Weekend Picks – LDW 2025

One More Week to See these exhibitions at the ICA Watershed
It’s the last week to take in Chiharu Shiota: Home Less Home and Our Memories, Our Stories at the ICA Watershed! The last day is September 1st. Get the details here!
New Edition Day Events
New Edition is being honored by The City of Boston with their own street naming followed by a community block party! The event is happening Saturday, August 30th starting at 10am. The street naming ceremony will take place at the corner of Ambrose Street and Albany Street in Roxbury, honoring the group at Orchard Gardens, formerly known as Orchard Park, where the founding members of New Edition grew up. The community block party will take place in front of the Orchard Gardens Boys & Girls Club, featuring music, a backpack giveaway for youth, free food, fun activities and a special appearance by New Edition. Get all the details here!
Hop on a ferry for a fun summer adventure
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!
Host a LDW celebration this Weekend
Treat yourself! EBO Co. Grocery can help you with everything from oysters, caviar, chips + dips, lobster roll kits, beer and wine and more to make your get-together perfect!
Pitch in!
Join in the neighborhood clean up of the Greenway on Saturday from 10am-12pm. Meet by the Blue Caboose (Marginal Street Enterence)!
Outdoor Yoga at Piers Park
Join Marisa from The Point Yoga for a rejuvenating Vinyasa Flow yoga class set outdoors in the stunning Piers Park on Friday at 5:30pm, where the beauty of nature enhances every breath and movement. As the sun sets over the Boston Harbor, you’ll move through a dynamic sequence of postures designed to build strength, flexibility, and inner calm. Reserve your spot here!
Drinks + Apps on the Roof
Enjoy some tropical summery cocktails and appetizers on the Layover’s Rooftop Bar!
Take a sunrise or sunset kayak tour
What better way to start or end your day than with a guided sunrise or sunset kayak tour of Boston Harbor? The Piers Park Sailing Center offers guided sunrise and sunset tours this weekend! It’s a great way to explore the city from the ocean! You can book the morning session here and the evening one here! Kayaking at Piers Park helps support its public access, youth, and adaptive programs. They are also open for regular public kayaking; you can reserve a time to kayak the Piers Park Cove by booking here.
Tall Ship Fun
Enjoy some fun in the sun this weekend along the water at the Tall Ship! Live music all weekend plus Tall Ship’s legendary White Party on Monday! You can get all the details here!
Brace Yourself! It’s Moving Day!
September 1st is upon us, and you know what that means – it’s Moving Day in Southie aka Southie Christmas! The next few weeks are sure to promise lots of double-parked cars and moving vans, “no parking” moving permits (which residents will ignore), and trash galore! Here is some helpful info to make sure things go smoothly on your block!
SPORTS!!:
Red Sox vs. Pirates – Friday, August 29th at 7:10pm, Saturday, August 30th at 4:10pm, Sunday, August 30th at 1:35pm
Red Sox vs. Guardians –Monday, September 1st at 1:35pm.
US Open Matches – 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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