Small-town surprise: The new Port of Leonardtown Winery is home of the Southern Maryland Winegrowers Cooperative. Besides a tasting room for sampling vino, enjoy tours and demonstrations during the crushing cycle. 23190 Newtowne Neck Road, 301-690-2192, portofleonardtownwinery.com
Stay here: Marble bathrooms and soaking tubs are among the amenities at the Executive Inn and Suites, a new upscale hotel in the downtown business district. 41655 Park Ave., 301-475-3000, http://www.execinnparkave.com.
Don't miss: The Religious Freedom Byway, part of the National Scenic Byways Program, traces the Potomac River in southern Maryland and features some of the nation's oldest churches, including the Francis Xavier Church, the state's oldest Roman Catholic Church in continuous use.
Info: visitstmarysmd.com or leonardtown.somd.com
Maryland's Coolest Small Towns
There's nothing official about this list, but here are some more of our favorite small towns (population 10,000 or less):
Berlin (Worcester County)
Centreville (Queen Anne's)
La Plata (Charles)
North Beach/Chesapeake Beach (Calvert)
North East (Cecil)
Ocean City (Worcester)
Pocomoke City (Worcester)