Explore Chestertown
Dining
Dining
Dining
From upscale dining restaurants to authentic pizza joints, you won't be disappointed with the food here. Check out a list of some of our favorite spots to dine.
Events
Dining
Dining
Check out our local events like the famous Chestertown Tea Party or the National Music Festival.
Shopping
Shopping
Shopping
Downtown Chestertown features a range of shops from Fashionable apparel, fine jewelry, sportswear, collectibles and antiques, eclectic galleries, and so much more can be found. These independently-owned businesses not only create jobs and support our local economy, they are here to cater to customer’s individual needs.
Outdoors
Shopping
Shopping
From hiking to biking, our area boasts tons of opportunities to enjoy the great outdoors. Our favorite parks for hitting the trails are Eastern Neck Island Refuge and Sassafras NRMA
Our Dining Recommendations
Evergrain Bread Co.
Located just across the street from 114 High, this is our go-to for coffee, espresso, and incredible house made bread and pastries. You won't be disappointed when you start your day at Evergrain.
Our Menu Pick: Mini "Everknots" and an iced brown sugar latte
Bad Alfreds
Bad Alfred’s is a brewpub and distillery featuring house-made spirits, local craft beer and wood-fired pizzas. Just a short walk from 114 High.
Our Menu Pick: The High Street Pizza
Watershed Alley
A fine dining experience. The menua reflect the long-held commitment of Watershed Alley’s Chef to a combination of fresh ingredients, tasteful simplicity, and beautiful presentations - all inspired by the resources of the Chesapeake Bay watershed. Reservations recommended.
Our Menu Pick: Any housemade dessert!
Luisa's Cucina Italiana
A Chestertown staple for over 20 years, Luisa's offers authentic Italian cuisine, wood-fired pizza, and something for everyone to enjoy. Luisa's is located uptown, in the Redner's shopping plaza.
Our Menu Picks: The Fancy Salad, Crab Dip, Tortellini Emiliani
Modern Stone Age Kitchen
Scratch-made, industrial nut and seed-oil free artisan breads, pastries, delicious coffees and sandwiches.
Out Menu Picks: Housemade Granola, Iced Vanilla Latte and Friday Night Pizzas!