Weekend Picks – MDW 2026

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. The ICA Watershed will reopen on Thursday, May 21st.
Visit the Fallen Heroes Memorial in the Seaport
At the northern edge of Seaport Common, surrounded by the ever-changing light of the waterfront, stands a powerful tribute to those who made the ultimate sacrifice for a grateful nation. The first of its kind in the country, the memorial honors the Commonwealth’s brave servicemen and women who lost their lives fighting for our freedoms since September 11, 2001. Over 4000 flags have been planted to commemorate Memorial Day.
The rededication for the Massachusetts Fallen Heroes Memorial is scheduled to take place on Friday, May 22, 2026 in the area of 85 Northern Avenue. The ceremony will take place from 10:00 a.m. to 1:00 p.m. and will require the closing of Northern Avenue from Fan Pier Boulevard to Harbor Shore Drive. Northern Avenue is expected to be closed from 8 a.m. to 2 p.m.
Run to Remember
The 2026 Boston Run To Remember will take place on Sunday, May 24, 2026, in the Seaport. Boston’s Run To Remember is a Half Marathon or 5 Mile race (live or virtual) that pays tribute to fallen 1st Responders. “We honor all 1st Responders by celebrating their service and giving back to the community.” You can get all the details, including registration info, here.
¡Viva Chile Boston!
The 12 annual festival ¡Viva Chile Boston! this year featuring special guests coming directly from Chile! You’re invited to enjoy a one-of-a-kind show presented by the Verónica Robles Cultural Center (VROCC). This year, local groups El Ballet Folklórico de VROCC and Corazón Chileno, will bring you the very best of Chile’s traditional music and dance. You’ll also be able to taste delicious Chilean food, cooked and prepared in La Cocina VROCC, bringing you the flavor of Chile. Come and immerse yourself in the cultural richness of Chile, this beautiful South American country—right here in East Boston! This event takes place on Saturday, May 23rd at 5:30 at the VROCC. Get more details here.
Celebrate Memorial Day Weekend at the Tall Ship
If eating oysters and drinking rosé on a tall ship sounds like fun, then you’ll love The Tall Ship! The Tall Ship on the East Boston Waterfront is officially back for the 2026 season. The ship features three custom-built mahogany bars, built around the grand mast and forward and aft of the ship, while guests enjoy uninterrupted views of the city skyline and harbor. The galley kitchen offers local oysters, shellfish, and charcuterie boards. Alongside the majestic tall ship, Navy Yard Hospitality has activated and built out the pier into a 40,000 sq ft waterfront experience featuring live entertainment, retail, food vendors, food trucks, pop-ups, and more! You can learn more here!
Memorial Day Observation via East Boston Chamber
Join the East Boston Chamber of Commerce on Monday, May 25, from 11:00 am to 1:00 pm for a flag display and ceremony just outside their office.
Hop on a water taxi!
Looking for a fun activity around the neighborhoods? Check out the boat shuttle service that connects you from ReelHouse East Boston to Charlestown’s waterfront and the Seaport. Boston Launch Company runs their boat shuttle service daily from 11 am until 11 pm, making stops at Pier 6, Reel House East Boston, The Tall Ship, and ReelHouse Oyster Bar in the Seaport. The service costs $4 a ticket but is free during Sumner Tunnel closures. It is such a fun, easy, and convenient way to get around the city! Get all the fun details here!
Senator Lydia Edwards Veterans Event
State Senator Lydia Edwards hosts a free Annual Memorial Day Brunch for veterans and military families on Friday, May 22, from 10:00 am to 12:30 pm. It takes place at the Beachmont VFW Post 6712 (150 Bennington St., nearby in Revere).
It’s Lobster Roll Season at EBO Grocery!
Okay, so the weather this Memorial Day Weekend might not be giving “beach day,” but this news could brighten your mood. 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 weekend – it pairs perfectly with a bottle of rosé! Available for pick up starting on Thursday afternoon.
SPORTS!
Red Sox vs. Twins – Friday, May 22nd at 7:15pm, Saturday, May 23rd at 4:15pm and Sunday, May 24th at 1:35pm.
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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