‘Tis the season for Santa appearances and bar crawls across town. Charlestown’s unmatched charm and lively events make it worth staying home for the holidays. See all of this year’s events below, and be sure to check back as new events are added!
Polar Express Pajama Party by Mini Movers Studio
Sunday, November 24th | 3 p.m. – 5:30 p.m. at Mini Movers Studio, 14 Green St
Have your little one(s) kick off the holiday season with a PJ Party at Mini Movers Studio! Sign Up today!
✨Write Letters to Santa (and they’ll get a mailed response back!)
✨Fun Polar Express Themed Dance Class
✨Decorate a cookie
✨Enjoy Hot Chocolate and Popcorn as we watch the Polar Express!
Confetti the Yeti at Monument
Monday, November 25th | 4-6 p.m. at Monument
@theconfettiyeti will be popping up at @monumentcharlestown THIS Monday, November 25th, from 4–6 PM! Stop by for giveaways and grab your copy of The Confetti Yeti Celebrates #Christmas Kindness as we gear up for the holiday season!
If you’ve pre-ordered and selected local pick-up, this is your chance to grab your book! Shipped orders will be arriving next week, and they can’t wait to hear your feedback on the newest release.
Breakfast with Santa
Sunday, December 1st | 10:30am at Saint Francis de Sales Bishop Lawton Hall
Don’t miss your chance to take a photo with (and even get a gift from) Santa! Enjoy breakfast from Warren Tavern, sponsored by Bunker Hill Associates and the City of Boston.
*Gifts aged up to 10 years old
Hood Park’s Winter Village
Sunday, December 1st | 11 a.m. – 4 p.m. Hood Park
(Yes, this is different than Hood Park’s Winter Fest, which starts on December 5th) Hood Park‘s Winter Village is back! Free for all ages, and dogs are allowed! Enjoy a local artisan holiday market, curling, igloos, food and beverages, games, and activities! Don’t forget, you get 3 hours of free parking in Hood Park.
Wreath Workshop with Baby Boyle Bouquets
Thursday, December 5th | 6pm Bishop Lawton Hall
This year’s beloved Wreath Workshop with Baby Boyle Bouquets is fundraising for the 2025 Bunker Hill Day Parade, which will commemorate the 250th anniversary of the Battle of Bunker Hill. $50/ticket, Venmo: Kathleen-noonan-8
Hood Park’s Winter Fest
Thursday, December 5th – January 25th | Exact Days and Times Posted Here
Winter Fest, a large-scale immersive two-acre winter experience from the creative team behind Wicked Haunt Fest, is transforming Hood Park into a dazzling wonderland featuring a breathtaking festival of lights and a huge ice skating rink. Opening December 5th in Charlestown, guests can enjoy an Après Ski Veuve Clicquot Gondola Lounge, charming shopping vendors, festive food & beverage, a life-size ice castle adorned in twinkling lights, and ice skating. Check it out!
USS Constitution Tree Lighting
Friday, December 6th | 3 p.m. to 6 p.m. at the USS Constitution Museum
“Old Ironsides” and her crew invite the public to join for their annual tree-lighting ceremony! Tour the ship, snap a photo with Santa, and enjoy the festive Christmas lights aboard USS Constitution!
This free event will feature:
• Visits and photo opportunities with Santa
• Complimentary hot chocolate and cookies
• Holiday music
• Ship tours
• Remarks from the ship’s commanding officer
Guests can also witness the ship’s gun firing during evening colors, a ceremony marking the lowering of the American flag at sunset, scheduled for 4:11 p.m. The tree-lighting ceremony will begin at 4:30 p.m., with photos with Santa Claus available immediately afterward.
Warren Tavern’s Annual Toys for Tots Open House
Sunday, December 8th | 4 to 8 p.m. at Warren Tavern
Bring an unwrapped toy or gift card to Warren Tavern and enjoy complimentary hors d’oeuvres and lots of giveaways! You can also donate directly to the Kennedy Center’s website. Donate here, and be sure to designate your donation for the Toy Drive.
Enchanted Trolley Tour and Tree Lighting with Mayor Michelle Wu
Sunday, December 8th | 5 p.m. at Winthrop Square (the Training Field)
For the 28th year, the Mayor’s Enchanted Trolley Tour will continue the festive tradition of lighting holiday trees while bringing holiday spirit to children across Boston. The event is sponsored by Bank of America, and includes visits with Santa, tree lightings, and more.
Santa Hat Social: Charlestown Women’s Club Christmas Party
Sunday, December 8th | 4:30 to 7 p.m. at Bacco North End
The Charlestown Women’s Club is hosting their second annual Christmas party! Get ready to Sip & Sleigh (in Santa hats!). Only $20 a ticket and the money goes straight to Charlestown Community Cares, a nonprofit that provides holiday gifts for kids in the Bunker Hill Housing Development. Over 50% of their event attendees are first-timers, so don’t hesitate if you don’t know anyone!
Holiday Night Out
Wednesday, December 11th | 5pm Downtown
Join Charlestown’s local shops, restaurants, artisans, and organizations for a night of festive holiday revelry taking place all throughout the neighborhood. Come out to support our local small businesses and enjoy discounts, pop-up shopping, dining specials, and maybe even a visit from Santa himself! Make sure to follow us here on @visitcharlestown for all the details. We hope to see you there!
Monument’s Ugly Sweater Party
Thursday, December 12 | 7 – 10 p.m. at Monument
Charlestown Holiday Festival
Sunday, December 15th | 11 a.m. – 3 p.m. at the Training Field
Previously named the ‘Holiday Stroll’, the Holiday Festival is back, with your help! Consider donating to the fund that will keep this Charlestown tradition going. This festival brings local vendors together to provide a neighborhood shopping experience and celebration of the holidays.
YMCA’s Holiday Coat Drive
Now – Friday, December 20th | YMCA Charlestown
Feast of the Seven Fishes at Prima
Sunday, December 22nd and Tuesday, December 24th| Starting 4pm at Prima
The traditional Italian-American Christmas Eve meal known as the “Feast of the Seven Fishes,” which consists of a large spread of various seafood dishes, usually includes seven different types of fish, representing a rich and celebratory meal on the eve of Christmas. Make a reservation and celebrate with Prima!
New Years Eve Party at Urban Wild
Tuesday, December 31st | 8 p.m. to 1 a.m. at Urban Wild
Celebrate the start of 2025 at Urban Wild! Enjoy a live DJ, dancing, passed appetizers, a Champagne toast, party favors, ball drop on big screens, and the option to reserve VIP tables or bowling lanes. Early bird tickets are just $20, until November 30th!
Local Gift and Shopping Ideas
Shop Small for Black Friday and Small Business Saturday
Check out our roundup of sales in the neighborhood that you don’t want to miss!
You don’t need to hit the dreaded mall or hike over to downtown Boston to get your fix of holiday cheerful shopping. Junebug and Place & Gather have fully turned their stores over and are a magical wonderland of holiday gifts and decor!
Not-so-ugly Christmas Sweaters and Seasonal Fashion at Kaybea Collection
Head to Kaybea Collection and shop her amazing, curated holiday crewnecks and knit sweaters, along with amazing fashion and gifts!
Handmade Chocolate Advent Calendars at Anna’s Cafe
Go check out Anna’s Cafe for the cutest Boston-themed handmade chocolate advent calendars!
Abbey is the face behind Caught in Charlestown. In 2023 she migrated from Southie to Charlestown and brought the spirit of the ‘Caught In’ community with her. She is a new momma, creator, real estate agent, yogi, and so much more.
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