Roads Less Travelled

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 trai...

 🚀 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...

🚀 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 dow...

🚀 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...

🚀 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...

🚀 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...

🚀 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. Th...

🚀 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 al...

🚀 In this inspiring episode, Craig Della Penna sits down with Peter Stanton and Walter Henritze, co-founders of the Union Station Alliance, to discuss the extraordinary grassroots effort that helped save and restore Worcester’s historic Union Station. From abandoned ruins and political resistance to civic pride and urban revival, this conversation explores how passion, persistence, and community...

🚀 In this insightful conversation, host Craig Della Penna interviews Dan Hodge and Ann Ormsbee about the newly completed economic impact study for the New Haven and Northampton Canal Greenway. The discussion explores how shared-use trails generate economic activity, attract tourism, support local businesses, and influence policymakers to invest in long-distance trail infrastructure. Dan and Ann e...

🚀 In this episode, we sit down with Jenelle Cruz, owner of a stunning historic vegan bed & breakfast in Northeastern Washington. From leaving a 15-year career as a registered dietitian to restoring a former convent built in 1873, Jenelle shares her journey into hospitality, sustainable living, and creating a destination experience rooted in nature, history, and plant-based living. 🎧 Hosted b...

🚀 In this episode, Craig Della Penna sits down with Glenn Pransky, President of the Mass Central Rail Trail Alliance, to explore the transformative power of rail trails. From Glenn’s early cycling adventures to his leadership in developing a 100-mile trail across Massachusetts, this conversation dives into how bike tourism revitalizes communities, boosts local economies, and improves public healt...

🚀 In this episode, we sit down with Mike Kowalczyk to explore how grassroots efforts are transforming abandoned rail corridors into thriving trail networks across New Hampshire and beyond. From overcoming community resistance to building cross-state partnerships, Mike shares how small wins, collaboration, and persistence are turning vision into reality—connecting towns, boosting tourism, and pres...

🚀 In this episode, we explore how cooperative living and sustainable business models are reshaping modern communities. Featuring Alex Jarrett and Daniel Trenner, the conversation dives into co-living, intergenerational housing, human-powered transportation, and the future of community-centered living. Learn how these innovative approaches address affordability, reduce environmental impact, and co...

🚀 In this episode, we sit down with Jeff Anzevino, Director of Land Use Advocacy at Scenic Hudson, to explore how rail trails are reshaping communities across the Hudson Valley. From abandoned railroads to thriving public spaces, Jeff shares how projects like Walkway Over the Hudson and the Empire State Trail are driving economic growth, tourism, and community connection. 🎧 Hosted by: Craig Dell...

🚀 Marianne Borowski joins us to discuss the 83-mile Cross New Hampshire Adventure Trail and its rise as a top cycling route in New Hampshire. Learn how this trail connects communities, boosts cycling tourism, and transforms Northern New Hampshire into an emerging outdoor destination.. 🎧 Hosted by: Craig Della Penna 👤 Guest: 🏡 Marianne Borowski – Trail Developer & Outdoor Recreation Advocat...

🚀 In this episode, we sit down with Kurt Gaertner, Assistant Secretary of Environmental Policy at the Executive Office of Energy and Environmental Affairs, to explore how Massachusetts is leading the way in trail development. From the growth of the Mass Trails initiative to the vision behind long-distance rail trails like the Mass Central Rail Trail, Kurt shares insights on funding, environmental...

🚀 In this episode, hospitality expert David Mayfield shares powerful insights on growing and optimizing small lodging businesses. From dynamic pricing strategies to leveraging OTAs and building a regional hospitality network, this conversation explores how entrepreneurs can create thriving bed & breakfast ecosystems—especially in emerging tourism corridors like central Massachusetts. 🎧 Hoste...

🚀 In this episode, trail advocate Don Burn shares decades of experience working to transform historic rail corridors, trolley lines, and aqueduct routes into modern shared-use trails. From his early exposure to the Illinois Prairie Path to championing trail networks in Massachusetts, Don explains the challenges of navigating utilities, working with state agencies, and convincing communities and d...

🚀 In this episode, longtime trail advocate George Eckert shares the story behind the development of the Natick rail trail in Massachusetts. From childhood memories walking old railroad tracks to decades of community advocacy, George discusses how local partnerships, grassroots efforts, and persistence helped turn a dormant rail corridor into a thriving community trail. The conversation explores t...

🚀 In this episode, host Craig Della Penna sits down with Lindsay Barron Labonte , a top-ranked mortgage professional with over 19 years of experience and Branch Manager of the Applied Mortgage Team at HMA Mortgage in Northampton, Massachusetts. Lindsay shares insights into why Western Massachusetts has become a desirable lifestyle destination for homebuyers, how today’s competitive housing market...

🚀 In this powerful and deeply personal episode, we sit down with longtime civic leader Dan Fitzpatrick , whose decades of service helped shape modern Belchertown. From transforming the school system and managing explosive population growth to leading one of Massachusetts’ most controversial rail trail battles, Dan shares behind-the-scenes stories of leadership, resistance, and perseverance. 🎧 Ho...

🚀 In this powerful episode, host Craig Della Penna sits down with longtime community leader Cynthia Allen Bourcier to discuss the future of Ware, Massachusetts. From rural healthcare reform and the repurposing vision for the former Mary Lane Hospital site to the expansion of the Mass Central Rail Trail, Cindy shares how volunteers shape the destiny of small towns. With over 40 years of nonprofit...

🚀 In this energizing episode, Craig Della Penna sits down with Peter Sutton, Bicycle and Pedestrian Program Coordinator at MassDOT, to explore the future of rail trails, active transportation, and statewide collaboration. From the 25th Annual Moving Together Conference to the ambitious expansion of the Mass Central Rail Trail, Peter shares how Massachusetts is transforming infrastructure to suppo...

🚀 In this inspiring episode, we sit down with Brian Sutton—former emergency physician, medical director, and founder of his own occupational health clinic—to explore his remarkable journey from hospital medicine to cycling across America on the Great American Rail Trail. From riding through Yellowstone and battling headwinds in Montana to launching his FAA aviation medical examiner practice in We...