This list of Washington, DC’s “Best Road Trips” is, admittedly, an arbitrary list of crowd favorites, which I have sorted based on driving distance and general awesomeness.
- 10. The Shore (2.5 hr)
- 9. Westward Ho! Harper’s Ferry to Deep Creek along the Potomac River & National Road
- 8. Western Chesapeake to Solomon’s Island (1.5 hr)
- 7. Pennsylvania Amish Country (2 hr)
- 6. Williamsburg, Jamestown & Yorktown (2.5 hr)
- 5. Richmond (1.5 hr)
- 4. Virginia Hunt Country (1 hr)
- 3. Annapolis (1 hr)
- 2. Wilderness: Shenandoah NP, George Washington & Monongahela NF
- 1. What else, hon? BALTIMORE! (1 hr)
10. The Shore (2.5 hr)
Folks in DC tend to pick their beach and stick to it. For a quick getaway, consider the many beaches along the Chesapeake that are within an hour’s drive. The most popular is Sandy Point, just this side of the Bay Bridge. If you’re looking for something less crowded, consider Chesapeake Beach or, just beyond Sandy Point, the many beaches on Kent Island.
And if you’re willing to stretch your definition of a beach even further, you can find the closest beach to DC at Freestone Point, just half an hour from the city.
But for a true beach experience with big waves and a boardwalk, you’ll need to commit to a longer drive. The most direct route to the ocean will take you to the mouth of the Deleware Bay. South from there will get you to many beaches in Maryland (such as Ocean City).
The Virginia shore south of there is the place to go for a truly remote experience. A 3-hour drive will take you to the National Seashore along the MD / VA border, which is an open expanse of salt scrub and wild horses.
Rehoboth (and its quieter cousin, Dewey) is the closest ocean beach to DC 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 (just north of Rehoboth) in 2 hours. From there, you can hit up Cape Henlopen State Park, which has gorgeous white sand beaches and giant canons from a strategic fort guarding the mouth of the bay.
From there, A mere 80 minute ride on the Lewis ferry will take you to the charming Victorian resort of Cape May. This is our favorite family beach because it has so much to offer for kids and history buffs alike. Of course, the beach is the main attraction, and you’ll find plenty to do along the boardwalk from Poverty Beach to the marshland to the south of the city.
The town itself is jam packed with beautiful Victorian homes that have been immaculately restored to their original glory. For those who are bored of the sand, strolling the streets to gawk at the architecture is a favorite pastime. There are also many superb restaurants downtown, but be advised, many do not serve alcohol or take credit card, so bring cash and your own bottle.
There’s also plenty to do beyond the city and the beach. The Cape May Zoo is free, and is one of the top zoos in the country. For a modest fee, you can also enjoy the zip lines and rope course on the edge of the zoo.
There are also some interesting spots nearby for naturists. South Cape May Meadows is a short bike ride from town and is a favorite stopping point for migratory birds, which may be one reason Birdwatching Daily has named Cape May the #2 birdwatching destination in the nation. 
A good spot to stop with the kids is Beach Plum Farm, a free farm that you can stroll before picking up lunch in their outdoor cafe. Make sure you show your kids the rope swing in the northern corner of the farm, right along the WMA.
If you’re interested in exploring the WMA further, there’s a secret dirt road that you can bike through the marsh lands. You won’t see the road on Google Maps, but you can find it with satellite view. just across the street from the WWII tower. It’s an easy 20 minute ride with lots of wildlife peeping. Best of all, it empties out on the most secluded beach in the area.
9. Westward Ho! Harper’s Ferry to Deep Creek along the Potomac River & National Road
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. Best of all, it’s only an hour’s drive from DC (for closer-in Potomac access, see our Guide to the Potomac).
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.
American pioneers continued their journey on the Potomac as far as Cumberland, MD, a coal and industrial hub that was originally the headquarters of George Washington during the French and Indian war. They would then pick up the trail to the Ohio on what would become known as The National Road.
Fort Necessity National Battlefield
Early settlers often stopped to spend the night at The Washington Inn, which has been restored to show the furnishings of early America. But a far more important piece of history lies in its back yard.
