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Roads Less Travelled

Hosted by Craig

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

Area focus: New Hampshire

Themes: Expertise Across Industries

Want To Be A Guest?

Seeking

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.

Meet Your Host

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.