5 Things You Should Know This Week – September 22nd

Colin’s Joy Project 5K
Lace up your sneakers and participate in the Annual Colin Joy Project 5K on September 27, 2025. The day will begin with two youth races, followed by a 5 km course along scenic South Boston beaches. After the race, there will be light refreshments and entertainment to go along with the awards. The fun starts at 8am. Get the details here.
Nominate a Legacy Business
Today, Mayor Michelle Wu announced the launch of the nomination period for the fourth annual Legacy Business Awards. Nominations will be accepted through Friday, October 31, 2025. Residents are encouraged to nominate long standing businesses that have been located within the city of Boston for at least 10 years and contribute to the cultural, historical, and societal fabric of their community or neighborhood. To nominate a business, residents can use the online form, visit their local Boston Public Library branch for assistance filling out the form, or call the Office of Small Business at 617-635-0355 for assistance. You can get more details here!Â
If you’re riding your bike around Castle Island, please stop.
The Department of Conservation and Recreation (DCR) recently put up a few signs out of Castle Island, reminding visitors that bike riding is prohibited around Fort Independence or the Causeway. If you do ride your bike out to Sullivan’s or Fort Independence, kindly get off your bike and walk it. This policy, which has been in place for many years, is designed to ensure the safety and enjoyment of all park-goers. Bikes must be walked throughout Castle Island, and the DCR has provided bike racks at the entry plaza on the Pleasure Bay side, opposite Sullivan’s for convenience.
Community Meeting to discuss development at 662-666 East Broadway
The Boston Planning Department will host a virtual community meeting to discuss a development project at 662-666 East Broadway on Monday, September 29th from 6:00pm – 9:00pm. Register: bosplans.org/662-666EBroadway-09-29 Toll Free: (833) 568 – 8864 Meeting ID: 161 402 9009. You can learn more here.Â
Let’s Pick some Apples
Venture out of Southie and pick yourself a bushel and peck of farm-fresh apples. Make sure to check all orchard’s websites for up-to-date safety info, restrictions, etc. Some require reservations, so double-check before you head out! Here are our picks for
Have a wonderful week!Â

Maureen Dahill is the founder of Caught in Media. Once a longtime wardrobe and prop stylist for brands such as Rue La La, TJ Max & Hasbro, she is a devoted lover of vintage clothing, Martini Mondays, Castle Island, AND a 4th generation South Boston native. Mother of three, married to Peter G.


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