Cash prizes up to $500, incredible inflatable Festivus Village, Elfie Selfies supporting local food programs & more.  

Union Square Main Streets (USMS) and 30+ local businesses crank up the jolly for the 8th Annual Holiday Stroll featuring rad retail, unique eats, an incredible inflatable Festivus Village, the Keep Small Strong Challenge, and much more. This free and family-friendly celebration makes spirits bright on Saturday, December 10 from 12-6pm throughout Union Square.

30+ local businesses entice customers to keep small strong with festive fares. Be sure not to miss the African Twist Foodie Holiday Gift Basket at Adorn Me Africa; Christmas in July…in December at The Independent; Peruvian Algarrabina at Machu Picchu; Holiday Nova, a Somerville good time and holiday celebration, at Somernova; and Winter Fest, featuring vendors, live music, and ice sculpting at Boynton Yards, among many other holiday happenings. 

Three people who bundle up and come on down will win cash prizes of $100, $250 or $500. Winners will be announced on December 13.

“For an 8th year, Union Square’s specialty shops, award-winning eateries, and generous Stroll sponsors have come together to host this joyous and meaningful neighborhood holiday tradition.” said Jessica Eshleman, Executive Director of Union Square Main Streets who produces the Holiday Stroll. “Shopping local helps you find the perfect gifts and keeps the Square strong with more of your dollars staying in Somerville. Businesses are decking the halls, ready to welcome you and yours this Saturday for another uniquely-Union day of fun festivities.” 

People who Stroll will score multiple chances to win up to $500 when participating in these activities:

• Keep Small Strong Challenge: Stay loyal to local Union Square businesses by shopping, dining, or visiting them online. Save three of your receipts from purchases at Union Square businesses then email a photo to Stroll@unionsquaremain.org. **Shopping in person or online allowed. Multiple entries encouraged for repeat visits and purchases.**

• Visit incredible inflatables at the Festivus Village: Snap an Elfie-Selfie, post and tag @unionsquarems & @somernova on social media for a chance to win one of three prizes up to $500. For every tagged post, SOMERNOVA will donate $25 to the Union Square SNAP match, supplementing the food budget of needy families. Thanks to SOMERNOVA, the chance to win and the chance to give to fight food insecurity is just a selfie away.  

“We’d like to thank Union Square Main Streets for the tireless work they do every day to support Union Square’s small and independently owned businesses,” said Collin Yip, Managing Partner, Rafi Properties (owner of SOMERNOVA). “These local entrepreneurs are the heart and soul of community. This holiday season, we are especially grateful to bring together old friends and new, to celebrate the people that define this dynamic neighborhood.’

The 8th Annual Holiday Stroll is presented by Union Square Main Streets, Inc. and made possible by generous support from SOMERNOVA, Boynton—Yards, a DLJ + Leggat McCall Project, Sira Naturals, Rockland Trust, USQ, Kristin Chalmers Photography, Tiny Turns Paperie, and Thalia Tringo & Associates Real Estate.