Roads Less Travelled

Craig Della Pena

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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.

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Recent episodes

  • How E-Bike Tours Are Connecting Vermont’s Trail Towns | Yva and Jim RoseOct 30, 2026 · 34 min
  • Buying a Home in Greater Boston: Costs & Challenges | Bonnie LaiOct 23, 2026 · 30 min
  • The Real Cost of Pricing Like It’s 2021 | Bill SkerryOct 16, 2026 · 43 min
  • Bike Tourism and the Business of a Trail Town | Alison LeathersOct 9, 2026 · 31 min
  • How Rail Trail Cyclists Drive 25% of This Inn’s Revenue | Pecco BeaufaysSep 25, 2026 · 19 min
  • Bike Tourism: The Service Behind the Stay | Pecco BeaufaysSep 18, 2026 · 49 min
  • Affordable Housing Starts with Cooperative Living | Craig Della PennaSep 11, 2026 · 46 min
  • Rail Trail Adventures & Cycling Tourism in New Hampshire with Marianne BorowskiSep 4, 2026 · 32 min
  • Sustainable Farming and Trail Access with Kristen SykesAug 28, 2026 · 33 min
  • How One Advocate is Transforming Rail Trails for Wheelchair AccessAug 7, 2026 · 44 min

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