Last week, while driving through his hometown of Holyoke and giving me a windshield tour of the city's historic neighborhoods, by chance Craig Della Penna spotted a tour bus parked next to the former passenger rail station. Without a second thought, he did a U-turn.

There was a model railroad convention in Hartford that week, and a crowd of tourists with cameras were snapping shots of the H.H. Richardson-designed station at the intersection of Lyman and Bowers streets. Della Penna pulled his car into the lot and jumped out, flagging down the first rail fan he could find.

In short order, he'd announced his extensive credentials as a rail historian and successful advocate for the preservation of abandoned rail corridors, and his good humor and passion for the subject emptied the bus. It was a hot July morning, and people who had just been sitting back in air-conditioned comfort and beginning to consider lunch options suddenly found themselves standing on the pavement, listening to the station's story and an overview of the demise of passenger rail in the Northeast. Della Penna explained, too, why, despite the possibility of federal stimulus money re-energizing rail in the region, he was less than certain that commuter rail would benefit Western Massachusetts.

It was far from a stale lecture; he kept the tourists laughing with tales of his personal experience working with rail companies, politicians and the public. He found out where people in his ad hoc audience were from and usually had a good idea of what rail lines or rail trails were near them or being planned. In 10 minutes it was over, and people were asking how to spell his name and where they could contact him to learn more. In parting, he explained he was a local real estate agent, specializing in selling homes near rail trails, and that he also owns a bed and breakfast in Florence, next to a trail. Next time they were in the area, he said, they should definitely look him up.

As we drove away, Della Penna admitted that there was a time when he wasn't so extroverted about his passion for the rails, and the idea of public speaking left him "knock-kneed." He remembers the exact moment, though, when he decided he needed to overcome his anxiety and speak out.

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Long before he devoted himself to preservation and advocacy, "I marketed rail freight for 20 years," Della Penna said. "I operated big trans-loads. We'd identify commodities coming across the country on trucks and then find ways to put those commodities back on the rails, coming to our railroad.

"I worked for Pinsley Railroad Company, based in Westfield," he said. "They were one of the country's earliest operators of short-line railroad, and they run them all over the country. Short-line industry is booming right now. After the Staggers Rail Act of 1980, a number of things happened that changed the rail landscape dramatically. The act made it easier for the big railroads to abandon branch lines that were no longer tenable. Up until then, they had to go through a lengthy federal process. After that, it became a lot easier. Rather than being abandoned, though, a lot of those lines were taken over by short-line railroad operators. Bringing local management and expertise, a local face to call on, they found they could generate better business for the local railroads.

"Wherever Pinsley have a railroad, they have an outfit called Railroad Distribution Services (RDS) set up to help generate traffic. The railroad I worked with in partnership—we were different companies—was the Pioneer Valley Railroad, also in Westfield. I would market mail freight, and I brought customers on board. I learned how to make a railroad work."

He also learned about the rail lines Pinsley didn't acquire and those that had been abandoned. A publisher he met and befriended through his rail freight work suggested he write a guide to New England's unused rail lines.

"It was a minor league hit, and the publisher had asked me to write editions on both New York and New Jersey," Della Penna said. "So, back in 1996, each weekend my wife and I would drive out of state, find an abandoned rail line and ride our bikes along it, documenting it and doing research for the books. Around this time, I heard about this little war—this little 'to-do'—going on in the town of Southampton, Massachusetts. Pioneer Valley Railroad had donated the town track they weren't going to use anymore with the idea that it might be turned into a rail trail.

"But there was a lot of angst in the community," Della Penna said. "I went to the last public meeting, sat at the back and watched. The opponents had gotten people to believe that if they didn't vote to block the trail, the town would become flooded with outsiders." Initially, he dismissed the opponents and thought anyone would see how narrow their perspective was. "But then the trail was voted down! I was aghast. I couldn't believe it. It didn't even register that it was possible to be against a trail. That's when I realized that maybe it was time I began speaking up."

At the time, as an author, Della Penna had ridden nearly 50 different trails.

While he was a member of the Rails to Trails Conservancy and he hoped his books would promote exploration and understanding of the abandoned infrastructure, he had not yet become a political advocate for their preservation. Around the time of the Southampton vote, he had gradually become enlightened that beyond being a weekend hobby for him, rail trails were vital to the health of a community.

