Short bio of Craig Della Penna 

For twelve years, Craig Della Penna worked for one of the country’s earliest short-line railroad companies marketing rail freight and managing the planning and start-up operations of two of the northeast’s largest railroad-owned trans-loading facilities.


Having a background in railroad history, he was invited by a regional publisher to write a series of books about the history of old railroad lines and their conversion to bike and hike trails. He was later hired by Rails-to-Trails Conservancy as an organizer and for seven years covered the New England region.

He has been involved in much of the rail trail development in the northeast.

For the past 18 years, he has been a Realtor in Northampton Massachusetts, with a special niche. He specializes in the sale of houses near rail trails, greenways and other conservation lands.

He is the first Realtor in the U.S. with this niche and has been written about in numerous national Realtor trade magazines and local newspapers. In November of 2017 the National Association of Realtors awarded him the EverGreen award for his work in getting rail trails built in the northeast.

He is one of the top Realtors in his marketplace and with over 1,200 lectures in 21 states he is also one of the most in-demand speakers in the U.S. on various topics related to real estate and rail trail development. He and his wife Kathleen also operate an award-winning bed & breakfast in Northampton—that sits eight [8] feet from one of New England’s earliest municipally-built rail trails. Full bio/CV is HERE

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