Roads Less Travelled

Craig Della Pena

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.

  1. 6d ago

    How the Empire State Trail Created a $1.87B Economy

    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 annually for New York's economy. 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. 🎧 Hosted by: Craig Della Penna  👤 Guest:Dylan Carey – Director of Policy & Planning, Parks & Trails New York Dylan Carey 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.  💡 What You'll Learn: ✔️ How the Empire State Trail generates $1.87 billion in annual economic impact ✔️ Why trails increase tourism, local business revenue, and property values ✔️ The role of trail-oriented development in community revitalization ✔️ What makes a bike-friendly business or bed & breakfast successful ✔️ The future vision for expanding New York's statewide trail network 🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights! 💼 Connect with Dylan Carey: 🌐 Website → https://www.ptny.org/ 📸 Instagram → https://www.instagram.com/parkstrailsny/ 👻 Facebook → https://www.facebook.com/parksandtrailsny 🔗 LinkedIn → https://www.linkedin.com/in/dylan-carey-08611a76/ 🔗 LinkedIn → https://www.linkedin.com/company/parks-&-trails-new-york/ 🎧 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/

    How the Empire State Trail Created a $1.87B Economy

  2. Jul 3

    How Cities Can Fix Housing Using “Tax Per Acre” Thinking

    🚀 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. 🎧 Hosted by: Craig Della Penna 👤 Guest: 🏡 Scott Graves – Principal, SMG Graves Associates | Construction Project Manager | Mixed-Use Housing Developer | Economic Development Strategist 💡 What You’ll Learn: ✔️ How jazz improvisation mirrors real estate development and urban planning ✔️ Why zoning and housing policy shape community health and economic resilience ✔️ The hidden cost of suburban sprawl and underused urban land ✔️ Why “tax revenue per acre” matters more than expansion-based growth models ✔️ How cities can unlock housing by activating vacant lots and reforming land use 🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights! 💼 Connect with Scott Graves: 🌐 Website → http://smgravesassociates.com/ 📸 Instagram → https://www.instagram.com/arewehereyetpodcast/ 🎧 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/

    How Cities Can Fix Housing Using “Tax Per Acre” Thinking

  3. Jun 26

    How Mixed-Use Housing Can Revive Small Towns

    🚀 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 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. 🎧 Hosted by: Craig Della Penna 👤 Guest:🏡 Scott Graves – Principal, SMG Graves Associates | Construction Project Manager | Mixed-Use Housing Developer | Economic Development Strategist 💡 What You'll Learn: ✔️ Why affordable housing and quality job creation must be developed together ✔️ How mixed-use downtown developments benefit both young professionals and empty nesters ✔️ The economic value of rail trails, walkable communities, and connected neighborhoods ✔️ Why locally driven investment and entrepreneurship outperform grant dependency ✔️ Practical strategies for creating resilient small-town economies 🎵 Whether you're an investor, developer, planner, entrepreneur, or community leader, this episode offers valuable insights! 💼 Connect with Scott Graves: 🌐 Website → http://smgravesassociates.com/ 📸 Instagram → https://www.instagram.com/arewehereyetpodcast/🎧 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/

    How Mixed-Use Housing Can Revive Small Towns

  4. Jun 19

    Why Most Adults Quit Cycling Too Soon

    🚀 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. Elizabeth shares her personal journey from rediscovering cycling through the Norwottuck Rail Trail to becoming a passionate advocate for trail networks throughout Massachusetts and New England. The conversation explores adaptive cycling solutions, trail towns, community building, public health benefits, and how trail-oriented development is shaping the future of real estate and transportation. 🎧 Hosted by: Craig Della Penna 👤 Guest:🏡 Elizabeth Johnson – Retired Educator, Cycling Advocate & Rail Trail Advocate Elizabeth Johnson is an adult cycling advocate who discovered her passion for riding on the Norwottuck and Mass Central Rail Trails. She actively promote adult cycling, sharing her journey to show that biking is a fun and healthy way to enjoy life. 💡 What You’ll Learn: ✔️ How Elizabeth rediscovered her passion for cycling through the Norwottuck Rail Trail ✔️ The physical and mental health benefits of rail trail access ✔️ How adaptive bike modifications can make cycling accessible at any age ✔️ Why trail towns create economic opportunities and community growth ✔️ How trail-oriented development is influencing the future of real estate 🎵 Whether you're an investor, planner, cyclist, community leader, or outdoor enthusiast, this episode offers valuable insights! 💼 Connect with Elizabeth Johnson: 🌐 Website → https://www.youtube.com/@RideandShineBicycling 📸 Instagram → https://www.instagram.com/rideandshinebicycling/ 🎧 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/

    Why Most Adults Quit Cycling Too Soon

  5. Jun 12

    How a Forgotten Railroad Revived an Entire Small Town

    🚀 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 valuable community assets, the process of earning National Recreation Trail certification, balancing conservation with recreation, and the economic and cultural benefits trails bring to small towns. He also explores trail tourism, forestry, environmental stewardship, and the future of Oregon’s trail networks. 🎧 Hosted by: Craig Della Penna 👤 Guest:🏡 Michael Calhoun – Conservationist, Trail Advocate, and Board Chair of the Columbia Soil and Water Conservation District 💡 What You’ll Learn: ✔️ The history behind Oregon’s first rail-trail conversion ✔️ How National Recreation Trail certification works ✔️ The economic impact of trail tourism on rural communities ✔️ Balancing recreation with environmental conservation ✔️ Strategies for preserving railroad heritage and local history ✔️ The importance of urban forestry and dark-sky initiatives ✔️ Advice for grassroots advocates working to save historic rail corridors 🎵 Whether you're a trail enthusiast, conservation advocate, community leader, or history buff, this episode offers valuable insights into preserving the past while building a sustainable future. 💼 Connect with Michael Calhoun: 🌐 Website → https://shorturl.at/E8yBJ 🔗 LinkedIn → https://www.linkedin.com/in/michael--calhoun 🎧 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/

