1 hour to 90 minutes

Ellicott City, Md.

The walking trails around Centennial Lake at Centennial Park. (Michael S. Williamson/The Washington Post)

1 hr, 7 min (36.5 miles) | Directions
At nearly 250 years old, the former Quaker mill town looks its age, though it acts more like the 10th-generation grandkid. The downtown district, a proud member of the National Register of Historic Places club, is a blast from centuries past, with dozens of buildings dating from the 1700s and 1800s. Visitors can weekend-binge on such historical sites as the Colored School, the Thomas Isaac log cabin and the B&O Railroad Museum, the oldest surviving train station in America. Ghosts add to the throwback feel, and their legendary pranks add comic relief to a history marked by two devastating floods. To rejoin modern times, simply open the door to a Narnia of quirky shops (so many animal-shape gewgaws!) spin-the-globe restaurants (Indian, pan-Asian, French country, USA burgers, etc.) and animated bars (several with microbrews and live music). Indeed, in one afternoon, you can leap across several time periods and bring back the shark-face mittens and raised hairs to prove it. www.visithowardcounty.com
Annapolis, Md.

Annapolis is known as America’s sailing capital, evident on any clear day on the Chesapeake Bay. (Marvin Joseph/The Washington Post)

1 hr, 2 min (31.7 miles) | Directions
Gaze down the Severn River toward Annapolis on any but the coldest, wettest days and you’ll see more than a few sailboats, from tiny daysailers to massive yachts. Maryland’s historic state capital is also known as America’s sailing capital. The U.S. Naval Academy, which sits at the mouth of the harbor, sets the sea-based tone. Sailing classes, kayak rentals, boat sightseeing tours and charter fishing trips draw crowds of tourists, but landlubbers are also included in the fun. On Wednesday nights in the summer, line up on the Spa Creek drawbridge to watch 150 crews compete in a race that ends at the Annapolis Yacht Club. The Naval Academy’s year-round guided walking tours introduce visitors to its 338-acre campus . Annapolis boasts more 18th-century buildings than any other U.S. city, with many of them now home to bars, shops, galleries and restaurants. And it’s one of the few places in America where you can do a pub crawl among taverns that have been pouring for 200-plus years. www.visitannapolis.org
Harpers Ferry, W. Va.

A woman rests on Jefferson Rock at Harpers Ferry National Historical Park. Harpers Ferry has a spider’s web of trails, including a section of the mother of them all, the Appalachian. (Amanda Voisard/The Washington Post)

1 hr, 28 min (63.4 miles) | Directions
The West Virginia town is one big confluence — history and culture, mountains and rivers, urbane strollers and outdoorsy folks. The national historical park dominates the Lower Town, where the Potomac and Shenandoah rivers converge and Maryland, Virginia and West Virginia meet. The park spotlights seminal events including Civil War battles (and the revolving door of occupiers), the rise of industry and transportation, the arsenal raid by abolitionist John Brown and the movement to educate African Americans. Etsy-spirited boutiques, art galleries and snug cafes line Washington Street, the main drag, and outlying lanes. The area also has a spider’s web of hiking trails, including a section of the mother of all treks, the Appalachian Trail. The trail conservancy’s visitor center is a resource to all guests — long-distance marchers as well as day-walkers wearing flip-flops and carb-loading on waffle cones from Scoops. historicharpersferry.com

90 minutes to 2 hours

Winchester, Va.

Take a tour of the childhood home of country legend Patsy Cline. (Steve Helber/AP)

1 hr, 37 min (75.8 miles) | Directions
The Stonewall Confederate Cemetery, Stonewall Jackson’s headquarters, battlefield sites and Civil War museums can all be found in this Shenandoah Valley town in Virginia. But why not tour, instead, the childhood home of country music legend Patsy Cline? She lived in a white two-story house on South Kent Street from 1948 to the mid-’50s, longer than she did anywhere else. It’s decorated with ’50s furniture and memorabilia, including a wooden ironing board, floor-standing ashtrays, doilies and some of the singer’s costumes. Knowledgeable docents describe the hardscrabble life she lived with her siblings and mother, Hilda, who was only 16 years older than Patsy and who sewed her daughter’s costumes. Elsewhere in and around the picturesque town — seemingly all of which is on the National Register of Historic Places — check out the strollable Loudoun Street pedestrian mall or the Family Drive-In, one of the state’s few remaining movie theaters of that style. www.patsyclinehistorichouse.org
Gettysburg, Pa.