"I began to notice," he said, "that where these old rail lines were in the worst condition—dead and derelict—the nearby neighborhoods generally reflected that. And as they became improved, the neighborhoods improved."

More than simply saving a piece of esoteric history, he began to see that converting rail lines to pedestrian greenways had a direct and positive impact on the people around them. He began giving lectures, and he got himself a job with the conservancy as a legislative agent and political organizer covering the New England region. (His card identifying him as a registered lobbyist has a front row position in his wallet, beating out even his driver's license). Since then, he's been involved in preserving over a thousand miles of rail trail, and the 10th anniversary issue of Ride Magazine named him the most effective advocate of his kind in the region. He now runs his own consulting firm, Northeast Greenway Solutions, which helps communities win wars over new rail development, avoid potential conflicts, and seek out new potential trails.

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"Now when I go to community meetings about these issues," he said, "and people tell me I have no idea what it's like to live next to a rail trail, I offer anyone who's interested a complimentary stay in my inn. But I tell them they have to come during a weekday in the spring or fall, so they can wake to the sound of kids riding their bikes to school."

People rarely take him up on his offer, but he said it often did the trick for separating fence-sitters who had had some unfounded fears from the "dead-end extremists."

Many opponents of rail trails refer to them as "bike paths," Della Penna said, in an effort to minimize their significance and create factions. "The argument goes that the many people who don't ride bikes will think, 'What do I need that for?', and if you're an equestrian, snowmobiler or ATV driver, 'bike path' might sound exclusionary." While he has enjoyed biking the trails (he pointed out that the activity helped him lose nearly 80 pounds), he said that the thrust of his efforts "isn't about bikes."

Rather, he says, "I'm the right-of-way guy. I'm defending people's right to turn these routes into pathways because if I don't, the adjacent land owners gain control and it would be nearly impossible then to put Humpty Dumpty back together again." These historically important corridors were the trade routes that provided a backbone to American industry; even now that they are no longer used for their original purpose, these uninterrupted pathways can still be valuable, but only if their integrity is maintained. Much of Della Penna's work is identifying who owns land on and along abandoned rail lines. Sometimes the state owns it, and he needs to make certain towns don't end up "paying for it twice" by buying it from their own government. Other times, he's working with local conservancy groups to buy parcels from multiple owners.

"New England's rail infrastructure was way overbuilt," he explained. "We have a rail inventory that was overbuilt by a factor of three. Rail started here first, and it didn't benefit from years of planning, so lines were sometimes built without a lot of thought when another line would do. But this means New England's got an abundance of natural greenways just outside our door. …"

Often it's how and whether a trail is to be paved that is the crux of many of the battles communities fight over turning an abandoned rail line into a trail, Della Penna says, and until recently, Massachusetts was the only state in the region to require pavement. Bicyclists enjoy it, equestrians don't, xenophobes fear it will attract outsiders like bears to honey, and the fiscally conservative worry about the cost of future upkeep and potential liability. Della Penna has ridden his bike over thousands of miles of both surfaces and maintains the difference is negligible, and at least for his central purposes, unimportant.

"I'm about getting to 'yes,'" Della Penna said. "And you don't do that by division, you do that by addition." Saving the pathway's integrity is what is critical, and he works to tailor a plan that meets the needs of as many constituents as possible. Ideally, he thinks the best solution would be to pave sections of rail paths that run through towns and cities, but keep the connecting, more rural paths unpaved.

While for the time being the preservation of these historic corridors might be seen as a chiefly recreational enterprise, as the network of rail paths begins to connect cities, states and entire regions, he anticipates they'll be seen as more practical. He points to a path along the Erie Canal that he knows is used by many residents as their commute between towns to work. Della Penna thinks big and long term: he's also not opposed to the pathways one day returning to their use as railways. In communities with sufficient population and resources to support light, electric rail (such as some areas in and around Boston, like Somerville and Needham), trolleys and rail trails have worked well together to cut down on traffic pollution.

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Despite his enthusiasm for preserving and rehabiltating old railways, though, Della Penna is less than enthusiastic about the plans recently announced by the Pioneer Valley Planning Commission (PVPC) to extend commuter rail service from Connecticut through Springfield and Holyoke and along the towns on the west bank of the Connecticut River.

