Roads Less Travelled
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Roads Less Travelled

Hosted by Craig Della Pena
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Expertise Across Industries

About Roads Less Travelled

Roads Less Travelled is a podcast hosted by Craig Della Penna that explores the fascinating intersection of real estate, railroads, and tourism. From homes near historic rail corridors to the booming bike tourism industry along rail trails, Craig shares expert insights, engaging stories, and practical advice for buyers, investors, and enthusiasts. Each episode highlights the potential of railway-related properties and educates listeners about owning bed and breakfasts, rail trail tourism, and regional development

Topics Covered

Expertise Across Industries

Meet Craig Della Pena

Craig Della Pena

Craig Della Pena

Craig Della Penna is a pioneering Realtor based in North Haptions, MA, specializing in properties near railway tracks and rail trails, a unique niche he was the first in the U.S. to develop. With a deep background in railroad history and a veteran in the “railroad war,” Craig combines his passion for railroads with real estate expertise as a Certified Residential Specialist (CRS). He is also an accomplished author with several books on railroad history. Craig educates buyers and investors about owning homes near railway corridors, rail-trail tourism, and the opportunities in bed and breakfast properties along these historic routes.

How to Get on Roads Less Travelled

What We're Looking For

Craig Della Penna is looking to feature experts in railroads
bike tourism
regional tourism councils
bed and breakfast operators
real estate professionals
and community leaders involved in rail trail development and historic railway preservation.

Booking Process Through HUB

1
Create Your Guest Profile Sign up on HUB and build your guest profile with your bio, headshot, production stats, and speaking topics.
2
Submit Your Application Apply to this podcast with a clear pitch, what you can teach, and why you're a strong fit for the audience.
3
Get Booked & Record Once approved, coordinate scheduling through HUB and record your episode with the host team.

Featured Episodes