Roads Less Travelled
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.
Episodes
How can an e-bike tour help more people experience Vermont’s 93-mile Lamoille Valley Rail Trail? Founders Yva and Jim Rose share how they built a bike-tour business around the trail and connected riders with local communities along the way.
On Roads Less Travelled, Craig Della Penna, REALTOR®, author, and nationally recognized rail-trail advocate, speaks with Yva and Jim Rose, founders of Lamoille Valley Bike Tours in Johnson,...
Can first-time homebuyers afford a home in Greater Boston? Explore homebuyer assistance, condo costs, and the challenges of buying in Massachusetts.
On Roads Less Travelled, host Craig Della Penna, REALTOR®, author, and nationally recognized rail-trail advocate, speaks with Bonnie Lai, founding partner of 1st Knock Realty and the Luxe Home Team, about navigating Greater Boston’s real estate market. As the first U.S. REALTOR® t...
Still pricing a home like it’s 2021? In today’s market, that mistake can cost sellers time, leverage, and real money.
Craig Della Penna, a Realtor specializing in homes near rail trails in Western Massachusetts, brings his local real estate perspective to Roads Less Travelled. In this episode, he speaks with Bill Skerry about mortgage rates, downsizing, seller pricing mistakes, negotiation, home equity, and how parks and...
How does a town of just over 700 residents generate more than $3 million a year in overnight lodging revenue?
On the Roads Less Travelled podcast, Craig Della Penna—the first U.S. REALTOR to specialize in homes near rail trails—talks with Alison Leathers, manager of Cottage House Inn in Lanesboro, Minnesota. Alison shares how bike tourism, rail trails, arts, outdoor recreation, and local businesses working together helpe...
Pecco Beaufays, owner of Highland Lake Inn and Andover Barn, explains how cyclists using New Hampshire’s Northern Rail Trail now account for about 25% of the inn’s revenue.
With host Craig Della Penna, Pecco shares practical lessons on cyclist-friendly hospitality, luggage logistics, flexible cancellations, e-bike charging, and the business opportunities created by rail-trail tourism.
🎙️ Host / Guest
Host: Craig Della Pen...
What turns a rail-trail stop into an overnight stay? At Highland Lake Inn, Pecco Beaufays says cyclists generate 25% of revenue.
Craig Della Penna hosts Roads Less Travelled to explore how trails connect communities and local businesses. As the first U.S. REALTOR to specialize in homes near rail trails and the author of five books on greenway development, Craig brings a rail trail real estate perspective to Pecco’s experience ...
What if the people who used to feel like strangers could become the family you choose? Craig Della Penna talks with Alex Jarrett (Petal People Cooperative) and Daniel Trenner (a 17-year intentional co-living household) about cooperative business, shared living, and the insurance and policy challenges still standing in the way.
🎧 Hosted by: Craig Della Penna
👤 Guest:
🏡 Alex Jarrett - Co-Founder, Petal People Cooperative
Alex Jarrett ...
Marianne Borowski joins Craig Della Penna on Roads Less Travelled to discuss the creation and expansion of the 83-mile Cross New Hampshire Adventure Trail. Learn how historic rail corridors, multi-use collaborations, and local business partnerships are transforming rural tourism.
🎧 Listen to the full episode of Roads Less Travelled now.
🎙 What you'll learn:
The layout and geography of the 83-mile Cross New Hampshire Adventure Tr...
Host Craig Della Penna welcomes conservationist and organic farmer Kristen Sykes to discuss the vital connections between local agriculture, trail infrastructure, and community well-being in Massachusetts.
🎙 What you'll learn:
How local trail networks and organic farms support community health and active transportation.
The reality of managing an 8.5-acre organic farm on protected floodplain land.
Why pedestrian infrastructure is ...
How one resident transformed a muddy path into an accessible community lifeline.
Steven Hawk joins Craig to explore the powerful impact of ADA-compliant rail trails in small towns like Ware, Massachusetts. Steven shares how he advocated for safer access points, leading to rapid infrastructure improvements that benefit everyone from wheelchair users to local dog walkers. This episode covers practical strategies for communicating with...
Explore how Western Massachusetts is balancing modern transit shifts, trail safety, and community engagement with former eMarketer analyst David.
Joined by host Craig, David shares insights from his transition to Northampton, discussing everything from e-bike regulations on local trails to creative solutions for vacant downtown landmarks.
🎧 Hosted by: Craig
🎤 Featuring: David
David is a retired communic...
🚀 In this episode, host Craig Della Pena sits down with Tara Brewster, VP of Business Development at Greenfield Savings Bank, to explore the power of community banking, social entrepreneurship, and kindness in local development. Tara shares her journey from entrepreneur to banker, her passion for giving back, and her vision for Western Massachusetts’ future. From partnerships between nonprofits and businesses, to the i...
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 ameniti...
🚀 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 connec...
🚀 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 investme...
🚀 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 expl...
🚀 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 trai...
🚀 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 mappi...
🚀 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 explo...
🚀 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 tie...
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