A teenager at Gettysburg National Cemetery in 2013, the 150th anniversary of the Battle of Gettysburg. (Matt McClain/ The Washington Post)

1 hr, 48 min (85.1 miles) | Directions
Although it may have seemed otherwise during the 150th anniversary of the Battle of Gettysburg two summers ago, this town offers more than Civil War history. In just the past few years, a notable culinary scene has emerged. Restaurants have added more local ingredients to their menus, and Savor Gettysburg is in its second season of food tours, with a new Savory Sweets tour this year. For hard cider, visitors can go to the year-old Reid’s Orchard & Winery tasting room or Hauser Estate Winery, home of Jack’s Hard Cider. Even if you’re not hard-core into Civil War, Gettysburg makes history lessons fun, whether it’s visiting the battlefields on horseback or Segway, or viewing the famous cyclorama painting, in the Gettysburg National Military Park Museum and Visitors Center, which underwent a $13 million renovation in the past decade. You can’t ignore history here, nor would you want to; even the longtime mayor is one of the rigorously tested licensed battlefield guides. www.destinationgettysburg.com
St. Michaels, Md.

The H.M. Krentz sets sail on the Chesapeake Bay near the Maritime Museum in St. Michaels. (André Chung/The Washington Post)

1 hr, 57 min (79.3 miles) | Directions
This waterfront town on Maryland’s Eastern Shore dates to the mid-1600s, but it’s only within the past 30 years that crowds of tourists have discovered its charms. For most of its history, St. Michaels was intimately linked with the Chesapeake Bay, with residents working as shipbuilders and seafood processors. That link continues, but now the boats that ply its waters are far more likely to be ferrying tourists. Quaint streets are dotted with art galleries, bistros and antique stores. Grab a cone of homemade ice cream from Justine’s before heading to the Chesapeake Bay Maritime Museum, a 38-acre waterfront facility whose attractions include a historic lighthouse and a working boatyard. Rent a bike and head 14 flat miles to Tilghman Island or set out along one of several trails that stretch from St. Michaels to adjacent farmlands. Don’t forget that connection to the sea: Water-going choices include a trip to Oxford aboard the nation’s oldest privately operated ferry and a narrated tour on a 70-foot skipjack. www.stmichaelsmd.org.

2 to 3 hours

Luray, Va.

Luray Caverns, a geological attraction that’s equal parts natural wonder and kitsch. (Hello, Great Stalacpipe Organ). (Karen Bleier/AFP via Getty Images)

2 hrs, 9 min (92.9 miles) | Directions
If you prefer ridgelines to tan lines and like to soak up scenery rather than sun, there are few better ways to show your allegiance to Team Mountain than heading to Luray, Va. Tucked into the Shenandoah Valley, it’s the kind of place where you want to plant yourself on the front porch and drag out your morning coffee until lunchtime. The small town has a gently rolling main drag presided over by the Mimslyn Inn, an Old South-style hotel that sits atop a hill at one end. The sleepy county seat is largely free of commercial trappings, save for the touristy atoll that is Luray Caverns, a geological attraction that’s equal parts natural wonder and kitsch (e.g., the Great Stalacpipe Organ). Skyline Caverns, a relatively gritty alternative, is also along the route from the District. Luray is a great home base for exploring Shenandoah National Park, with the multitudinous outdoor ad­ven­ture and scenic-vista-ogling options the 200,000-acre park offers — whether it be hiking through a panorama of fall leaves or sitting in a line of cars stopped to let a bear cub amble across Skyline Drive. www.luraypage.com
Dover, Del.

Dunlins, a type of migratory shorebird, hunt up and down the shore for horseshoe crab eggs in the Ted Harvey Wildlife Area. (AJ Chavar/The Washington Post)

2 hrs, 14 min (105 miles) | Directions
Sports, politics and Lady Luck drive Delaware’s state capital. Depending on the season, race cars, horses and/or legislators go around and around the track. Visitors can (mock) gamble on lawmakers’ votes during a tour of Legislative Hall or (for-real) gamble on the live harness races at Dover Downs Casino. To connect the city’s dots, First State Heritage Park, a “park without boundaries,” links eight attractions, including the Old State House and Biggs Museum of American Art. Curious minds with niche tastes can chase down the obscure at institutions specializing in such topics as aircraft, state police memorabilia, farm life and victrolas. Those still in a betting mood should swing by Constitution Park and challenge a friend to name the 13 colonies. Go double or nothing on the dates the states ratified the Constitution. Stumped? Check the low wall inscribed with the answers. www.visitdover.com
Charlottesville, Va.

