Weekend Picks – October 23rd

4.3 min readBy Published On: October 23rd, 2026Categories: See & Do, See & Do0 Comments on Weekend Picks – October 23rd

Have a great weekend, Ctown!

Bring your dog to Howl-O-Ween on Saturday

Calling all Ctown dogs! The annual Howl-O-Ween event is this Saturday, October 24th from 11am-1pm

Join Charlestown Dogs on Saturday, October 24th, 11am at the training field. Bring family, friends and neighbors for a morning of fun! There will be prizes for best costumes in these 3 categories: single dog, dog + human, and dog + 2 or more humans. Rain date is Sunday, October 25th.

And bring the kids to Halloween in the Gardens on Sunday!

This Sunday, October 25th from 10:30am-1pm, join Gardens for Charlestown for some spooky fun: arts & crafts, face painting, balloon twisters, pony rides (10:30-12:30), and games with Knucklebones. Costumes are encouraged for guests of all ages!

Admission is $10 per child. Pony rides, face painting, hot dogs and drinks are available for purchase at additional cost.

Tickets will be available to purchase at the Gardens the day of the event, or buy them now, here, at a discount. Save 20% if you buy a $20 ticket today, which includes admission for one child + a pony ride, face painting, a hot dog, and drink.

All proceeds benefit Gardens for Charlestown, a local 501(c)(3) corporation dedicated to greenspace preservation, community gathering, and education.

Nightmare in the Navy Yard is back at The Anchor this Saturday!

This Saturday, October 24th, head to The Anchor between 6pm and 11pm for their annual Halloween Party! You can expect live fire performers, cirque acts, haunted attractions, a scary movie lounge, live DJ, costume contests, and so much more! General admission is free, but you can purchase a VIP group experiences:

Here for the Boos – Group VIP Experience

$325 per group | Up to 4 guests

Gather your favorite ghouls for a fiery night on the waterfront.

  • Reserved VIP lounge or preferred table seating with viewing of the fire performances and cirque acts
  • (4) Signature Cocktails
  • Dedicated VIP server
  • $40 food & beverage credit
  • Fall dessert platter featuring cider donuts and seasonal sweets
  • Group photo at a Halloween backdrop
  • Priority access to the Scary Movie Lounge
  • Anchor fleece blankets + hand warmers for each guest
  • Trick-or-treat bags filled with sweet + spooky surprises
  • Entry into the group costume contest

Love at First Bite – Date Night Package

$95 per couple

A little heat, a little fright, and a Halloween night on the Boston waterfront made for two.

  • Guaranteed VIP reserved seating for two with preferred viewing of the fire performances and cirque acts
  • Anchor fleece blankets + hand warmers to stay cozy
  • One seasonal cocktail per person, with mocktail options available
  • Fall dessert plate to share
  • Pumpkin centerpiece with paint supplies—decorate it together and take it home!
  • Couple’s photo at a Halloween backdrop
  • Reserved seating for the Scary Movie Lounge
  • Trick-or-treat bags filled with sweet + spooky surprises
  • Entry into the couples’ costume contest

Charlestown now has an official Running Club – and the kickoff is this Sunday

Charlestown Running Club, the Town’s first official run club, is here! And they’re teaming up with @flighthousefitness for their first group run this Sunday, October 25th! RSVP now so they can get a headcount and plan accordingly.

📅 Sunday, October 25th | 8:00 AM
📍 Flight House – 465 Medford Street, Charlestown
🏃 5 Miles – 2.5 miles out to the Navy Yard and back
☕ Post-run coffee & food from Waverly!

You can VOTE early in Charlestown this weekend!

Election Day is Tuesday, November 3rd, but why wait? Early voting in Boston kicks off on Saturday, October 17th, and runs through Friday, October 30th. Registered Boston voters can cast their ballots at any early voting location in the city, regardless of where they live. No excuse or special reason is needed!

Where to Vote Early in Charlestown:

Harvard/Kent Elementary School
50 Bunker Hill Street, Charlestown

  • Saturday, October 24th: 11am–7pm
  • Sunday, October 25th: 11am–7pm

Who/What Are We Voting For?

This year’s general election includes some important races! Voters will be choosing Massachusetts’ governor and lieutenant governor, a U.S. senator, members of Congress, state lawmakers, and other statewide officials. There are also nine ballot questions for voters to consider. Here is our breakdown on WHAT TO KNOW before you vote!!

Want to see exactly who’s on your ballot? Visit the Massachusetts Secretary of State’s voter information website to look up your ballot based on your address.

Important Dates to Remember

  • October 17th: Early voting begins
  • October 24th: Deadline to register to vote
  • October 27th: Deadline to apply for a mail-in ballot (5pm)
  • October 30th: Early voting ends
  • November 3rd: Election Day! Polls are open 7am–8pm.

Try Prima’s October ‘Cocktail for a Cause’, which supports Breast Cancer Patients

Prima has announced their October ‘Cocktail for a Cause’ which supports the Ellie Fund. They provides essential, free support services that ease the daily burdens that breast cancer patients face. Here’s the drink:

Pink Ribbon Sour

  • Tequila
  • Sarti Rossa
  • Vanilla
  • Lime
  • Egg white

SPORTS!

Bruins vs. Sharks – Saturday, October 24th at 7pm.

Celtics vs. Knicks – Friday, October 23rd at 7pm.

MLB Playoff Schedule

Here are 9 places to watch the game in the neighborhood!

Check back as this list may be updated. Thank you to our Caught in Charlestown readers and Neighborhood Partners for supporting our local journalism efforts!

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