Trusted allies. Safe houses. Secret meeting locations. Boats. Trains. Wagons.

The Underground Railroad was an intricate network of people, buildings and transport that helped enslaved people escape to freedom from their slave owners. The Underground Railroad was active in the years prior to Civil War when abolitionists were working towards creating an equal country where everyone was equal. The network was based entirely on trust and never fully documented when it was active to avoid harm and danger to the enslaved.

The network used the terminology of the railroad and had ‘conductors’ who would lead the enslaved, many times those who escaped slavery became future conductors. The network began with ‘pilots’ who would head south to seek the enslaved who yearned for freedom, they were then lead by conductors. The enslaved people were called ‘passengers’, and the safe houses were called ‘stations’.

Both black and white abolitionists offered their homes and business establishments as safe houses. Every aspect of the Underground Railroad was critical because any lapse in communication meant that slave catchers would catch the enslaved people and take them back to their slaveowners, and those aiding the enslaved would face jail!

Today, the vestiges of the Underground Railroad can be seen in preserved historical homes, museums, institutions like churches, across the country. We have listed five experiences including road trips and trails, where you can learn about the Underground Railroad, witness the hardships and feel the desire of everyone involved to create an equal and just world.

1) Take a road trip along the Harriet Tubman Byway in Maryland

Harriett Tubman mural
Photo by Kirt Morris / Unsplash

Harriet Tubman is one of the most prominent figures associated with the Underground Railroad and wore multiple hats throughout her life. Born into slavery in Maryland, she escaped to her freedom in Philadelphia and returned multiple times as a conductor on the Underground Railroad helping many others find their freedom.

The Harriet Tubman Byway is a wonderful road trip and starting point to learn about her life and how she impacted history. The byway goes through 125 miles of Maryland’s Eastern Shore, Delaware and Philadelphia. More than 45 sites along the byway narrate the stories of Tubman’s life and bravery, as well as the struggles of the enslaved.

Stops on the Harriet Tubman Byway –

  • Harriet Tubman Memorial Garden
  • Harriet Tubman Museum & Educational Centre
  • Webb Cabin
  • Brodess Farm
  • Bucktown General Store

2) Go on the Frederick Douglass Driving Tour in Maryland and the Capital Region

​English Wikipedia user Daniel Case, CC BY-SA 3.0 <>, via Wikimedia Commons

Orator, Writer, Abolitionist – Frederick Douglass donned many hats during his life. One of the most inspiring figures in American History, Douglass’ story is one of courage and perseverance. Born into slavery, he worked under many slave masters learning to read and write by himself before escaping via the Underground Railroad. He made his home in New England but soon became a conductor on the Underground Railroad and went on to actively help others escape slavery.

A driving tour through Maryland and Washington D.C will take you through the scenic Eastern Shores and across all the places where Frederick Douglass was born, lived, and advocated for the enslaved and marginalized. His intellect and oratorial skills stunned all as he championed the message that all humans were equal.

Spots on the Frederick Douglass Driving Tour –

  • Frederick Douglass Park on the Tuckahoe
  • Talbot County Jail
  • Asbury United Methodist Church
  • Banneker-Douglass Museum
  • Frederick Douglas – Isaac Myers Maritime Park

3) Walk the Black Heritage Trail in Massachusetts

Rhododendrites, CC BY-SA 4.0 <>, via Wikimedia Commons

Many Underground Railroad routes, both over land and water, culminated in Boston. The community in Boston enabled the enslaved to head towards safety and freedom across the border in Canada. Many of them also included those who escaped slavery like Lewis and Harriet Hayden, who continued to help others by harboring them in their homes. The Hayden house was the most active safe house in Boston before the Civil War.

The Black Heritage Trail in Boston offers visitors a glimpse into the past and all the places where the antislavery movement took place. The 1.6 mile trail is located in the Beacon Hill neighborhood and showcases community buildings and homes where the enslaved found refuge.

Stops on the Black Heritage Trail –

  • African Meeting House
  • Lewis and Harriet Hayden House
  • Robert Gould Shaw and Massachusetts 54th Regiment Memorial
  • John J. Smith House
  • Smith Court Residences

4) Drive through the historical Cass County in Michigan

rossograph, CC BY-SA 4.0 <>, via Wikimedia Commons

Cass County was once called ‘the hot bed of abolitionism’ at the peak of the antislavery movement in the 1800s. It became an important destination on the Underground Railroad and was led by the Quakers who harbored the fugitive slaves in their homes, barns and other buildings. Hundreds of enslaved would travel from across the Ohio River and then onto Detroit where they crossed into freedom to Canada.

The region’s leading abolitionists were Stephen Bogue, William Jones, Ishmael Lee, and James E. Bonine, whose Carriage House can be visited today. It was also here that the pivotal 1847 Kentucky Raid took place whose trial changed the course of the antislavery movement and eventually led to Civil War. A driving tour across Cass County will take you through the important spots where history took place.

Stops on the Cass Driving Tour –

  • Birch Lake Cemetery and Meeting House
  • Brownsville School
  • Bonine House and Carriage House
  • Stephen Bogue House
  • Cass County Courthouse

5) Travel across the Freedom Trail in Iowa

Jim Roberts, CC BY-SA 4.0 <>, via Wikimedia Commons

Hundreds of enslaved people escaped into Iowa on their road to freedom. Many of them were lead by radical abolitionist John Brown, whose last trip to Iowa is documented along the Freedom Trail. John Brown famously wrote ‘All men are created equal’ that now is a part of the Declaration of Independence. He came to prominence during the Bleeding Kansas crisis and faced his ultimate challenge when he led the raid on Federal Armory at Harper’s Ferry. Unfortunately, the raid wasn’t successful, and he became the first person in the US to be executed for treason.

Trace his and his entourage’s footsteps on his last trip to Iowa when he helped free twelve men, women, and children. Along the Freedom trail are homes and institutions, including the courthouse where the trial of Kentucky Raid was conducted.

Stops on the Freedom Trail –

  • Tabor Antislavery Historic District
  • Reverend George B. Hitchcock House
  • Jordan House
  • Todd House

Wish to on these experiences and learn more about the Underground Railroad and black history? Plan a trip with family and friends with the help of our expert travel designers at Voyay!ge.