Halloween Happenings in Dorchester 2026
Things are getting a little spooky around the neighborhood! Here’s a roundup of some festive and fun Halloween events. Check back, as this list will be updated!
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!
Magic Halloween Castle Island
The Castle Island Magical Castle – Halloween Celebration will take place on Saturday, October 24th and Sunday, October 25th from 12 noon- 4 p.m. at Fort Independence at Castle Island. FREE ADMISSION: No food or drink available. 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.
McGonagle’s Halloween Party
McGonagle’s is hosting a very spooky Halloween party on Friday, October 31st starting at 10pm with live music. No cover. Prizes for best costumes!
Halloween Fun at Boston Lights at Franklin Park Zoo
Get into the Halloween spirit at Boston Lights at Franklin Park Zoo! Stroll through dazzling lantern displays featuring glowing wildlife, colorful flowers, and larger-than-life creations inspired by nature. Keep an eye out for talking pumpkins and skeletons adding some spooky fun along the way! It’s a fun fall adventure for the whole family! Learn more and get tickets at Franklin Park Zoo.
Annual Pumpkin Parade Returns to Dorchester
Get the costumes and pumpkins ready! The Annual Pumpkin Parade returns to Pope John Paul II Park on Thursday, October 29th, from 5:30–7pm! Bring the whole family for a fun-filled evening of music, games, candy, and Halloween festivities! Don’t forget your decorated or carved pumpkins for a chance to win a special treat! This event is FREE! Get all the details here!
Halloween Bash at Landmark Public House
Get your costumes ready! Landmark Public House is hosting a Halloween Bash on Saturday, October 31st, featuring a costume contest, pizza bar, and DJ spinning tunes from 9pm–2am! Special guest Katie Nolan, the 2026 “Mayor of Dorchester,” will be hosting the festivities. Grab your friends and celebrate Halloween at 772 Adams Street!
Spooky Skate at Chez Vous
Lace up those skates and get ready for some Halloween fun! BCYF is hosting a Spooky Skate at Chez Vous Roller Skating Rink on Thursday, October 29th, from 5–8pm! Kids and teens ages 17 and under can enjoy a festive night on wheels! Registration is required. Get the details here!
Halloween Fun at BCYF Draper Pool
Make a splash this Halloween! BCYF Draper Pool is hosting a Spooky Swim on Saturday, October 31st, from 12–3pm! Girls ages 14 and under can enjoy swimming, sweets, and Halloween fun! A parent or guardian must accompany participants, and registration is required. Learn more here!
Bears, Brews & Boys at Dorchester Brewing
Get into the Halloween spirit at Dorchester Brewing Company on Sunday, October 25th, from 4–8pm! Enjoy a DJ spinning tunes upstairs, beer, special drinks, and plenty of festive fun at Bears, Brews & Boys, co-sponsored by Mass Bears and Cubs. Costumes are optional, but encouraged! Get all the details here!
Did we miss your Halloween celebration? Drop us an email at [email protected]
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.
