Weekend Picks – May 1st

It’s officially May!! Happy May Day Weekend to all!
May Day is this weekend!
May Day is finally here! It will be held on Saturday with a rain date of Sunday, but as of now both are looking a bit wet so we are continuing with Saturday! It’s time to celebrate Spring in Charlestown, support our local businesses, and have some fun with the community. Here are some highlights:
- Tour De Spritz ft. Waverly, Prima, and Monument: Get a punch card and order a Spritz at each restaurant to be entered to win gift cards! BONUS: Caught in Charlestown is also giving away a $50 gift card to each location!! Just post a photo of you with your Spritz, tag us and the restaurant, and you’ll be entered to win!
- Crate Escape will host the Park Clean Up at the Monument from 10am-12pm, and will be offering dog cookies, bandanas, and raffle prizes for participants at the High Street steps!
- Flight House, Charlestown’s newest gym, will be popping up at The Method. Read all about how this massive, new gym will be more than just another place to work out.
- LexRX is doing 20% off skincare and hosting Puffy Clouds Boston who will be giving out gourmet cotton candy!
Here is our Guide to May Day with all the happenings!
Celebrate Derby Day in Charlestown
Pier 6’s Derby Day party is back! Big hats, bourbon cocktails, and waterfront views. Join Pier 6 to celebrate Derby Day with their annual Derby Day Party, presented by Ketel One Botanicals and your ticket includes one drink ticket for a Ketel One specialty drink. Dapper fits, bold cocktails, waterfront views, and live music all afternoon. Get your tickets now!
What to Expect
Prizes for Best Hat + Most Dapper
Waterfront patio + multiple bars
Love Your Block is on Saturday in Charlestown
Love Your Block is a city-wide initiative hosting neighborhood cleanups, and Charlestown’s is on Saturday. The Charlestown Preservation society will host at Preservation Park (corner of Austin and Main St) from 10:30am-12:30pm. Anyone can join! They’ll provide bags, pickers, gloves, and limited tees from the City of Boston.
Haven’t tried MYSTRYDE? Here’s your chance!
MYSTRYDE is having a spring sale – 6 classes for $144. They have a 6-week expiration, and monthly members save 10% at checkout. Sale ends Friday, May 8th! Haven’t been before? They also have a new client special: first 3 classes for $49!
Watch the playoffs this weekend at Urban Wild
Don’t want to miss any playoff games? Well, you’re in luck. Head to Urban Wild for 12 different TVs so you get to see all the action. The Bruins play Friday night at 7:30pm and will be on the huge 16ft drop down screen. A DJ will also play between periods. They lose or go home, so it’s a big one! Reserve a table by emailing [email protected]
Parents Night Out at the YMCA
The Y’s Pre-Mother’s Day Parent’s Night Out is the perfect chance for parents to enjoy a few kid-free hours while the little ones have a blast at the Y! This Sunday, May 3rd from 3:30–5:30 PM kids ages 3–12 can enjoy arts & crafts, snacks, and games. Family membership required. To register, email [email protected] or stop by the Welcome Center. Spots are limited!
Check out Flight House Fitness at an Open House
Head to Flight House Fitness for an open house this weekend! They are getting ready to open a massive new gym in Charlestown early June—and it’s aiming to be more than just another place to work out. Located at 465 Medford Street along the Mystic River, the 50,000-square-foot space is designed to bring everything fitness-related into one spot. Members will have access to a traditional open gym, group classes that blend strength and cardio, and even private recovery suites. The idea is simple: instead of juggling multiple memberships, you can do it all in one place. Read all about it, here!
SPORTS!
Bruins vs. Sabres – Friday, May 1st at 7:30pm and again on Sunday TBD
Celtics vs. 76ers– Saturday, May 2nd TBD
Red Sox vs. Astros – Friday, May 1st at 1:35pm, Saturday, May 2nd at 4:10pm and Sunday, April 3rd at 1:35pm.
Here are 9 places to watch the game in the neighborhood!
Check back as this list may be updated. Thank you to our Caught in Charlestown readers and neighborhood partners for supporting our local journalism efforts!

Abbey is the face behind Caught in Charlestown. In 2023 she migrated from Southie to Charlestown and brought the spirit of the ‘Caught In’ community with her. She is a new momma, creator, real estate agent, yogi, and so much more.

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