour at Bennington Street Cemetery
Take a walk through Eastie’s past with the East Boston Historical Society’s 5th Annual Tombstone Tour on Saturday, October 24th. The historic Bennington Street Cemetery, normally closed to the public, will open its gates from 1–5pm for this special event. Guided tours will take place at 2pm and 4pm, offering a chance to explore the cemetery and learn about East Boston’s history. A unique way to celebrate spooky season.
Pocket’s Billiard Club Halloween Party
Show off your costume at Pockets Billiard Club Halloween Party on Saturday, October 31st at 7pm. There will be drinks, food, fun, pool and specialty shots. Pockets is also hosting spooky movie nights every Wednesday in October at 7pm.
Haunted Greenhouse at Eastie Farm
Get ready for some spooky family fun! Eastie Farm is hosting a free Haunted Greenhouse event on Saturday, October 24th, from 6–8pm at 6 Chelsea Terrace in East Boston! Enjoy pumpkin painting, a movie, snacks, prizes, and plenty of Halloween fun for all ages! Get the details here!
Children’s Magical Halloween Castle Walk
It’s Back! Have a hiatus, the Children’s Halloween Castle Walk will take place on Saturday, October 24th and Sunday, October 25th from 12noon-4pm at Fort Independence at Castle Island. FREE ADMISSION. Storyteller. Costumes encouraged. All children must be accompanied by an adult.
Park City Pumpkinfest
Get the costumes ready! Park City Southie is hosting its annual Pumpkinfest on Sunday, October 25th from 1–4pm with pumpkin decorating, face painting, fall treats, live music, games, and plenty of family-friendly fun. There will also be a costume parade, so costumes are definitely encouraged! Get the details and tickets here.
Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Co-host of Caught Up, storyteller, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.


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