Places in Chestertown
Two centers, 624 places in Chestertown
624 places in Chestertown: 56 places to eat and drink, 58 shops, 85 things to do and 8 places to stay. Local spots first, with directions to every one.
All places
624
112 per 1,000 residents
Eat & drink
56
10 per 1,000 residents
Shops
58
14 gifts · 5 antiques · 5 books
Things to do
85
21 outdoors · 28 arts · 14 landmarks
Places to stay
8
1.4 per 1,000 residents
What kind of places does Chestertown have?
Read from every listing. The page puts what stands out first.
Two town centers240 places within a five-minute walk of High St, and 68 more around Washington Ave.Galleries & stages28 galleries, museums, theaters and music venues.A food town56 places to eat and drink, 10 per 1,000 residents.A coffee town12 independent cafés, coffee shops and bakeries, 14 with the sweet shops and chains.
★ What stands out · The map
Where Chestertown gathers
240 of Chestertown’s 624 places sit within a five-minute walk of High St. A second center gathers around Washington Ave.
240places in a five-minute walk of High St38% of Chestertown’s places
68around Washington Ave11% of Chestertown’s places
Things to do
See all →85 things to do
28 arts & culture, 22 fitness & sports, 21 parks & outdoors. Local spots first.
Garfield Center For The Arts At The Prince Theatre
Theaters and performance venues · 210 High St
Johnson Fitness Center
Gym · Johnson Lifetime Fitness Center, 300 Washington Ave., Bldg# JFCATH1
Casey Swim Center
Sports and recreation venue · 300 Washington Avenue, Bldg# CSATH3
Rose O'Neill Literary House at Washington College
Campus building · 300 Washington Ave
Washington College Alumni House
Campus building · 226 Washington Ave
Chestertown Landing Apartments
Landmark and historical building · 100 Schooner Way
Kent Crossing and Colonial Manor Apartments
Landmark and historical building · 101 Morgnec Rd
Chestertown Tea Party Festival
Landmark and historical building · 400 High St
Eat & drink
See all →56 places to eat & drink
33 restaurants, 14 cafés & treats, 7 bars & breweries. Local spots first.
Shops
See all →58 shops
14 gifts & boutiques, 7 home & hardware, 6 clothing. Local spots first.
Hooked On The River
Hunting and fishing supplies · 903 Washington Ave
Mill Pond Outfitters / Eastern Shore Decoys
Sporting goods · 102 Sutton Way
Places to stay
See all →8 places to stay
7 hotels & inns, 1 camping & rentals. Local spots first.
Everyday
See all →325 errands & services
Groceries, gas, the barber, the vet, the bank.
Health care 69Walgreens · Labcorp · Um Smg - Women's Health At ChestertownOffices & pros 66Coldwell Banker Chesapeake Real Estate · Benchworks · Beth Ostrander - Doug Ashley Realtors, LLCBanks & insurance 33Western Union · Bruce Valliant - Raymond James · Chesapeake Bank & TrustHair & beauty 26Emily's Salon · Black Opal Piercing · Confidence Beauty LoungeHome services 23Smith Bennie Funeral Homes · Adept Home Services · Allstate Building CompanyAuto & gas 22AUTO PLUS · Bennett's · Chestertown Auto Plus and MarineGroceries & convenience 12Redner's Warehouse Markets · Chestertown Natural Foods · Jj's Deli & Liquors LlcPets 4Cat Colloquium · Coco's Pet Center · High Street Veterinary PracticeOther services 70Bitstop Bitcoin ATM · Bitstop Bitcoin ATM · Kent County Tourism
Community
See all →92 schools, churches & public places
Where Chestertown learns, worships and gets things done.
Community groups 34Main Street Chestertown · Foreman's Branch Bird Observatory at Washington College · Allyson Stewart International MinistriesTown & public services 25United States Postal Service · Chestertown Volunteer Fire Company · Town of ChestertownSchools & childcare 22HH Garnet Elementary School PTA · Washington College · Chester River Adventist SchoolPlaces of worship 11Sacred Heart Catholic Church · Christ First United Methodist Church · 30th Annual Christmas Bazaar by Emmanuel Church
Talk & tips
Favorites, openings and closings from Chestertown neighbors.
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Is Cafe Sado the best place to eat in Chestertown?
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Some place details from Overture Maps (CDLA-Permissive-2.0), checked against the Census town line. Places added by neighbors go live once a second neighbor confirms them. Spot a mistake? Open the place and tap Edit mode.
How we sort and count
Each list puts neighbor favorites first (ratings and photos), then the most complete listings (a website, a phone number, a note), with local, independent spots ahead of national chains. Categories come from each place’s map category, so a café filed under “Shops” still shows up with the cafés. “A five-minute walk” is a quarter mile from the busiest spot on the map. Per-1,000 figures use the Census population.