Chestertown is an unforgettable destination along the Eastern Shore of Maryland. The area is home to countless outdoor activities, making it the ideal place for wildlife viewing, hiking, boating, hunting, and more.

As a guest of Brampton Inn, you are just minutes away from the Chester River and the Chesapeake Bay. It’s the ultimate setting for your next romantic getaway. Explore the best Eastern Shore of Maryland activities when you access your free copy of our Travel Guide! Inside, you’ll find even more recommendations on ways to experience the great outdoors in Chestertown, MD.

your travel guide to eastern shore of Maryland

Eastern Shore of Maryland Activities You’ll Love

Spending an afternoon in the great outdoors is one of our favorite things to do in Chestertown, MD. What does the Eastern Shore have in store for you?

Explore Local Gardens

Brampton GardenBrampton Inn Gardens

One of the most magnificent things about our property is the gorgeous garden. The inn sits on 20 intricately landscaped acres, four of which are listed on the National Register of Historic Places and require even more extensive care.

Our gardens are lovingly tended by Geoffrey DeMeritt and Manick Burton. This expert duo of gardeners tends to the property’s vegetable garden, flowers, perennials, grass, trees, and English boxwood shrubs. We are so grateful that they work hard every day to keep our gardens beautiful!

Adkins Arboretum

Plan a visit to Adkins Arboretum and explore the 400-acre native garden and preserve on Maryland’s Eastern Shore. Adkins is dedicated to promoting the appreciation and conservation of the region’s native plants. It’s the perfect spot for an afternoon stroll, art exhibition, or seasonal community event.

Visit Nature Preserves

egret in the reedsEastern Neck Wildlife Refuge

This 2,300-acre island habitat features nature trails, picnic areas, and wildlifeviewing areas for visitors to enjoy. When you’re at the Eastern Neck Wildlife Refuge, you’ll have the chance to see bald eagles, migratory waterfowl, amphibians, and more. Be sure to check out the colorful butterfly garden and take a walk along the rocky shoreline while you’re there.

Sassafras NRMA

The Sassafras NRMA is a scenic spot featuring waterfront bluffs and nature trails. While you’re there, take advantage of the excellent hiking, mountain biking, wildlifeviewing, and equestrian trailriding opportunities along the banks of the Sassafras River. You can also explore over 1,000 acres of farmland, mature forests, sandy beaches, tidal ponds, and marshland.

Millington Wildlife Management Area

Visit Millington W.M.A. and discover four ponds stocked with bass and bluegill inside the 3,800-acre preserve. Observe woodpeckers, woodcocks, Scarlet tanagers, and beavers as you hike your way through the area.

More Eastern Shore of Maryland Outdoor Activities

Chesapeake Bay Sunset

Golf & Pool

The Chester River Yacht and Country Club is about a mile from Brampton. Our guests have access to the pool during the summer months and can play golf at this gorgeous facility.


The Chesapeake Bay area is home to hundreds of bird species. Bald eagles, osprey, Tundra swans, Canada geese, and Snow geese are just a few of the region’s most recognizable visitors. The National Wildlife Federation named the Brampton Inn a Certified Wildlife Habitat, making it an excellent spot to watch some of your favorite bird species. Birding at the Brampton has never been more exciting!

Take a Trip to Sandy Point State Park

Sandy Point State Park is the ideal location for an outdoor adventure. Spend the day fishing, swimming, or wildlife viewing while soaking up stunning views of the Chesapeake Bay. Bring your sweetheart, because a picnic at Sandy Point is one of the top romantic things to do in Annapolis, MD.

Are you ready to book your stay with Brampton Inn? Browse our luxurious accommodations and start planning your trip today!


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