    How a Forgotten Railroad Revived an Entire Small Town

  6. Jun 5

    How Massachusetts Is Building Trails Faster Than Ever

    🚀 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 across the Commonwealth. Amanda shares how MassTrails is connecting communities through a statewide network of recreational trails and shared-use paths, the impact of the MassTrails Grant Program, innovations in trail mapping and accessibility, the launch of MassTrails10, and what lies ahead for trail development in Massachusetts. Whether you're a trail advocate, planner, municipal leader, or outdoor enthusiast, this conversation offers valuable insights into the power of trails to transform communities. 🎧 Hosted by: Craig Della Penna 👤 Guest:🏡 Amanda Lewis – Director of MassTrails, Massachusetts Department of Conservation and Recreation (DCR) 💡 What You’ll Learn: ✔️ The vision behind MassTrails and how agencies collaborate statewide ✔️ How the MassTrails Grant Program has funded over 500 trail projects ✔️ The role of GIS, digital mapping, and trail data in improving public access ✔️ Why accessibility and equity are central to modern trail planning ✔️ How MassTrails10 is promoting trail tourism and outdoor recreation across Massachusetts 🎵 Whether you're a planner, trail advocate, municipal leader, cyclist, hiker, investor, or outdoor enthusiast, this episode offers valuable insights into the future of trails and recreation in Massachusetts! 💼 Connect with Amanda Lewis: 🔗 LinkedIn → https://www.linkedin.com/in/amanda-krchak-lewis-b250662a/ 🎧 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/

  7. May 29

    How Massachusetts Could Save Its State Parks Before It’s Too Late

    🚀 In this insightful episode, Doug Pizzi, Executive Director of Mass Parks for All, joins Craig Della Penna to discuss the history, funding, and future of Massachusetts state parks. From the origins of America’s first public parks to today’s challenges surrounding conservation funding, Doug shares how public lands impact environmental protection, recreation, public health, and economic growth. The discussion also explores the Mass Central Rail Trail, DCR funding priorities, and why investing in parks is critical for future generations. 🎧 Hosted by: Craig Della Penna 👤 Guest:🏡 Doug Pizzi – Executive Director, Mass Parks for All Doug Pizzi is the Executive Director of Mass Parks for All, a nonprofit organization advocating for the protection and modernization of public lands. He previously served as Executive Director of Massachusetts Conservation Voters and brings extensive experience in environmental policy, communications, and nonprofit advocacy, including work with organizations such as Friends of the Earth and the National Wildlife Federation. 💡 What You’ll Learn: ✔️ The history of Massachusetts state parks and conservation ✔️ Why public parks are essential for mental and physical wellbeing ✔️ How Mass Parks for All advocates for better park investment ✔️ The economic and environmental impact of rail trails and outdoor recreation ✔️ How communities can help protect and improve public lands ✔️ The future outlook for conservation and state park funding in Massachusetts 🎵 Whether you're an investor, advocate, outdoor enthusiast, or community leader, this episode offers valuable insights! 💼 Connect with Doug Pizzi: 🌐 Website → https://www.massparksforall.org/ 📷 Instagram → https://www.instagram.com/dougpizzi/ 🔗 LinkedIn → https://www.linkedin.com/in/pizzicommunications/ 🎧 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/

    How Massachusetts Could Save Its State Parks Before It’s Too Late

  8. May 22

    How to Protect Your Mental Health During a Move

    🚀 In this episode, Craig Della Penna sits down with Beth Agostino-Evans, a licensed independent clinical social worker with more than 20 years of experience in behavioral health and trauma-informed care. Beth shares her expertise on mental health, emotional resilience, mindfulness, and how outdoor spaces and community wellness initiatives positively impact emotional wellbeing. The conversation also explores the emotional stress tied to buying and selling homes, how repeated relocations affect families, and why having trusted support systems during major life changes is so important. From evidence-based therapy approaches to the long-term impacts of chronic stress, this episode offers practical guidance for anyone navigating transitions, anxiety, or personal growth. 🎧 Hosted by: Craig Della Penna 👤 Guest:🏡 Beth Agostino-Evans – Licensed Independent Clinical Social Worker Beth Agostino-Evans, MSW, LICSW is a clinical social worker with more than 20 years of experience specializing in focused, evidence-based treatment. She serves as the Director of Clinical Services at a mental health agency in the Pioneer Valley. A graduate of Assumption College and Boston University’s Master of Social Work program, Beth brings deep expertise in trauma-informed care, behavioral health, and community-based mental health services. 💡 What You’ll Learn: ✔️ How outdoor spaces and nature support emotional wellness ✔️ Why buying or selling a home creates emotional stress ✔️ Evidence-based therapy approaches that help clients thrive ✔️ The mental health impact of repeated relocations and life transitions ✔️ Practical mindfulness and self-care strategies during stressful times ✔️ Common misconceptions about therapy and mental health support ✔️ How COVID changed the mental health profession and therapy delivery 🎵 Whether you're an investor, agent, homeowner, or someone navigating life transitions, this episode offers meaningful mental health insights and practical wellness strategies! 💼 Connect with Beth Agostino-Evans: 🌐 Website → https://www.psychologytoday.com/profile/1380412 🎧 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/

    How to Protect Your Mental Health During a Move
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About

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.

Information

  • Creator
    Craig Della Pena
  • Years Active
    2025 - 2026
  • Episodes
    38
  • Rating
    Clean
  • Copyright
    © Craig Della Pena
  • Show Website
    Roads Less Travelled

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