2.7 min readBy Published On: October 13th, 2025Categories: See & Do, See & Do0 Comments on Your 2025 Charlestown Halloween Roundup

There are so many awesome, local Halloween events in the next few weeks – so here’s your official neighborhood round up!! Keep checking back in as more events get added to the schedule.

YMCA’s Pumpkin Splash and Costume Party

Saturday, October 18th

Suit up in your best Halloween costume and join the Y for Halloween fun on Saturday, October 18th. There will be a family swim pumpkin splash 1:30p – 2:30p in the pool (Must register to receive a sugar pumpkin, while supplies last). Then you will move up to the gymnasium 2:30p – 4:30p for trick or treating, crafts and music. Email [email protected] to register today!

Halloween Music Bingo to benefit Bunker Hill Associates

Friday, October 24th

Tickets for Bunker Hill Associates‘ highly-anticipated Halloween Music Bingo event go on sale Monday, October 6th! The event will take place at Urban Wild on Friday, October 24th. Bunker Hill Associates was established in 1985 and is a community nonprofit from Charlestown, MA raising funds for youth programming and civic engagement. Stay tuned on their Instagram and website for a link to purchase tickets.

Halloween in the Gardens

Sunday, October 26th

Calling all ghosts, ghouls, and goblins (and fairies, firefighters, and farmers), Halloween in the Gardens is on October 26th from 10:30am to 1pm!! Enjoy games by Knucklebones, arts and crafts, balloon twisters, face painting, and pony rides. Just $10 for children to enter, and $20 for entry, pony ride, face painting, a hot dog + a drink! Advance tickets can be purchased on Gardens for Charlestown’s website.

Howl-o-ween Pup Pageant at The Anchor

Sunday, October 26th

Save the date for a spook-tacular fashion show on October 26th! Join Crate Escape and Charlestown Veterinary Hospital for the Howl-o-ween Pup Pageant at The Anchor from 12 to 3 p.m.

Dress your pup in their cutest, creepiest, or funniest costume for a chance to win prizes, enjoy pup cups, and have a fang-tastic time. Bring your boos, your ghouls, and most importantly… your pups!

Boo Bash at The Tall Ship in Eastie

Sunday, October 26th

Sneak over to East Boston for something spooktacular docking at The Tall Ship! Join for the 4th Annual Boo Bash on Sunday, October 26th from 12-4pm… a day of fun for friends and family of all ages!

Enjoy pony rides, inflatables, a petting zoo, face painting, costumed characters, food specials, kids games & more – all with those unbeatable harbor views. Admission is FREE.

Haunted Harbor Halloween Party

Thursday, October 30th

Mark your calendars, sailors…something spooky is surfacing at Pier 6. Thursday, October 30th from 7pm to 12am they will host a Haunted Harbor Halloween Party. Enjoy DJs, a costume contest, specialty cocktails, bites and all the eerie ocean energy you can handle.

Monument Monster Mash

Thursday, October 30th

The second annual Monument Monster Mash will be held at Monument on Thursday, October 30th! There will be drink specials, a costume contest, halloween treets, and spooky tunes. Best dressed award gets announced at 8pm!

Charlestown Dogs’ Annual Halloween Parade

Sunday, November 2nd

Head to the Training Field on Sunday, November 2nd from 11am to 1pm with your pups for Charlestown Dogs‘ annual Halloween Parade! Costumes are encourages, and there will be voting on best dressed! Check out last year’s winner, Ponti, for Best Solo Costume!

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