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history • 2 days, 1 night

Private Trip: Tracing the Steps of Tubman & Douglass

history • 2 days, 1 night

Private Trip: Tracing the Steps of Tubman & Douglass

See Dates
  • Group Size 6 People Maximum
  • Activity Level
  • Travel Style
    Road Trip

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  • Implemented expansive new safety protocols
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Trip Overview

On this privately guided, self-drive experience, trace the trails of abolition blazed by Harriet Tubman, Frederick Douglass, and the 19th-century Black communities they drew from. Meet your local guide in Cambridge, Maryland and begin by learning about Tubman’s early life in Dorchester County, where, after escaping from slavery, she returned 13 times to usher 70 enslaved people to freedom. Step inside the shop where she first defied her white oppressors and visit a former safe house along the Underground Railroad. Journeying north on your second day, you'll visit Easton, where Frederick Douglass met the free Black individuals living and working in the Hill Community, escaped from slavery, and came back decades later to deliver a speech next to the jail in which he’d once been incarcerated. While our two days together will be largely dedicated to Tubman and Douglass, we’ll visit Methodist churches, centuries-old schoolhouses, and residential neighborhoods, casting an ear to the stories of the countless Black community members who contributed to the rich historical fabric of Maryland’s abolitionist movement. For those interested in exploring the surrounding area further with a guide on on their own, we're happy to provide additional information.

For a day-by-day itinerary description, either inquire with us directly or visit the group trip page, here.

Note on Safety:

We’ve designed this two-day trip with current health and safety precautions in mind. To maintain adequate physical distancing, participants will be traveling in their own vehicles and will reserve their own accommodations. Staff and participants will be expected to follow the latest CDC guidelines, which include wearing face masks in public and group settings, and keeping six feet of distance between parties who are not traveling together. Visit our Trips FAQ for more information, and feel free to contact us directly with any questions.

  • Stories and sites chronicling the early life of Harriet Tubman
  • History of Frederick Douglass’s later years as a writer and orato
  • Tour of a community built by and for free Black individuals in the 1780s
  • Visit to historic Black schoolhouses, churches, and neighborhoods
  • Privately guided experience for you and your companion(s)


Itineraries and daily schedules are subject to change. We expect to do everything listed in the itinerary, though the order may be rearranged based on weather or other local conditions.

Trip Leader

Alex Green
Alex has spent over eight years researching the life and legacy of Harriet Tubman and sharing her powerful story with visitors from around the U.S. and the world. Alex grew up in a family of storytellers; his maternal grandfather, in particular, took Alex under his wing and recounted vivid stories of his experience as one of the first Black captains on the Chesapeake Bay. After retiring from his work as a diesel mechanic, Alex, along with his wife Lisa, continued the storytelling tradition and founded Tubman Tours. Alex has now lived along the Harriet Tubman Byway for 20 years, and still continues to discover new historic details.

Additional Info


The cost of this private trip is $980, based on two participants. The rate for each additional participant will be $90, up to a maximum group size of six guests. Note that participants are responsible for their own transportation and accommodations.


Accommodations for this weekend trip are not included; we encourage locals to join us, and would like to provide participants with as much flexibility as possible. There are a variety hotels, motels, campsites, and boutique B&Bs in the Cambridge, Maryland area.

Arrival & Departure

You'll need your own means of transport for both days of this trip, as you and the guide will be driving caravan-style between locations. The tour begins at 9 a.m. on the first morning at the Dorchester County Visitor Center. If you’re joining from out of town, we recommend you arrive the night before. Your trip concludes on the second day at around 4 p.m. From here, you can depart for home or, if you'd like to extend your trip, we’d be happy to provide suggestions for things to do and see in the area on your own. Note that you'll be a private group, we can provide some flexibility with timing, topics of interest, and additional inclusions. 

Activity Level

Participants should feel comfortable walking three to four miles over the course of each day, spending most of the day outdoors, and remaining on their feet for long periods of time, including walking on uneven terrain. We encourage participants to bring a water bottle, some snacks, a hat, and sunscreen in preparation for two active, outdoor days.

  • An experienced guide accompanying you for the duration of the trip.
  • Admission to all proposed activities, locations, and events.
  • All meals described in the itinerary.
  • 24/7 emergency assistance during your trip, provided by Global Rescue.
  • Built-in donation to the Harriet Tubman Museum and Education Center.
  • Special access to unique places and extraordinary experiences.
  • Transportation to Cambridge, Maryland and from Easton, Maryland, as well as during the tour.
  • Accommodations throughout the trip.
  • Pre- and post-trip accommodations.
  • Travel insurance (recommended).
  • Additional meals and drinks outside of Atlas Obscura offerings, including alcoholic beverages.
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Trip FAQ

Most dietary restrictions can be accommodated as long as we’re notified in advance, though in most cases ingredients can't be substituted or omitted from particular dishes. The trip includes two lunches, though you’re also welcome to bring your own. If you have a severe allergy, please contact us in advance, and be sure to include this information in your reservation form.

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