Weekend Picks – May 28th

Free Watercolor Workshop
Enjoy a free, fun activity in a park near you! Join one of Boston Parks Dept. watercolor painting workshops, led by a local artist in various parks throughout the City of Boston! The Watercolor Painting Workshops enable artists of all skill levels to create their own inspired masterpieces. Tips and techniques are provided by an instructor. These workshops take place in May and June 2026. All classes are from 10:00am to 12:00pm at the designated location. One takes place on Saturday at LoPresti Park, 33 Sumner Street. Register Now.
Paddle all Summer
Piers Park Sailing has a new kayak pass that will have you paddling all summer long! Get moving on the ocean. You can learn more here!
Portraits of Us
On May 30, “Portraits of Us” will hold its capstone event, including performances of the fellows’ original songs. The event will be hosted at ZUMIX and emphasizes community participation, storytelling, and intergenerational collaboration. At 11 a.m., attendees will learn and participate in a community sing of original songs written by Ballesteros and Botticelli. Lunch provided, no prior musical experience required. Following at 1 p.m., there will be performances of the fellows’ portrait songs and by the ZUMIX Streetwise ensemble. This event is free to attend, but registration is required. Donations to the “Portraits of Us” workshop can be made via Venmo with the message “Portraits.” Proceeds will be distributed among the participating songwriters, youth included. Get all the details via our feature here.
Live Music + Cocktails at The Tall Ship
Enjoy cocktails and live music on Friday, Saturday and Sunday at the Tall Ship! You can check out the schedule of who’s playing. here!
Celebrate National Burger Day in the Neighborhood
It’s National Burger Day! Whether you like it with the works or just a little ketchup, today is your perfect excuse to eat one! We are sharing our picks for some of the best burgers in the neighborhood! Check out our roundup here.
Free Ferry to Georges Island
Looking for a free way to get out on Boston Harbor? Free Ferry Weekend returns Saturday, May 30 and Sunday, May 31, offering free round-trip ferry service from Boston to Georges Island. The annual event, presented by Boston Harbor Now in partnership with the Massachusetts Department of Conservation and Recreation, the National Park Service, and Boston Harbor City Cruises, gives families, residents, and visitors an easy way to experience one of Boston Harbor’s signature destinations without the cost of ferry tickets. Get the details here.
Update: Due to inclement weather, Saturday, May 30th’s Free Ferry Weekend has been postponed to Saturday, June 6th. Free Ferry Day on Sunday, May 31st will continue as planned with regular scheduled departures to Georges Island.
It’s Lobster Roll Season at EBO Grocery!
It’s officially summer season. EBO + Co Grocery announced on Instagram that their legendary Lobster Roll Kits are back for the season! Each kit includes one pound of fresh Maine lobster meat (knuckle & claw) and a pack of Martins Potato Rolls and makes six lobster rolls. “Ain’t nowhere else you’ll be getting six lobster rolls for $75!” Truth! Pick one up this week– it pairs perfectly with a bottle of rosé!
Treat Yourself to Slush King
With warmer temps and longer days, the summer season is perfect for enjoying ice-cold treats! Enter Slush King, offering everything from homemade slush to ice cream sandwiches! Slush King has been around since 1965, operating push carts at Boston Common and at festivals throughout New England. In 2020, Slush King opened a window at 211 Bennington Street, where you can order your favorite ice cream treats every day from 1pm-10pm. You can check out the full menu here!
Zumix at the Hatch Shell
Join Zumix on the Esplanade as they kick off this FREE riverfront concert series celebrating Boston’s vibrant music scene! The evening of live music will feature students from the Sprouts program, group programs, and teen ensembles, as well as local alumni artists. Each concert is produced by local creators and showcases a diverse lineup of artists, bringing communities together through music, culture, and connection. Takes place on Sunday, May 31st from 4pm-7pm. You can learn more here.
ICA Watershed is back for a new season!
The ICA Watershed—a seasonal space in East Boston dedicated to large-scale artist projects—will reopen for the season with Lucy Raven: Rounds. This is a major new exhibition by Lucy Raven (b. 1977 in Tucson, Arizona) includes the United States premieres of Hardpan, a large-scale kinetic sculpture co-commissioned with Barbican Centre, London, and Murderers Bar (2025) a new moving image installation and the final installment of Raven’s series The Drumfire. Check it out this weekend!
SPORTS!
Red Sox vs. Guardians – Friday, May 29th at 7:10pm, Saturday, May 30th at 4:10pm and Sunday, May 31st at 1:40pm.
NBA Playoffs – schedule here
NHL Playoffs – schedule here
Here are 7 Places to Watch in the Neighborhood!
Check back as this list may be updated!
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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