Happy Halloween Weekend, Ctown!

Crate Escape’s Howl-O-Ween Extravaganza

Here’s another opportunity for you and the pups! Join Crate Escape on Friday, October 30th from 5-6:30pm for their Howl-o-ween extravaganza at the lawn behind Harborview in the Navy Yard (250 1st Ave in Charlestown). There will be drinks and desserts for two-legged friends and a costume contest, cookies, and prizes for four-legged friends!

Halloween Social Night at PickleBOS

On Halloween night, Saturday, October 31st from 5-8pm, PickleBOS will host a Halloween Social Night! Your admission gets you one free drink ticket, access to 3 hours of social skill based open play, and our private event and lounge space for relaxing between games. Make sure to bring your best costume since they will be doing a “Best Costume Contest” throughout the night!

Th’ll have courts available for all skill levels from beginner through to 4.5+ DUPR. Something for everyone! The bar will be open all night to keep the fun going.

🏓 3 hours of social open play for all levels
🍻 One drink ticket included
🏆 Best Costume Contest

Kids eat FREE at Pier 6 on Saturday!

All treats, no tricks! This Saturday, October 31st, your little monsters eat FREE at Pier 6 with the purchase of an entrée! Come hungry, wear your costume, and let them treat the kiddos to something delicious. This offer is valid all day long, doors open at 11am!

Fright House Fitness x Battista Boo-Camp, with 100% of proceeds going to the Charlestown Boys and Girls Club

Join Flight House Fitness and Battista Boot Camp on Halloween (Saturday, October 31st)! Sign up for classes at either 8am or 9:30am, and 100% of proceeds benefit the Boys & Girls Club of Charlestown. There will also be Recovery, Vendors & a DJ! Registration is now live.

8 AM + 9:30 AM — Full Body Strength with the Flight House & Battista Bootcamp Teams

8 AM + 9:30 AM – Studio Classes

FREE for members | $25 for non-members

Monument will host a Grave Rave on Sunday

Who says the halloween party has to end in October? You’re invited to a neon-themed monster mash on Sunday, November 1st at Monument! Spooky tunes will be brought to you by @patdowlingmusic starting at 7pm. Neon costumes encouraged! No neon? no problem! They’ve got you covered 😉

Take a Spooky Stroll Through Charlestown and Vote for Your Favorite Halloween Decorations

Charlestown knows how to do Halloween, and this year, neighbors are taking their decorations to the next level. This weekend, take a stroll through the neighborhood and check out the decorated homes, stoops, and yards participating in the Caught in Charlestown Halloween Decorating Contest.

From spooky skeletons and glowing pumpkins to over-the-top displays, there’s plenty to see. And the best part? You get to vote for your favorites. – VOTE HERE! Participating homes will have a special yard sign with a QR code. Simply scan the code to cast your vote for the best-decorated house. First-, second-, and third-place winners will receive gift cards to local favorites Prima, Waverly, or Monument.

The decorating contest also supports Harvest on Vine, a local organization helping Charlestown families in need. Proceeds from the $20 homeowner registration fee benefit the organization. So get outside this weekend, enjoy the decorations, and show your neighbors some Halloween love.

FREE Family Hour at PickleBOS every Sunday!

Every Sunday from 4-5pm at PickleBOS Charlestown, they do a relaxed, family-friendly open play hour where parents and kids can rally, laugh and enjoy Pickleball side-by-side. Paddles and balls are provided, juice and snacks for the kids, plus the bar is open and the NFL games are on. What is normally $30 for an hour with the family, is free!

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

Check out 4 Cook Street, Unit 1, a charming and thoughtfully designed 2-bedroom, 1.5-bath condo in the heart of Ctown

Warm and welcoming, this home offers an efficient layout with two generously sized bedrooms, a beautifully renovated full bath (2023, refreshed in 2026), central air, in-unit laundry, and excellent storage throughout.The private-use patio provides a wonderful outdoor retreat—perfect for morning coffee, summer dinners, grilling, or gathering with friends. Here are the open house times this weekend:

Saturday, 10/31 from 10:30am-12:30pm
Sunday, 11/01 from 10:30am-12:30pm

You can get more information and photos of this property by visiting here!

Listed by Deacon Swift of Compass | (508) 404-6579 | [email protected]

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!