5 Things You Should Know This Week – December 1st

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Get your tickets to the Caught in Southie Festive Stoop Stroll
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!
The Annual Christmas Stroll in South Boston
The South Boston Chamber of Commerce and South Boston Neighborhood Development Corporation are excited to once again make the Broadway business district and surrounding areas a festive place for the community to shop and dine locally during the holiday season. The annual South Boston Christmas Stroll will take place on Thursday, Dec. 4, starting at 4 p.m., officially kicking off the “Shop, Dine, and Celebrate” campaign, a month of holiday activities that encourage everyone to support local businesses and restaurants throughout the season. Get all the details here including Santa!
Light Up Seaport
Friday, December 5th
Light Up Seaport is the perfect way to kick off the Holiday Season. The event will be held on Friday, December 5th, from 5-9pm. Now in its seventh year, the community event will feature a tree lighting, live entertainment, and can’t-miss offers and surprises from Seaport’s incredible mix of retailers and restaurants. You can get the full details here!
Enchanted Trolley Tour and Tree Lighting
Sunday, December 7th
Mayor’s Tree Lighting at Medal of Honor Park will take place on Sunday, December 7th at 2pm. Enjoy hot cocoa, face painting and more!
Massport Winter Festival
Celebrate the season, support local, and experience the magic! Join Massport for a joy-filled celebration at the new 10 World Trade (401 Congress Street) in the South Boston Waterfront on Saturday, December 6th from 12pm-5pm. All throughout the day, enjoy festive activities for all ages. Perfect for families, friends, and neighbors.
- FREE Photos with Santa
- FREE Holiday Movie Screening
- Gifts & Crafts from Local Vendors
- Seasonal Food & Drink Stalls
- Tree Lighting & Kid’s Brass Band to Close the Day!
Reserve your spot for this free event here!
Bonus: Pick up the First Ever Caught in Southie Holiday Zine
Be on the lookout for it in the neighborhood! It’s FREE!
With the holidays this year, we couldn’t think of a better way to celebrate than by creating something collectable…something delightfully nostalgic that bridges the past/present/future and shows our local love in the BIG way – our first-ever (very tiny) limited-edition Caught in Southie Holiday ZINE!
What the heck is a ZINE? It’s a real, offbeat printed piece of Southie that you can flip through, share, and cherish (we hope!) Plus, there are some “Golden Tickets” hidden inside some of them, where you can win a prize and old-fashioned coupons that you clip and use at local neighborhood spots!
So where can you find it? At these local small businesses in the neighborhood on Saturday, November 29th! While your there – show them some love, order a drink, pick up a gift card, do a little shopping!
Get one before they are gone! Make sure to tag us in your photos with them in the wild! One per customer, please!

Maureen Dahill is the founder of Caught in Media. Once a longtime wardrobe and prop stylist for brands such as Rue La La, TJ Max & Hasbro, she is a devoted lover of vintage clothing, Martini Mondays, Castle Island, AND a 4th generation South Boston native. Mother of three, married to Peter G.


Seaport Holiday Stroll is Saturday
5 Things You Should Know This Week – December 8th
Weekend Picks – December 5th