Need weekend plans? We’ve got you covered!

Ugly Sweater Run MYSTRYDE

Saturday December 20th at 9:30am

Join MYSTRYDE for a 2.5 or 4.5 mile casual run! Your $40 ticket includes brunch, first drink from Surfside, MYSTRYDE credit, and raffle entries. Show up on Saturday, December 20th to join!

Cookies with Santa at the Y

Sunday, December 21st from 12 to 2:30pm

Cookies, Santa, and holiday cheer! Bring the family and enjoy an afternoon of fun at the YMCA on Sunday, December 21st. Please email [email protected] to register. Check out the schedule, here!

Holiday Cookie Decorating Party at La Saison

Saturday, December 20th from 1:30 to 3pm

Kids decorate, parents caffeinate!! La Saison is hosting a Holiday Cookie Party on Saturday, December 20th for $30 per child … and free coffee for the parents! Sign up here.

Boston Winter Festival

December 6-7, 12-14, and 19-30 (closed December 24 & 25)

Boston’s most magical holiday tradition returns this December as Winter Fest 2025 transforms The Yard at Hood Park in Charlestown into an enchanting winter wonderland. Running on December 6-7, 12-14, and 19-30 (closed December 24 & 25), this year’s event has been completely revamped to deliver a new immersive, family-friendly experience. Produced by Giancarlo Natale, Founder of the Boston Pizza Festival and one of Boston’s most recognized event producers, Winter Fest 2025 introduces a refreshed layout, new attractions, with a focus on community, comfort, and fun. Guests can enjoy an immersive amusements, classic carousel, and carnival-style arcade games, combining the charm of a traditional fair with the magic of the holidays.  Get the details here! 

Menorah Lighting in the Seaport

On Sunday, December 21st at 4pm, join the Chabad of Downtown Boston at One Seaport in Seaport as they light up the 9-foot Menorah for Hanukkah.

Do some (local) holiday shopping!

You don’t have to leave Charlestown to check gifts off your holiday shopping list! Check out our roundup of Charlestown shops and gift ideas! Also, HandleBar just announced their gift card sale which you will not want to miss!

HB GIFT CARD SALE STARTS NOW!

Give love, get love from December 15th – Jan 1st

Every $50 you give, we’re sending $15 back your way!
✨ GIVE $50 → GET $15
✨ GIVE $100 → GET $30
✨ GIVE $250 → GET $75

How it works:
1️⃣ Purchase an E-gift card online or a physical gift card in-studio
2️⃣ Forward your receipt to [email protected]
3️⃣ We’ll add the HB rewards straight to your account

Dedicate time (or funds) to give back to the Ctown community

Charlestown has always taken care of its own, and there are plenty of ways—big and small—to make sure no one goes hungry or without gifts this holiday season. Whether you can donate canned goods or gifts, volunteer your time, or give a few dollars, your kindness will go a long way. Here’s your guide to giving locally!

SPORTS!

Bruins vs. Canucks – Saturday, December 20th at 7pm

Bruins vs. Senators – Sunday, December 21st at 7pm

Celtics vs. Heat – Friday, December 19th at 7pm

Celtics vs. Raptors – Saturday, December 20th at 7pm

Patriots vs. Ravens – Sunday, December 21st at 8:20pm

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