The Best Things to Do Around Chestertown, MD

Some of the best vacations take place in destinations that feature a harmonious combination of rich history, a thriving arts scene, and plenty of stunning sights. The Eastern Shore of Maryland is one of those rare spots! In the heart of the Eastern Shore, you’ll discover the charming town of Chestertown. This is home to Washington College, one of the oldest universities in America, and countless other attractions. Below, we’ve compiled just a few of the best things to do around Chestertown, MD! For a complete guide to our favorite local activities:

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The Top Reasons Why You Need a Getaway in Chestertown, MD

To Experience Unique Culture and History

You’ve probably heard the phrase “Everyone you meet can teach you something new.” The same wisdom applies to destinations! Travel opens your mind and exposes you to new and different ways of life. The Eastern Shore of Maryland is the perfect place to learn all about the Mid-Atlantic’s vibrant culture. Historic Chestertown boasts an array of museums and historic sites that encourage visitors to get to know a unique piece of the country’s storied past. Here are the best places to encounter Eastern Shore history:

To Reset in Nature

If you find yourself hopping from one enclosed space to the next, it may be time to reset in nature! Studies show that just being outdoors can improve your memory, spark your creativity, and ignite your senses. Luckily, The Eastern Shore of Maryland is an ideal place to unplug and recharge in the fresh air! Here are some of the best ways to refresh and reset in the great outdoors of Eastern Maryland:

To Experience Fantastic Food and Wine

You may have heard about Maryland’s delicious coastal cuisine (crab, anyone?), but have you actually tried it for yourself? There’s no time like the present! One of the best aspects of travel is trying new cuisines and indulging in an extra dessert or glass of wine. Here in Chestertown, there’s no shortage of delicious restaurants to try for a taste of the region. Here are our top suggestions for delighting your taste buds:

To Think Like an Artist

Art appreciators and creators will feel right at home on The Eastern Shore of Maryland! There are so many high-quality galleries, theaters, and one-of-a-kind architectural structures here in Chestertown. There’s no better way to get to know an area than by exploring its local art scene, so here are just a few of the ways to enjoy the work of Maryland’s best creatives:

To Celebrate the Season

No matter what your favorite time of year is, The Eastern Shore of Maryland offers an assortment of festive events for every season! Chestertown in particular is a true year-round destination. Here’s how to enjoy it when you come to visit:

To Go on a Shopping Spree

To relieve stress, some people do crafts. Some people cook. Some people get lost in nature for a little while. Others engage in a little retail therapy! Historic Chestertown is brimming with local boutiques where you can find countless one-of-a-kind creations. If you’re a shopaholic, there’s no better place to be! Here are just a few of our favorite local shops on The Eastern Shore of Maryland:

To Get a Good Night’s RestRussell's Cottage at Brampton Inn, close to the Chestertown, Maryland, Farmers Market and Other Chestertown, MD, Things to Do

There’s only one place on The Eastern Shore of Maryland that offers a perfect blend of private countryside location, storied past, immaculate manor house architecture, and premium amenities. Brampton Inn is a family-owned bed and breakfast in the heart of historic Chestertown offering bright and airy accommodations including spacious rooms and romantic cottages. There’s no other place in town that provides each guest with exceptional service, beautiful grounds, fun events, and proximity to everything The Eastern Shore has to offer.

Ready for the ultimate getaway to one of Maryland’s hidden gems? Check our availability today and start planning your trip!