Weekend Picks – September 19th

2.9 min readBy Published On: September 19th, 2025Categories: See and Do0 Comments on Weekend Picks – September 19th

History in Motion – USS Constitution Underway on Friday

USS Constitution is scheduled to get underway on Friday, September 19th, from Charlestown Navy Yard at 10:00 A.M. The cruise will be visible from the Boston Harborwalk, Castle Island, and Charlestown Navy Yard. A 21-gun salute will be fired at approximately 11:30 A.M., viewable from Fort Independence on Castle Island. This sail will commemorate Purple Heart Recipients.

Let the Cheeseburger Celebration Continue!

As if you really needed an excuse to eat a burger. Well, it’s National Cheeseburger Day and we can’t think of a better reason to eat one! Whether you like it with the works or just a little ketchup, today is the perfect day to eat one! We are sharing our picks for the best burgers in the neighborhood!

Eastie Welcome Weekend is Saturday!

East Boston Main Streets is pleased to announce Eastie Welcome Weekend, a new event designed to engage new residents, celebrate the neighborhood’s diversity, and strengthen bonds between local businesses, non-profits, and the broader community. The outdoor event will take place on Saturday, September 20, 2025, from 2:00–6:00 PM (Rain date: Sunday, September 21) at the intersection of Havre, Brooks and Bennington Streets.  This event will feature food, art, a beer garden and more! You can learn more here! 

Local Artists Transform The Eddy into a Pop-Up Waterfront Exhibit, The Water’s Edge

The East Boston Artists Group (EBAG) presents The Water’s Edge, a collaborative exhibition featuring four local artists whose work is inspired by the natural beauty, color, and energy of the waterfront. The show will run from September 15 to October 20, 2025 in a unique pop-up gallery space at The Eddy (10 New Street, East Boston), with an opening reception on Friday, September 19 from 6–8 PM.  Visitors can view the exhibition Monday through Friday, 11 AM–4 PM, or by appointment.

Fried Chicken Tower at Cunard Tavern

If you love fried chicken, you’ll live this news!  Cunard Tavern now features a tower of fried chicken. Perfect for game watching!

Trash to Treasures Event

“Trash to Treasure / De basura a tesoro” East Boston harbor cleanup and trash-to-art project. This free, family-friendly event will bring neighbors together for a morning of fun by the water, featuring a shoreline cleanup and a collaborative art project led by art activist Rebecca McGee Tuck using materials collected from the cleanup. The event will celebrate East Boston’s waterfront while creating space for connection, creativity, and coastal care. Informational signage will also be displayed to raise awareness about public shoreline access rights. Takes place at 126 Border Street on Saturday September 20th from 10:00 am – 1:00 pm

Celebrate National Pepperoni Pizza Day

Friday, September 20, is National Pepperoni Pizza Day, and what better way to celebrate than with a Santarpio’s Pizza? Located at 111 Chelsea Street, this family-owned and operated pizza joint is a fan favorite among residents!

Live Music + Workouts at the Tall Ship

Enjoy some fun in the sun this weekend along the water at the Tall Ship!  Live music all weekend – you can check out the schedule here!  Plus two workouts will be popping up on Saturday and Sunday.  Get the details here! 

Pick Your Own Apples

Venture out of the neighborhood and pick yourself a bushel and peck of farm-fresh apples.  Here are our picks for 5 Places To Pick Your Own Apples! 

SPORTS!

Red Sox vs. Rays – Friday at 7:30, Saturday at 7:05pm and Sunday at 7:35pm.

Patriots vs. Steelers –Sunday at 1:00pm.

Here are  7 Places to Watch in the Neighborhood! 

Check back as this list may be updated! 

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