Downtown Chestertown Association

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Chestertown, MD
Downtown Chestertown Association

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Historic Downtown Chestertown on Maryland's Eastern Shore: where art, history and nature meet.

Dedicated to promoting businesses and services in Chestertown, as well as hosting events and activities to increase tourism and encourage residents to shop locally

10/30/2026

🎄❤️ ADOPT A SENIOR – SPREAD A LITTLE HOLIDAY JOY! ❤️🎄

The holiday season is a time for giving, and here’s a wonderful way to make a difference right here in our community!

Chestertown Nursing & Rehab is inviting the community to participate in their Adopt a Senior program. By choosing a tag from the tree and purchasing a few requested gifts, you can help make the holidays a little brighter for one of their residents. 🎁

Here’s how you can participate:

Choose a tag from the tree and register it with the receptionist.
Purchase the gift(s) listed on the tag.
Wrap the gifts and attach the tag.
Return your gifts to the Activities Department by the due date.

It doesn’t take much to make someone’s holiday special. A small gift can bring a big smile and remind someone that they are loved and remembered.

Let’s come together as a community and make this holiday season a little brighter for our local seniors! ❤️

Small gifts. Big smiles. A whole lot of kindness! 🎅🎄

10/28/2026

10/28/2026

10/27/2026

🍂🎃 SCARECROW CONTEST WINNERS! 🎃🍂

The Downtown Chestertown Association would like to thank everyone who participated in this year’s Scarecrow Contest! We loved seeing all the creativity and festive spirit throughout downtown.

Congratulations to our winners:

🥇 First Place: The Bookplate
🥈 Second Place: The Kitchen and Pub at The Imperial
🥉 Third Place: Mimi’s Closet

📸 Pictures are included below in order, from first place through third place.

Thank you again to all of our participants for helping make downtown Chestertown so much fun this fall! 🍁

10/27/2026

🎄🎅 BE A PART OF CHESTERTOWN’S HOLIDAY TRADITION! 🎅🎄

The Downtown Chestertown Association is getting ready for our Hometown Holiday Parade on Friday, November 27th, at 5:30 PM, and we want YOU to be part of the fun!

✨ We’re inviting local businesses, schools, clubs, community organizations, and families to join the parade lineup!

Whether you want to decorate a float, show off your organization, dress up for the holidays, or come up with something creative, we’d love to have you participate. Let’s fill downtown Chestertown with holiday spirit and make this a parade to remember! ❤️💚

🎁 Want to participate? We’d love to hear from you!

We’re also looking for sponsors to help bring Santa to town, make Santa’s House festive, and provide prizes for parade participants.

📧 For parade entry forms, sponsorship information, or questions, email [email protected].

Let’s make this holiday season extra special for our community. Gather your group, get creative, and join us in welcoming Santa to Chestertown! 🎅🎄

10/23/2026

10/21/2026

🎄🎅 SAVE THE DATE! 🎅🎄

The Downtown Chestertown Association’s Hometown Holiday Parade & Santa’s Arrival is coming!

📅 Friday, November 27, 2026
⏰ 5:30 PM
📍 Downtown Chestertown

✨ Want to be part of the parade? Businesses, schools, clubs, organizations, and families are invited to join the fun!

📧 Email [email protected] for parade entry and sponsorship information.

Mark your calendars and get ready to kick off the holiday season with us! ❤️💚

10/15/2026

🎃 IT’S TIME TO DECORATE CHESTERTOWN! 🎃

The 2026 Chestertown Scarecrow Contest is coming, and we want to see what you can dream up! 👻🍂

Since the parking meters are no more, you have even more freedom to get creative with where you display your scarecrow. Alternate “posts” and locations are welcome — use your imagination!

🧙‍♀️ A few things to know:

📅 Registration Deadline: Wednesday, October 14

🎃 Set Up: Friday, October 16 – Thursday, October 22
📍 If you’d like to display your scarecrow in front of a business, please coordinate directly with the business.

🏆 Judging: Saturday, October 24
💰 Cash prizes will be awarded!
⤵️Link to register below

🍂 Scarecrow Removal: Sunday, November 1 – Tuesday, November 3

Please make sure your scarecrow is clearly marked with your organization’s name.

🚫 No political messaging, please.

Whether you go spooky, silly, creative, or completely over the top, let’s fill Downtown Chestertown with scarecrows and get everyone in the Halloween spirit! 🎃👻🍁

Get your group together and start creating!

https://www.surveymonkey.com/r/DLT29HS

Address

Chestertown, MD
21620

Website

http://www.downtownchestertown.org/

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