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Craig Della Penna tells about his TRAILSIDE family of companies: "What They Are: How They Came to Be: And Why I Just Might be Living Your Dream Life."

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Creating four careers from a life in the world of rail trails


photo of women sith strollers

Moms on the Minuteman Trail in Lexington, MA

In a past life I marketed rail freight and operated large transloading facilities for railroads. I identified commodities that were coming across the continent on trucks and found a way to get the "move" back onto the railroad— and into one of our facilities in western New England, and then ultimately onto the end user.

One of my customers was a fellow, Chris Ryan, who converted obsolete topo maps into stationery, known in stores as Geo-lopes or Topo-lopes. We handled that move from USGS depots out west then to our facility and finally to paper converters who created the stationery. Chris was in my office one day back in February of 1994 and noticed a book on my desk called “The Lost Railroads of New England” by Ronald Dale Karr (The new Third Edition of Karr's classic book is available from Branch Line Press.)

He picked up the book, looked at it and said to me; “You know, they’re taking a lot of these old, unused railroad lines and converting them to bike and hike trails.” I said; “Yes, I have a background in railroad history and am a member of Rails-to-Trails Conservancy.” I pointed out that there were a lot of potential pathways that could be built here in New England. I said; “That book is about a thumbnail sketch of the history of them, but doesn’t tell much about where they are in the context of finding or visiting them.“

After chatting for a while longer, he mentioned that his main line of business wasn’t the topo-maps, but that he was the publisher of outdoor recreational guide books and maps, New England Cartographics. He said that if I would write a manuscript on the subject of OPEN trails that were safe for families— with a strong bent towards the history of the corridor— he’d publish it.

photo of runner with rusty bridge

Runner on Windsor Locks Trail crossed by old railroad bridge

I said to myself; Wow! Imagine that! A publisher will publish a book that I’d write. How fun! Little did I know that this conversation would be the opening of a new chapter in my life.

Early that spring of 1994, my wife Kathleen and I bought bikes and after we laid out the program, started to bike every mile of every open rail trail in New England. Back then, these rail to trail conversions were a new-fangled idea around here and there were scarcely more than two dozen open in all of New England. [My wife would dispute that many of trails were really "open" because of their "forgotten" nature and lack of build out, but that’s for another story— another day.]

We would bike along, me with a bike odometer, and I’d recite into a tape recorder, the location all the railroad history and bits of railroad archaeology that we’d find along the way. In the end, the book had 26 trails, and all the chapters laid out— by way of that detailed, odometer based mileage guide— not only all the railroad history, but why it was there and what purpose it once served.

This take was much different from the typical bicycling book with turn-by-turn cue sheets. Those sorts of books allow the rider/reader to blaze on by and miss the details. My book encouraged you get off the bike and to explore the surroundings a bit. A little bit different. The book was a minor league hit in the railfan world and a major league hit in the railfan/trailfan world.

photo of family on roadside trail

ex New Haven RR Arch Bridge at Leeds, Mass shortly before construction
began on the trail there in the fall of 2008

That first book, called Great Rail Trails of the Northeast and published by New England Cartographics, came out in 1995. I’ll never forget when I started to see families and even troops of Boy Scouts or Girl Scouts using that book as a sort of treasure hunt. It was such a niche hit that the editor suggested that I should start doing a slide lecture series based on pictures in the book. I declined. My take was that I was shy and couldn’t speak in public. After all, I flunked out of speech class in high-school because I was so shy. Life went on.

Though I continued to go out on weekends to open rail trails in New York and New Jersey for future books on those places. By the end of 1996, I had visited and in a detailed way, cataloged over 50 rail trails in the northeast. Around that same time was beginning to hear about a "to-do" regarding a proposed rail trail in a small community not far from where I lived. The community of Southampton, Massachusetts was actually the scene of a little "war" about the possibility of converting their unused railroad into a publicly accessible trail. That fall, I went to my first political meeting and watched how the opponents rallied support to defeat the trail project. I was naïve, but none-the-less stunned. I began to get educated about trail advocacy. Quickly.

As I said, I had been to over 50 such projects and never saw one that was seen by the host community as a negative and couldn’t really imagine people being against them. Yet here, there were definitely people fearful of such a change. I then began looking closer into the places where conversions were early in the process; places where the discussions were taking place. The fact that I such detailed knowledge of all the finished projects around the region meant that I that I probably had something that was needed— a first-person experience. I did start the slide lecture series. Armed with a borrowed Kodak Carousel slide projector and some Kodachrome slides of trails, I began to speak. Knock-kneed and sweating bullets at first, but always speaking with passion, I began to develop a presentation that included some “then-and-now” scenes, but focused on the transformation that happens when the trail was built. I also began to develop an extensive inventory of photos of design issues where people said that it "couldn’t be done."

photo of bikes in mountains

interpreter kiosk at the Northampton, Mass end of the Norwottuck R
ail Trail (MassCentral Rail Trail)

I would typically go into places where the war was already underway— though it was always more beneficial and effective if I could get into town before the war broke out. I took several courses on Mediation Training and began to work with the trail proponents in several areas of New England and getting to know the trail opponents and their take as well— all while working my day job with the railroad at the same time.

Then one of those little moments in life happened— whose importance we discover only sometime in the future. My publisher told me that a fellow in eastern Massachusetts was buying the book by the case and GIVING it away at the trailhead of the famous Minuteman Rail Trail. He was passing the book out to passers-by, telling them that the trail wasn’t merely a "cute path in the woods," so to speak, but actually an important and historic route. We had to meet him.

It turned out that he was a railfan/trailfan of the first degree AND a major supporter of Rails-to-Trails Conservancy. The eventual outcome was that I was hired as RTC's New England Field Representative— essentially their lobbyist in New England. I had a few tasks. To figuratively "parachute into the wars," teach the locals how to move their project forward, and become an on-the-ground resource for both transportation agencies and communities. And to speak out wherever, whenever. I began to do two to three lectures or public meetings a week— all over New York and New England. I eventually left the railroad job in 2000 and began life full-time with RTC.

I was going to all the pressurized and packed public meetings where people would invariably say to me, "Don’t tell us how great it will be to convert that old railroad corridor into a bike trail— pedophiles will be snatching our children out of our backyard." Etc., etc., etc. And then they’d invariably end up with: "Don’t tell us what to do; you don’t live near one." I knew that eventually I’d have to graduate from merely "talking-the-talk" to actually "walking-the-walk." That is to say, I’d have to be moving to a place that was near a rail trail.

photo of house by trail

Our house undergoing renovations in the spring of 2003—with one of our
neighbors on the trail

Well, one night while coming back from one of my lectures before an embryonic group of rail-trail advocates in New Hampshire, I decided to stop off in Northampton, Massachusetts, or more specifically, Florence— a village within Northampton. I wanted to see if any houses were for sale near the rail trail. Low and behold, there was. I stumbled upon an old revival style farmhouse that was barely visible from the street, hidden behind years of neglected brush and over-growth. The best part was that it sat a mere eight feet [!] from the rail trail.

We called the realtor the next morning, toured the place and found it to be in even worse condition than it looked from the outside. Nevertheless, we saw the potential and jumped right into a bidding war with three other bidders. We prevailed and in September of 2001, we moved in and started to restore the 1865 house. We (and a slew of contractors) spent the next fourteen months restoring not only the interior and exterior of the house, but also the grounds outside. This landscape work included the installation of "period gardens" with plants and themes that were common to the Civil War era. Although we had many surprises in the restoration, most of them unpleasant, there was one interesting oddity.

