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Downtown Chestertown, Maryland

Chestertown, MD

484 local businesses in and around Kent County. Locally owned first. Every listing dated.

Popular in Chestertown

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Only 3 Featured spots per category in Chestertown.

Recently checked in Chestertown

Browse Chestertown by category

Home services

Plumbers2 listingsElectricians2 listingsHeating and Air3 listingsRoofing1 listingContractors and Builders16 listingsLawn and Landscaping8 listingsCleaning Services2 listingsPest Control1 listingPool ServiceNone yet. Add the first oneLocksmithsNone yet. Add the first oneHome InspectorsNone yet. Add the first oneStorage Units7 listingsLaundromats and Dry Cleaning2 listings

Auto

Auto Repair19 listingsAuto Dealers3 listingsAuto Parts6 listingsGas Stations4 listings

Food and drink

Restaurants and Catering42 listingsCafes and Bakeries11 listingsBars and Pubs10 listingsGrocery and Markets10 listings

Shopping

Shopping and Gifts20 listingsPawn ShopsNone yet. Add the first onePhones and Computers7 listingsGuns and Outdoors1 listingClothing and Shoes9 listingsHardware and Farm Supply6 listingsFurniture and Home Goods5 listingsFlorists7 listings

Health and beauty

Salons, Nails and Barbers28 listingsDoctors and Clinics39 listingsDentists2 listingsCounseling and Therapy7 listingsSenior Living and Home Care7 listingsPharmacies5 listingsGyms and Fitness19 listingsVets and Pet Care9 listings

Professional

Real Estate33 listingsInsurance8 listingsLawyers9 listingsBail BondsNone yet. Add the first onePrinting and Signs1 listingAccountants, Tax and Notary5 listingsBanks and Credit Unions5 listings

Community

Churches31 listingsSchools and Childcare13 listingsColleges and Trade Schools5 listingsWeddings and Events6 listingsCity and Public Services14 listingsFuneral Homes3 listingsHotels and Lodging12 listingsFun and Entertainment17 listingsOther Local Businesses2 listings

Eastern Shore

About local business in Chestertown

Chestertown is a town of about 5,500 people in Kent County, Eastern Shore. Small Town Pages lists 484 businesses here, and 450 of them are locally owned. The most listed kinds are restaurants and catering (42), doctors and clinics (39) and real estate (33). 428 list a phone number and 9 post their hours.

Nearby towns

Questions about Chestertown

How many local businesses are listed in Chestertown, MD?

484 businesses are listed in Chestertown across 48 categories. 450 are locally owned, and 34 national brands are shown after them. Listings were last checked in September 2026.

What kinds of businesses can I find in Chestertown?

The most listed are restaurants and catering (42), doctors and clinics (39), real estate (33), churches (31), salons, nails and barbers (28) and shopping and gifts (20). Every category has its own page for Chestertown.

Which towns near Chestertown are on Small Town Pages?

Centreville (12 miles), Aberdeen (22 miles), Havre de Grace (24 miles), Clayton (24 miles) and Perryville (24 miles). Many local businesses serve more than one town.

Do businesses in Chestertown offer military, senior or first responder discounts?

None have posted one yet. Owners can add military, senior, first responder and other discounts to their listing free.

How do I add or fix a business in Chestertown?

Owners can claim their listing free and update the phone, hours and photos. Anyone can add a business we are missing with the Add a business form, and a person checks it before it goes up.

Own a business in Chestertown?

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