Happy Holidays, Charlestown! Here is your lineup of Holiday Happenings in and around the neighborhood!

Oyster Shell Ornament Making at Pier 6

Saturday, December 13th from 1 to 4 p.m.

Get Crafty by the Pier! Join Pier 6 on December 13th from 1-4pm for a festive Oyster Shell Ornament Making event! Create two unique DIY ornaments (all materials included), enjoy a complimentary freshly shucked oyster with your ticket, and sip on holiday-themed cocktails! Grab your ticket while you still can!!

Frozen Fire Festival

Friday, December 12th through Saturday, December 14th

You do not want to miss the hottest (and coolest) event of the season! The Anthem Group’s Frozen Fire Festival is coming to The Anchor … this weekend!! Friday, December 12th through Saturday, December 14th, celebrate winter with mesmerizing fire and ice installations, live music, craft food and drinks, a holiday artisan market, curling, and captivating fire and cirque performances. The fire and cirque performers are coming from all over the world, bringing an unforgettable event to our own neighborhood. Along with in-house BBQ, get excited for the Donut Pub, Soup Shed, and a Smores and Hot Cocoa bar! Speaking of a bar – the festive libations are guaranteed to impress. From a Fire & Ice Sangria to the Jingle Spritz, a Snow Globe Mimosa, and staples like Warm Mulled Sangria and Spiked Eggnog, you’ll want to try them all! This is a free event, but you can secure guaranteed front row seats, reserve a heated igloo, or enhance your experience with one of the VIP packages (available daily!)

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! 

Mini Movers Holiday Classes

Monday, December 15th and 22nd from 4 to 5 p.m.

Each holiday class will transport kids into a winter wonderland! They will move, breathe, and CREATE! Each class includes a story, yoga, and art project to take home!

December 15: Gingerbread Registration
December 22: Polar Express Registration – come in pajamas if you wish!

Sign up at 2mindfulgirls.com

Annual Ugly Sweater Party at Monument

Thursday, December 18th starting at 7pm

It’s back! Unpack your ugliest holiday sweater for Thursday, December 18th as we host our 8th annual ugly sweater fundraiser for the Charlestown Boys and Girls Club featuring our top notch silent auction, tons of raffle prizes, awesome drink specials and a prize for ugliest sweater!

5th Annual Christmas Singalong

Friday, December 19th at 5pm

Join Essem Art Studio for their 5th Annual Christmas Singalong with Miss Sophia on Dec 19th at 5 PM. (Doors open at 4:50) It will take place at Christ Church Charlestown, who has generously offered their beautiful space again. The Charlestown Mothers Association also sponsors this even every year so the concert may remain free! It is family friendly and open to all ages, but all children must be accompanied and cared for to ensure the safety of all. There is limited stroller parking so please plan accordingly!

This year, you’ll be joined by the musical talents of Masataka Yamamoto on keys, Nic McGehee (drums), and Nat Mangrum (hand percussion) to bring you a festive singalong.

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.

Feast of the Seven Fishes is Back at Prima

December 23rd & 24th

Feast with Prima for Christmas! Join as they celebrate the holidays on December 23rd & 24th for a spin on the traditional Italian family style feast, Feast of the Seven Fishes. You’ll experience fresh and fun takes on traditional dishes with some of the best seafood New England has to offer. The Feast of Seven Fishes Menu is a Chef’s Tasting menu with 4 courses for $115 per person and an optional $50 wine pairing! This menu will be optional but the wholetable has to commit as it is served family style. Book your table now!

Santa Hangover Brunch at Blackmoor

Friday, December 26th starting at 10am

Save the date! After the presents are unwrapped and the fun winds down, join Blackmoor for a relaxing Santa Hangover Brunch on December 26th at 10 AM — delicious food, festive drinks, and the perfect way to recover from Christmas!

Pier 6’s New Years Eve Cocktail Party and Fireworks Show

Wednesday, December 31st from 8pm to 1am

Shuck yeah, it’s almost New Year’s! Join at Pier 6 for a waterfront NYE bash stacked with oysters, cocktails, music, and fireworks.

🦪 Raw Bar Display
🍤 Apps & Bar Bites
💥 Harbor Fireworks at Midnight
🍾 Champagne Toast
🎧 Top 40 All Night
📺 Live Ball Drop
🎉 Party Favors

Harbor views + champagne? That’s how you start 2026 right. Get your early bird ticket now!!

Something new comes our way: Boston Frostival, Reimagining Winter in the City

Meet Boston announced today the inaugural Boston Frostival – a dynamic lineup of winter events and activations that will commence in late November and run through February. This programming will completely transform and reimagine winter in Boston, taking the iconic seasonal experiences that the city is known for – holiday lights, ice skating, tree lightings, games at the Garden, live theater, and more – and couple them with first-time events. Read more about it, here!

Give Back To Charlestown Families This Holiday Season

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!