Working on the Rail-Trail

His extensive knowledge of the converted railroad-to-trail system in Northampton, Mass., has turned Craig Della Penna into the go-to expert on the history of his area (not to mention the go-to real estate pro).

April 7, 2014

Craig Della Penna, GREEN, GRI
Associate broker
The Murphys, REALTORS®
Northampton, Mass.

What exactly is a rail-trail, and why are they important in your neighborhood?

The Rails-to-Trails Conservancy describes them in this way: “Rail-trails are multipurpose public paths created from former railroad corridors. Most often flat or following a gentle grade, they traverse urban, suburban, and rural America. Ideal for many uses, such as bicycling, walking, inline skating, cross-country skiing, and equestrian and wheelchair use, rail-trails are extremely popular as recreation and transportation corridors.”

In the context of southern New England, the railroad network was overbuilt, and we have many rail-to-trail conversion projects underway. In fact, within 100 miles of my house, there are over 200 such projects underway. This is the densest network under development in the United States, and what makes it interesting is that the former railroad corridors here went to village centers — places where huge antediluvian mill complexes once produced heavy things. Today, these places are converted to offices or residences, and the old railroad corridors are being redeveloped as nonmotorized pathways that connect where people live, work, and play — places where kids can safely bike to school. So many kids bike to school on the trail network here that the city plows it in the winter.

You specialize in selling homes near rail-trails and other land conservations. How did this become your niche?

When I was looking to get into real estate, it seemed to me that the most successful agents were those who had some kind of niche practice. I had credentials in the transportation industry (I marketed rail freight for many years and have a background in railroad history), and more recently, I was a political organizer building “Friends of the Trail” groups all over the Northeast. When I became a real estate practitioner, it was destined that my niche would be houses near rail-trails because I knew from my research that millions of people were using these facilities, and it stood to reason that a segment of them would like to live near them. And besides, I became more committed to this niche when the lead opponent against a trail project in his community told me that his reasoning was because he’d not be able to sell his house easily because the trail would reduce interest in it. I set out to prove him wrong. And I have.

You’re also on the board for the Regional Tourism Council, and you and your wife run a bed and breakfast next to a rail-trail. What inspired you to get so involved in your community’s tourism sector?

I’ve written three books on rail-trails. For the research on the longer trails, I would bike from inn to inn, and I thought, wouldn’t it be fun to run a B&B? So here we are, years later, running our B&B in a massive “fixer” house that sits eight feet from New England’s oldest municipally built trail. And since I’m both a high-altitude fellow and a burrower — working my way into all sorts of organizations — it was a natural for me to gravitate into the tourism and hospitality realm. And besides, our B&B sits at the intersection of the northern end of the longest interstate trail in the Northeast (84 miles from New Haven, Conn., to Northampton, Mass.), and we’re at the western end of the longest developing trail in Massachusetts (104 miles from Boston to Northampton). It’s easy to think of tourism when looking at the map and considering inn-to-inn touring.

How does knowing so much about the local greenways and rail-trails make you an expert on your community?

As I mentioned, in southern New England, the rail-trail network here is not off in some far-off hinterland place. It is right where people live, work, and play. The rail-trail network is a perfect way to introduce people to the communities here. Knowing why they were here, how they got built, what they were used for after they stopped being used by the railroad, and how the neighborhoods around them became developed — all these factor into becoming an expert on the context of place in a community.

How does it improve your real estate business?

I get between four and seven real estate transactions a year from our B&B. Our area looks much different from other parts of the country, and people are stunned to see it for themselves. Over breakfast, I give visitors to our B&B a synopsis as to how this place came to be and what it took for this place to avoid the destructive forces that did in many communities in the United States. Four to seven of my visitors a year end up relocating here.

Being an expert on something as forgotten or mundane as an old railroad line — and bringing it back to life as a trail — means that I have scores of stories of inspirational things that people have told me about what it means to them to have the trail in the community. In the past, the butcher, the baker, and the candlestick maker were the de facto go-to people in the community. Today, the real estate professional in the community is one of those go-to people. And today, doing inspirational and uplifting work for the long-term good of the community is something people appreciate and value, and they’ll refer buyers and sellers to you.

You sometimes give clients showings by bike. What kind of experience does this give them versus a traditional showing?

I’ll do second showings of houses by bike if my buyers are interested or inclined. Touring a neighborhood by bike is much different than by car. The sights, sounds, smells, and flavor of a neighborhood by bike are quite simply imprinted in an unforgettable and stimulating way. My buyers will then have firsthand knowledge about the possibility of their kids being able to bike to school or to the commercial areas. Very important stuff when you think about it.

I’ll also lead Tuesday evening bike tours of the three different segments of the rail-trail network here. I’ll point out and describe the railroad history and bits of archeology we come upon, talk about how the trail got built in terms of overcoming the initial opposition to it. And, of course, I point out the recent residential sales and the effects that the trail has had on the values and sales performance of various neighborhoods. All the money I collect for these tours go to local nonprofits, and I get an abundance of both buyer and seller leads from these tours.

What is your favorite characteristic of your neighborhood and why?

I’m a transportation policy geek and I love the obscure and small transportation details that make a city livable. Here in Northampton, whenever you step off a sidewalk and into a crosswalk, traffic screeches to a halt. For many places in the United States, this is not the case. This basic cultural cue will transform your community.

For people who want to get more involved in their community, what steps would you advise them to take?

  1. Volunteer on the bicycle and pedestrian committee for your community.
  2. Advocate to get a traffic-calming program underway.
  3. Organize a “Complete Streets” program.
  4. Work to convert that dead and derelict old railroad corridor into becoming something attractive and useful.
  5. We are real estate pros, and we must do real things. Stop golfing.
Graham Wood
Senior editor

Graham Wood is senior editor for REALTOR® Magazine. He can be reached at