Downtown Chestertown Association

10/21/2026

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

10/13/2026

🎅🎄 SANTA IS COMING TO TOWN! 🎄🎅

Mark your calendars! The Downtown Chestertown Association’s Hometown Holiday Parade is coming to downtown Chestertown on Friday, November 27th, at 5:30 PM!

And the holiday fun doesn’t stop with the parade! Santa’s House will be back this year, with visits with Santa on Saturdays from 10 AM to 2 PM🎅

🎄 BE PART OF THE HOLIDAY MAGIC! 🎄

✨ Have a business? Decorate a float and show it off!
✨ Have a youth group or organization? Get everyone together and join the parade!
✨ Want to support the community? Become a sponsor!

This is a wonderful opportunity to celebrate the season, bring our community together, and make downtown Chestertown shine for the holidays!

📣 Interested in participating, volunteering, or becoming a sponsor? Reach out to the Downtown Chestertown Association, [email protected]

Let’s make this year’s Hometown Holiday Parade one to remember! ❤️💚

10/12/2026

🎃 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
👉 Link Below to Register

🎃 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!

🍂 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!

Take this survey powered by surveymonkey.com. Create your own surveys for free.

10/05/2026

Whether you’re looking for a new piece, considering a custom design, have jewelry you’d like to sell or trade toward something new, I’d love to help you find the right piece.

Visit the link to book your one-on-one appointments in downtown Chestertown.

A limited number of appointments are available next week so it’s a great time to get on the schedule!

443-480-8482
www.NelsonGold.com
License 2952

10/05/2026