Spooky Street Block Party in Eastie
Halloween and the Harvest season are the perfect time to host a block party, creating a fun, traffic-free environment where kids and families can enjoy their community. Explore the City of Boston’s interactive map to discover events happening in Boston. Zoom in or use the search bar to find events in your neighborhood! You can check out the map here!
East Boston Spooky Street Block Party Address: Liverpool Street between Maverick Street & Decatur Street Time: October 25th from 5:00 PM to 8:00 PM
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.
Zero Waste Pop-Up
The next Zero Waste Pop-Up is this Saturday, October 25 at East Boston Memorial Park from 8:30am-12pm! All Boston residents are welcome. Bring your yard waste, e-waste, paint, motor oil, household chemicals, clothing, textiles, and paper for shredding. Questions about what you can drop off? Visit boston.gov/zero-waste-pop-drop
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!
New Cocktail List at Cunard Tavern
Sweater weather is better with your favorite cocktail in hand 🍂🥃🧡 Come taste Cunard Tavern’s fall drink menu this weekend!
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.
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!
SPORTS!
Patriots vs. Browns –Sunday, October 26th at 1pm.
Bruins vs. Avalanche – Saturday, October 25th at 3pm
Bruins vs. Mammoth– Sunday, October 19th at 7pm
Celtics vs. Knicks – Friday, October 24th at 7:30pm
Celtics vs. Pistons – Sunday, October 26th at 3:30pm
Here are 7 Places to Watch in the Neighborhood!
Check back as this list may be update!
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.



Weekend Picks – November 14th
5 Things You Should Know This Week – November 10th
Weekend Picks – November 7th