She’s going on a road trip! What’s up fam. If you’re looking for a unique road trip, then look no further than the Harriet Tubman Underground Railroad Byway! On this trip, you and your favorite history buff will learn about one of our country’s greatest heroines!  I took this trip with one of my best friends and we did it in four days, so this is perfect to take over a long weekend.

The Harriet Tubman Underground Railroad Byway is a self guided drive that follows Harriet’s route to freedom through Maryland, Delaware and Pennsylvania. It was designated as one of the best driving tours in the nation in 2009 by the Federal Highway Administration and is one of only 31 distinctive “All-American Roads” nationwide. Most of the sites featured were connected with the Underground Railroad and offer either indoor exhibits or outdoor plaques that you can read to learn more. (You can learn more about it here.) I visited some of the Maryland sites on a trip with the Community College of Baltimore County a few years ago but my bestie couldn’t make that trip. We’ve been talking about doing our own trip ever since and finally decided that this is the year we would make it happen. 

We decided to do this trip over a long weekend, from Thursday to Sunday, to save PTO. That gave us four days to tackle all the sites. Once we decided what days we wanted to go, I planned our itinerary using the Driving Tour Guide (you can get a copy of the guide and map here). Since we are both amateur genealogists and love learning about African American history, I tried to choose sites that would give us more in depth information. 

Thursday

On Thursday, our first stop was the Dorchester County Visitor Center. Here, we checked out their exhibit about life on the Eastern Shore, picked up paper copies of the guide and chatted with the super helpful front desk staff who gave us recommendations on the best places to eat in the area and helped us download the app. I highly recommend downloading the app. It provides audio narration for all the stops in Maryland and really draws you into the past. For instance, we were not able to go into the Stanley Institute and Bucktown Village Store. The Stanley Institute is open by appointment only and Bucktown Village Store is closed during the pandemic. But the app filled in the blanks on how these buildings were significant and what was happening in the area during Harriet’s lifetime. 

The audio on the app called Brodess Farm holy ground. And you could feel it. Other than the rather large dragonflies circling the area, there was no other sound. It was eerie and yet peaceful, providing the perfect backdrop to imagine what it was like to live and work there and how it felt to plan an escape. This stop was definitely one of the highlights of the day. 

We also spent some time hanging out in downtown Cambridge. We had lunch at Snappers (eat the crabby nachos and thank me later!), checked out the historic buildings on High Street and visited the Downtown Cambridge Farmers Market at Long Wharf. If you’re in the area on a Thursday, stop by and try one of Mandala Pies Oreo cookies. She only makes them for the market and they sell out quickly. 

The Crabby Nachos at Snappers. Yum!
Quilt on display at the Harriet Tubman Museum.
Portrait on display at the Harriet Tubman Museum

Friday

On Friday, our first stop was the Harriet Tubman Underground Railroad State Park and Visitor Center. The Visitor Center has a vast amount of information about Harriet and a well stocked book store. This is not a site that you want to rush through. Plan to be here for at least an hour, take your time and steep in the history. 

When we finished, we wanted to take a photo at the mural which we thought was located at the visitor center.  A ranger informed us it was at the Harriet Tubman Museum in Cambridge! Despite the fact that we were just there on Thursday, we drove all the way back to Cambridge to find this mural. Don’t be like us. When you visit the Harriet Tubman Museum (which is different from the state park and visitor center), ask the staff how to get to the mural. Since we were back in Cambridge, we had lunch at Ava’s Pizzeria (two words: Meatball Breeze!). 

The famous mural at the Harriet Tubman Museum (not the Harriet Tubman Visitor Center!)

Another way the app is helpful is letting you know which sites are accessible to the public. The Driving Guide is a little outdated and we learned the hard way that the Jacob Leverton House was one of the sites without public access. My suggestion – listen to the narration for the next site before you drive there. We also visited Linchester Mill but when we arrived the parking area was closed for a private event. Thankfully, the app was able to fill us in on its significance.

The guide also doesn’t mention that the William Still Family Interpretive Center is still being restored. While trying to find the center, we met Michael McCrea, who was restoring the house that will be the future site. Mr. McCrea lives in the Jacob Leverton House and also helped restore the Webb Cabin. When we stopped by, he was full of stories about the Still family and the work he’s doing to restore other historical sites in Caroline County. If you happen to make this one of your stops and see a lone man working on the house, stop in and say hi. Mr. McCrea recommended we visit Choptank Landing, a pretty slip that is also in the guidebook. That and dinner at Portside rounded out our day.

