Home  / Profile

Craig Della Penna Northampton, MA 

I have had an interesting life journey. I worked in the railroad industry for many years, marketing rail freight and planning the start-up and management of large scale, contemporary, transloading facilities. In the mid-1990s, while working for the railroad, I was invited to write a series of books on the history of old railroad lines converted to walking and biking trails (rail trails).
Two years after the first of three books on this subject came out, I got involved in the politics of how these paths did or did not get built and I began to actively organize “friends of the trail” groups in scores of communities all across New England and eastern New York.
In the late 1990s, I was hired by the national organization, Rails-to-Trails Conservancy, as a political organizer/lobbyist in the New England region to not only prevent bad policy at the state and local level, but to also “parachute” into some of the most notable rail trail wars in the northeast. I am a “battle-hardened veteran” of every rail trail war in the Northeast.
In late 2001, while working for RTC, my wife Kathleen and I bought a badly run-down, 1865 farmhouse next to (eight feet from) the rail trail in Northampton’s Florence village center. We began a far-reaching renovation and had contractors there for fourteen months. Then, in the spring of 2003, we opened as a bed & breakfast called Sugar Maple Trailside Inn. The renovation was featured on HGTV’s Restore America television program and the house won a historic preservation award from the City of Northampton as well. I am on the Board of Directors for the Hampshire County Regional Tourism Council.
In 2004, I entered the real estate field and quickly became one of the top Realtors at a long respected local firm—the Murphys Realtors. I have a unique niche real estate practice—specializing in houses near to walking or biking pathways and antique or historic houses. This niche was featured in two National Realtor Association magazines, a Massachusetts Association of Realtors magazine, a Boston Globe editorial, an article in the Wall Street Journal, and even in United Airlines in-flight magazine, Hemispheres. I am also one of only a small handful of Realtors in the Northeast to receive Green designations from both the National Association of Realtors and the U.S. Green Building Council. I also hold the Certified Residential Specialist designation—CRS. Only 3% of Realtors in the U.S. have this designation.
I am the top Realtor at the firm and am ranked as a top-producing Realtor in my community of Northampton, MA. In their 10th anniversary issue, The Ride magazine named me as the most effective advocate for rail-to-trail issues on the Eastern seaboard, and I have helped build over 1,000 miles of rail trails in scores of communities in New England and New York.
Today, having given over 1,200 lectures in twenty states, I am one of the country’s most in-demand public speakers on the subjects of rail-to-trail conversions and their tie-in to the issues surrounding smart growth, land preservation, effects on nearby residential real estate values, and other similar topics.
Just in the past few years, I have been the keynote or plenary speaker at state or regional conferences in New York, California, Virginia, Connecticut, Michigan, and Massachusetts.
In 2015, I was the keynote speaker at NH DOT’s annual conference. And in 2016, I’ll be one of the plenary speakers at VT’s Bike/Ped conference and also at that conférence, I’ll be teaching a course about these issues to scores of VT Realtors for their Continuing Education requirements. Later this year, I’ll start taking this presentation to various Realtor associations in southern New England.


Life Stage:
Real Estate/Mortgage
Biking, walking, public speaking.


Current Location

Northampton, MA