Roads Less Travelled

🚀 In this episode, Craig Della Penna sits down with filmmaker Tom Adam, founder of  Reelife  Documentary Productions, to explore the intersection of storytelling, rail trails, biking culture, and community transformation. From analog tape decks to digital filmmaking, and from grassroots trail advocacy to cross-country bike adventures, this conversation highlights how media and movement shape thri...

🚀 In this powerful and inspiring episode, host Craig Della Penna sits down with Steven Hawk, a wheelchair user and passionate rail trail advocate from Ware, Massachusetts. Steven shares how accessible trail design has transformed his independence, mobility, and connection to community. Together, they explore why ADA-compliant public spaces matter, how residents can advocate for inclusion, and how...

🚀 In this episode, host Craig Della Penna sits down with conservationist and organic farmer Kristen Sykes to explore the powerful connection between local recreation, sustainable land use, and vibrant communities. Kristen shares firsthand stories from her organic farm, discusses the importance of bike and pedestrian infrastructure, and explains how accessible trails, local farms, and small busine...

🚀 In this thoughtful episode, host Craig Della Penna speaks with community advocate and former communications executive David Hallerman about the future of Northampton, Massachusetts. The conversation explores bike trails and e-bike regulation, eminent domain and downtown revitalization, community-building beyond screens, sustainable transportation ideas, and how culture, history, and even time i...

🚀  In Part 3 of this special episode of Roads Less Traveled , the mic is turned toward the show’s own host, Craig Della Penna. Craig shares the remarkable journey that shaped his life’s work, from growing up alongside railroads to becoming one of North America’s leading advocates for rail trails and a real estate professional who proves that living near a trail is not a liability, but a lifestyle...

🚀 In Part 2 of this special episode of Roads Less Traveled , the mic is turned toward the show’s own host, Craig Della Penna , as he shares the deeper chapters of his life’s work. From fierce rail-trail battles and community resistance to rebuilding abandoned rail corridors across Massachusetts and the Northeast, Craig reflects on advocacy, history, resilience, and why trails are not a liability—...

🚀 In this special “Flip the Script” episode, host Craig Della Penna steps out from behind the mic to share the remarkable journey that shaped his life’s mission. He opens up about his early fascination with transportation, life in trolley-built neighborhoods, dramatic shifts in New England’s mill towns, and how abandoned rail corridors became the backbone of modern linear parks. Craig also reveal...

🚀 In this episode of Trails, Transit & Transformation , host Craig Della Penna sits down with Bill O’Neill , retired engineer, principal at Fuss & O’Neill , and one of the early champions behind the East Coast Greenway . Often called the Father of the East Coast Greenway , Bill reflects on his decades of work connecting communities through trails, family involvement in multi-use path plan...

🚀 In this inspiring episode, host Craig Della Penna sits down with engineer and lifelong rail trail enthusiast Michael Akrep to discuss the magic of New England’s historic rail trails. From abandoned railway routes to vibrant biking corridors, Michael shares stories of adventure, preservation, and the communities thriving along these trails. They explore the Lamoille Valley and Mass Central Rail...

🚀 In this insightful episode, host Craig Della Penna sits down with Bruce Donald , Southern New England Manager for the East Coast Greenway Alliance , to explore how regional trail systems are transforming communities. From the challenges of long-term rail-to-trail projects to the power of data-driven advocacy, Bruce shares decades of experience in trail planning, funding, and community partnersh...

🚀 Host Craig Della Penna talks with Kristin Vevon , realtor with Murphy’s Realtors and founder of The Real Estate Book of Western Massachusetts , about the growing connection between real estate, lifestyle, and greenway development. They explore how properties near bike trails are reshaping communities, the impact of print-to-digital transitions in real estate marketing, and the economic revival...

🚀 In this episode, host Craig Della Penna sits down with Tara Brewster , VP of Business Development at Greenfield Savings Bank, to explore the power of community banking, social entrepreneurship, and kindness in local development. Tara shares her journey from entrepreneur to banker, her passion for giving back, and her vision for Western Massachusetts’ future. From partnerships between nonprofits...

Passionate about real estate, rail trails, and the lifestyle they inspire? Join Craig Della Penna—Realtor and trail advocate—as he shares insights on buying homes near green corridors, bike tourism, and B&B opportunities. With decades of experience turning historic railroads into thriving assets, Craig offers inspiring stories, tips, and insider knowledge. Whether you’re a homebuyer, investor,...