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!
The Tall Ship Boo Bash
It’s the Fourth Annual Tall Ship Boo Bash on Sunday, October 26th from 12-4 pm. Featuring:Pony Rides, Inflatables, Petting Zoo, Face Painting, Costumed Characters, Food Specials, Kids Games *Event is Weather-Dependent. * * It is suggested that kids bring a helmet if they would like to ride the ponies.
Greenway Halloween Bike Ride
On Saturday from 10-12 enjoy a morning of Halloween fun complete with a bike ride, costumes, pumpkin decorating, and more! Meet at the East Boston Library bring your bikes, scooters or wheelchairs – spooky bike decorations and free Bluebikes available!
Tombstone Tour of the Bennington Street Cemetery in East Boston
Looking to get into the spooky spirit as Halloween approaches? Are you searching for the chance to walk through an old cemetery on a crisp autumn afternoon? Want to learn about a historically authenticated ghost story? Join the East Boston Museum & Historical Society for our 4th annual Tombstone Tour of Bennington Street Cemetery! Our highly anticipated tour returns this year, with more options to explore than ever before, and new activities for kids! Gates will be open from 1-5pm on Saturday, October 25, 2025. Tours will run at 2pm and 4pm, lasting approximately one hour. Not interested in a group tour? Self-guided tour options allow visitors to explore at their own pace.
This year we will be offering new activities for kids of all ages: A crafts table, where kids can do some seasonal decorating, and a scavenger hunt of the cemetery, allowing kids to run around and explore in their own way!
This event is free, although donations to the Museum are always welcome. Light refreshments will be provided.
Creepy Crawlies with Animal World Experience at Eastie Library
It’s the season for things that creep and crawl. Matt from Animal World Experience will teach us about some not-too-scary live animals from around the world. Recommended for ages 4 and up. Takes place ,
Cunard Tavern
You’re invited… if you dare! 👻🍸 Join Cunard Tavern for a Halloween Party at the Tavern with a costume contest, bites, and specialty cocktails. See you Friday 10/31 at 10 PM. Don’t ghost them!
Pocket’s Billiard Club Halloween Party
Show off your costume at Pockets Billiard Club Halloween Party on Friday, October 31st at 7pm. There will be drinks, food, fun, pool and specialty shots. Pockets is also hosting spooky movie nights every Tuesday in Oct. at 8pm.
Pazza on Porter Kids Halloween Brunch
On Saturday, October 25th Pazza on Porter will host a spooktacular kids Halloween brunch from 12pm-2pm with Halloween-themed pancakes and a photo shoot for your little ghosts and goblins!
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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