Maryland’s most inspiring road trip follows Harriet Tubman’s path to freedom

One of only 31 All-American Roads

A 125-mile road runs through Maryland’s Eastern Shore, and every turn carries a piece of Harriet Tubman’s story. The Harriet Tubman Underground Railroad Byway threads through Dorchester and Caroline counties, connecting more than 30 sites with outdoor markers and interpretive signs.

In 2009, the Federal Highway Administration named it an All-American Road, one of just 31 in the country. You drive the same land where Tubman was born into slavery around 1822, escaped in 1849, and came back 13 times to lead about 70 people to freedom.

Much of the countryside looks the way it did more than 150 years ago, and that’s what hits you first.

Twenty-seven years enslaved in Dorchester County

Tubman came into the world as Araminta Ross in Dorchester County around 1822. She spent 27 years enslaved before she escaped.

As a child, different farms hired her out for labor. Working alongside her father in the timber industry, she picked up survival skills like navigation and foraging that would later save lives.

In 1849, she made her break north to Philadelphia. Then she turned around and came back, again and again, guiding family and friends to freedom on the Underground Railroad.

A Union spy who led an armed raid

Tubman did not stop at the Underground Railroad.

During the Civil War, she served as a Union spy and scout, and she became the first woman in U.S. military history to lead an armed raid.

After the war, she threw herself into the fight for women’s suffrage. She founded a home for elderly African Americans in Auburn, New York.

You trace her entire arc on this drive, from the fields where she worked as a child to the routes she used to change history.

Pick up your map at Sailwinds Park

Your trip starts at the Dorchester County Visitor Center at Sailwinds Park in Cambridge. A 100-foot sail-shaped landmark marks the spot, right on the Choptank River.

Inside, you’ll find exhibits about Tubman and the region, free maps, and staff who know the byway well.

The park wraps around a mile-long waterfront boardwalk with a nautical-themed playground and wide views of the Choptank.

Cambridge itself goes back to 1684, one of the oldest colonial cities in the country, so you’re standing on history before you even start the drive.

Walk the grounds Tubman once crossed

About 20 minutes from Cambridge, the Harriet Tubman Underground Railroad State Park and Visitor Center sits in Church Creek on 17 acres of land that looks much like it did in Tubman’s time.

The 10,000-square-foot center opened in March 2017, and the National Park Service and Maryland Park Service run it together.

Exhibits walk you from Tubman’s birth through her 13 rescue missions, her Civil War service, and her suffrage work.

A theater, research library, gift shop, and Junior Ranger program for kids round it out. Outside, you’ll find a meditation garden, nature trails, and a pavilion.

The iron weight that changed everything at Bucktown

The Bucktown Village Store dates to the 1820s and still stands along the byway.

When Tubman was a young girl, an overseer sent her to this store and demanded she help restrain an enslaved man who had left without permission.

She refused. The overseer hurled a two-pound iron weight that struck her in the head and cracked her skull.

The injury nearly killed her and left her with seizures and vivid visions for the rest of her life. Today the store operates as a museum with guided tours and artifacts from Tubman’s era.

A bronze sculpture reaches across 200 years

The Dorchester County Courthouse in downtown Cambridge once held slave auctions and trials. In 1850, Tubman’s niece Kessiah and her two children were set to go on the auction block here.

Kessiah’s husband, a free Black ship carpenter, outbid everyone and escaped with his family before anyone collected payment. They later met Tubman in Baltimore, and she led them to Philadelphia.

In 2022, artist Wesley Wofford’s 13-foot bronze sculpture “Beacon of Hope” went up on the courthouse lawn, unveiled during Tubman’s bicentennial year.

It shows Tubman reaching down to her younger self.

A mural that went viral on social media

Over on Race Street, the “Take My Hand” mural covers the side of the Harriet Tubman Museum and Educational Center.

Local artist Michael Rosato painted it in 2019, and it shows Tubman with her hand stretched out toward the viewer.

A photo of a young girl reaching up to touch the painted hand spread across social media and landed on the Today Show.

Inside, a newer mural called “Minty’s Act of Courage” recreates the Bucktown Store scene across all four walls.

The volunteer-run museum has preserved Tubman’s legacy since the 1980s, but it was undergoing renovations as of 2025, so check before you go.

Paddle 17 miles of trails through the marsh

You can explore Blackwater by car, bike, or on foot along the 3.6-mile Wildlife Drive, a favorite with photographers and birders.

The refuge also has more than five miles of hiking trails and 17 miles of paddling trails through its waterways. More than 250 bird species have been recorded here.

Keep your eyes up for bald eagles, ospreys, herons, Canada geese, snow geese, and the formerly endangered Delmarva fox squirrel. The visitor center has wildlife exhibits, an observation deck, a gift shop, and live wildlife cameras.

Safe houses and a log cabin that still stands

Near Preston, Linchester Mill marks a site where mills have operated since the 1680s.

Free and enslaved African Americans worked side by side here, and Quakers nearby secretly helped freedom seekers cross Hunting Creek.

The mill sat within a network of safe houses run by the Levertons, the Hubbards, and Tubman’s own parents, Ben and Rit Ross, at nearby Poplar Neck.

Choptank Landing at Poplar Neck is likely where Tubman made her first escape and later returned to rescue her brothers and parents.

Close by, the 1852 James Webb Cabin is considered the only surviving pre-Civil War log dwelling on the Eastern Shore known to have been built by and for an African American.

The byway ends where Tubman found freedom

North of Preston, the route passes through Denton, Greensboro, and Goldsboro in Caroline County. A side road from Denton takes you to Hillsborough, where Frederick Douglass was born.

The Maryland portion of the byway ends at the Delaware border near the Mason-Dixon Line, and the full route continues through Delaware all the way to Philadelphia, where Tubman first tasted freedom.

The 125 Maryland miles can fill a few hours or stretch across a couple of days, depending on how many stops you make.

Either way, you leave knowing the ground under your feet carried people toward something worth everything they had.

Drive the Tubman Byway in Cambridge, Md.

You can pick up the byway at the Dorchester County Visitor Center at Sailwinds Park, 2 Rose Hill Place in Cambridge.

The Harriet Tubman Underground Railroad State Park and Visitor Center is at 4068 Golden Hill Road in Church Creek, open Wednesday through Sunday from 10 a.m. to 4 p.m., with free admission.

Grab a free driving guide and download the audio app before you go. September is International Underground Railroad Month in Maryland, and the state celebrates Harriet Tubman Day around March 10 each year.

This article was created with AI assistance and human editing.

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