Downtown Chestertown Association

09/06/2026

❤️ THANK YOU, CHESTERTOWN! ❤️

What a wonderful First Friday in Downtown Chestertown!

A huge thank you to everyone who came out, walked our streets, visited our shops, enjoyed the food, listened to the music, and helped make the evening such a great one. Your support means so much to our local businesses and to our community.

And to all of our downtown businesses and participating organizations — thank you for staying open, welcoming visitors and creating specials. First Friday simply wouldn’t happen without you!

We also want to thank our partners who helped make this special Welcome Back First Friday possible. It was wonderful to see our community come together to welcome students back and celebrate all that makes Downtown Chestertown such a special place.

Thank you for supporting local, shopping local, and being part of our downtown community. We’ll see you at the next First Friday! 🎉

Downtown Chestertown — where our community comes together. ❤️

09/04/2026

🎉 CHESTERTOWN FIRST FRIDAY IS TODAY🎉

Welcome Back, Students!

Join us Friday, September 4th from 5–8 PM on High Street for a fun evening in downtown Chestertown!

This First Friday is a combined community celebration featuring the United Way Non-Profit Fair, food trucks, shopping, games, and more!

🍴 FOOD TRUCKS
• Walker Family
• Ricks Rolling Restaurant
• Sassy Sips

🎨 RIVER ARTS
Enjoy a pop-up exhibition at River Arts.

🎯 OUTSIDE GAMES FOR ALL!
Come out and enjoy some fun outdoor games on High Street!

🎓 STUDENT ID = GREAT DEALS!
Students can show their ID and enjoy discounts offered at:
• Bespoke Chocolate
• Bee Crafty
• Riverside Unique
• And others!

Come downtown, bring your friends, grab some food, shop local, and enjoy the evening!

Shop Local. Eat Local. Support Local. 💙

We can’t wait to see everyone on High Street!

09/03/2026

09/03/2026

09/02/2026

09/01/2026

🎉 FIRST FRIDAY IS THIS FRIDAY! 🎉

Downtown Chestertown is the place to be this Friday, September 4th!

September’s First Friday is a community-wide Welcome Back celebration for Washington College students and a special event supporting the United Way.

This First Friday is a combined effort of Washington College, United Way, Main Street and the Downtown Chestertown Association, working together to bring our community and students downtown for a fun evening.

Come out, enjoy downtown, support our local businesses, grab something to eat, and help us welcome the students back to Chestertown! ❤️

🛍️ Stores will be open late
🍴 Food & fun downtown
🎶 A great night to be in Chestertown

Bring your friends, bring the family and come celebrate First Friday with us!

See you downtown this Friday! 🥳

09/01/2026

Celebrating all of our recent joys...

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🎼 A great summer semester of music classes!

🎵 An upcoming fall semester, with spots still open.

🎶 Our wonderful staff & friends !!

🎧 Our amazing staff pizza party today (Thanks to Procolinos in Chestertown!)

🎹 All of our loyal customers, students, and supporters :)

🎤 And... 15 years of our store, MusicLife! How exciting is that?!

Feel free to comment and let us know what YOU love about MusicLife. And of course, thank you to everyone who is a part of our musical family. Our gratitude is beyond words, always.

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