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Natural Charters

Fishing charters on the Chesapeake Bay. Max charter size is 6 people.

Schmankerl Stube Bavarian Restaurant

Authentic Bavarian cuisine. Entrée’s prepared by order, Strassen Café, five Bavarian draftbier served in authentic glassware.

Ava's Pizzeria & Wine Bar

Since opening in 2008, Ava’s Pizzeria & Wine Bar has been awarded “Best New Restaurant” and “Best Pizza” by the readers of What’s Up Magazine 8 years in a row as well as “27 Points” for Food Quality from Zagat. On the Maryland Crab and Oyster Trail.

Gilpin's Falls Covered Bridge

View from Rt. 272; 119-ft. red wooden bridge built circa 1860.

Port of Leonardtown Winery

The agricultural cooperative consists of 15 members' vineyards from a small 1/2 acre to several acres to produce the best wine from the best Southern Maryland growers.

Cherry Hill Park

campground with RV sites, tent sites, cabins and resort-style amenities. Tours and transit to Washington DC

Bayard House

Famous umbrella bar right on the C & D Canal. On the Maryland Crab and Oyster Trail.

Hilton Garden Inn Baltimore/White Marsh

Offering amenities galore and is within walking distance of shopping, entertainment dinning and local pubs. Complimentary shuttle available within a five-mile radius.

Gillis Grier Bed & Breakfast

Enjoy the old world charm of a Queen Anne Victorian inn in the heart of the Eastern Shore of Maryland. Built in 1887 and carefully restored to its grandeur, our inn provides a unique opportunity to step back in time while you get away from it all.

Comfort Inn & Suites-Chestertown

Set in a suburban shopping area half a mile from Washington College and not far from Chestertown's town center.

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