Your Guide to May Day 2026

3.6 min readBy Published On: April 30th, 2026Categories: See & Do, See & Do0 Comments on 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

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