A three-day road trip through Maryland's Black history

As a devoted scholar of Black history and a long-time Maryland resident, I cannot resist the call of the state’s Eastern Shore. This region is the birthplace of two titans of the abolition movement: Frederick Douglass and Harriet Tubman. And for my family, spending a long weekend absorbing the remarkable tales of these two legendary Americans is a great way to unlock an immersive lesson in Black history.

It may seem like you could tackle this itinerary—which in part follows the Harriet Tubman Byway—in a day or two, but to get the most out of the trip, it’s best to break it up into a three-day journey that starts in Washington, D.C., for a comprehensive look at what these two heroes accomplished before stepping back in time to experience landscapes and waterways on the Eastern Shore that helped to shape their lives.

Total mileage: 43 miles

Our family road trip begins with a bacon, egg, and cheese sandwich from the historic Florida Avenue Grill, the self-proclaimed “oldest soul food restaurant in the world.” This no-frills eatery located near Howard University is only open Friday through Sunday and has very limited seating, so don’t plan to stick around too long.

Once you've had breakfast, make the 15-minute drive over to the National Mall for a visit to the National Museum of African American History and Culture (we usually pay about $30 to park at the Ronald Reagan Building across the street). Since opening in 2016, this museum has stayed crowded, so make sure to snag your timed entry passes online a few weeks before visiting.

Grab lunch at Sweet Home Café, the museum’s restaurant. The menu changes with the seasons, but staples include roasted chicken, potato salad, and mac and cheese.

In the afternoon, drive to D.C.’s Anacostia neighborhood to visit Cedar Hill, the estate of the famed abolitionist and author Frederick Douglass. The National Park Service manages the 21-room manor, and the mansion-turned-museum provides a snapshot of the life of Douglass as a successful 19th-century statesman, orator and author, on timed tours available on Tuesdays, Wednesdays, and Saturdays (reservations required).

After watching a brief film about Douglass's life, a park ranger will lead you to the mansion for a guided tour where you'll see several rooms where Douglass worked and entertained guests. My favorite room was the study where he crafted some of his famous speeches and correspondence. After the tour, take in the breathtaking panoramic views of the D.C. skyline from the front porch.

For dinner, head back into the city to enjoy mouth-watering fine dining at Georgia Brown's. The restaurant specializes in southern classics like buttermilk fried chicken, Carolina gumbo, and shrimp and grits.

Total mileage: 81 miles

Before you hit the road, grab breakfast at the U Street location of Busboys and Poets. This restaurant-meets-bookstore is a cultural hub that’s popular for not only its great food, but its nods to Black culture in everything from decor to its poetry slams and community engagement. Then, load up the car for a 1.5-hour drive to Talbot County on Maryland's Eastern Shore, the birthplace of Frederick Douglass.

The first stop on the road trip is the Frederick Douglass Park on the Tuckahoe, in Queen Anne. This site is located very close to the farm where Douglass was born, and there are plans to build a scenic overlook and walking trails. Next, make your way to the Talbot County Courthouse in Easton to see the bronze, life-sized Douglass statue on the lawn out front. As a young man, Douglass was once jailed here for attempting to escape slavery, and 42 years later, he delivered the fiery "Self-Made Men" speech on the same lawn. The statue was erected to commemorate that speech.

Finally, drive west on Maryland Route 33 to St. Michaels, a waterfront town where Douglass was forced to work while enslaved, and where he was caught teaching other enslaved people how to read. Take a break at Legal Assets for a lunch of shrimp and grits, then walk along the waterfront on the grounds of the Chesapeake Bay Maritime Museum to find the Eliza Bailey Mitchell House. Eliza was Douglass’s sister, and the structure is an example of a middle-class house owned by free African Americans in the 19th century.

In the evening, drive a quarter of a mile south to Bistro St. Michaels for French-inspired cuisine on Talbot Street. After dinner, wander a few doors down to spend the night at The Old Brick Inn, where Douglass was the first free African American to stay as a guest in 1878.

Total mileage: 37 miles

As you leave Talbot County, stop by The Coffee Trappe for a quick French Toast or pancake breakfast. Then, it’s off to Dorchester County, the birthplace of liberator, wartime nurse, spy, and legend, Harriet Tubman. Today, you’ll be driving along the Eastern Shore portion of the Harriet Tubman Byway, a 125-mile self-guided driving tour that starts in Maryland's Dorchester and Caroline counties before continuing onto Wilmington, DE, and Philadelphia. The drive is marked by idyllic marshlands and inlets—and very little of the landscape has changed in the 150 years since Tubman and others risked their lives for freedom.

Make your first stop at the Harriet Tubman Museum and Educational Center in Cambridge, which houses murals and painted displays that tell the story of Tubman’s life. The biggest draw here is the popular "Take My Hand" mural on the side of the building, where hundreds of visitors patiently wait their turn to snap a photo for Instagram. Afterwards, stop by Black Water for a casual lunch of salads and sandwiches.

Next, head over to the Harriet Tubman Birthplace Marker on Greenbriar Road. There's a graveled parking lot off the highway where you can stop and look at the field that was once the home to Tubman's family. From there, drive by the Bucktown General Store, where Tubman, at the age of 13, suffered a significant head injury at the hands of the owner of the store that caused seizures for the rest of her life. You’ll have to call ahead to schedule a tour of the store’s interior, which is frozen in time to the early 19th century.

Finally, end your afternoon at the Harriet Tubman Underground Railroad National Historical Park, a 480-acre park with immersive exhibits, programs, and tours that educate visitors about Tubman's life. Tubman’s story comes to life through displays depicting critical life scenes: bronze renderings of Tubman as a child in ankle-deep water, surrounded by reeds catching a muskrat; another statue has Tubman in a boat reaching out to save people struggling to swim in the water below. Another moving exhibit lists the names of some of the enslaved people she helped escape to freedom.

After your busy drive, wrap up your trip at local watering hole RAR Brewing for dinner with a side of locally brewed beers. Then, check into a local hotel to rest up for your quick, two-hour drive back to D.C. the next day.