Thomas Jefferson's Monticello. (Sonya Doctorian/The Washington Post)

2 hrs, 49 min (116.3 miles) | Directions
This historic university town is for more than college students, although the University of Virginia is certainly a looming presence, as is its famous founder, Thomas Jefferson. To appreciate both, we suggest at least a brief excursion to the scenic school, a UNESCO World Heritage Site. Its crown jewel, the Rotunda, is undergoing an extensive renovation, but the real hidden gems are the surrounding pavilion gardens. Make a picnic out of lunch grabbed from one of the nearby Corner’s restaurants or local provisions from neighborhood gourmet stores. For a slightly more adult scene, stroll the brick-lined downtown mall for some more food and shopping. Jefferson groupies shouldn’t miss his famed home, Monticello, and if you’d like to pay further tribute to the oenophilic third president, spend an afternoon visiting some of the region’s many acclaimed vineyards. www.visitcharlottesville.org.

3 to 4 hours

Ocean City, Md.

A summer day at the Ocean City beach. Don’t head home without eating at least one Dumser’s cone. (Nikki Kahn/The Washington Post)

3 hrs, 18 min (146.2 miles) | Directions
Generations have looked forward to that one week each summer when the family heads to Ocean City (known as “goin’ downy oshun” in Baltimore). Taking a dip along its 10 miles of beach, eating Old Bay-steamed blue crabs off tables covered in brown paper, hitting the boardwalk for iconic Thrasher’s french fries and Fischer’s popcorn, and spending a day at the amusement park are still part of the essential Ocean City experience. But this seaside town, which got its big shot in the arm in 1952 when the Bay Bridge opened, is not just a throwback to simpler times. Seventeen nearby golf courses, a new 1,200-seat performing arts center, a burgeoning eco-tourism scene and an explosion of craft breweries have attracted a different clientele, perhaps equally intrigued by recent bans on beach and boardwalk smoking. But in with the new doesn’t mean out with the old: We still couldn’t head home without eating at least one Dumser’s ice cream cone, dancing in the sand at Seacrets and taking a ride to Assateague Island to see wild ponies. www.ococean.com.
Canaan Valley, W. Va.

Blackwater River in Blackwater Falls State Park, in the Allegheny Mountains of W. Va. (D. Trozzo/Alamy)

3 hrs, 26 min (176.8 miles) | Directions
For skiers in the Washington region, conditions at local resorts often come up short, which is why those who like their powder deep and their trails steep head to this valley in Tucker County, W.Va. With its high elevation and a location that gets hammered with Great Lakes snow coming in on northwesterly winds, Canaan typically gets more than 150 inches of snow each year. (In 2010, 242 inches fell.) Canaan Valley Resort & Conference Center and Timberline Four Seasons Resort, both with summits of more than 4,200 feet, attract downhill skiers, while cross-country and snowshoe enthusiasts head to White Grass or Blackwater Falls State Park. In warmer seasons, mountain biking, golfing, trout fishing and hiking take top billing. Don’t like to break a sweat? Head about 15 miles to the tiny town of Thomas, which, with a nice selection of cafes and shops, does its part to provide a hub for local artists and musicians — check out the Purple Fiddle for live bluegrass. www.canaanvalley.org.
Cape May, N.J.

The Emlen Physick Estate, built in 1879, is among homes you can tour on Washington Street. The mansion is among scores of late 19th-century structures in the town. (AP Photo/Beth J. Harpaz)

4 hrs, 5 min (186.8 miles) | Directions
See the light? Now walk toward it and then up it. The Cape May Lighthouse has one of the most arresting panoramas on the point — even at night. (The next full-moon climb takes place July 31.) Back on solid ground, red trolleys cart guests around the country’s oldest seaside resort town, idling before Victorian homes dolled up like beauty pageant contestants. The Mid-Atlantic Center for the Arts and Humanities is the mega-event planner in town, packing the calender with such excursions as harbor safaris, treasure hunts and WWII Lookout Tower visits. If you’re for the birds, the Cape May Bird Observatory organizes a slew of winged outings, a local pastime that goes back several centuries. Of course, you won’t be faulted for just wanting to slump down on the beach and letting Cape May wash over you. www.capemaychamber.com
  • 1 hr to 90 minutes
  • 90 minutes to 2 hours
  • 2 to 3 hours
  • 3 to 4 hours