1map logoGo to main page

Annapolis, MD, USA to Chestertown, MD, USA from $8: 3 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Annapolis, United States of America
to
Chestertown, United States of America

How to Get from Annapolis to Chestertown: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$8 - OtherBest price
76 kmDistance
1h 3m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Annapolis to Chestertown with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Bus
Taxi
Average Duration
1h  48m
Estimated price
$40-55
Recommended
Company
various
Drive
Average Duration
1h  3m
Estimated price
$8-13
Cheapest
route map
Distance: 76 km
Duration: 1h 3m

See more options

Company
various
Taxi
Average Duration
1h  3m
Estimated price
$110-140
Browse car rentalsExplore flights

Traveling From Annapolis to Chestertown

The journey from Annapolis offers a transition from a lively waterfront city brimming with historic charm to the tranquil, small-town atmosphere of Chestertown, where you can enjoy a slower pace and picturesque river views.

Best Neighbourhoods in Chestertown

Chestertown features charming neighborhoods, each offering unique experiences for visitors.

Historic District
• Home to beautiful colonial-era architecture.
• Bustling with art galleries and local shops.
Chestertown Waterfront
• Scenic views of the Chester River.
• Great spot for waterfront dining and strolls.
Fowler Beach
• Serene beach area for relaxation and picnics.
• Ideal for birdwatching and nature walks.

Best Times To Visit Chestertown's Attractions

Timing your visit can greatly enhance your experience in Chestertown's attractions.

Chestertown Historic District
Weekdays in the morning offer a quieter stroll through its charming streets.
Chester River
Early mornings or late afternoons provide stunning views without the crowds.
Washington College
Visit during campus events or tours to connect with local culture.

Chestertown Weather: What to Expect Year-Round

Chestertown experiences a humid subtropical climate, with warm summers and cool winters, making spring and fall the ideal seasons to visit. Understanding local weather patterns helps you plan activities, ensuring a more enjoyable and comfortable travel experience.

Dining Recommendation in Chestertown

For a taste of Chestertown's local flavor, try the crab cakes at The Fish Whistle, where the focus is on fresh, locally-sourced ingredients and a laid-back, riverside atmosphere. This dining experience contrasts with Annapolis's more upscale seafood venues, inviting you to savor dishes that capture the essence of the Chesapeake Bay in a cozy setting.

Annapolis - Chestertown operators

Explore transport companies operating between Annapolis and Chestertown, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Bus
Website
qac.org

Bus from Church Circle Annapolis to Kramer Center Centreville

Average Duration
1h 25m
Estimated price
$430-430
Taxi

Taxi from Kramer Center Centreville to Chestertown

Average Duration
23m
Estimated price
$40-431

Taxi from Annapolis to Chestertown

Average Duration
1h 3m
Estimated price
$110-140

Annapolis to Chestertown: Overview of Bus, Train, Flight, and Car Trips

Traveling between Annapolis and Chestertown offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Departing from charming Annapolis your scenic road trip to Chestertown spans 47 miles and promises a delightful drive through Maryland's picturesque landscapes. 🌳 Expect a journey of approximately 1 hour and 3 minutes filled with opportunities to explore quaint towns and enjoy the peaceful countryside as you make your way to Chestertown. 💸 With prices ranging from $8 to $13 for the trip, driving from Annapolis to Chestertown offers an affordable and enjoyable way to discover the beauty of Maryland's Eastern Shore.
Average price
$8 - $13

Frequently asked questions

Find out more about the route from Annapolis to Chestertown.

Or choose the category:
The distance between Annapolis and Chestertown is approximately 28 miles by air or direct route. However, the road distance is around 47 miles. By taking a combination of bus and taxi, it typically takes around 1 hour and 48 minutes to travel from Annapolis to Chestertown. On the other hand, if you prefer driving by car, it usually takes around 1 hour and 3 minutes to travel from Chestertown to Annapolis.
The most cost-effective transportation option for traveling from Annapolis to Chestertown is to drive. It is estimated to cost around $8 to $13 for the road distance of 47 miles, and the journey takes approximately 1 hour and 3 minutes. Alternatively, taking a taxi is the quickest way, also taking 1 hour and 3 minutes, but it is more expensive, costing around $110 to $140.
To get from Annapolis to Chestertown without using public transportation, the best option is to drive. The driving distance between Annapolis and Chestertown is 47 miles, and it takes approximately 1 hour and 3 minutes to complete the journey. The cost varies depending on factors such as fuel prices, but typically ranges from $8 to $13 for a one-way trip by car.
To travel from Annapolis to Chestertown without a car, the best option is to take a bus and then a taxi. The journey takes approximately 1 hour and 48 minutes and the cost ranges from $40 to $55. The bus is the primary mode of transportation, while the taxi is required for the final leg of the trip.
There are multiple accommodation options in and around Chestertown. You can choose from at least 11 hotels in the area. Prices for these hotels start at $73 per night. It is recommended to do some research and compare the amenities, location, and customer reviews to find the best option that suits your needs and budget.
Yes, you can get from Annapolis to Chestertown by bicycle. Keep in mind that road conditions and traffic may affect your travel time.