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.
13 locals raden deze aan
BAD Alfred's Distilling
323 High St
13 locals raden deze aan
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.
22 locals raden deze aan
Chester River Wine & Cheese Co.
117 S Cross St
22 locals raden deze aan
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
25 locals raden deze aan
Harbor Shack
20895 Bayside Ave
25 locals raden deze aan
Waterfont, dock bar vibe. Great food, tropical drinks. 15-20 min drive. Family Friendly
21+ only.
9 locals raden deze aan
LTO
337 1/2 High St
9 locals raden deze aan
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!
37 locals raden deze aan
Evergrain Bread Company
201 High St
37 locals raden deze aan
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
8 locals raden deze aan
Stam's Luncheonette
215 High Street
8 locals raden deze aan
Old fashioned lunch counter
Breakfast and lunch/ coffee bar. Great place to and get remote work done with a cup of coffee.
25 locals raden deze aan
Play It Again Sam
108 S Cross St
25 locals raden deze aan
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
17 locals raden deze aan
Sultana Education Foundation
200 S Cross St
17 locals raden deze aan
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.
16 locals raden deze aan
Washington College
300 Washington Ave
16 locals raden deze aan
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!
12 locals raden deze aan
Twigs & Teacups
111 S Cross St
12 locals raden deze aan
Gifts, books, everything!