Welcome to Chestertown

Elisabeth
Welcome to Chestertown

Food scene

Fantastic wood-fired pizza and drinks! Make sure to tell the owners, Al and Jen, that we sent you.
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BAD Alfred's Distilling
323 High St
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Fantastic 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.
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Chester River Wine & Cheese Co.
117 S Cross St
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Gourmet 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
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Harbor Shack
20895 Bayside Ave
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Waterfont, dock bar vibe. Great food, tropical drinks. 15-20 min drive. Family Friendly
21+ only.
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LTO
337 1/2 High St
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21+ only.
Soft Serve ice cream, burgers, fries, ect. BEST Sundaes
The FREEZE
717 Washington Ave
Soft 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!
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Evergrain Bread Company
201 High St
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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!
Old fashioned lunch counter
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Stam's Luncheonette
215 High Street
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Old fashioned lunch counter
Breakfast and lunch/ coffee bar. Great place to and get remote work done with a cup of coffee.
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Play It Again Sam
108 S Cross St
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Breakfast 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 St
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Learn 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.
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Washington College
300 Washington Ave
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Walk around the campus, check out their events page. They have daily events open to the public, most are free.

Shopping

Interior design store, curated by our lovely locals
Village House
103 S Cross St
Interior design store, curated by our lovely locals
Gifts, books, everything!
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Twigs & Teacups
111 S Cross St
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Gifts, books, everything!