5 Things You Should Know This Week – May 18th
Welcome to the neighborhood, Dot Fun Day
A new summer tradition is coming to Dorchester! Dot Fun Day, a new open-air market, is set to debut on Sunday, May 24th, in the former Dorchester Tire space — and it sounds like there will be a little something for everyone. Organizers are planning a fun, community-focused setup featuring local food and shopping vendors, craft workshops, kid and pet zones, and, maybe, even a beer garden. The vision? Creating a space where neighbors can gather, hang out, and connect all summer long. The first market will kick off with a smaller group of vendors, with plans to reach full capacity as the season progresses. Dot Fun Day is expected to run every Sunday through October. Make sure to follow Dot Fun Day on Instagram for the latest!
It’s Officially Ice Cream Season at Landmark Ice Cream Bar
It’s officially ice cream season – who are we kidding, it’s always ice cream season – and Landmark PublicHouse ice cream bar in Adams Village is officially open! Enjoy scoops of your favorite flavor, sundaes, frappes, and Richie’s Italian slush. They’ve launched a new Instagram account for their ice cream bar here! Give them a follow for the latest scoop (get it?)!
Apply: MCCA Community Partnership Grants + Hospitality Scholarships Program
The Massachusetts Convention Center Authority invites eligible organizations and students to apply for the Community Partnership Grants and
Register to Participate in the Dot Day Road Race – June 7
Lace up your sneakers and participate in the 2026 Dot Day Road Race on Sunday, June 7! You can register here! The out-and-back course begins and ends at the ADSL building at 1565 Dorchester Avenue, running down Dot Avenue past Ashmont and turning around at St. Gregory Parish. Each registration includes a finisher medal and a t-shirt! Food will be available for purchase.
Now Open: The Chester Tavern
The Chester Tavern is officially open for business in Savin Hill. The new restaurant is located at 1121 Dot Ave. and features a menu of classic comfort favorites like fried pickles, nachos, sliders, steak frites, salads and bowls, pizza, and more! You can check out the full menu here! They are now open for business – Monday – Thursday at 4pm and at 11am Friday – Sunday. Make sure to follow The Chester on Instagram for the latest!
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.
