Craig Della Penna, Realtor® | Northampton Real Estate, Amherst Real Estate, Florence Real Estate

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About Craig Della Penna, Realtor®

Craig Della Penna, Realtor®

     In 2003, I became a realtor with The Murphys Realtors. I focused on a special niche: the sale of houses near to rail trails, greenways, or other conservation lands. This unique real estate practice was recently featured in two national realtor trade magazines, a Boston Globe editorial, an article in the Wall Street Journal, and in United Airlines’ in-flight magazine, Hemispheres.
       I am consistently listed among the top performing realtors in the Five-College area of the Pioneer Valley because I bring innovation and creative marketing to the local real estate market. Earlier in the spring of 2013, I had my 5th book come out and also that same spring, a third book came out that featured some aspect of my creative marketing as a case-study. 

      For 20 years, I marketed rail freight, planned the start-up, and then operated two of the Northeast’s largest railroad-owned trans-loading facilities.   I have a background in RR history, and in 1994, was invited by a regional publisher to author a series of books on old rail lines and their conversion to bike and hike trails. I then got involved in the politics of how these conversions took place and in 1998, was hired by Rails-to-Trails Conservancy as a legislative agent and political organizer in the New England region.
       Because of this work, 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 for several years now, I an one of the country’s most in-demand public speakers on the subjects of how rail-to-trail projects impact residential real estate and how they foster sustainable economic development—improve communities. I have given over 1,200 lectures on these subjects in 19 states and Canadian provinces.  And I have helped advance the building of over 1,000 miles of rail trails in the past 15 years.          

         My wife Kathleen and I operate Sugar Maple Trailside Inn, a bed & breakfast located in a restored 1865 farmhouse-style home on Chestnut Street in Florence. The house sits eight (8) feet from southern New England’s first municipally built/operated rail trail. The renovation was recognized in 2003 with a Historical Preservation award by the City of Northampton and around the same time our house was featured on HGTV’s Restore America program. The B&B was also featured in Yankee Magazine’s "Best of New England” 70th Anniversary issue and we typically win "Best in the Valley."

          Because of my demonstrated interest in historic preservation, I am now on Northampton’s Historical Commission and the Board of Historic Northampton, Inc. My real estate practice has reflected this area as well because I’ve sold some of the most dramatic, famous AND historic properties in the Five College area.  Links to more info and all my businesses can be found  at or
Professional Realtor® through the National Association of Realtors®
Member of the Realtor Assoc. of the Pioneer Valley's Presidential Advisory Group for Green Initiatives
Member of the Massachusetts Association of Realtors®
Governor’s Bicycle Pedestrian Advisory Board
Former Co-chair of Mass Highway’s Trails & Greenways Taskforce
Former Chair of the East Coast Greenway’s Massachusetts Committee
Coordinator for the MassCentral Rail Trail Coalition
Member of the City of  Northampton's Historical Commission
Board member of Historic Northampton, Inc.
Board member of the Hampshire County Tourism Council
Board Member for Mass DCR’s Massachusetts Recreational Trail Advisory Board
Board Member for Friends of Schell Bridge, Inc.
Member of the Association of Pedestrian and Bicycle Professionals
Member of the Congress of New Urbanism
Advisory Board Member of the Massachusetts Bicycle Coalition [MassBike]
Professional Association of Innkeepers International