The first link in a chain of events that would eventually lead to the American Revolution happened here, in a sad little hog-pen known as Fort Necessity.
It was also the first battle in an otherwise distinguished military career for the 21-year-old colonel, George Washington. Prior to the battle — and to defend his interests in a pelt-trading firm — Washington and a local Indian chief named Tanacharison (called the Half King by the British) led a massacre on a camp of French regulars under the command of Joseph Coulon de Villiers, Sieur de Jumonville.
According to one history of the battle, Tanacharison washed his hands in Jumonville’s brains to make sure he was dead. Determined to avenge his brother’s death, Louis Coulon led a counter-assault on Fort Necessity. Washington had half the troops in the ill-fortified Necessity and most of them were drunk, so he surrendered. While making his ignoble retreat, the French forces raided his supplies and sent him limping back to Williamsburg, where he would eventually win the support of the British Crown.
After winning the war, the crown sent the bill to the colonies, the colonies rebelled, and eventually won their independence. It is thus a strange coincidence that the Battle of Fort Necessity was on July 3rd, but it’s no accident that July 4th weekend is the best time to go to Fort Necessity. On that weekend there is an encampment of re-enactors depicting British and French regulars and Indians, and it is a good time to learn the customs of this land before it was a country.
If you can’t make it to the Independence Day celebrations, there are tours and musket demonstrations nearly every morning. This is an important place to visit, but be prepared for disappointment (as my kids were) on your approach to the fort. It’s little more than a few upright sticks hammered in a circle of earthen works. But the surrounding natural meadow is beautiful, and your imagination can supply the rest.
Deep Creek Lake, MD
While not strictly on the National Road, Deep Creek is a short detour. It was here that Thomas Edison, Henry Ford and B. F. Goodrich spent their summers in the early 20th Century. It’s easy to see why.
8. Western Chesapeake to Solomon’s Island (1.5 hr)
THE CHESAPEAKE BAY is huge. So big that it’s hard to get your head around it. But consider this: with over 11,000 miles of shoreline, it’s bigger than the West Coast. The entire coast of Great Britain is a rough match.
Along the Western Chesapeake — the side closest to our fine city — you’ll find beaches and crab shacks that will take you back to a simpler time. Our favorite place to get crabs for the neighborhood boil is Mel’s Crabs in Huntington, well worth the hour drive. While there, stop at Breezy Point to fish the pier or just hang out on the beach.
Further south is Solomon’s Island. 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 (2 hr)
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 (2.5 hr)
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. Nearby 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. The small colonial town there also makes for a pleasant stroll, particularly where it tends downward to the breezy beach and boardwalk along the York River.
5. Richmond (1.5 hr)
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.
Plantations east of Richmond
Among the many plantations between Williamsburg and Richmond is Westover Plantation (pictured above). Along with Berkeley and Shirley, you can tour the gardens anytime, but the houses sometimes require special reservations.
4. Virginia Hunt Country (1 hr)
From the Scottish Highland Festival to Oatlands Plantation and 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 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.
Also out that way is a stunning portion of the Appalachian Trail known as Raven Rocks. This is something you should only do when you have the whole day. Parking is tight in the trailhead lot, so if you’re there after 10 on a spring weekend, you may have to bail. The hike is also long, traversing three ridges on the AT.
3. Annapolis (1 hr)
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. Wilderness: Shenandoah NP, George Washington & Monongahela NF
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.
Dolly Sods Wilderness
Just west of Shenandoah National Park is George Washington and Jefferson National Forest, known for its lake retreats and tall waterfalls. Continuing into West Virginia, you will eventually arrive at Monongahela National Forest, the gem of which is Dolly Sods Wilderness.
Dolly Sods is by far the most remote wilderness I have experienced on the East Coast. The drive up the plateau follows a single-lane dirt road with no shoulder between you and steep cliffs down to the valley below. Once on top, the atmosphere changes immediately, as thick forest yields to a wind-swept plain of scrub brush and tundra.
1. What else, hon? BALTIMORE! (1 hr)
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 of our Best Road Trips destination 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.
- “Birdwatchers’ 15 Favorite Birding Destinations in the U.S. and Canada” BirdWatching, 20 Feb. 2019. Accessed 17 Aug. 2020.