Main Street Chestertown

10/15/2026

🎃 Black Cat Art Trails, Scarecrows, Cult Classic Theater, and, Costume Parades, and Tall Ships Pack the pre-Halloween Season. 👻

Check out our latest round up of late October events happening in downtown Chestertown from Chestertown Lion's Club, Sultana Downrigging Festival, the Garfield Center for the Arts, Downtown Chestertown Association, and more!

https://mainstreetchestertown.org/spooky-season-arrives-in-downtown-chestertown/

10/14/2026

Downtown Property Owners Step Up to Create New Diaster Relief Fund

In response to the recent fire on Cannon Street, our downtown business and property owners are taking action to build long-term support for affected neighbors. To help local households displaced by fires or other catastrophic events, several have partnered with the Chester Valley Ministers Association (CVMA) to establish the Chestertown Area Disaster Relief Fund—kickstarting the effort with an initial $5,000 personal donation.

Managed under CVMA’s 501(c)(3) Good Neighbors Fund, this new initiative provides tax-deductible grants of up to $2,500 to local households facing extended displacement (30+ days) to help cover immediate needs alongside insurance and government aid.

Learn more and donate today: https://chestervalleyministers.org

10/12/2026

ICYMI - Chestertown was featured in Garden & Gun Magazine!

We’re thrilled to share that Chestertown made a splash in Garden & Gun’s October/November Southern Agenda! The piece spotlights our town’s rich maritime tradition along the Chester River and highlights Sultana Downrigging Festival (October 30–November 1)—calling out the tall ships, live music village, and warm community spirit that make our historic port town so special. Read Mayor Efland’s comments in this month’s issue out now:

G&G staff, editors, and contributors share their picks for the top ways to spend your time this autumn season

09/29/2026

We are thrilled to spotlight Down on Main Street—our dedicated storytelling partnership between Main Street Chestertown and The Chestertown Spy! 🗞️✨

This joint initiative brings you stories, progress, and news directly from downtown Chestertown, celebrating the local businesses, people, and ideas that make our community so vibrant and welcoming.

To kick things off, check out this heartwarming featured story on Stam’s Luncheonette and their Stam's Sweet Readers program! 🍦📚

In partnership with The Bookplate, Stam's is launching Year 2 of their reading incentive initiative—expanding to all public, private, and homeschool elementary students across Kent County from October through May! Students who log their monthly reading goals earn custom stickers, free sundae vouchers from Stam's, and book vouchers to The Bookplate.

👉 Read the full story on The Chestertown Spy:

https://chestertownspy.org/2026/09/23/childrens-literacy-with-a-cherry-on-top/

💡 How You Can Participate:

• Teachers, Administrators & Homeschool Coordinators: Register your students and view program guidelines at stamsluncheonette.com/stams-sweet-readers.

• Have a story idea for Down on Main Street? We want to hear from you! If you have a tip about a downtown business, resident, visitor, or upcoming happening for us to consider featuring, email us directly at [email protected].

Together, let’s keep supporting local reading, local businesses, and our downtown community! ❤️

As local kids head back to school this month, downtown ice cream shop and much beloved lunch spot Stam’s Luncheonette is celebrating the return and expansion of its popular reading incentive initiative, Stam’s Sweet Readers. Launched in early 2026 in partnership with local bookstore The Bookplat...

09/17/2026

Happy 1-Year Anniversary to the Main Street Chestertown Community Bike Share! 🚲✨ Launched in partnership with the Town of Chestertown, our 10-bike fleet is keeping our town connected.

Year 1 Highlights:

300+ Rides Logged: Averaging ~30 rides per bike each month.

Rapid Adoption: 71 new registered users per month in 2026 alone.

Tourists love them: 61% of all rides originated at the Chestertown Marina location, serving as a key gateway for waterfront visitors, downtown shoppers, and diners.

Master Plan in Action: Creating safe, bikeable routes between the Rail Trail, Heritage Trail, and waterfront.

It’s just $1 to unlock and $1 per 30 mins via the Movatic app!

📲 Download via QR codes at the Chestertown Marina or Washington College depots, or visit https://www.tandem-mobility.com/bikeshare-town-of-chestertown.

09/16/2026

🎩 **DICKENS OF A CHRISTMAS IS BACK!** 🎄✨

Mark your calendars! Main Street Chestertown's premier holiday event returns **December 4 & 5, 2026**. Get ready for classic favorites, exciting new additions, and returning crowd-pleasers!

Here’s a quick look at what’s in store this year:

* 🐎 **Classic Holiday Favorites:** Enjoy carriage rides, antique bikes, Victorian Tea, live music, bonfires, children's activities, and holiday shopping throughout town!

* 🔥 **Fire Dancers Returning:** Catch the thrilling Fire Dancers performance on **Friday, December 4th**!

* 👻 **New Dark Victorian Attractions:** Look out for spooky new ghostly additions bringing an immersive twist to Olde London.

* 🛍️ **Vendor & Performer Call:** We have a few remaining spots for Victorian London and Christmas-themed vendors or entertainment! Email `[email protected]` to apply.

Stay tuned—big announcements about brand-new events and attractions are coming very soon!

👉 Visit our festival website to learn more: https://mainstreetchestertown.org/dickens-festival/

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