Article published in Northampton Living
(February 2023)

My career has always centered on railroads – marketing rail freight and managing the operations of several transloading facilities in the northeast. In 1994 a regional publisher who admired my background in railroad history contracted me to write three books on the conversion of former railroad corridors into trails. The books were hits, but some people were still fearful or angry about trail conversions. I couldn’t understand why and wanted to help. I became an advocate for the conversions and helped to organize local “Friends of the Trail” groups. Eventually, I was hired by Rails-to-Trails Conservancy (RTC) and worked for them for seven years in policy development at the state level. I like to say that I am a battle-hardened veteran of nearly every rail-trail war within 150 miles of Northampton. When RTC left the region, I became a realtor with a related niche: I sell houses near rail trails. The primary reason people opposed trail conversions was a decrease in property value. But I’m very successful in my specialty. You could say I’ve cornered the market.

I also specialize in selling antique homes, like the one my wife and I transformed into our award-winning bed-and-breakfast. The renovation of our farmhouse, built during the Civil War, earned us a Historic Preservation Award. And guess what? The Sugar Maple Trailside Inn sits 8 feet from the Mass Central Rail Trail, the longest developing trail in New England. Guests fall in love with the area, and several a year decide to buy a home from me.

One B&B guest told me that I was living their dream life! But I’ve had a real impact on rail-to-trail issues. In addition to my books, I’ve written more than a dozen op-ed pieces on the value of rail-trail conversions. In their 10th anniversary issue, Ride Magazine cited me as the most effective advocate for bike and rail-to-trail issues on the Eastern Seaboard. I’ve given more than 1,200 lectures in 21 states.  

Recently, I found a niche-within-a-niche: promoting the wellness benefits of linear parks created from railroad corridors. While most people travel between home and work, I’ve found that a third significant place, like a church or a civic organization, can be integral to well-being. When that place is a linear park, it becomes a treasured part of the neighborhood – and an entire community’s touchstone for wellness.

When not selling homes or running the B&B, I work with land trusts, helping them reassemble old railroad corridors that were sold-off and fragmented. Nearly 200 rail-to-trail projects are currently underway within a few hours of Northampton! Besides being sought after as a rail-trail expert and advocate, I have been recognized for creative and innovative marketing, 21st-century branding, and the courage to do what I love. In these intertwined roles, I’m proud to redefine what it means to come and go home.

More contributions from Craig Della Penna