BEYOND REAL ESTATE
Real estate has always been just one part of my story.
For decades, I've been writing, speaking, and advocating for the preservation of historic places, the development of rail trails, and the communities they connect. Through my books and podcast, I share the ideas, experiences, and conversations that have shaped my career—and continue to inspire the way I help clients buy and sell homes.
books
Stories That Preserve History & Inspire Community
Long before becoming a Realtor, I began documenting the history of railroads, rail trails, and the communities built around them. Over the years, I've authored and contributed to several books exploring the transformation of historic railroad corridors, community development, and the lasting impact these places have on how we live today. These publications reflect decades of research, advocacy, and firsthand experience helping communities preserve their history while planning for the future.
Browse the collection to learn more about:
Rail trails and greenway development
Historic railroads and local history
Community planning and placemaking
The stories behind some of New England's most significant transportation corridors
GREAT RAIL TRAILS OF THE NORTHEAST by Craig Della Penna New England Cartographics June 2, 1995
IMAGES OF AMERICA: HOLYOKE by Craig Della Penna Arcadia Publishing July 7, 1997
24 Great Rail Trail of New Jersey: The Essential Guide to the Garden State's Best Multi-use Recreational Trails by Craig Della Penna. New England Cartographics May 7, 1999.
THE OFFICIAL RAILS TO TRAILS CONSERVANCY GUIDEBOOK By Craig Della Penna and Tom Sexton Globe Pequot Press September 2002
IMAGES OF AMERICA: Florence By Jason A. Clark and Craig P. Della Penna Arcadia Publishing September 22, 2013
Pathfinder: Blazing a New Wilderness Trail in Modern America by Ron Strickland Oregon State University Press May 15, 2011
REINVENTING YOU: Define your brand. Imagine your future by Dorie Clark Harvard Business Review Press April 9, 2013
Legendary Locals of Holyoke by Jacqueline M. Sears. Arcadia Press April 13, 2015
WHY NOT DO WHAT YOU LOVE: An Invitation to Calling and Contribution in a World Hungry for Your Gifts by Martha Johnson. Pearl Meadow Press April 28, 2017
From Rails to Trails: The Making of America's Active Transportation Network by Peter Harnik University of Nebraska Press May 1, 2021.
ROADS LESS TRAVELED
EVERY ROAD HAS A STORY.
On Roads Less Travelled, I sit down with guests from across the worlds of real estate, rail trails, tourism, historic preservation, community planning, and local leadership. Together, we explore the people and ideas shaping the places we live—and why thoughtful communities create a better quality of life.
Whether you're buying a home, passionate about active transportation, interested in regional history, or simply enjoy meaningful conversations, each episode offers fresh perspectives and practical insights from experts and advocates alike.
Topics include:
Rail trails and greenway development
Historic homes and preservation
Real estate and community planning
Bike tourism and outdoor recreation
Walkable neighborhoods and placemaking
Stories from leaders making a difference in their communities
IN THE MEDIA
RECOGNIZED FOR A DIFFERENT APPROACH TO REAL ESTATE
As the first Realtor in the United States to build a real estate practice focused on historic homes and properties near rail trails, my approach has been featured in national publications, industry magazines, television, and books on marketing and branding. My work continues to be recognized for demonstrating how a clear niche, community involvement, and authentic expertise can redefine what it means to be a real estate professional.
Featured In
The Wall Street Journal
The Boston Globe
United Airlines' Hemispheres magazine
National Association of REALTORS® trade magazines
Massachusetts Association of REALTORS® publications
Certified Residential Specialist (CRS) Magazine
HGTV's Restore America
Featured as a marketing and branding case study in multiple published books
Speaking & Industry Recognition
I am one of the country's most sought-after speakers on the relationship between rail trails, community development, and residential real estate. Over the course of my career, I have delivered more than 1,200 presentations across the United States and Canada, helping communities, planners, and fellow Realtors better understand the lasting value of connected, walkable places.
My work earned me the National Association of REALTORS® Evergreen Award, recognizing both my leadership in creating one of the nation's first rail trail-focused real estate practices and my decades of advocacy for trail development throughout the Northeast.
