- 51
- Episodes
- 1
- Ratings
- Weekly
- Cadence
- 2025
- First episode
About 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.
- Publisher
- Craig Della Pena
- Category
- business
- Language
- en
- Explicit
- No
- First episode
- 24 Sept 2025
- Latest episode
- 6 Nov 2026
Latest episodes
51 episodes in the feed.
6 Nov 2026
How Rail Trails Drive Local Tourism & Business | Yva and Jim Rose
E-bikes can help families and visitors experience more of Vermont’s Lamoille Valley Rail Trail. On Roads Less Travelled, Craig Della Penna talks with Yva and Jim Rose of Lamoille Valley Bike Tours about making trail rides accessible and connecting riders with local communities. They discuss the growth of e-bike rentals and tours, bike-and-brew and cheese outings, shuttle service, multi-day trips, and the local partnerships that make a rail-trail visit more than just a ride. They also share how trail use can extend into winter and why new trail businesses need patience as local tourism grows. 🎙️ Host & Guest Host: Craig Della Penna REALTOR®, author, nationally recognized rail-trail advocate, and host of Roads Less Travelled. Guests: Yva and Jim Rose Founders of Lamoille Valley Bike Tours in Johnson, Vermont. Their business offers e-bike rentals, guided tours, sales, and shuttle service along the completed 93-mile Lamoille Valley Rail Trail. 💡 Key Topics Covered - How e-bikes make multi-generational trail rides more accessible - How bike tours connect visitors with local businesses and attractions - How to plan multi-day rides with rentals, shuttles, and luggage support - How rail trails support four-season tourism, from biking to winter activities - How local partnerships support trail maintenance and community growth 💡 Key Questions Answered Q: Who can benefit from an e-bike tour? A: E-bikes can help newer riders and family members of different ages enjoy a trail outing together. Q: What local experiences can riders find along the Lamoille Valley Rail Trail? A: Yva and Jim discuss brewery and cheese tours, local food, lodging, shops, and other community destinations. Q: What does it take to plan a longer rail-trail trip? A: Visitors may need to coordinate bikes and gear, transportation, food, and lodging. The available options continue to grow as the trail’s tourism infrastructure develops. Q: How can a new rail trail support local communities? A: The trail can bring visitors to local businesses and create opportunities for partnerships, new services, and tourism growth. Q: What winter activities can visitors enjoy along the Lamoille Valley Rail Trail? A: Snowmobiling, cross-country skiing, and fat biking. Fat biking can be an alternative when snow conditions are poor. ⏱️ Chapters (00:00) – Meet Yva and Jim Rose (02:02) – The E-Bike “Great Equalizer” (05:07) – Riding Farther and Visiting More Towns (07:49) – Bringing Customers to Local Businesses (12:15) – Brewery and Cheese Trail Tours (20:00) – The Wider Rail-Trail Community (24:00) – Multi-Day Trip Planning (30:17) – Winter Activities and Changing Seasons (34:10) – Local Trail Committees and Maintenance (39:22) – Being Patient and Moving Forward Here's a 2,000+ word Op-Ed piece I wrote for the Hardwick, VT newspaper back in November of 2003 that helped to ensure that the conversion from rail-to-trail took place. https://www.norevisionisthistory.org/stj-lc (https://www.norevisionisthistory.org/stj-lc) 💼 Connect with Yva and Jim Rose 🔗 Website →https://www.lamoillevalleybiketours.com/ (https://www.lamoillevalleybiketours.com/) 📸 Instagram →https://www.instagram.com/bikelamoille/ (https://www.instagram.com/bikelamoille/) 📘 Facebook →https://www.facebook.com/bikelamoille/ (https://www.facebook.com/bikelamoille/) 🎧 Follow Craig Della Penna 🌐 Website →https://www.northamptonrealtor.com/ (https://www.northamptonrealtor.com/) 📘 Facebook →https://www.facebook.com/craig.dellapenna/ (https://www.facebook.com/craig.dellapenna/) 📸 Instagram →https://www.instagram.com/craigdp413/ (https://www.instagram.com/craigdp413/) 🔗 LinkedIn →https://www.linkedin.com/in/craigdp/ (https://www.linkedin.com/in/craigdp/) 📌 Don’t forget to LIKE 👍, SUBSCRIBE 🔔, and COMMENT 💬 below! ⭐ Produced by Icons of Real Estate — iconsofrealestate.com (https://iconsofrealestate.com/) #RoadsLessTravelled #YvaAndJimRose #LamoilleValleyRailTrail #VermontEbikeTours #EbikeRentals #VermontTourism #TrailTowns #RailTrailBusiness #VermontCycling #RealEstatePodcast
30 Oct 2026
How E-Bike Tours Are Connecting Vermont’s Trail Towns | Yva and Jim Rose
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, Vermont. They discuss starting with seven e-bikes and a truck and trailer, then growing into a hub for e-bike rentals, guided tours, sales, and trail shuttles. Discover how e-bikes can make trail riding more accessible, why riders should stop to explore the towns along the route, and what local assets and partnerships can mean for a trail-focused small business. 🎙️ Host & Guest Host: Craig Della Penna REALTOR®, author, nationally recognized rail-trail advocate, and host of Roads Less Travelled. Guests: Yva and Jim Rose Founders of Lamoille Valley Bike Tours in Johnson, Vermont. Founded in 2016, they were the first company in Vermont to offer e-bike rentals and tours. Their business has grown from a mobile truck-and-trailer operation into a hub with 50+ bikes, guided tours, e-bike sales, and trail shuttle service along the completed 93-mile Lamoille Valley Rail Trail. 💡 What You’ll Learn Why e-bikes can introduce more people to the Lamoille Valley Rail Trail. The path from a mobile rental setup to a business offering tours, bike sales, and trail shuttles. Local food, historic stations, and village stops riders can discover along the route. The role rentals, tours, and shuttle service play in longer rail-trail adventures. Why local assets, strong partnerships, and patience matter when building a trail-focused business. ❓ Key Questions Answered Q: How did Yva and Jim Rose start Lamoille Valley Bike Tours? A: They began in 2016 with a truck, trailer, and seven e-bikes, offering rentals and tours on the trail’s first 17-mile section. Q: How long is the Lamoille Valley Rail Trail? A: The completed trail is 93 miles long and connects 18 Vermont towns. Q: How can e-bikes make rail-trail riding accessible to more people? A: E-bikes can help people who aren’t regular cyclists enjoy a trail ride, including families riding with visitors of different ages and abilities. Q: What can riders see and do along the Lamoille Valley Rail Trail? A: Riders can explore Vermont villages, local food stops, historic train stations, scenic viewpoints, and other community destinations along the trail. Q: What advice do Yva and Jim offer entrepreneurs starting a rail-trail business? A: Identify the trail’s local assets, find experiences and partners that can attract visitors, and allow time for the business to grow. ⏱️ Chapters (00:00) – Meet Yva and Jim Rose (01:17) – Starting an E-Bike Tour Business (05:06) – Growing With the Rail Trail (08:30) – Connecting Trail Towns (10:48) – Trail Partners and Access (17:49) – E-Biking for More Riders (20:01) – