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On the Right Track

A CRS trains his sights on abandoned rail lines

Craig Della Penna, CRS

Craig Della Penna, CRS, has built an impressive track record as his career path has taken the road less traveled. He has developed a unique niche in his real estate practice over the past 15 years. He has written five books, four books feature him as a case study in creative marketing and 21st century branding, and his activities have been described in the Boston Globe and Wall Street Journal.

As is the case for many CRSs, real estate was not his first career. He worked in the railroad industry for many years, and in the mid-1990s, he wrote a series of books on the history of old railroad lines converted to walking and biking trails (aka rail trails), and got involved in the politics of how these paths did or did not get built.

Over the past 25 years, Della Penna has given over 1,200 lectures in 21 states on rail-to-trail conversions and their tie-in to issues surrounding smart-growth, land preservation, brownfield redevelopment, place-making, effects on nearby residential real estate values and sustainability. He has helped develop over 1,000 miles of rail trails in the northeast U.S., and has taught groups how to overcome local opposition to rail-to-trail conversion.

In Northampton, post-civil war mills were built that produced wealth, but when industrial uses were scaled back, the railroads started to disappear. “I began to actively organize ‘friends of the trail’ groups in communities across New England and eastern New York,” Della Penna says. “In the late 1990s, I was hired by the national organization Rails-to-Trails Conservancy [RTC] as a political organizer to ‘parachute’ into some of the most notable rail trail wars in the northeast. I am a battle-hardened veteran of nearly every rail-trail war within 150 miles of my home in Northampton, Massachusetts.”

In 2005, Della Penna set up two entities. One was the Northeast Greenways Solutions (NEGS) to teach communities and groups how to get their trail development projects moving forward. He also set up Central Highlands Conservancy LLC (CHC) as a hybrid land acquisition vehicle to purchase former railroad corridors in Massachusetts to block sales to adjacent landowners. CHC purchased 3.2 miles and gave the local land trust two years to buy him out. After purchasing it, they got grants to build out and rehab the trail. CHC has also been used to teach others how to do this.

The Inside Track

“I was involved in all the wars in the Northeast—homeowners would attend meetings and say that the conversions would devalue their homes,” Della Penna says. “They didn’t want a trail because they thought it would devalue their property.” The homeowners would also claim that Della Penna didn’t understand their perspective because he didn’t own a home near a proposed rail-to-trail conversion. “They would say to me, ‘You don’t live near one, so don’t tell us what to do’—so I bought one that’s 8 feet from the trail,” Della Penna says.

“When RTC scaled-out of the region, I decided I would become a REALTOR® to prove that all those who said they couldn’t sell their house were wrong. I developed a unique niche real estate practice, specializing in houses near to walking or biking pathways and antique or historic houses.”

“I’ve been a REALTOR® in Massachusetts for about 15 years now and I am consistently among the top REALTORS® in the Northampton area. I came onboard with The Murphys REALTORS®—it’s a locally owned company and we have three offices in Northampton.

Della Penna is an accredited teacher of REALTORS® in both Massachusetts and Vermont, where he has taught CE courses about these issues to hundreds of REALTORS®. He has also been a keynote or plenary speaker at state or regional conferences in New York, California, Virginia, Connecticut, Missouri, Michigan, and Massachusetts.

“In the world of 21st century real estate, you have to have core beliefs and a niche that you can hang your hat on,” Della Penna says. “As a REALTOR®, I have focused on a special niche: the sale of houses near rail trails, greenways or other conservation lands.

Della Penna and his wife, Kathleen, bought a badly run-down, circa 1865, farmhouse next to the rail trail in Northampton’s historic Florence village center, and in spring 2003, it opened as a bed & breakfast called Sugar Maple Trailside Inn. The renovation was featured on HGTV’s Re-store America television program. “Now I go into the meetings and tell them I own a B&B 8 feet away, and if you’re really fearful of this coming to your neighborhood, I’ll give you a complimentary stay.” “Has to be on a weeknight though because I want you to wake up to the laughter of kids biking to school.” Della Penna says.

Getting Back on Track

The B&B also attracts potential homebuyers. “Millennials don’t want to live where they grew up—in meandering suburbs with no sidewalks,” Della Penna says. “They want the convenience of being able to walk or bike to amenities. I do several transactions each year with folks who want a second home, or who want to relocate to Northampton. The existence of the trail has been a significant factor in attracting potential buyers.”

“As REALTORS®, we see that places with grid-pattern streets, porches, sidewalks and high Walk Scores have come out of the recession stronger than the typical suburban layout,” Della Penna says. “People want to live near these things, and they want their kids to be able to bike to school. With climate change increasingly a concern, the smallest possible step they can take to make life better is to not have to drive everywhere. In late 2017, the National Association of REALTORS® awarded me the 2017 EverGreen award for being the first REALTOR® with my special niche of developing these green pathways.

The Fast Track

Della Penna sends out a free, monthly e-newsletter to more than 10,000 people. He searches online for articles in every paper in the U.S. about greenways, bike trails and similar key words.

The search results arrive every day at 5 am. He scans primarily for stories that are within 100-150 miles of Northampton. “We pull an image and the headline into the Constant Contact format, plus 2-3 sentences, and add a ‘read more’ link that readers can click-on, to go directly to the newspaper article at the papers’ website. The publications love it because it brings additional eyeballs to their stories.”

The e-newsletter Della Penna publishes about ongoing development of rail trails throughout the northeast has been named a 2018 All Star Award winner by Constant Contact, a leader in small business marketing solutions. The annual award recognizes the most successful 10% of Constant Contact’s customer base, based on their significant achievements using email marketing to engage their customer base and drive results for their organization during the prior year. The newsletter rated highly in terms of engagement with readers, opens, click-throughs, forwards to friends and social media posts.

What does the future hold for Craig Della Penna? Della Penna doesn’t get paid for his advocacy, newsletter or lectures—it’s all part of his legacy project. He’s currently assembling what would be the longest rail to trail project in the Northeast at 104 miles. And he’s still involved in three rail conversion wars in eastern Massachusetts where there is opposition to the conversion, so he continues to fight the good fight.