3.7 min readBy Published On: May 15th, 2025Categories: See and Do0 Comments on Weekend Picks – May 16th

National Bike to Work Day is May 16th

Join a neighborhood-based group ride, or just show up for the fun. Going to work after the event is optional. 😉 Find more information about this year’s event on the City of Boston’s Bike to Work Day page. On Bike to Work Day, you can join a bike commuter neighborhood-based group ride from one of dozens of locations throughout the Boston metro area. Guided group rides with experienced ride leaders will follow a fixed schedule and route and finish together in Downtown Boston. Head to City Hall between 7 and 9 a.m. on Friday, May 16th. Enjoy some breakfast snacks and coffee. Stop by tents and tables to learn about local businesses and organizations that support our cycling community in the Boston region. The event is free, but registration helps the City to know you’re coming. Registration will close at 5 p.m. on Wednesday, May 14. You can still attend the event if you don’t register, but you will not be able to get a t-shirt during the event. Register here. 

USS Constitution is Underway on Friday

USS Constitution is scheduled to get underway Friday, May 16, 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. Check her out!

Greenway Garden Club

Join the friends of Mary Ellen Welch Greenway for a spring garden cleanup on Saturday, May 17th at 10am at Memorial Garden at Marginal.

Live Music at the ReelHouse

Sunday Funday! Enjoy a cocktail and an appetizer while you listen to live music on Sunday, May 4th from 2pm-6pm!

Italian Apertivo Hour at Pazza on Porter

Pazza on Porter is celebrating patio season with an Italian Apertivo Hour on Sunday  from 12pm-2pm. There will be special menu additions including arancini, fritto misto, flatbread plus specialty cocktails like Aperol Spritz and more!

New Show at Atlantic Works Gallery: The Art of Letting Go

The Art of Letting Go features work by two AWG artists, Elsa Campbell and Daniel Gaviani. Letting go is not about losing; it’s about release. It’s the moment you exhale after holding your breath for too long. It’s the acceptance that change is natural, and that chaos can be art.  Opening reception takes place on Saturday.  You can get the details here! 

New to the Neighborhood:Caffe dello Sport

The wildly popular espresso bar in the North End has officially expanded to Eastie!  Caffe dello Sport has opened a new shop at 973 Saratoga Street in Orient Heights. The shop serves espresso, gelato, pastries, paninis, and more. The original Caffe dello Sport has been in the North End for over 30 years. You can learn more by visiting the website here. Open 7 days a week 7am-11pm

Hunt + Gather

Grace Church will be hosting a rummage sale on Saturday from 10am-2pm.  Grace Church is located at 762 Saratoga Street.

Spring Fling in The Seaport

Get ready for Seaport Spring with a picnic for all ages on Saturday, May 17th from 12 to 3pm. There will be live music, complimentary bites, and beer to purchase from Castle Island Brewery. Dancers from Superette Salsa Nights, Seaport Sketch Artist, and Seaport Smalls will also be there! It is free to all and will be taking place at 111 Harbor Way.    

Free Ferry Weekend

Celebrate Boston Harbor Islands opening weekend with a FREE trip to Spectacle Island! Explore Spectacle Island’s beaches and winding trails. Catch the ferry to Spectacle right from Downtown Boston’s Long Wharf North… for free!

  • Saturday, May 17
  • Sunday, May 18

Getting Tickets:

  • Tickets are first come, first served, and can be picked up at the Boston Harbor City Cruises Ferry Center at Long Wharf North  beginning at 8:00am. No advance reservations. Arrive early, as this event will sell out fast!
  • This event cannot accommodate groups – 5 tickets allowed per adult

Ferry Schedule: Ferries depart from Gate 5 . Ticketed passengers should plan to be in line at least 15 minutes before their ferry departure time. 10:30AM  |  12:30PM Ferries from Spectacle back to Boston depart the island at 1:30PM & 3:30PM

SPORTS!

Celtics vs. Knicks on Friday at 8pm

Red Sox vs. Braves– Friday, May 16th at 7:10pm, Saturday, May 17th at 7:15pm, Sunday, May 18th at 1:35pm

Here are  7 Places to Watch in the Neighborhood! 

Check back as this list may be updated! 

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