Chestertown
Chestertown
Annapolis
Annapolis
Driving

Chestertown to Annapolis

Updated: 31 May 2026

The trip from Chestertown to Annapolis is about 40 miles. You can drive via US-301 S, which takes about 1 hour. This is a very short and easy drive.

Total Distance: Driving distance 65 km; Air distance 50 km.
Fastest Way
Driving is the fastest at 1 hour.
Cheapest Way
Driving is the most cost-effective for individuals and groups.
Compare Chestertown to Annapolis Routes
Driving
Direct
Duration
1 hour
Avg Price
$10 - $20 in fuel
Operator
Personal Vehicle
Route
US-301 S.

The drive is very direct and easy to navigate.

Travel Tips
  • Transportation
    A car is recommended for exploring the city.
  • Dining
    Try the local seafood; it is fresh and delicious.
  • Weather
    Be prepared for hot summers and mild winters.
  • Booking
    Stay near the downtown area for easy access to attractions.
  • Walking
    Downtown is very walkable; bring comfortable shoes.
Safety Tips
  • Neighborhoods
    Research areas before booking accommodation.
  • Night Safety
    Avoid walking alone in isolated areas at night.
  • Emergency
    Keep emergency contacts handy.
  • General
    Stay aware of your surroundings in public spaces.
People Also Ask
  • Is there a train?
    No, there is no direct train service from Chestertown.
  • What is the best way to travel?
    Driving is the best way.
  • How long is the drive?
    Approximately 1 hour.
  • Is it safe to drive?
    Yes, the route is well-traveled.
  • Are there tolls?
    Yes, there may be tolls on the Bay Bridge.
Quick Info
  • From Chestertown, Maryland, United States
  • To Annapolis, Maryland, United States
  • Modes
Best Time to Travel

Spring and Fall for mild weather and outdoor activities.

Things to Do in Annapolis
1
Maryland State House
The oldest state capitol in continuous legislative use.
2
U.S. Naval Academy
A historic campus with beautiful architecture.
3
City Dock
A historic waterfront area with shops and restaurants.
4
William Paca House
A historic home with beautiful gardens.
Tags
Chestertown to Annapolis driving to Annapolis from Chestertown Maryland travel Annapolis travel guide best way to Annapolis travel from Chestertown historic city trip
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