It seems that in 1868, three years after this house was built, the railroad came to Florence. The railroad was built so close to the house that the railroad officials offered a creative mitigation for the homeowners who were wary of cracked ceilings from the shaking the house was sure to experience. The railroad came in and reinforced all the plaster ceilings in the house with lath-strips nailed every few inches. Below that, they installed canvas ceilings. The thinking was that if the passing trains cracked the ceilings, they would not be noticeable since they would be above the taut, but flexible canvas. When we came onto the scene 130-odd years later and restored the house, two rooms still had these canvas ceilings.

After the restoration of our house, we were honored when we received both the city's Historic Preservation Award and shortly after that, our work was featured on House & Garden Television's acclaimed series, "Restore America."

During the restoration, we decided to go one-step further and open a bed & breakfast. We call it Sugar Maple Trailside Inn— see our website at This was the first of what turned out to be my “Trailside” family of companies. SMTI is the first bed and breakfast in New England that sits next to a rail trail— and that also heavily markets to the bicycle tourism industry.

photo of people and bikes

Trailside businesses along the MassCentral Rail Trail in Hadley, Ma

Our house was one of the closest houses ever to have a railroad built next to it— and it is certainly one of the closest houses to sit next to a rail trail. In addition, as an advocate, it is a just a perfect place to offer up complementary room nights to people fearful or concerned about the rail trail in their community. We make only weeknights available to trail opponents however because we want these people to wake up to the laughter of children biking to school— as they remember, but probably don’t see any more in their community. Though I’ve offered up this stay to many anti-path extremists, only one couple actually took me up on my offer.

Through it all I kept giving lectures and talks before myriads of different groups. I was being called to speak before groups all over the country. By late 2009, I had given over a thousand lectures in 18 states as well as in Canadian provinces— on a wide range of topics. Real estate and rail trails, smart growth aspects of building out these places, various advocacy and political organizing topics, running a successful bed & breakfast and tourism aspects of rail trail development. I was flattered when a regional bike magazine called me "the most effective rail trail advocate on the east coast." Pretty heady stuff indeed.

In August of 2004, when RTC pulled out of New England and made the office in Pennsylvania, the regional office for the northeast, I did not go. I decided to become a Realtor with a local independent firm called, The Murphys Realtors. I also set up a couple of other trail related entities— Northeast Greenway Solutions (NEGS) and Central Highland Conservancy (CHC).

photo of house by trail

Ribbon Cutting ceremony on a newly opened section of trail

NEGS was set up to essentially do the same advocacy and technical assistance I was doing with RTC— while CHC was set up to do things I wasn’t able to do at RTC. CHC was a land acquisition company that I used to swoop in and buy former railroad corridors in Massachusetts that were in danger of being sold to adjacent land owners. I would buy the corridor and then sell the property to the local land trust a couple of years later when they could raise the money to buy me out— for my costs plus expenses. No mark-up. Since 2005 this model has directly or indirectly saved over 12 miles of former railroad corridor that would have been lost. At one time, I also owned three large former railroad bridges including the last standing, boxed pony truss railroad bridge in southern New England.

One of the most notable things about New England—that most people do not realize— is the super-abundance of unused former railroad corridors. There are about 200 projects underway right now within a 100-mile radius of Northampton and Florence. In fact, since the 1960s, there have been over 70,000 miles of former railroad corridor taken out of the nation’s inventory— and the majority of this mileage is here in the northeast. The network of off-road paths that can be built in eastern New York and New England is simply unmatched anywhere else in the U.S. and they connect where people live, work, and play.

Though I was extremely busy with trail development in the region— still doing 2-3 lectures a week— the real estate career was blossoming. From a standing start in late 2004— having never sold anything in my life (except maybe rail trails)— I became the 2nd top agent at the firm and stayed right up there till the end of 2009 when I left The Murphys to open my own firm. The reason I was successful was because I had a special niche. I specialized in the sale of residential property near rail trails. Because of my notoriety in advocating for the creation of rail trails, I had a burgeoning following of buyers who wanted me to help them find houses near such places.

