Distance from DC: 79 miles; one hour and 45 minute travel time
Where to stay: Rest your head where Wedding Crashers was filmed: the Inn at Perry Cabin, a colonial mansion on the waterfront with 78 rooms, antique fireplaces, an infinity pool, and seafood restaurant. The inn's winter indulgence package is available until March 31st.
The Eastern Shore town of St. Michael’s feels like a place frozen in time, back when the maritime industry dominated the landscape and a stroll down Talbot Street was the busiest part of your weekend. There is plenty to explore here, like the Chesapeake Bay Maritime Museum, quirky stores like the Preppy Redneck, and boozy destinations Eastern Shore Brewing Company, St. Michael’s Winery, and Lyon Distilling for rum and whiskey samples.