Ep. 1
with Josh
Roads Less Travelled is a podcast hosted by Craig Della Penna that explores the fascinating intersection of real estate, rail trails (linear parks), and tourism. From homes near historic, former rail corridors to the booming bike tourism industry along rail trails, Craig shares expert insights, engaging stories, and practical advice for buyers, investors, and enthusiasts. Each episode highlights potential of properties near these linear parks and educates listeners about experiencing--or even owning bed and breakfasts in the 21st century, rail trail tourism, and regional development.
Craig Della Penna is a pioneering CRS Realtor, a nationally recognized rail-trail advocate, and the host of the Roads Less Traveled podcast. As the first U.S. Realtor to specialize in properties along scenic rail-trail corridors, Craig blends his expertise in real estate with decades of experience transforming “dead” railroads into thriving community assets.
A former New England organizer for the Rails-to-Trails Conservancy, he has delivered over 1,200 lectures in 21 states, authored five books, and was hailed by Ride Magazine as the most effective rail-to-trail advocate on the Eastern Seaboard. He and his wife Kathleen also operate Sugar Maple Trailside Inn, a traditional bed & breakfast that sits 8 feet from one of the northeast’s earliest municipally-built rail trails in Northampton’s village of Florence, a completely intact, Civil War era industrial village.
