Main Street Chestertown

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Chestertown, MD
Main Street Chestertown

Welcoming all to one of the Eastern Shore’s most charming towns. | Preserving what makes Chestertown special. Building what comes next.

Main Street Chestertown, Eastern Shore Life at its Best... Downtown Chestertown is a vibrant place where locals love to live, work, and play, and where visitors choose to come time and again. Main Street Chestertown strives to create a more engaging and prosperous downtown.

09/03/2026

🎉 WELCOME BACK, WASHINGTON COLLEGE STUDENTS! 🎉

First Friday is officially this Friday, September 4th, and Main Street Chestertown couldn't be more excited to help kick off the fall semester! We are proud to co-sponsor this community-wide Welcome Back celebration alongside United Way of Kent County, the Downtown Chestertown Association, and Washington College, bringing our vibrant downtown and college students together for an unforgettable night.

While you're out exploring the festivities, be sure to make the rounds:

🚲 Visit our Main Street Table: Come chat with us to learn all about our downtown Bike Share program and how you can easily get rolling around Chestertown.

🤝 Discover Local Non-Profits: Explore the booths showcasing incredible non-profit organizations serving our local area.

🛍️ Shop & Dine Late: Check out downtown stores open late and grab a bite to eat from our amazing local businesses. We're co-sponsoring some special treats from local joints especially for students.

Bring your friends and let’s show our Washington College students what makes Chestertown so special!

📍 Where: Downtown Chestertown

📅 When: This Friday, September 4th from 5-8pm

08/21/2026

Gearing up for those classic Chestertown Saturday morning views. See you out there as we make our way through the Chestertown Farmers' Market and down to the Chestertown Marina. 🚲 Need an easy way to get around without the parking hassle? Grab a Main Street Chestertown bike and head on out! More info here: https://www.tandem-mobility.com/bikeshare-town-of-chestertown

08/13/2026

Local business owners: Major financial tools are available right now to help you invest in your property and grow your business!

The Maryland Department of Housing and Community Development (DHCD) and the Maryland Historical Trust (MHT) have announced two key programs:

🔹 DHCD Small Business Direct Loans: Low-interest financing applications officially open on August 17.

🔹 MHT Historic Revitalization Tax Credits: Earn up to a 20% state tax credit on historic rehab expenses. Note: Large project applications are due August 31 (Small Commercial credits up to $50k remain open on a rolling basis).

Main Street Chestertown strongly encourages our local businesses to take advantage of these opportunities. If you need assistance navigating the application process or have questions about how these programs fit your business, reach out to us—we are here to help!

07/31/2026

The wait is over! Bespoke Chocolate has officially opened the doors to its brand-new, expanded location at 103 S. Cross Street—and you have to see this space in person!

👀 What you can look forward to right now:

An expanded retail area where you can watch artisan chocolates, fresh fudge, and roasted nuts being made right in front of you!

Coming soon: The Koko Lounge, a walk-up window for specialty chocolate drinks and gelato, and second-floor chocolate-making classes and community events!

🛠️ Why we're so proud:
Main Street Chestertown was thrilled to support this expansion through our Building Interior Improvement Grant—funding critical plumbing, electrical, framing, and carpentry work to make this incredible transformation possible. In just one year, our interior grants program has backed multiple local project applications that are driving real, positive progress in our downtown!

Stop by 103 S. Cross Street today to congratulate Kurt, explore the new shop, and grab a sweet treat (or three)!

🔗 Read the full story in our newsroom: https://mainstreetchestertown.org/bespoke-chocolate-opens-with-new-renovations/

📍 Location: 103 S. Cross Street, Downtown Chestertown
🌐 Learn more about Bespoke Chocolate: bespokechocolate.net

07/29/2026

We all know our town has serious historic charm—and the numbers prove tourists agree! In June alone, we welcomed 758 visitors to our Visitors Center - more than 200 more than June of last year. People from as far as Poland and the Philippines have joined travelers from Arizona, Tennessee, and Oregon to visit Chestertown in the last 90 days.

A huge shout-out to Robin Sesplankis, our newly promoted Visitors Center Manager, for making sure every guest gets the warmest Chestertown welcome. We love seeing our community thrive and showing off what makes Chestertown so special!

🔗 Read more about Robin's promotion and our latest visitor stats: https://mainstreetchestertown.org/robin-sesplankis-dedicated-public-servant-named-visitors-center-manager/

07/27/2026

How's your Chestertown vacation (or staycation) been going?

07/23/2026

Happening now in downtown Chestertown! Now through July 25 head on down for Downtown Chestertown Association's annual Crazy Days of Summer! 🌞 Enjoy sidewalk sales, a scavenger hunt, tasty local food, and fun events. 🍔🎉 Don’t miss this summer celebration—bring friends and family for a memorable experience!

07/16/2026

Proud moment for Chestertown and the 3 local businesses/organizations featured in this summer's Destination Main Street campaign - Sultana Education Foundation, Modern Stone Age, and Park Row Floats!

Check out the interactive map to discover all 85 featured destinations chosen by Maryland Department of Housing and Community Development: https://tinyurl.com/mrmr7e9c

At Main Street Chestertown, we are always happy to showcase all that our beautiful historic town has to offer to every kind of visitor. We are incredibly proud of these three for representing the unique character and vibrant spirit of our community.

07/09/2026

Hop on Chestertown! 🚲 Did you know our town has its very own bike share program? June was officially our highest usage month yet, and with summer in full swing, we are just getting started!

These bikes are a key part of Main Street Chestertown's Master Plan, reflecting our community’s growing commitment to making our historic streets accessible, connected, and inviting for everyone.

Whether you’re a visitor exploring our downtown shops, a local hitting the nature trails and riverfront, or a Washington College student commuting from campus, these bikes make seeing the best of Chestertown incredibly easy and affordable.

📍 Where to find a ride:
The Chestertown Marina
Washington College (Gibson Center for the Arts)

📱 How to ride:
All you need is pedal power and your phone. Simply scan a bike using the MotoVac app at either depot and you’re on your way.

Ready to ride? Get all the details on our website at https://mainstreetchestertown.org/ or check out the program dashboard at https://www.tandem-mobility.com/bikeshare-town-of-chestertown 🙌

07/02/2026

It takes a village! We're so grateful to Bill and Kay MacIntosh, Ellen Hurst, and Patricia Pheiffer for filling the planters down at the marina with beautiful greens and vibrant blooms, readying the waterfront for another wonderful summer season.

Read on here to learn more about our volunteers' dedicated efforts and how our board and staff's work has been recognized nationally yet again: https://mainstreetchestertown.org/national-recognition-and-waterfront-planters-showcase-the-collective-spirit-keeping-chestertown-vibrant/

Address

122 N Cross Street
Chestertown, MD
21620

Telephone

+14107782991

Website

https://mainstreetchestertown.org/

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