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