Roads Less Travelled
Roads Less Travelled

Roads Less Travelled

Craig Della Pena

Overview
Episodes

Details

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.

Recent Episodes

Why Cities Fail at Urban Revitalization Projects
MAY 15, 2026
Why Cities Fail at Urban Revitalization Projects
🚀 In this inspiring episode, Craig Della Penna sits down with Peter Stanton and Walter Henritze, co-founders of the Union Station Alliance, to discuss the extraordinary grassroots effort that helped save and restore Worcester’s historic Union Station. From abandoned ruins and political resistance to civic pride and urban revival, this conversation explores how passion, persistence, and community activism transformed one of Massachusetts’ most iconic transportation landmarks into a symbol of Worcester’s rebirth.🎧 Hosted by: Craig Della Penna👤 Guests:🏡 Peter Stanton – Former Publisher of Worcester Business Journal🏡 Walter Henritze – Entrepreneur & Civic AdvocatePeter Stanton and Walter Henritze are co-founders of the Union Station Alliance, the group that helped drive the successful restoration of Worcester’s historic Union Station. Peter recently retired after 40 years as Publisher of the Worcester Business Journal, while Walter is a serial entrepreneur who has led startups across media, technology, and nonprofit arts. Together, they offer firsthand perspective on the station’s revival and its impact today.💡 What You’ll Learn:✔️ How a small grassroots group helped save Worcester’s Union Station✔️ The emotional connection communities have to historic train stations✔️ Why persistence and “showing up” matters in civic activism✔️ The role historic preservation plays in urban revitalization✔️ How Union Station became a symbol of Worcester’s momentum and rebirth🎵 Whether you're an investor, urban planner, preservationist, or community advocate, this episode offers valuable insights!💼 Connect with Peter Stanton:🌐 Website → https://www.wbjournal.com/staff/Peter-Stanton🔗 LinkedIn → linkedin.com/in/peter-stanton-02a34a17💼 Connect with Walter Henritze:🔗 LinkedIn → https://www.linkedin.com/in/whenritze🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/
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35 MIN
How Connected Bike Trails Become Economic Engines
MAY 8, 2026
How Connected Bike Trails Become Economic Engines
🚀 In this insightful conversation, host Craig Della Penna interviews Dan Hodge and Ann Ormsbee about the newly completed economic impact study for the New Haven and Northampton Canal Greenway.The discussion explores how shared-use trails generate economic activity, attract tourism, support local businesses, and influence policymakers to invest in long-distance trail infrastructure. Dan and Ann explain the mechanics behind economic impact studies, including direct, indirect, and induced spending, while also discussing trail connectivity, transportation synergies, and the broader vision for interconnected interstate trail systems across New England.🎧 Hosted by: Craig Della Penna👤 Guests:🏡 Dan Hodge – Economic Development & Transportation Planning Expert🏡 Ann Ormsbee – Economic Impact & Community Development SpecialistDan Hodge, Executive Vice President at Cambridge Econometrics, brings 25+ years of experience in economic development, transportation planning, and economic impact analysis, backed by prior roles at the UMass Donahue Institute, HDR, and Cambridge Systematics. Ann Ormsbee, Senior Economist at Cambridge Econometrics, specializes in economic development strategy and fiscal and economic impact studies, including major shared-use path projects. Together, they lead analyses that shape transportation and community planning across the U.S.💡 What You’ll Learn:✔️ How rail trails generate economic impact and tourism spending✔️ Why completing trail gaps dramatically increases economic potential✔️ How policymakers use economic impact studies to justify trail investments✔️ Why connected interstate trail systems matter for regional development✔️ The role of Amtrak and multimodal transportation in trail tourism✔️ Why recreational use statutes impact trail expansion projects🎵 Whether you're an investor, planner, policymaker, trail advocate, or community leader, this episode offers valuable insights!💼 Connect with Dan Hodge & Ann Ormsbee: 🌐 Website → https://www.camecon.com/ 🔗 LinkedIn → https://www.linkedin.com/in/danhodge-econ/ 🔗 LinkedIn → https://www.linkedin.com/in/annormsbee/ 🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/
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41 MIN
The Biggest Mistake New B&B Owners Make
MAY 1, 2026
The Biggest Mistake New B&B Owners Make