Saturday

On Saturday we drove to our first stop in Delaware, the Historic Odessa Foundation, which offers tours of three historic homes. This was the only site where we needed to pay a fee. It was only $20 a person and totally worth it. When you arrive, let them know you’re there for the Harriet Tubman Underground Railroad Byway and they will tailor the tour. We toured all three homes but the main draw for us was the Corbit-Sharp House where we learned how the Corbit family hid slaves in their tannery and hid one in a small cubby in the attic. The foundation has period events all year round so check them out.  

This photo shows how Sam, a runaway slave, was hidden in a cubby hole in the attic of the Corbit-Sharp House.

We also visited the Jane and Littleton Mitchell Center for African American Heritage in the Delaware History Museum and checked out their exhibits on Delaware history and the history of African Americans in the state.

We ended the day with an early dinner at Two Stones Pub.

The bread pudding at Two Stones Pub.

Sunday

We started our last day at the Tubman-Garrett Riverfront Park, named after Tubman and Thomas Garrett, an abolitionist. The park houses the statue, Unwavering Courage in the Pursuit of Freedom, which is a stunning tribute to the two freedom fighters. We took a leisurely walk through the park before heading to the New Castle Court House Museum where Garrett was tried and convicted for helping enslaved people to escape. Here we watched a short movie depicting Garrett’s trial, saw the court house where the actual trial was held and visited their exhibit room that explained the state’s connection to the Underground Railroad and highlighted the accomplishments of prominent African American Delawareans. Among the exhibits was a plaque that discussed Delaware’s free unless proven enslaved policy and manumission papers from the 1700s. The docent, who was very personable and passionate about history, made our last stop in Delaware a memorable one.

Unwavering Courage in the Pursuit of Freedom. My photos did not do this statue justice.
Manumission papers at the New Castle Court House Museum.

Our first order of business after crossing the Pennsylvania line into freedom was to find William Still’s house. Still was a conductor of the Underground Railroad who kept very detailed records of those he helped to freedom so that they could be reunited with their families later. We used Google Maps for directions to the house but it took us South Delhi Street, the site of one of his former homes that was discovered in 2018. The street was extremely difficult to get to on a busy Sunday afternoon and much to our chagrin, didn’t reward us with a marker when we were finally able to see it. We checked the guide and figured out we were at the wrong location and eventually found our way to the site of his last residence on South 12th Street.  

I decided that the only way I could officially end this trip was to get a shot of the Liberty Bell. That was easier said than done. Due to the traffic, we arrived at the Liberty Bell Center, sweaty, hot and just 5 minutes before closing. But we got our shot.

We officially ended our trip with a visit to the Liberty Bell.

For this trip we stayed in the Comfort Inn & Suites Cambridge and the Holiday Inn Express & Suites Wilmington Newark. The Comfort Inn & Suites could have used some updates but what they lacked in that area they more than made up for in charm. The famous Eastern Shore hospitality was on full display during our stay. Every time we walked by the front desk, someone checked in with us, asking if we needed anything and how our stay was going. This hotel does offer breakfast. In addition to the standard continental items, they also had a waffle bar and breakfast sandwiches you could heat up.

The Holiday Inn Express & Suites was our favorite hotel for this trip because it was recently renovated, there was a restaurant a short 5 minute walk away and we loved their breakfast set up. Instead of guests handling items themselves, you come to the designated area and place your order with the staff. They relay it to the staff in the kitchen and hand you your order. You have the option of eating in your room or in the dining area. The tables in the dining area were spaced far apart and cleaned as soon as the occupants left. Overall, we had good experiences at both hotels. 

A few important things to note, some of these businesses are still working out the kinks that come with navigating this new post COVID universe. So be patient and kind. That being said, this trip is very safe to take during the pandemic. Most of the sites are outdoor sites. The only time we were in a place with a large group of people was in the Harriet Tubman Museum, the Harriet Tubman Underground Railroad State Park and Visitor Center and the restaurants where we ate. The restaurants we visited in Cambridge had indoor and outdoor seating available. The hotels where we stayed required masks indoors in the public spaces. 

The trip is also very customizable. You can do it over a long weekend or stretch it out to a week. There were a ton of sites in the guide that we didn’t get to see so you can easily pick and choose the sites that are of interest to you. 

And that’s how we did the Harriet Tubman Underground Byway in 4 days. I hope this helps you plan a similar road trip of your own. Don’t forget, you can go somewhere too!