ICONS Real Estate Podcast Network
Roads Less Travelled
Hosted by Craig Della Penna · 48 episodes
Exploring how rail trails, real estate, bike tourism, and community development are transforming communities across New England!
About Roads Less Travelled
The Roads Less Travelled, hosted by Craig Della Penna, highlights the New England people, communities, and ideas shaping the future of former rail corridors and the towns surrounding them. Episodes feature conversations with experts, community leaders, real estate professionals, trail advocates, and others who understand the opportunities and challenges connected to rail-trail development.
With a strong connection to New England, the podcast offers practical insights into how rail trails can transform small towns, create economic opportunities, encourage outdoor recreation, and bring communities together. Whether you’re interested in real estate, cycling, sustainable development, or discovering how overlooked corridors can become vibrant community assets, The Roads Less Travelled offers an engaging look at the possibilities waiting just beyond the pavement.
Latest episodes of Roads Less Travelled
- The Real Cost of Pricing Like It’s 2021 | Bill Skerry
Oct 16, 2026 · 43 min
- Bike Tourism and the Business of a Trail Town | Alison Leathers
Oct 9, 2026 · 31 min
- How Rail Trail Cyclists Drive 25% of This Inn’s Revenue | Pecco Beaufays
Sep 25, 2026 · 19 min
- Bike Tourism: The Service Behind the Stay | Pecco Beaufays
Sep 18, 2026 · 49 min
- Affordable Housing Starts with Cooperative Living | Craig Della Penna
Sep 11, 2026 · 46 min
- Rail Trail Adventures & Cycling Tourism in New Hampshire with Marianne Borowski
Sep 4, 2026 · 32 min
From Apple Podcasts, checked Oct 17, 2026.
About Craig Della Penna
Craig Della Penna is a rail-trail advocate, real estate professional, author, speaker, and the Principal of Northeast Greenway Solutions. Based in Northampton, Massachusetts, Craig has spent decades working at the intersection of rail trails, real estate, community development, tourism, and sustainable growth. Before entering real estate, Craig worked in the railroad industry, marketing rail freight and managing large-scale transloading operations. Today, Craig is an associate broker with The Murphys Realtors, where he specializes in properties near rail trails and greenways.
As host of Roads Less Travelled, Craig brings his extensive experience to conversations about rail-trail living, real estate, bike tourism, community development, and sustainable lifestyles. He has delivered more than 1,200 lectures across the United States and Canada and has authored multiple books on rail trails and smart-growth development.
Be a guest on Roads Less Travelled
Do you have insight into rail trails, real estate, bike tourism, or community development that New England needs to hear? Join Craig for a conversation that puts your expertise in front of listeners who care deeply about the future of former rail corridors and the towns surrounding them.
Showcase Your Expertise
Share your knowledge and position yourself as a thought leader in Western Massachusetts and New England real estate and trail development. Your insights will build credibility and elevate your personal brand.
Gain a Competitive Edge in Western Massachusetts & New England’s Growing Market
Western Massachusetts and New England’s rail-trail communities are drawing new interest from buyers and investors, and your appearance on the podcast lets you tap into this growing demand. Share strategies that set you apart from the competition.
Engage a Focused, High-Impact Audience
Connect with an audience of real estate professionals, trail advocates, and community members eager for actionable insight into rail trails and the towns they run through.
