Your Guide to May Day 2026

May Day will be held on Saturday, May 2nd with a rain date of Sunday, May 3rd
May Day is finally here! It’s time to celebrate Spring in Charlestown, support our local businesses, and have some fun with the community.
Shops and Restaurants
JPPilates’s FREE Outdoor Pilates Fusion Class
A kickoff to May Day! JPPilates will host a FREE Pilates Fusion class at the Bunker Hill Monument (9am) followed by studio open house and trunk show with Twin Lion (shop your favorite workout brands!)
Crate Escape will host the park clean up at the Monument
Along with hosting the Park Clean Up at the Monument from 10am-12pm, Crate Escape will be offering dog cookies, bandanas, and raffle prizes for participants at the High Street steps.
Junebug’s Floral Bench
Visit Junebug’s floral bench in the Training Field for a wonderful photo op! The shop will also be buzzing with new inventory and product lines.
The Waverly, Monument, and Prima Tour de Spritz is back!
Tour de Spritz is back this year, with punch cards for drinks at each location. Visit all 3 locations and get entered into a raffle for gift cards. Prima & Waverly will be selling prints of the restaurant by a local artist. The Monument patio open will be open – and it’s dog friendly!
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
Enjoy 20% off skincare and Puffy Clouds Boston is giving out gourmet cotton candy!!
Kaybea’s Stuff the Bag Sale
It’s back! Kaybea is hosting another Stuff the Bag Sale from 10-11am. Plus, Sweets by Cella will be popping up outside with cookies for sale!
The Method
The Method will be hosting an open house! There will be fun and interactive challenges.
Joy Street
Celebrating Joy Street’s 1st Birthday in Charlestown with the Betti the Confetti Yetti! Enjoy an extra % off sale on select items and pick up free Charlestown washable tattoos!
Dovetail
Enjoy Aperol Spritz’s on the patio!
Cut-Splice
25% off product! Plus 10% off gift cards. Both in store, mention ‘mayday’.
Place & Gather
Get ready for new Charlestown product drops – follow along on their Instagram for sneak peeks!
Slate
7&Sun returns to Slate from 11am-5pm in celebration of spring – unveiling a fresh collection of Sacred Strands and gem-set 14k charms.
Pier 6’s annual Derby Day Party is back!
Big hats, bourbon cocktails, and waterfront views to finish up May Day. Join Pier 6 on Saturday, May 2nd from 3-7pm to celebrate Derby Day with their annual Derby Day Party, presented by Ketel One Botanicals. 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
Pop-Ups
Daphne Rae Creative
Location: Main Street to the Left of Junebug
Floral paintings, prints and cards to welcome in Spring!
Savvy Sitter
Location: Main Street to the Right of Junebug
Handing out Fun things for the kids!
Charlestown Coffee
Location: Main Street to the Right of Monroe
Cups of coffee for the stroll and bags of coffee to bring home.
AJ Skye Designs-Nicole Saez-Armand-Custom Drinkware
Location: Main Street at the Halligan Club
Ronald McDonald House
Location: Training Field for families to visit floral bench. Hood Park has graciously provided their shuttle for families to go from the Ronald McDonald House to the Training Field!!
DIY pinwheels and sun catchers to embrace the spring vibes!
Monument Dental
Location: Main Street to the right of 231 Main Street
Charlestown Candle Company
Location: Main Street to the left of Barber Shop
Ruthie’s Juice
1) JPPilates studio: 10am Juice Drop
2) Main Street: Right of Joy Street at 11am
Juice tasting, Juice, Wellness Shots & Energy Balls for sale
IONI Olive Co.
Location: Main Street to the left of Monroe
Olive Oil tasting w/freshly baked sourdough from La Saison
Boston Belle Embroidery
Location: Inside Monroe
From Print to Press
Location: Main Street in front of Fitness Together
Raffle for free custom stationery
Charlestown Kids PMC
Location: Main Street to the left of 231 Main Street
Warren-Prescott School
Location: Main Street in front of La Saison
Raffle to win $10,000 at Spring Fling fundraiser
Harvest on Vine
Location: Main Street Halligan Club

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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