Have a great week, Ctown!

Charlestown, It’s Time to Get Spooky: Join our Halloween Decorating Contest & Give Back to Harvest on Vine!

Year after year, Charlestown just keeps upping the game when it comes to all things Halloween. Not only are there awesome annual, can’t-miss events and an epic evening of trick-or-treating, but people are also going all-out to decorate their buildings, stoops, and yards. Folks from all over the city are making their way over the bridge to take a stroll through these streets.

So, it’s time to up the game even more… with a decorating contest!

Here’s the deal:

• Sign up and pay the $20 entry fee. You get a small yard sign to display so people can vote, and the proceeds from your sign-up go towards supporting Harvest on Vine
• People will scan the QR code on your sign to view our Voting Form, and can vote for your address
• 1st, 2nd, and 3rd place winners get a Gift Card to Prima, Waverly, or Monument (your choice)!!!

Anyone can sign up – whether you have the time to create something out of a movie, or just have an array of pumpkins on your stoop and want to join in on the fun while supporting the community.

Tag us in your photos (@caughtincharlestown) so we can share your work with the community!

Outdoor Dining Season Extended in Boston Through November 15th

Good news if you’re not ready to say goodbye to patio season just yet! The City of Boston has extended its 2026 Outdoor Dining season through November 15th, giving restaurants a couple more weeks to keep the tables and chairs outside. Restaurants participating in the program can continue outdoor dining, weather permitting. The City reminds businesses not to use outdoor setups during inclement weather or when snow is on the ground.

The extension also applies to Boston’s Food Truck Program, allowing participating food trucks to continue operating at their approved locations through November 15th. So, grab that sweater and enjoy a few more meals and drinks outside before winter officially takes over!

An interactive map with restaurants with outdoor dining can be found here.

You can register for 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 10/31! 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

MYSTRYDE has announced Baby Friendly Classes

Because parents need to sweat, too! If you have a 4 month old or younger, you can bring them to a Parent + Baby Power Class. These classes will take place on Tuesdays at 11:15am with Becca, 10/13, 10/20, 10/27, and 11/3. Sign up now!

Or, you can take a free hour-long Stroller Walk on Thursday, 10/22 at 11:15am with Becca. It will start and end at MAC Charlestown!

Nightmare in the Navy Yard is back at The Anchor on 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