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.
Roads Less Travelled
Claim This Podcastby Craig Della Pena
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38 episodes
Updated Daily
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Podcast Overview
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.
Language
🇺🇲
Publishing Since
9/24/2025
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Recent Episodes
July 10, 2026
How the Empire State Trail Created a $1.87B Economy
<p>In this episode, Craig sits down with <strong>Dylan Carey</strong>, Director of Policy & Planning at Parks & Trails New York, to discuss the newly released economic impact report showing the trail network generates <strong>$1.87 billion annually</strong> for New York's economy.</p><p>From boosting local businesses and increasing property values to creating healthier communities and expanding tourism, Dylan explains why trails are far more than recreational amenities—they're powerful economic development tools. The conversation also explores trail-oriented development, bike-friendly communities, and the future vision for expanding interconnected greenway systems across New York and beyond.</p><p>🎧 <strong>Hosted by:</strong> Craig Della Penna </p><p>👤 <strong>Guest:Dylan Carey</strong> – Director of Policy & Planning, Parks & Trails New York</p><p><strong>Dylan Carey</strong> is the Director of Policy and Planning for Parks & Trails New York, leading advocacy efforts to expand the state's greenway networks and support public lands. Leveraging a background in politics and government, he collaborates with local communities to maximize the economic impact of these resources and promote the Empire State Trail. </p><p>💡 What You'll Learn:</p><p>✔️ How the Empire State Trail generates <strong>$1.87 billion</strong> in annual economic impact</p><p>✔️ Why trails increase tourism, local business revenue, and property values</p><p>✔️ The role of trail-oriented development in community revitalization</p><p>✔️ What makes a bike-friendly business or bed & breakfast successful</p><p>✔️ The future vision for expanding New York's statewide trail network</p><p>🎵 <strong>Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!</strong></p><p><strong>💼 Connect with Dylan Carey:</strong></p><p>🌐 Website → https://www.ptny.org/</p><p>📸 Instagram → https://www.instagram.com/parkstrailsny/</p><p>👻 Facebook → https://www.facebook.com/parksandtrailsny</p><p>🔗 LinkedIn → https://www.linkedin.com/in/dylan-carey-08611a76/</p><p>🔗 LinkedIn → https://www.linkedin.com/company/parks-&-trails-new-york/</p><p>🎧 <strong>Follow Craig Della Penna:</strong></p><p>🌐 Website → https://www.greenwaysolutions.org/</p><p>🌐 Website → https://www.northamptonrealtor.com/</p><p>🌐 Website →https://www.sugar-maple-inn.com/</p><p>📷 Instagram → https://www.instagram.com/craigdp413/</p><p>🔗 LinkedIn → https://www.linkedin.com/in/craigdp/</p><p>📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!</p><p> ⭐ Produced by Icons of Real Estate -<a href="https://iconsofrealestate.com/"> <u>https://iconsofrealestate.com/</u></a><br></p>
July 3, 2026
How Cities Can Fix Housing Using “Tax Per Acre” Thinking
<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 Massachusetts, Scott explains how housing policy, zoning, and infrastructure design shape the health of communities—and why America’s built environment may be undermining both economic opportunity and social connection.</p><p>🎧 <strong>Hosted by:</strong> Craig Della Penna</p><p>👤 <strong>Guest:</strong> 🏡 <strong>Scott Graves</strong> – Principal, SMG Graves Associates | Construction Project Manager | Mixed-Use Housing Developer | Economic Development Strategist</p><p>💡 <strong>What You’ll Learn:</strong> </p><p>✔️ How jazz improvisation mirrors real estate development and urban planning </p><p>✔️ Why zoning and housing policy shape community health and economic resilience </p><p>✔️ The hidden cost of suburban sprawl and underused urban land </p><p>✔️ Why “tax revenue per acre” matters more than expansion-based growth models </p><p>✔️ How cities can unlock housing by activating vacant lots and reforming land use</p><p>🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!</p><p><strong>💼 Connect with Scott Graves:</strong></p><p>🌐 Website → http://smgravesassociates.com/</p><p>📸 Instagram → https://www.instagram.com/arewehereyetpodcast/</p><p>🎧 <strong>Follow Craig Della Penna:</strong></p><p>🌐 Website → https://www.greenwaysolutions.org/</p><p>🌐 Website → https://www.northamptonrealtor.com/</p><p>🌐 Website →https://www.sugar-maple-inn.com/</p><p>📷 Instagram → https://www.instagram.com/craigdp413/</p><p>🔗 LinkedIn → https://www.linkedin.com/in/craigdp/</p><p>📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! </p><p>⭐ Produced by Icons of Real Estate -<a href="https://iconsofrealestate.com/"> <u>https://iconsofrealestate.com/</u></a><strong></strong></p>
June 26, 2026
How Mixed-Use Housing Can Revive Small Towns
<p>🚀 In this episode, <strong>Craig Della Penna</strong> sits down with <strong>Scott Graves</strong> to explore how affordable housing, entrepreneurial ecosystems, and connected transportation networks can transform communities. Drawing on decades of experience in construction, mixed-use development, and economic research, Scott explains why housing and job creation must go hand in hand. He also shares how rail trails, walkable downtowns, and locally driven investment strategies are helping revitalize small cities and rural communities across New England.</p><p>🎧 <strong>Hosted by:</strong> Craig Della Penna</p><p><strong>👤 Guest:</strong>🏡 <strong>Scott Graves</strong> – Principal, SMG Graves Associates | Construction Project Manager | Mixed-Use Housing Developer | Economic Development Strategist</p><p><strong>💡 What You'll Learn:</strong></p><p>✔️ Why affordable housing and quality job creation must be developed together</p><p>✔️ How mixed-use downtown developments benefit both young professionals and empty nesters</p><p>✔️ The economic value of rail trails, walkable communities, and connected neighborhoods</p><p>✔️ Why locally driven investment and entrepreneurship outperform grant dependency</p><p>✔️ Practical strategies for creating resilient small-town economies</p><p>🎵 Whether you're an investor, developer, planner, entrepreneur, or community leader, this episode offers valuable insights!</p><p><strong>💼 Connect with Scott Graves:</strong></p><p>🌐 Website → http://smgravesassociates.com/</p><p>📸 Instagram → https://www.instagram.com/arewehereyetpodcast/<br><strong>🎧 Follow Craig Della Penna:</strong></p><p>🌐 Website → https://www.greenwaysolutions.org/</p><p>🌐 Website → https://www.northamptonrealtor.com/</p><p>🌐 Website →https://www.sugar-maple-inn.com/</p><p>📷 Instagram → https://www.instagram.com/craigdp413/</p><p>🔗 LinkedIn → https://www.linkedin.com/in/craigdp/</p><p>📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! </p><p>⭐ Produced by Icons of Real Estate -<a href="https://iconsofrealestate.com/"> <u>https://iconsofrealestate.com/</u></a><strong></strong></p>
38 total episodes available
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- What is Roads Less Travelled?
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This podcast updates daily.
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This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
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Yes, this podcast regularly features guests.
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