Looking for a paving contractor in Chestertown, MD? Describe your project once and up to three paving contractors who work in Chestertown and Kent County get back to you with a quote. It's free and there is no obligation.
Chestertown is home to about 5,702 people (2024 Census Bureau estimate), a growing community (+3.0% since 2020). With 1,981 people per sq mi, it is a suburban area. Freeze-thaw cycles, heat and heavy vehicles wear out local driveways.
Chestertown at a glance
- Population (Census Bureau estimate, 2024)
- 5,702 (+3.0% since 2020)
- Rank in Maryland
- 41st of 157 cities and towns
- Land area
- 2.9 sq mi
- Population density
- 1,981 people per sq mi (suburban)
- Type
- Town (Chestertown town)
- Main county
- Kent County
What to check before hiring in Chestertown
- Base: ask how deep the base will be and how it is compacted.
- Permit: in Maryland, street aprons may need a city permit.
- Scams: avoid unsolicited "leftover asphalt" offers.
- Price drivers: area, base work, thickness and access.
Useful official resources
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National Asphalt Pavement Association
Official information and guidance.
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FTC: home improvement scams
Official information and guidance.
Services available in Chestertown
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Asphalt driveway
New or replacement asphalt driveway with base preparation.
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Repairs and sealcoating
Crack filling, patching and sealcoating of an existing driveway.
Frequently asked questions in Chestertown
How much does an asphalt driveway cost in Chestertown, MD?
It depends on area, base work and thickness. Describe your driveway: contractors who serve Chestertown reply with a quote.
How long before I can drive on it?
Often a couple of days; longer in hot weather.
Asphalt or concrete?
Asphalt usually costs less upfront; concrete lasts longer with less maintenance.
Which paving contractors will contact me?
Up to three independent paving contractors who serve Chestertown and the surrounding area, chosen for the service you need. Your details are shared only with your consent.
Source: U.S. Census Bureau, Population Estimates Program (Vintage 2024) and Gazetteer Files (public domain), imported on 10/31/2026. Figures describe the incorporated place or county as published; they are shown for information only.