How do I get to Chestertown, MD?

To get to Chestertown, you can drive via Route 213 or Route 301 if you are coming from the north or south. If you are traveling by air, the nearest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI), which is approximately 70 miles away. From BWI, you can rent a car or take a shuttle service to Chestertown.

Where can I park downtown?

There are several parking options available in downtown Chestertown, Maryland. Here are a few options:

  1. On-street parking: There are parking spots available on High Street, Cross Street, and Queen Street.
  2. Municipal lots: There are several municipal parking lots located throughout downtown Chestertown. The lots are free to use, but they do have time limits. The lots are located on Spring Street, Cannon Street, and Calvert Street.

Overall, parking in downtown Chestertown is fairly easy and convenient. However, it’s always a good idea to arrive early prior to a downtown event to ensure you can find a spot!

When is the best time to visit Chestertown?

The best time to visit Chestertown is during spring (April to June) and fall (September to November) when the weather is pleasant and the town is less crowded. Additionally, Chestertown hosts several events throughout the year, such as the Tea Party Festival and the Chestertown Jazz Festival, which attract visitors from all around.

Are their any accommodations available in Chestertown, MD?

Yes, there are various accommodations available in Chestertown to suit different budgets and preferences. You can find charming bed and breakfasts, boutique hotels, and vacation rentals in and around the town. It is advisable to make reservations in advance, especially during peak tourist seasons.

Are there any local events or festivals in Chestertown that I can attend?

Yes, Chestertown hosts several events and festivals throughout the year. The Tea Party Festival in May, the Chestertown Jazz Festival in September, and the Chestertown First Friday events are some of the highlights. These events showcase local culture, music, arts, and provide a great opportunity to experience the community spirit. You can view the Signature Events here.

What colleges are located in Chestertown, MD?

Chestertown is home to Washington College, the 10th oldest college in the nation!

Is there a visitor information center available?

Yes, there is a visitor information center located in downtown Chestertown. It provides maps, brochures, and helpful advice regarding local attractions, dining, and activities. The friendly staff can assist you in planning your visit and answer any questions you may have about the area.

Is there public transportation available?

Chestertown does not have a comprehensive public transportation system; however, there are some options available. You can take advantage of local taxi services or hire a car rental for convenient transportation within the town and nearby areas.

Are there any dining options available in Chestertown, MD?

Chestertown offers a diverse range of dining options to cater to different tastes. From seafood restaurants to farm-to-table eateries, you can find something to satisfy your palate. The town also boasts several charming cafes and bakeries that offer delicious snacks and desserts.

What popular attractions are there in Chestertown, MD?

Chestertown offers a range of attractions for visitors to enjoy. Some popular ones include Washington College, the Cray House and Garden, the Schooner Sultana, the Chestertown Farmers Market, and the Garfield Center for the Arts. The historic downtown area also offers charming shops, galleries, and restaurants to explore. Start your visit here!

Are there outdoor recreational activities in Chestertown, MD?

Yes, Chestertown offers various outdoor recreational activities. For nature enthusiasts, you can visit the Wilmer Park, where you can enjoy picnicking, walking trails, and waterfront views. You can also go kayaking, canoeing, or paddleboarding on the Chester River or nearby Chesapeake Bay. Additionally, there are several golf courses and parks in the area for outdoor enthusiasts.

Is Chestertown, MD a good place to live?

Yes, Chestertown is known for its rich history, low cost of living, and charming downtown area! It is a great place to live and work!


5 Things to Do in May in Chestertown

5 Things to Do in May in Chestertown

In May, Chestertown, Maryland offers a range of activities and experiences to enjoy. Here are five things you can do: Attend the Chestertown Tea Party Festival: Join in the town's iconic annual event that commemorates the historic Tea Party incident. Enjoy...

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How to get involved in Main Street Chestertown

How to get involved in Main Street Chestertown

There are a variety of ways to get involved with Main Street Chestertown. You can volunteer to help with clean-ups, community events, or join one of the many Main Street Chestertown committees. Additionally, you can attend special events, like art walks, festivals, or...

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Top Five Reasons to Shop Small

Top Five Reasons to Shop Small

1. Supporting Local Businesses: Shopping small helps to support local businesses and the economy of a community. By shopping small, you are helping to keep money local and stimulate the economy of the area. 2. Personalized Shopping Experience: Small businesses are...

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Why Should You Become a Corporate Sponsor?

Why Should You Become a Corporate Sponsor?

As a corporate sponsor, you have the opportunity to create a lasting connection with your target audience. You can use your sponsorship to reach new customers and build brand awareness. Corporate sponsors also have the ability to leverage their resources to support a...

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First Friday’s in Downtown Chestertown

First Friday’s in Downtown Chestertown

First Friday in Chestertown is a monthly event that celebrates the town's vibrant arts and culture. Held the first Friday of each month, First Friday is an evening of music, art, food, and fun in downtown Chestertown. Local businesses and organizations partner with...

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Curious about frequently asked questions like "Where to park?" and "What time does First Friday start?" Click here to find all the answers you need in our comprehensive FAQ section.


Discover the insider knowledge on where to find the best cream of crab soup in town, indulge in the tastiest ice cream, and plan your visit to the art galleries. Let us guide you to create a spectacular experience in Chestertown that combines culinary delights, sweet treats, and a journey through the town's vibrant art scene.


Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!

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(410) 778-2991


Chestertown Town Hall
118 N. Cross Street
Chestertown MD 21620


PO Box 427
Chestertown MD 21620

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