Commuter rail, in his experience, often doesn't strengthen the communities it serves. Instead, the towns along a commuter rail line become bedroom communities in which a majority of residents don't work where they live. Unless Massachusetts steps up more seriously and invests more deeply, Della Penna sees the potential for this dynamic developing between Connecticut and Massachusetts. The best and brightest in the PVPC's proposed Knowledge Corridor would not be working where they sleep.

"The Connecticut Department of Transportation [DOT] has been working on commuter rail for years, devoting a lot of money to it," Della Penna said, "and they're the driving force behind this effort. This is not driven at all by Massachusetts transportation agencies."

The reason the rail systems along the rivers in the Pioneer Valley are now largely defunct is because the industries that once supported them have folded, fled or now rely on roads. Without another source of income, reintroduction of passenger rail service needs to be funded federally or by the state. For years, Connecticut taxpayers and businesses have been investing in building a rail infrastructure they hope will feed their industries and economy. While Massachusetts can spend federal stimulus money to extend the electric tracks northward into the state, the trains running on them and the bureaucracy behind keeping the state-funded enterprise alive will all belong to Connecticut.

"Most people don't realize this," Della Penna says, "but there will be zero chance for people in Connecticut to take jobs up here. It will be reverse flow. It'll be important for the Connecticut DOT to get people to Connecticut jobs, not to feed businesses in Springfield or Northampton. You'll have a schedule that's packed with southbound trains in the morning and the reverse in the evening."

With the train schedule determined by our southern cousin, and without a matched dedication to rail service by Massachusetts, the schedule will not be balanced to serve northern and southern interests equally.

"I've seen it happen," Della Penna says. "I was the first paying tenant in the Worcester Union Station when they reopened that. I set up my regional Rails to Trails office there, thinking with the new train service coming up from Connecticut and between there and Boston, it would be a good hub for me to work from.

"The city of Worcester was thrilled to have this beautiful renovated station and there was a lot of private investment. I was in there with all these fancy stores, gift shops and a beautiful restaurant—every service you could imagine a rail station having—and they all thought with the new commuter rail, they'd be sitting pretty. But a lot of them weren't open early enough to get the morning rush, all through the day it was a ghost town, and come the end of the day, the commuter trains would arrive, and instead of heading back along the platform to go through the fancy station, I'd see commuters climbing down the embankment strewn with rocks and broken glass, making a beeline for their cars in the parking lot.

"Unless I wanted to spend the whole day someplace, I had to drive everywhere. There wasn't a westward-bound train out of Boston until 4:30," he said. Things have improved since then, he's heard, but it was a rude awakening at the time for a city that had been anticipating an economic boost, and it took 10 years. He doesn't see the same kind of clout in this region to create balanced scheduling.

But, he reiterates, even with a more balanced schedule and an equal investment from both states, he's uncertain if commuter rail is the best use for the historic corridors he works to protect. With it easier to get to work in distant places, he fears "people will become delusioned (sic) into thinking it's normal and healthy to live up here and work down there."

He continued, "Some of my fellow realtors don't like it when I say this, but a bedroom community isn't really worth living in unless you're asleep. There's nothing there. I used to live in one. I came home, put the car in the garage and mowed my lawn on the weekends. I didn't know my neighbors."

Additionally, the plan in Connecticut currently is not to build stations in downtown urban areas, but to build them outside of town where more land is available for parking. He refers to these lots as "parking slums" and the cheap, prefabricated stations as "Am-shacks." While he doesn't doubt that a commuter line would be popular in the Pioneer Valley, he fears that without proper planning and resources it could have "a negative impact on the area," working against the advantages and ideals of living locally that he promotes through his work preserving greenways.

Since taking on his cause, he's given over a thousand lectures in 18 states and Canadian provinces on rail corridor preservation. Recently, after more than a decade of work, a canal path in Holyoke appears to be making headway, and he's heard that the town that launched his crusade, Southampton, is revisiting the rail trail idea and conducting a feasibility study.

On a busy week, Della Penna logs over 900 miles giving talks and working with communities on preservation issues. While he claims to have been involved in preserving over a thousand miles' worth of corridor, few of his campaigns have been quick, and he's learned to be very patient.