Welcome to Chestertown
Food scene
Fantastic wood-fired pizza and drinks! Make sure to tell the owners, Al and Jen, that we sent you.
13 abantu bendawo batusa
BAD Alfred's Distilling
323 High StFantastic wood-fired pizza and drinks! Make sure to tell the owners, Al and Jen, that we sent you.
Gourmet cheese, wine and snack shop! The owner's Jen and John are FANTASIC. Check out their sister store, Welcome Home.
22 abantu bendawo batusa
Chester River Wine & Cheese Co.
117 S Cross StGourmet cheese, wine and snack shop! The owner's Jen and John are FANTASIC. Check out their sister store, Welcome Home.
Waterfont, dock bar vibe. Great food, tropical drinks. 15-20 min drive. Family Friendly
25 abantu bendawo batusa
Harbor Shack
20895 Bayside AveWaterfont, dock bar vibe. Great food, tropical drinks. 15-20 min drive. Family Friendly
LTO
337 1/2 High St21+ only.
The FREEZE
717 Washington AveSoft Serve ice cream, burgers, fries, ect. BEST Sundaes
Bakery and Coffee. Try any of their lattes over ice! Their grab and go sandwiches are my favorite. Don't be intimidated by the line. It moves fast!
37 abantu bendawo batusa
Evergrain Bread Company
201 High StBakery and Coffee. Try any of their lattes over ice! Their grab and go sandwiches are my favorite. Don't be intimidated by the line. It moves fast!
Stam's Luncheonette
215 High StreetOld fashioned lunch counter
Breakfast and lunch/ coffee bar. Great place to and get remote work done with a cup of coffee.
25 abantu bendawo batusa
Play It Again Sam
108 S Cross StBreakfast and lunch/ coffee bar. Great place to and get remote work done with a cup of coffee.
Sightseeing
Learn about the Chesapeake Bay, schedule kayak tours and sails aboard a Tall Ship
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Sultana Education Foundation
200 S Cross StLearn about the Chesapeake Bay, schedule kayak tours and sails aboard a Tall Ship
Walk around the campus, check out their events page. They have daily events open to the public, most are free.
16 abantu bendawo batusa
Washington College
300 Washington AveWalk around the campus, check out their events page. They have daily events open to the public, most are free.
Shopping
Village House
103 S Cross StInterior design store, curated by our lovely locals
Twigs & Teacups
111 S Cross StGifts, books, everything!