Explore how railroads shaped Eastern Shore economies throughout history – and consider what the future of rail transport might look like.

Trace the story of rail on Delmarva from its beginnings with the New Castle and Frenchtown Railroad in the 1830s through the booms, declines, and modern-day operations that continue to influence the region. This course connects the evolution of rail to the economic and social forces that defined Delmarva’s past and still shape its future.

What to expect: 

Tom will guide us through the major eras of railroad development on the Eastern Shore, showing how rail lines fueled industrial growth, reshaped local communities, and adapted to changing economic realities. We’ll examine the interplay between transportation infrastructure and regional industry, then turn to current trends and emerging technologies that may redefine rail’s role in Delmarva in the decades ahead.

Feedback from past courses:

“I loved this class. Tom provided an interesting narrative behind many aspects of our rail history. He had insightful stories and great pictures and artifacts that made the presentation come alive.”

“Tom is an excellent speaker —knowledgeable, engaging, and full of insight”

“As a longtime student of railroad history, I found this the most effective summary I’ve seen of this complex subject. The map and timeline were the best I’ve encountered —an excellent series.”

Thomas Mackay

Thomas Mackay is the owner of Last Mile Rail Strategies, LLC, specializing in capital project management, strategic planning, and funding solutions for rail infrastructure. From 2022–2026, he served as Rail Program and Policy Manager for the Maryland Department of Transportation, overseeing more than 150 miles of freight rail corridor—much of it on Delmarva. His background includes roles with MARC Train, CSX’s Mountain Subdivision, and the Western Maryland Scenic Railroad. He holds a degree in Geography from Frostburg State University.
Share this course
Related Courses You Might Enjoy

Chesapeake Forum Course Categories – Something for Everyone!