Birding & Boating the Tubman Byway: Caroline County

We will resume these tours on June 7, 2024! New dates will be added soon.

All tours will run 2:00 – 6:00 pm. From 2:00 – 4:00 pm, we will drive the Harriet Tubman Underground Railroad Byway to visit historic sites and go birding. From 4:00 – 6:00 pm, we will cruise the upper Choptank River north of Denton, MD. The cost is $100/person. Scroll down to read more about this tour!

Journeys to Freedom

Osprey photo courtesy of Frode Jacobsen. Harriet Tubman c. 1870-1880. River Run Cruises.

Birding & Boating the Harriet Tubman Byway (DRIVING/BOAT CRUISE)
Dates and Times: Friday, June 7, 2:00 – 6:00 pm
Cost: $100/person
Meeting location: the tour will begin at the Linchester Mill, located at Route 331 and Linchester Road in Preston, MD. The GPS Coordinates for the parking area are: 38.701391, -75.897370.

We need 10 participants to run this tour. As of 8:30 am on March 12,2024, we have 5 interested! If you wish to be added to the waitlist for this tour, please email dmvbirds@gmail.com with your name and the number in your party.


Discover the birds and wildlife that Harriet Tubman would have encountered during her journeys to freedom on the Underground Railroad on Maryland’s Eastern Shore.

Join Harriet Tubman Tours and Delmarva Birding Weekends as we go birding along the Harriet Tubman Underground Railroad Byway in Caroline County, MD. During the guided, self-driven tour, we’ll learn about the many daring escapes led by the famed freedom seeker and human rights activist known as “The Moses of Her People,” Harriet Tubman. In Caroline County, Harriet Tubman found shelter and assistance as she traveled along the Underground Railroad to Delaware.

River Run Cruises on the Choptank River

The driving route courses through the farms, forests and significant Underground Railroad sites of Caroline County. We’ll also tour the Choptank River with River City Cruise Company in Denton, MD. From there, we will explore the upper reaches of the Choptank during a two-hour cruise aboard a pontoon boat. Downriver, landings and points along the Choptank served as sites for perilous escapes by boat. The shallow waters of the Upper Choptank provided crossings for freedom seekers heading north towards Sandtown, DE.

Harriet Tubman was born around 1822 in Dorchester County, Maryland. She was brought into the world as Araminta “Minty” Ross, the middle of nine children born to Harriet “Rit” Green and Ben Ross, who were both enslaved. Her childhood was spent toiling on the plantation of Edward Brodess, who often hired his enslaved people out to neighboring farmers.

The James Webb Cabin in Preston, MD, a restored African American home c. 1852

In 1849, Harriet Tubman escaped Maryland’s Eastern Shore to Philadelphia, but she returned at least 13 times to rescue around 70 people, including her parents, family members, and friends. In the face of incredible danger, she guided them safely to freedom as a conductor of the Underground Railroad — a secret network of people, places and routes that provided shelter and assistance to escaping slaves. By 1860, Harriet Tubman had earned the nickname “Moses” for liberating so many enslaved people at great risk to her own life.

During her years as a conductor of the Underground Railroad, Harriet Tubman would have been intimately familiar with the birds and wildlife of Dorchester County. She used the call of a Barred Owl to alert freedom seekers that it was safe to come out of hiding and continue northward.

The same birds that Harriet Tubman would have known more than 170 years ago still inhabit the fields, forests and marshes of Caroline County. As we visit the sites on our driving tour, we will search for Summer Tanagers, Indigo Buntings, and Orchard Orioles. On the Choptank River cruise, we’ll likely encounter Bald Eagles, Osprey and Great Egrets.

Summer Tanager, Indigo Bunting and Orchard Oriole, photos courtesy of Frode Jacobsen.

These are the stops we will make along the ~20 mile, two-hour driving and walking tour:

These are sites we will pass by along the two-hour Choptank River Cruise:

Before your tour begins, we recommend that you visit Adkins Arboretum or Martinak State Park, or enjoy a walk and lunch in historic Denton, MD or Preston, MD.

Linchester Mill in Preston, MD will be the starting point for our Caroline County tour. Your guides (left to right): Jim Rapp of Delmarva Birding Weekends and Alex and Lisa Green of Harriet Tubman Tours.

Driving and Boating Route:

For June through October tours, we will meet at the small roadside pull-off at Linchester Mill, located at Route 331 and Linchester Road in Preston, MD. The GPS Coordinates are: 38.701391, -75.897370.

Please make certain to fuel up your vehicle and use the restroom before you arrive. We will have access to restrooms before and after the boat tour in Denton, and there is a “head” (toilet) on the boat.

Please note the following:

  • Please bring a $5-$10 tip for the First Mate on the boat.
  • Please make sure you have enough fuel in your vehicle for the trip, as we will not stop at gas stations along the route.
  • We encourage you to explore Caroline County before and after your tour. You will find museums, restaurants, farm stands and shops all within easy walking and driving distance of Preston and Denton.
  • We encourage you to support our friends at the Caroline County Historical Society. We thank them for their work promoting and protecting Caroline County’s rich history.

Some common sense approaches to make your birding and boating trips more enjoyable:

  • Wear appropriate clothing and shoes for weather on the water!
  • Carry sunscreen, sunglasses and/or a hat to protect yourself from the sun. You can still get sunburn in the winter.
  • Bring rain gear as all events are rain or shine.
  • Try to arrive a little before the scheduled trip departs.
  • Most trips are not appropriate for young children. Please use your discretion when registering.
  • Be courteous to your fellow birders. Speak quietly and turn off cell phones during trips.

We hope you’ll join us for Birding and Boating along the Harriet Tubman Byway!