Weekend Picks – December 12th
Take a field trip! Caught in Southie Festive Stoop Stroll – Get your tickets today!
Caught in Southie is hosting the second Annual Caught in Southie Holiday Stoop Decorating Competition + Festive Stroll, and you’re invited to join the merriment on Saturday, December 13th at 4 pm! This one-of-a-kind event is your chance to explore the neighborhood, admire some seriously impressive holiday decor, and enjoy the warm hospitality of participating homes. Each stop will offer festive refreshments and entertainment to keep the holiday vibes strong. And all proceeds benefit the South Boston Neighborhood House! Plus, there will be a trolley to hop on and off! Get your tickets here!
Haul out the Holly!
Christmas is coming. It’s time to deck the halls! Here are some places to pick up trees, wreaths, and more!
Eastie Elves
It’s the 22nd Annual Eastie’s Elves celebration, taking place on Friday, December 12th at 5pm at the Hyatt Regency Boston Harbor! The evening will include a buffet-style meal, live performances from local children’s dance groups, and our annual raffle. Admission to the event consists of donating one unwrapped toy for a child in need. With your support and participation, we hope to continue our tradition of brightening the holidays for families. YOu can still participate in the toy drive through December 11th- stop by one of the partner locations to donate a toy to a family in need this holiday season!
Holiday Bazaar at the ICA Water Shed
Please join the Veronica Robles Cultural Center and the Chamber of Commerce for its free annual holiday bazaar featuring vendors for holiday gift giving, musical/cultural performances, food and beverages for purchase, and the opportunity to visit with Santa. Sponsorships, volunteer positions, donations, and table opportunities are still available. Takes place on Sunday, December 14, 2025, 1:00 to 5:00 pm at the ICA Watershed, 356 Marginal Street, East Boston.
Get in the holiday spirit on Moore Street
Remember things looking pretty spooky on Moore Street this past Halloween? Well, scary spiders and singing pumpkins have been replaced with Frosty the Snowman, Rudolph and the rest of the reindeer, the Polar Express and more! It’s like a mini-Christmas festival right in the heart of East Boston! Clearly, a man who loves the holidays and the neighborhood of East Boston! Sneak a peek here! The display is located on Moore Street near Saratoga!
Ruggiero’s Christmas Tree Lighting
Please join the Ruggiero Family Memorial Home for its annual tree lighting. On hand will be refreshments, festive music, and performances. Sunday, December 14, 2025, at 6 p.m.
Fire Festival at the Anchor in Charlestown
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!).
Breakfast at Mi Pueblito Orient Heights
Breakfast is the most important meal of the day! Get yourself some breakfast this weekend at Mi Pueblito – try one of their delicious omelets!
Taco Trail Time
This fall, Taste of Eastie is rolling out the brand-new East Boston Taco Trail—a cultural and culinary adventure that highlights the neighborhood’s incredible Mexican taquerías, Salvadoran kitchens, and Colombian grills. So, what’s the Taco Trail all about? Think of it as your “passport to flavor”—a guided way to explore Eastie’s authentic taquerías, hidden gems, and local spots serving up everything from street-style tacos to lively bar bites. It’s the perfect excuse to gather your friends and eat your way through the neighborhood. November 15th – February 28th You can learn more here!
New Dessert Alert at Reel House
Always save room for dessert at Reel House. A new dessert just launched – a delicious winter mousse! Give it a try this weekend – pairs perfectly with an espresso martini!
Boston Frostival
Boston Frostival – is a dynamic lineup of winter events and activations that 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! Get all the fun and “frosty” details here!
Comfort Food at Cunard Tavern
Chicken Pot Pie season is officially at Cunard Tavern 🙌 Flaky puff pastry, creamy filling, and all the comfort you need! Try it this weekend!
SPORTS!
Bruins vs. Wild – Sunday, December 14th at 6pm
Patriots vs. Bills – Sunday, December 14th at 1pm
Here are 7 Places to Watch in the Neighborhood!
Wondering what’s happening in our sister neighborhoods this weekend? Check out our weekend picks below:
Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Co-host of Caught Up, storyteller, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.
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