Brampton Inn Is a Charming Escape by the Water in Maryland

Courtesy of Brampton Inn

Brampton Inn, located near the Chester River in Maryland, is a cozy getaway with historic significance and thoughtful touches.

Chestertown, Maryland
Drive time: 1 hour, 30 minutes

On a crisp fall evening, there’s nothing cozier than cuddling up next to a roaring fireplace at this charming inn tucked away on 35 wooded acres fronting the Chester River on Maryland’s Eastern Shore. Built in 1860, the Brampton Inn is listed on the National Register of Historic Places. It offers seven rooms and suites in the main house and six secluded cottages. Every detail has been thoughtfully designed for maximum comfort, right down to the heated towel bars.

Courtesy of Brampton Inn

The Yellow Room, Fairy Hill Suite, Sunset in the Garden Cottage, Marley’s Cottage and Mulberry Cottage all have jetted tubs. Other accommodations have jetted or steam showers. The Robin’s Nest Cottage has a fully equipped modern kitchen. You’ll find kitchenettes and grills in the Marley’s and Mulberry cottages, and Robin’s Nest and Russell’s cottages welcome your favorite four-legged friend.

- Advertisement -

A homemade multicourse breakfast is included with your overnight stay. You can savor it in the manor house or have it delivered to your cottage. Complimentary midday tea and treats will warm you up for afternoon excursions. Downtown Chestertown, with its eclectic array of shopping and dining options, is only two miles away.

River Rambles: The 1920s-style 65-foot Chester River Packet offers a variety of water adventures, including a Brampton Inn two-hour cocktail cruise on Nov. 7, a girls’ night out with dinner on Nov. 16 and a Black Friday lunch cruise on Nov. 25. The National Wildlife Federation has named the Brampton Inn a Certified Wildlife Habitat, so bring your binoculars. It’s a prime location to spot hundreds of bird species, including bald eagles, osprey, tundra swans, and Canadian and snow geese.

Courtesy of Chester River Packet Co.

More to Explore: Mount Harmon Plantation is a former tobacco plantation with a colonial manor house restored and furnished to reflect the period of 1760-1810. Outbuildings include a smoke house, tobacco barn and slave quarters. Take an hour-long golf cart tour of the 200-acre property or stroll its five miles of historic waterfront nature trails.

Chestertown is an artists’ mecca with numerous galleries and studios to peruse. Don’t miss the Holiday Show at RiverArts Gallery throughout the month, where over 50 local artists display their handmade seasonal gift selections. Stop in at Hegland Glass to see the latest works fresh from the kiln, and MassoniArt has two galleries of paintings and prints. Visit the studios of contemporary realist Diane Rappisi and Robert Ortiz, who crafts contemporary furniture in the Shaker and Japanese styles.

November Rates: $219-$599.

- Partner Content -

25227 Chestertown Road, Chestertown, Maryland, (410) 778-1860,

Related: Loews Regency New York Is a Top Escape for Fall in New York City

Our Best of the Main Line & Western Suburbs Party is July 25!