History on the Water
Chestertown, Maryland
Why go: Perched along the edge of the Chester River, the town would be worth a visit if only to stroll the tree-lined streets and look at the historic houses. But it’s also home to Washington College, a liberal-arts school that fuels the town’s cultural life. Downtown you’ll find art galleries, indie bookshops, and boutiques selling everything from handbags to Oriental rugs, along with a waterfront park. There’s a Saturday farmers-and-artisans market in the town square; traditional afternoon tea at the White Swan Tavern (231 High St.; 410-778-2300; whiteswantavern.com), a Colonial tavern; and brunch at the Imperial Hotel (208 High St.; 410-778-5000; imperialchestertown.com)—complete with a Bloody Mary bar.
Don’t miss: A sail on the Sultana (410-778-5954; sultanaprojects.org), a replica of an 18th-century schooner, on which you can help raise the sails and swing the seven-foot tiller. Or rent a kayak at Chester River Kayak Adventures (410-639-2001; crkayakadventures.com) and ply the river, home to ospreys, blue herons, and egrets.
Take a break: For local flavor, stop in at Play It Again Sam (108 S. Cross St.; 410-778-2688), a funky cafe where college students debating Nietzsche mingle with sailors, artists, and moms with strollers.
Travel time from DC: An hour and 45 minutes.
Old Haunts
Ellicott City
Why go: Ellicott City looks much the same as it did more than 200 years ago. Although some of the downtown was rebuilt after a 1999 fire, the streets are still lined with many 18th- and 19th-century-style stone buildings that house antiques shops, boutiques, cafes, and art galleries. There’s easy parking at signed lots off of Main Street. Need another reason to go? The city is considered the East Coast’s most haunted small town; ghost tours are offered Friday and Saturday evenings (howardcountymd.gov/hct/hct_ghosttours.htm).
Don’t miss: The B&O Railroad Museum: Ellicott City Station (2711 Maryland Ave.; 410-461-1945; ecborail.org), inside America’s oldest railroad station, circa 1831. The museum features toy trains that wind around a 40-foot-long scale model of the original 13 miles of track extending from Ellicott Mills to Baltimore. Another exhibit—on display November to January—shows model trains whooshing over hills, through tunnels, and past animated streetscapes. Outside, you can climb aboard a 1927 caboose.
Take a break: Nothing chases away the heat like an ice-cold lager or ale at Ellicott Mills Brewing Co. (8308 Main St.; 410-313-8141; ellicottmillsbrewing.com), which also serves pub fare, crabcakes, and rockfish.
Travel time from DC: About an hour.
Civil War Trails
Fredericksburg, Virginia
Why go: The area is rich in Civil War history, with four battlefields at National Military Park—Fredericksburg, Wilderness, Spotsylvania, and Chancellorsville. Start with an orientation film at the Fredericksburg Battlefield Visitor Center (540-373-6122; nps.gov/frsp); park rangers will then help you plan your day. Self-guided driving tours and ranger-led walking tours are available; the tours include stops at a former Union Army headquarters/hospital and a family cemetery at Ellwood Plantation that includes one of the oddest Civil War attractions: a granite marker denoting the burial site of Stonewall Jackson’s left arm, which was amputated after he was shot in 1863.
Don’t miss: The University of Mary Washington, with its elegant mix of Georgian and Jeffersonian architecture. The campus is only a few minutes from National Military Park, and a hill on the university grounds played a key role in the 1862 Battle of Fredericksburg. The historic downtown section of Fredericksburg is just a few blocks from campus; the brick-paved sidewalks are lined with shops, restaurants, and art galleries.
Take a break: Carl’s Frozen Custard (2200 Princess Anne St.; 540-370-4390) has been an institution since 1947, using Electro Freeze ice-cream machines from the 1940s to produce an egg-rich custard. For more substantial fare, try the fine vegetarian chili and other offerings at Sammy T’s (801 Caroline St.; 540-371-2008; sammyts.com).
Travel time from DC: About an hour.
