Unwrap Union Square for the 1st Annual Union Square Jingle!
Shop, Sip, and Mingle
Sunday, December 7, 2025
1-6pm
Revel in this festive neighborhood tradition as you sip in cozy cafes and bustling bars, shop at your favorite stores, and mingle with your community in celebration of everything Union Square has to offer!
Follow us on Facebook & Instagram for the latest
on stuffing your stockings and finding your favorite things right here in Union Square.
Stroll the Square Challenge
Grab a Stroll the Square stamp card and collect stamps as you shop the Square during this year’s Holiday Stroll. Present your card to a participating Stroll business to receive a stamp!
Fill up your card with wintry stamps and email us a picture to enter to win cash prizes. Multiple entries encouraged.
Make merry with live performances
The Eight Tracks rove the Square for pop-up caroling performances between 1-3pm. Shop, sip, and sing along this season as you make your merry way around Union!
Storefront Decoration Contest
Scores of local businesses will deck their halls! The snazziest Square storefront will win a prize!
2025 Storefront Decoration Contestants
Visit local businesses to check out their festive holiday decorations!
Dearly Studio
1 Bow Market Way #18
El Potro Mexican Grill
61 Union Square
Green Tiger & Co.
1 Bow Market Way #37
Machu Chicken
25 Union Square
Machu Picchu
307 Somerville Ave
Parkour Generations Boston
15 Properzi Way
Tiny Turns Paperie
339 Somerville Ave
Take an Elfie Selfie on the Festivus Trail
Check out our online Festivus Trail map (updated map coming soon!) to discover delights throughout the Square. Take an Elfie Selfie, share on social media, tag @UnionSquareMS & hashtag #LoveUnionSquare to be entered to win a cash prize!
Rad Retail & Unique Eats
Stuff your stocking (and your belly!) with tasty treats!
2025 Offers & Activities
Dearly Studio
1 Bow Market Way #18
Ornament decorating station
El Potro Mexican Grill
61 Union Square
Special holiday cocktail
F45 Training Somerville
442 McGrath Hwy
Complimentary InBody Scan, goal consultation, and F45 Somerville t-shirt
Green Tiger & Co.
1 Bow Market Way #37
Sustainable holiday market with Upstairs at Bow featuring local and low waste vendors, communal DIY gift wrapping station, and raffle to benefit Groundwork Somerville
Machu Chicken
25 Union Square
Peruvian dish and dessert
Machu Picchu
307 Somerville Ave
Special Peruvian drink and cookie
Parkour Generations Boston
15 Properzi Way
Holiday Parkour Challenge & holiday gifts and gear @ the Dojo
Tiny Turns Paperie
339 Somerville Ave
Free festive gift with $5+ purchase
Union Square Main Streets
Online here
Get your USFM & Fluff Stuff! What the Fluff? tees & more!
The 10th Annual Holiday Stroll is presented by Union Square Main Streets, Inc. with generous help from
The Eight Tracks Thalia Tringo & Associates Real Estate Rockland Trust
Union Square Main Streets, Inc. reserves the right to use any photograph/video taken at the Union Square Holiday Stroll without the expressed written permission of those included within the photograph/video. Photographs/videos may be used in publications, brochures, postcards, posters, newspapers, social media, television, websites, etc. for the purposes of event promotion and/or portraying Union Square as a destination. To ensure the privacy of individuals and children, images will not be identified using names or personal identifying information without written approval from the photographed subject, parent, or legal guardian. By participating in the Union Square Holiday Stroll you are agreeing to release, defend, hold harmless and indemnify Union Square Main Streets, Inc. from any and all claims involving the use of your picture or likeness. Thank you for your understanding and cooperation!