Top 10 Best Road Trips From Washington, DC

Updated: November 13, 2019

This is, admittedly, an arbitrary list of crowd favorites, which I have sorted based on driving distance and general awesomeness.

#10 The Shore   2.5h

Folks in DC tend to pick their beach and stick to it. Rahoboth is closest at 2.5 hours on a typical summer day, but if you leave early and have a lead foot you can make it to the Lewes Ferry in 2 hours and arrive in Cape May a mere 80 minutes later.

#9 Harper’s Ferry   1h

You’ve probably heard about John Brown’s raid, but did you know that Harper’s Ferry was also the embarkation point for the Lewis and Clark Expedition? Rich with history and stunning scenery that is reachable by even the smallest of adventurers, Harper’s Ferry is like a secret exit from our modern suburban sprawl.

For an easy entry into the hard-core outdoor opportunities, head over to nearby Waverton Cliffs (pictured above). A short hike that even my five-year-old can cover in half an hour affords a fantastic view of the mighty Potomac.

#8 Solomon’s Island   1.5h

We had a friend who called it Devil’s Island, probably because this is a place where people are known to cut loose. My first time there, we were greeted in the parking lot of the Annmarie Sculpture Garden with a steaming cup of spiked cider (which was delicious) and handed a number of free plants to bring back to our garden.

#7 Pennsylvania Amish Country   2h

Weird Al gave the Amish a bad rap, (and who can’t giggle at a postcard from Intercourse or Lititz?), but the rolling hills of Lancaster County provide ample opportunities for Family Entertainment. First on any family list is Hershey. Hershey also owns Dutch Wonderland, which sounds like something on the menu at a brothel, but is, in fact, an amusement park geared for the under 12 set. We call it Derivative Wonderland for the ersatz-Disney milieu, but it’s worth a spin at least once in your life. Budding railroad engineers and experienced train aficionados will both enjoy the Strasburg Railroad Museum. The Turkey Hill Experience (pictured) will titillate the milkaholics in your family.

#6 Williamsburg, Jamestown & Yorktown   2.5h

If you don’t know by now that America was born in Virginia, these people will beat it into you with a stick. Williamsburg is particularly excellent at Christmastime and the Fourth of July, but the historical demonstrations are open year-round. Jamestown serves up a trifecta of native village, English village, and a replica of the ship that started the whole catastrophe. Yorktown was at one time the last on the list, but the recently remodeled visitor center will impress.

#5 Richmond   1.5h

Richmond’s history surrounds you amid the cobblestone streets of Shockoe Bottom. After you’ve taken in the culinary masterpieces of downtown, head Northwest to the eclectic and funky Fan District and, just beyond, the Virginia Museum of Fine Arts and the excellent Science Museum of Virginia.

#4 Virginia Hunt Country   1h

From the Scottish Highland Festival to the dressed-up horse events like Gold Cup, Virginia Hunt Country is a celebration of posh tradition. The best wineries on the east coast dot the region as well, delivering views, at least, that compete with the best of Provence (Breaux takes the cake).

The less posh among us will find spectacular outdoor opportunities at Ravens Rock and, our personal favorite, Sky Meadows. This Virginia State Park has it all — a historic home, kid’s playgrounds, and serious hiking — all within an hour of DC. There’s also a stunning overlook that’s an easy half hour hike from the parking lot. If you’re up for more adventure, continue over the hill to #3 on CNN’s list of the World’s Best Hiking Trails. My son was three when he conquered the overlook on his own two legs, but by then I’d already carried him up on my back a half dozen times. Alcohol is prohibited in this park, but if you decide to crack open a bottle of wine from one of the nearby vineyards when you reach the top … Well, we won’t tell.

#3 Annapolis   1h

Most days you’ll find parking on State Circle or along Duke of Gloucester Street, but on Summer weekends and Festival Days you’re better off going to the city garage on West St. We enjoy just walking around the historic streets and cobbled alleyways, sampling seafood along the way.

Many people forget that the nearby US Naval Academy is open to the public (so long as you have valid government ID for all adults in your party. Beyond the soaring arches inside the chapel (pictured above), the USNA grounds include an excellent museum of Naval History, as well as a menagerie of well-preserved ship models.

#2 Shenandoah NP   1.5h

It is fitting that the first Americans found a poetic name for this valley: Schin-han-dowi, or “river that winds beneath the spruces.” Although you should budget more time for the valley itself, an easy day trip will afford you a glimpse of the promised land from the vantage of the spruces. Begin your journey along Skyline Drive at the Front Royal entrance to Shenandoah National Park.

#1 Baltimore  1h

With its edgy cultural festivals, tall buildings and historic ships, Baltimore feels like a world away from DC. Street parking is ample in all neighborhoods except the inner harbor (which has a paid garage off Pratt street). First time tourists will want to start an ambitious day by parking at the Visionary Art Museum and hiking up Federal Hill. Next, work your way around the Inner Harbor on foot, beginning at the Maryland Science Center and stopping off for a tour of the USS Constitution. Feast on crabs at Phillips and end your day at the National Aquarium.

Naturalists can take in a giraffe at The Maryland Zoo, and top off the day at the nearby Rawlings Conservatory. Another good option is the Walter’s Art Gallery in the morning, lunch at Fell’s Point, and a strong finish at The Baltimore Museum of Art. Little Italy is a can’t miss for pastavors.


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