How To Spend the Day in the Chestertown Historic District

Chestertown Historic District

When you stay at Inn at Huntingfield Creek, you’ll have everything you need for the ultimate Eastern Shore retreat at your fingertips. However, if you’re itching to explore our gorgeous area, pay a visit to the Chestertown Historic District. Chestertown is one of Maryland’s oldest counties and features charming brick sidewalks, antique stores, delicious restaurants, historic sites and tours, and scenic views of the Chester River.

Our Chesapeake Bay Area Guide is a valuable resource when it comes to planning your next getaway. It contains local insight on the area’s best attractions, events, and more!

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Getting To Chestertown From Inn at Huntingfield Creek

The drive from our inn to Chestertown only takes about 20 minutes. It’s the perfect distance for a leisurely day trip. You’ll head east towards MD-445 North and take MD-20 East for about 14 miles. You’ll arrive at a roundabout, which means you’ve arrived in Chestertown.

All About Chestertown Historic District

For History Buffs

A popular historical site in Chestertown is the Kent County Civil War Monument in Monument Park. The park is located on High Street and features a Civil War trail and the monument, which lists the names of Maryland soldiers sent to fight for the Union and Confederate armies.

One of the best ways to embrace Historic Downtown Chestertown is to go back in time with a walking tour. These fascinating tours focus on life in Chestertown before and during the Revolutionary War.  The tour concludes with a cup of tea at White Swan Tavern, which General George Washington would visit and enjoy a refreshment.

  • Walking tours are offered for five people up to 15 people per tour, at $15 a person
  • The Historical Society of Kent County has also made a paper version of this tour available to those who prefer to explore independently. Pick up a copy of the guide to the tour at the Visitor’s Center on Cross Street

For Foodies


Chestertown takes pride in providing farm-to-fork dining. After a day roaming the town, sit back and relax and enjoy incredible cuisine at one of the many outstanding eateries.

For Shopaholics

The two main streets in Chestertown are High Street and Cross Street. Here you’ll find an array of unique bookstores, antique shops, boutiques, and more. Stop in locally owned businesses and pick up a souvenir to remember your trip by!

Stay in Kent County’s Finest Accommodations

Woods Cottage Fireplace

Book a stay with us at Inn at Huntingfield Creek and be surrounded by the beauty of Maryland’s Eastern Shore. We’re happy to offer private cottages that will make you feel like you’re in your own oasis. Each cottage is fully-furnished and features a cozy bedroom, spacious living area, bistro kitchen, panoramic views of our expansive inn grounds.

Browse our availability and book a relaxing vacation with us. We can’t wait to host you.

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