Main Street Chestertown

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

04/26/2026

Sweet news for Chestertown: Brian’s Best Pastries & Cafe, now open on 328 Cannon Street, has brought some serious pastry talent to downtown. Founded by veteran pastry chef Brian Bennett, the new bakery/ cafe offers house-made croissants, cakes, cheesecakes, dessert bars, scones, signature pecan bars, and more—with tasting samples available so you can try before you buy. Stay turned for breakfast and lunch as they staff up.

Stop by for a sweet treat at 329 Cannon Street 🍰

04/24/2026

Downtown Chestertown has a new gallery space—Backwater Contemporary at 353 High Street.

After a renovation by owner Jeff McGuire, supported in part by a Project Restore 2.0 grant from Maryland Department of Housing and Community Development (DHCD), the building is now home to work by artist Jono Tew, whose paintings celebrate a sense of place through vivid landscapes. Stop by to take in his work and welcome Backwater Contemporary to Chestertown!

04/24/2026

Dickens of a Christmas is one of downtown Chestertown’s most magical weekends of the year, and Main Street Historic Chestertown is looking for the right event planning partner to help bring the 2026 festival to life.

From Victorian-inspired charm and live performances to vendors, family activities, sponsorships, volunteers, and downtown logistics, this event takes careful coordination behind the scenes to create an unforgettable experience for our community and visitors.

Main Street Historic Chestertown is now accepting proposals from qualified event planners or event management organizations to plan and coordinate the 2026 Dickens of a Christmas Festival, scheduled for December 4–5, 2026.

Proposal deadline: May 22, 2026
Questions may be submitted by May 8, 2026 to [email protected].

View the full RFP here: https://www.mainstreetchestertown.org/dickens-festival-event-planning-rfp/