First Friday
On the first Friday of the month, downtown shops stay open until 8 pm and galleries stage opening and special events.
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Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Featured
Chestertown Car Show
The Chestertown Car Show accepts all years, makes & models of cars, trucks in 10 classes. There will be over 10 trophies for specific classes, awarded on a judged basis. Food Trucks will be onsite. Beer and Wine will be sold by Mainstreet Chestertown. There’s more than just cars and trucks in Chestertown, we have a thriving arts district, […]
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Cars on High
High St. High St., Chestertown, MD, United StatesEvery third Thursday, April through October, weather permitting. Owners share classic, antique, and custom cars on High Street.
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
Featured
Downrigging Weekend
The Sultana Education Foundation's Downrigging Weekend highlights Tall Ships and Bluegrass, along with nautical history and Chesapeake Bay ecology.
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!
First Friday
On the first Friday of the month, downtown shops stay open until 8 pm and galleries stage opening and special events.
Farmers’ & Artisans’ Market
High St & Cross StVisit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts and more!