business
Hosted by Craig Della Pena · business · EN-US
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, or trail enthusiast, Roads Less Travelled releases new episodes every two weeks.
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Contact path
Verified email
Booking probability
32%
Guest openness
Selective
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Signup to Generate a PitchPassionate 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.
Roads Less Travelled is hosted by Craig Della Pena. The show has published 49 episodes to date.
Recent episodes include "How E-Bike Tours Are Connecting Vermont’s Trail Towns | Yva and Jim Rose" (30 October 2026, 34 minutes), "Buying a Home in Greater Boston: Costs & Challenges | Bonnie Lai" (23 October 2026, 30 minutes), and "The Real Cost of Pricing Like It’s 2021 | Bill Skerry" (16 October 2026, 43 minutes).
Roads Less Travelled publishes roughly weekly, with episodes averaging 36 minutes across 49 episodes.
Booking probability for Roads Less Travelled is 32%, and the host is rated Selective on guests. Roads Less Travelled requires a Pod Score of 80 or higher. Roads Less Travelled's contact route on record: verified email.
The strongest fits for Roads Less Travelled are Real Estate Agents and Fitness, Golf & Recreation. Roads Less Travelled has a business audience.
Craig Della Pena hosts Roads Less Travelled, a business podcast with 49 episodes published.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
Roads Less Travelled
How can an e-bike tour help more people experience Vermont’s 93-mile Lamoille Valley Rail Trail? Founders Yva and Jim Rose share how they built a bike-tour business around the trail and connected riders with local...
Roads Less Travelled
Can first-time homebuyers afford a home in Greater Boston? Explore homebuyer assistance, condo costs, and the challenges of buying in Massachusetts. On Roads Less Travelled, host Craig Della Penna, REALTOR®, author, and...
Roads Less Travelled
Still pricing a home like it’s 2021? In today’s market, that mistake can cost sellers time, leverage, and real money. Craig Della Penna, a Realtor specializing in homes near rail trails in Western Massachusetts, brings...
Roads Less Travelled
How does a town of just over 700 residents generate more than $3 million a year in overnight lodging revenue? On the Roads Less Travelled podcast , Craig Della Penna —the first U.S. REALTOR to specialize in homes near...
Roads Less Travelled
What turns a rail-trail stop into an overnight stay? At Highland Lake Inn, Pecco Beaufays says cyclists generate 25% of revenue. Craig Della Penna hosts Roads Less Travelled to explore how trails connect communities and...
Roads Less Travelled
What if the people who used to feel like strangers could become the family you choose? Craig Della Penna talks with Alex Jarrett (Petal People Cooperative) and Daniel Trenner (a 17-year intentional co-living household)...
Roads Less Travelled
Marianne Borowski joins Craig Della Penna on Roads Less Travelled to discuss the creation and expansion of the 83-mile Cross New Hampshire Adventure Trail. Learn how historic rail corridors, multi-use collaborations...
Roads Less Travelled
Host Craig Della Penna welcomes conservationist and organic farmer Kristen Sykes to discuss the vital connections between local agriculture, trail infrastructure, and community well-being in Massachusetts. What you'll...
Roads Less Travelled
How one resident transformed a muddy path into an accessible community lifeline. Steven Hawk joins Craig to explore the powerful impact of ADA-compliant rail trails in small towns like Ware, Massachusetts. Steven shares...
Roads Less Travelled
Explore how Western Massachusetts is balancing modern transit shifts, trail safety, and community engagement with former eMarketer analyst David. Joined by host Craig, David shares insights from his transition to...
Roads Less Travelled
<p>In this episode, Craig sits down with Dylan Carey, Director of Policy & Planning at Parks & Trails New York, to discuss the newly released economic impact report showing the trail network generates $1.87 billion...
Roads Less Travelled
In this episode, Craig sits down with Dylan Carey , Director of Policy & Planning at Parks & Trails New York, to discuss the newly released economic impact report showing the trail network generates $1.87 billion...
Roads Less Travelled
<p> 🚀 In this conversation, developer and former touring musician Scott Graves joins host Craig Della Penna to explore how jazz improvisation, economic theory, and urban planning intersect. From Vermont to...
Roads Less Travelled
🚀 In this conversation, developer and former touring musician Scott Graves joins host Craig Della Penna to explore how jazz improvisation, economic theory, and urban planning intersect. From Vermont to Massachusetts...
Roads Less Travelled
<p>🚀 In this episode, Craig Della Penna sits down with Scott Graves to explore how affordable housing, entrepreneurial ecosystems, and connected transportation networks can transform communities. Drawing on decades of...
Roads Less Travelled
🚀 In this episode, Craig Della Penna sits down with Scott Graves to explore how affordable housing, entrepreneurial ecosystems, and connected transportation networks can transform communities. Drawing on decades of...
Roads Less Travelled
<p>🚀 In this inspiring episode, host Craig Della Penna sits down with longtime cycling advocate and rail trail enthusiast Elizabeth Johnson to discuss how rail trails can transform lives, communities, and local...
Roads Less Travelled
🚀 In this inspiring episode, host Craig Della Penna sits down with longtime cycling advocate and rail trail enthusiast Elizabeth Johnson to discuss how rail trails can transform lives, communities, and local economies...
Roads Less Travelled
<p>🚀 In this episode, conservationist Michael Calhoun shares the remarkable story behind Oregon’s first rail-trail conversion, the Banks-Vernonia Trail. Michael discusses how abandoned railroad corridors became...
Roads Less Travelled
<p>🚀 In this episode, Craig Della Penna sits down with Amanda Lewis, Director of MassTrails at the Massachusetts Department of Conservation and Recreation (DCR), to explore the vision, growth, and future of trails...
Recent guests on Roads Less Travelled. Study who booked and why before you pitch.
Director of Policy & Planning, Parks & Trails New York
Principal, SMG Graves Associates | Construction Project Manager | Mixed-Use Housing Developer | Economic Development Strategist, California Budget and Policy Center
Retired Educator, Cycling Advocate & Rail Trail Enthusiast, Main Street Area Association
Director of MassTrails at the Massachusetts Department of Conservation and Recreation, Massachusetts Department of Conservation and Recreation
PitchCentric classifies Roads Less Travelled under these industries. Guests from them are the closest fit, and each links to the best podcasts in that industry.
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