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Icons of Real Estate

Craig Della Penna: A Rail-Trail Niche Show That Grew From a Few Episodes to 48

"You’re going to be amazed at the production values, the thoughtful interactions, the standardized onboarding of all your guests."

Craig Della Penna had a few episodes of Roads Less Travelled out and about 20 more in the queue when he recorded his testimonial. By October 2026 the show had 48 episodes on Apple Podcasts.

Before: decades of expertise in a niche few agents cover

Craig has been a Realtor in the Connecticut River Valley for more than 23 years. Before real estate he worked in the railroad industry, marketing rail freight. Today he is an associate broker with The Murphys Realtors, where he specializes in properties near rail trails and greenways, and Principal of Northeast Greenway Solutions in Northampton, Massachusetts.

He has written five books and given more than 1,200 lectures in 21 states, and he and his wife Kathleen run an award-winning bed and breakfast next to a former railroad corridor. His expertise doesn’t fit in one box: he talks about four areas, and real estate is only one of them.

What changed: one show for all four topics, with production handled

"I have four realms I talk about. I have four silos, let’s say. Real estate is one of them."
Craig Della Penna, host of Roads Less Travelled
  • One show for every topic: Roads Less Travelled covers rail trails, real estate, bike tourism and community development across New England.
  • Production values: the first thing Craig singled out in his testimonial.
  • Standardized guest onboarding: every guest goes through the same process, which matters when guests come from very different fields.
"I only have a few that are out there in the world. I got about maybe 20 in the queue waiting to be onboarded or made live."
Craig Della Penna

After: a steady run of episodes on Apple Podcasts, Spotify and YouTube

The queue turned into a publishing schedule. By October 2026 Roads Less Travelled had 48 episodes on Apple Podcasts, with conversations on bike tourism, trail towns, pricing and cooperative housing.

"You’re going to love it. You’re going to be amazed. You’re going to be amazed at the production values, the thoughtful interactions, the standardized onboarding of all your guests. It’s just thumbs up all the way."
Craig Della Penna

What agents with a niche can take from it

  • A niche is a strength, not a limit. A show built around what you know best gives listeners a reason to find you rather than any other agent.
  • Your topics can share one show. Real estate doesn’t have to be the only subject if the other topics connect back to your market.
  • Guests notice the process. Consistent onboarding makes every guest’s experience reflect well on the host.

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