Main Street Chestertown

06/04/2026

See you downtown! Here are some of the highlights happening during First Friday:

3-8 p.m. | The Grounded Frog
Grand Opening! Stop in to explore Chestertown's newest Pilates and yoga studio during its First Friday open house on High Street across from Evergrain.

5–7 p.m. | Sultana Education Foundation
Monthly First Friday gathering at the Holt Education Center with live music, beverages, games, and community activities. Check out this month's featured performer is Benji Price & Friends.

Family Fun Night | RiverArts Chestertown
Crafts, games, and indoor/ outdoor activities and snacks‚ fun for all ages!

5–8 p.m. | TwoTen with Say Grace
Grab dinner at TwoTen and enjoy golden hour sitting in an Adirondack chair savoring some delicious food, like a lemon pepper fried chicken or stuffed chicken breast platter.

5–7 p.m. | Slack Tide Yoga
Grand Re-Opening & New Location Open House featuring live music, refreshments, raffles, goodie bags, and a ribbon cutting celebration at the studio's new downtown location in Stepney Station.

Hope to see you there!

06/02/2026

Four reasons June might be the best month to visit Chestertown:

National Music Festival | May 31–June 13, 2026
Two weeks of concerts, free rehearsals, lectures, and performances by emerging and internationally acclaimed musicians. Learn more: nationalmusic.us

First Friday Art Walk | June 5, 2026
Downtown galleries, shops, restaurants, and creative spaces stay open late for an evening of art, music, and community.

Chestertown Farmers & Artisan Market | June 6, 13, 20 & 27, 2026
A Saturday morning tradition featuring local farms, food producers, artisans, flowers, baked goods, and more around Fountain Park. Learn more: chestertownfarmersmarket.org

Juneteenth Celebration | June 20, 2026
A community celebration honoring Black history, culture, resilience, and freedom through performances, activities, and educational programming.

06/01/2026

First Fridays aren't just for grownups! Stop by Chestertown RiverArts this Friday for some great crafty fun that will get everybody into the summer spirit 🌞

We are so excited to host our own KidSPOT First Friday this week. Make plans now to join us for an engaging evening of fun as we kick off our campaign to raise $12,000 to be matched by a generous donor!

05/29/2026

A very cool opportunity for an extra special River Packet cruise, hearing more about one of the Chester River's oldest living traditions. Paired with a quick drink at a downtown watering hole before you embark, it sounds like a perfect Chestertown night to us!

Join the crew of the Silver Heel for our very first fundraiser! An evening of dinner and stories celebrating the history of our favorite log canoe and enjoying a sunset cruise aboard the Chester River Packet! Tickets available at: https://donorbox.org/events/928998/steps/choose_tickets

05/28/2026

There’s something special about a downtown where you can still step inside a working artist’s studio, meet the person behind the work, and sign up to learn something new yourself.

Michael Bell’s new studio adds another layer to what makes downtown Chestertown distinctive—a historic main street shaped not just by shops and restaurants, but by working artists, makers, and creative people investing in the life of the community.

Part gallery, part classroom, and part creative gathering space, the studio brings more opportunities to experience art in an accessible, hands-on way right here in the historic district. Learn more, or sign up for classes here: https://mbellart.com/

05/27/2026

We are very excited to welcome Slack Tide Yoga Studio to Downtown Chestertown's growing wellness community. Stop by see their new space at their upcoming ribbon cutting ✂️ 🎉

WE’RE MOVING!

As of June 1, all classes will be held at our new home: 400 S. Cross St., Suite 4, Chestertown.

Stop by on Friday, June 5 from 5-7pm for our Grand Re-Opening & New Location Open House, featuring live music by Jude Strawley, a ribbon cutting, food by Happy Chicken - Bakery & Catering and Evergrain Bread Company, LLC.

We’ll be raffling some incredible prizes from local businesses like Unity Church Hill Nursery, Modern Stone Age, Stam’s Luncheonette, Revive Skn & Body Spa, Maryland Wellness & Aesthetics, Pink Moon Beauty Bar, Sultana Education Foundation, Java Rock and more!

Come back on June 6 and 7 for FREE YOGA WEEKEND at Slack Tide Yoga Studio, featuring free yoga classes all weekend, deals on special membership offers and new Slack Tide merch!

05/26/2026

Chestertown does day trips differently.

We’re launching a new series of curated itineraries designed to help visitors experience downtown Chestertown through its food, culture, waterfront, shops, history, and small-town character—and we’re starting with a day built around culture, cuisine, and cocktails.

Think gallery stops and bookstore browsing, river views and historic streets, long lunches, good drinks, and the kind of downtown where everything is close enough to discover on foot.

Whether you’re planning a summer day trip or looking for a new way to experience Chestertown like a local, this guide is a good place to begin.

Explore the itinerary here: https://bit.ly/4nUMrS7

05/20/2026

Deadline Extended: June 22!

Main Street Historic Chestertown is seeking an experienced event planning partner to coordinate the 2026 Dickens of a Christmas Festival, happening December 4–5, 2026.

This is one of Chestertown’s largest and most beloved annual events — bringing thousands of visitors downtown for a weekend of Victorian charm, live entertainment, vendors, family activities, and holiday tradition.

The RFP deadline has now been extended as we seek qualified candidates.

Event planners, production teams, and event management organizations are encouraged to apply! Please share with anyone who might be a good fit.

View the full RFP and submission details here: https://bit.ly/3Rjab67

05/18/2026

POV: Clam strips acquired, a cold lemonade in your hand, a parade of local marching bands and organizations right down High Street, and the promise of some red coats getting a good dunking in just a few hours.

Memorial Day weekend is headed our way and for downtown Chestertown, that means a weekend of Chestertown Tea Party Festival fun. Especially for the America 250 celebration, this feels like an even bigger year to celebrate, so we hope to see you there at the Festival, the raft race, the Sneaker Creeper, or the 5k foot race.

Just four more sleeps! ☕️ 🎉

04/29/2026

Enterprise zones? Improvement grants? 🤔 If you could use a little more guidance on what these tools are & how your downtown Chestertown business could benefit, we've got you!

Check out our latest Main Street Chestertown blog post for information about each of these great opportunities to invest in your business—and who to talk to if you'd like to know more! https://bit.ly/4cmHMnU