🚀 In this episode, we sit down with Jenelle Cruz, owner of a stunning historic vegan bed & breakfast in Northeastern Washington. From leaving a 15-year career as a registered dietitian to restoring a former convent built in 1873, Jenelle shares her journey into hospitality, sustainable living, and creating a destination experience rooted in nature, history, and plant-based living.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Jenelle Cruz – Innkeeper & Former Registered DietitianJenelle Cruz is the owner and operator of Gardenview Estate Bed & Breakfast, a historic vegan inn in northeastern Washington State. Built in 1873, the estate has served as Saint Francis Regis Mission, Sacred Heart Academy, and Lady of the Valley Convent. Jenelle, a former registered dietitian, restored the property and now welcomes guests seeking nature, history, and plant-based living near the Great American Rail Trail and Pend Oreille Wildlife Refuge.💡 What You’ll Learn:✔️ How Jenelle transitioned from healthcare to hospitality✔️ The history behind a former convent turned B&B✔️ Creating a vegan guest experience (even for non-vegans!)✔️ Marketing and managing a rural destination property✔️ The realities of running a B&B solo🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Jenelle Cruz:🌐 Website → https://www.gardenviewestatebnb.com/🌐 Website → https://www.wanderwithwonder.com/gardenview-estate-vegan-inn-washington-boutique-inn/ 🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/
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42 MIN
What No One Tells You About Bike Tourism
APR 24, 2026
What No One Tells You About Bike Tourism
🚀 In this episode, Craig Della Penna sits down with Glenn Pransky, President of the Mass Central Rail Trail Alliance, to explore the transformative power of rail trails. From Glenn’s early cycling adventures to his leadership in developing a 100-mile trail across Massachusetts, this conversation dives into how bike tourism revitalizes communities, boosts local economies, and improves public health. Learn what it takes to plan a successful cycling trip, overcome opposition to trail development, and why long-distance rail trails are shaping the future of travel and recreation.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Glenn Pransky – President, Mass Central Rail Trail AllianceCraig Della Penna is a pioneering Realtor and nationally recognized rail-trail advocate, and the host of Roads Less Travelled. As the first U.S. Realtor to specialize exclusively in properties along scenic rail-trail corridors, Craig blends his expertise in real estate with decades of experience transforming “dead” railroads into thriving community assets. A former New England organizer for the Rails-to-Trails Conservancy, he has delivered over 1,200 lectures in 21 states, authored five books, and was hailed by Ride Magazine as the most effective rail-to-trail advocate on the Eastern Seaboard.💡 What You’ll Learn:✔️ How rail trails transform local economies and communities✔️ Essential tips for planning a stress-free bike touring trip✔️ The history and growth of bike tourism in the U.S.✔️ Common challenges in trail development—and how to overcome them✔️ The public health and environmental benefits of cycling infrastructure🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Glenn Pransky:🌐 Email → [email protected]🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/
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53 MIN
The Biggest Mistake Killing Trail Development Projects
APR 17, 2026
The Biggest Mistake Killing Trail Development Projects
🚀 In this episode, we sit down with Mike Kowalczyk to explore how grassroots efforts are transforming abandoned rail corridors into thriving trail networks across New Hampshire and beyond. From overcoming community resistance to building cross-state partnerships, Mike shares how small wins, collaboration, and persistence are turning vision into reality—connecting towns, boosting tourism, and preserving history along the way.🎧 Hosted by: Craig Della Penna👤 Guest:🏡 Mike Kowalczyk – Rail Trail Advocate & Project LeaderMike Kowalczyk is the founder and president of the Monadnock Region Rail Trail Collaborative, leading efforts to rehabilitate and connect nearly 100 miles of rail trails across southwest New Hampshire and into Massachusetts and Vermont. Since retiring from a career in project management in 2017, Mike has become a key advocate for trail development, serving as chair of the Swanzey Rail Trail Advisory Committee, board member of the New Hampshire Rail Trail Coalition, and member of the Rails-to-Trails Conservancy.💡 What You’ll Learn:✔️ How to turn community resistance into support✔️ The “remove the excuses” mindset for progress✔️ How small trail projects lead to big regional impact✔️ The importance of cross-state collaboration in trail networks✔️ How rail trails boost tourism, community, and local economies🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!💼 Connect with Mike Kowalczyk:🌐 Website → https://monadnockrailtrails.org/📘 Facebook → https://www.facebook.com/p/Monadnock-Region-Rail-Trail-Collaborative-100083745592629/🎧 Follow Craig Della Penna:🌐 Website → https://www.greenwaysolutions.org/🌐 Website → https://www.northamptonrealtor.com/🌐 Website →https://www.sugar-maple-inn.com/📷 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/
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46 MIN