When you imagine the Eastern Shore of Maryland, what comes to mind? We think of the area’s rich history, thriving arts scene, and breathtaking views. The charming town of Chestertown, MD, is a gem nestled in the heart of the Eastern Shore. Spend your days here tasting delicious coastal cuisine, touring Washington College, and relaxing in nature.

Below, we’ve compiled a few of our favorite things to do in Chestertown, MD. For more local recommendations on the best attractions, restaurants, festivals, and more, access your free copy of our Travel Guide today.

brampton inn's eastern shore of maryland travel guide

The Top 7 Things to Do in Chestertown, MD

1. Experience Unique Culture and History

fall colors on a college campusYou’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. The Chestertown Historic District boasts an array of museums and historic sites that encourage visitors to get to know more about Kent County’s past. Here are the best places to encounter Eastern Shore history:

2. Reset in Nature

blackwater national wildlife refugeIf 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. Spend a day by the Chester River, 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:

3. Experience Fantastic Food and Wine

breakfast at brampton innYou 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:

4. Think Like an Artist

artist painting in a gardenArt 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:

5. To Celebrate the Season

fireworks displayNo matter what your favorite time of year is, The Eastern Shore of Maryland offers an assortment of festive events for every season! Chestertown is a true year-round destination. Here’s how to enjoy it when you come to visit:

6. Go on a Shopping Spree

shopping blousesTo 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:

7. Get a Good Night’s Rest at Brampton Inn

yellow room bedAfter you’ve explored the best things to do in Chestertown, MD, treat yourself to a night of pure relaxation at Brampton Inn. Our private countryside inn offers a storied past, immaculate manor house architecture, and premium amenities. Reserve your stay in one of our luxury suites and cottages for your next romantic getaway to the Eastern Shore of Maryland. 

Are you ready to make memories to last a lifetime? Start planning your trip today!

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