Downtown Chestertown Association

06/20/2026

🎉 Father’s Day is this Sunday! 🎉

It’s a beautiful weekend to stroll through Downtown Chestertown and find the perfect gift for Dad. Whether he’s into local art, books, sweet treats, apparel, or unique finds, our downtown shops have something special waiting for him.

And if you’re not quite sure what to get, give the gift of choice with Chestertown Cash! It’s accepted at many participating downtown businesses, allowing Dad to shop, dine, and explore his favorite local spots.
Shop local, support small businesses, and make Father’s Day extra special this year. ❤️

06/19/2026

06/17/2026

06/17/2026

06/17/2026

🎉 Give Dad the Gift of Local This Father’s Day!

Looking for the perfect Father’s Day gift? Give him something he’ll truly enjoy — Chestertown Cash!

Whether Dad loves great food, unique gifts, local art, sweet treats, or discovering hidden gems around town, Chestertown Cash lets him choose exactly what he wants while supporting the businesses that make our community special.

🛍️ Shop Local
🍽️ Dine Local
❤️ Support Local

This Father’s Day, skip the ordinary and give Dad the gift of a downtown experience he’ll love.

Chestertown Cash is accepted at many participating Downtown Chestertown businesses, making it the perfect way to celebrate Dad while keeping dollars local.

🎁 Treat your dad this Father’s Day with Chestertown Cash!

💙👔🎣🍔🛍️

06/07/2026

A huge THANK YOU to everyone who came out to enjoy First Friday in Downtown Chestertown! ❤️

We loved seeing our streets filled with friends, families, visitors, and neighbors supporting our amazing downtown community. A special thank you to all of our incredible shops, restaurants, galleries, and businesses for staying open late and helping make the evening so special.

Your support of our local businesses means so much and helps keep our downtown vibrant and thriving. We hope you had a wonderful evening, and we can’t wait to see you again next month for another fantastic First Friday!

06/05/2026

06/05/2026

Dont forget to swing by KidSPOT on First Friday for some wholesome fun for the whole family. It’s going to be a great evening in Chestertown!