I even had people who lived near pathways, asking for me specifically, to list their houses to sell. I was so busy that I was being noticed by national Realtor trade magazines; two stories were written there. Another story was written in the Wall Street Journal, and another in a well-read Boston area real estate blog. Even the United Airlines in-flight magazine Hemispheres did a mention.


Invitation to the grand opening of Pedal to Properties

In all the national press, there would also be a mention of a real estate company in Boulder, CO called Pedal to Properties— a firm with a bicycle aspect that includes a unique option to tour neighborhoods via distinctive cruiser bicycles. I met the founder Matt Kolb because of those articles, and I said to him “Matt, if you ever decide to franchise this, let me know.” Well in the fall of 2009 he did and I was approached by the franchisors.

After doing lots of investigations, I decided to step up. Some of my investigations also involved a look at the "inventory" of dead railroad corridor in New England. What was still out there and "un-adopted," shall we say. Or potential projects not yet moving forward in some fashion. Well it turns out that the vast majority of recoverable former railroad corridor IS moving forward— albeit slowly towards becoming trail. This meant that soon, I wouldn’t be having much more corridor to help shepherd towards becoming a trail. And the other aspect was more defensive in nature. If I didn’t step up to buy this franchise, I’m sure that someone else would have— and that would have disrupted my niche.

Thus in early 2010 we did create Pedal to Properties’ first franchise in the U.S.: PEDAL TO PROPERITES: Della Penna’s Trailside Realty, Inc. [my second "Trailside" business.] We sited the office in a very high-profile location in one of the most acclaimed and vibrant downtowns in the U.S.: Northampton, Massachusetts. Our lower level has a conference room and my office manager and I decided build out that space with the proper lighting one would find in an art gallery in New York City. We call it The Trailside Gallery [my third trailside business.] and we have a different artist there every month. We are a part of a community wide initiative called Arts Night Out.

photo of people and bikes

Bistro seating at Pedal to Properties Northampton during a summer
evening’s Arts Night Out event.

On the second Friday evening of each month, about 20 different galleries and venues in downtown Northampton have extended hours [and wine and cheese] and unveil that months’ new artist and his/her work. We regularly see over 50 people come through on those evenings. And since our office is right next to the newly opened rail trail, several of these people arrive via bike. See a story about the installation of my "bike corral":

Ever since we opened in the spring of 2010, we had an amazing amount of walk-in traffic. Much more than I’d ever seen before and more than I ever heard of at other real estate firms around town. Several people a week were coming in look for info about buying or selling a house AND several people were coming in, looking to rent apartments or houses.

So many people were looking to rent that we decided to not just let this traffic walk out the door. We knew that we couldn’t just set up a hap-hazard firm though. After a lengthy search for the right person to lead this effort and lengthy discussions as to how to make it work, we have launched Trailside Rentals— the fourth of the Trailside Family of Companies.

Since our office is in such a high-profile location, we will always have an abundance of walk-in traffic. However in order to build a sustainable and well regarded firm, you have to grow slowly, do things right, make sure all property owners and prospective tenants feel respected.

It also means making sure that thank you cards are sent out often. “Thanks for your referral!” is a phrase we’ll be repeating often. A rental office is the sort of business that will sink or swim on the number of referrals we get. If you are a fellow realtor and have a property owner with a vacancy or you have someone looking to rent while on the search for a new home, please rest assured that your referral will not only be welcomed but it will be honored. “Thanks for your referral!”

And now—as Paul Harvey used to say, “Now you know the Rest of the Story.”


Craig Della Penna is the Broker/Owner of Pedal to Properties: Della Penna’s Trailside Realty, Inc. He also owns The Trailside Gallery and Trailside Rentals— all located at 14 Strong Avenue in the heart of downtown Northampton, Massachusetts. He and his wife Kathleen also operate Sugar Maple Trailside Inn, an award-winning bed & breakfast that sits 8 feet from the rail trail. Click on the link for Info about all four of The Trailside Family of Companies. He has been building rail trails throughout the northeast for over 15 years.

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