Weekend Picks – December 6th

This weekend is filled with festive holiday events in the neighborhood! Check them out below, and tag us in your content using #CaughtInCharlestown on Instagram!
HO HO HO Boat Hop
Thursday, December 5th – Sunday, December 29th | Pier 6, ReelHouse East Boston, and ReelHouse Oyster Bar
Starting today, you can take part in a holiday boat hop! Hop aboard the heated, holiday-decked shuttle boat to Pier 6, ReelHouse East Boston, and ReelHouse Oyster Bar. Each restaurant is decorated and ready for you to enjoy!
Hood Park’s Winter Fest
Friday, December 6th – 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!
SPORTS!
Patriots – BYE Week
Bruins vs. Flyers – Saturday December 7th at 1pm.
Celtics vs. Bucks – Friday December 6th at 7:30pm.
Celtics vs. Grizzlies –Saturday December 7th at 8pm.
Here are 8 Places to Watch the Game in the Neighborhood!
Check back as this list may be updated!

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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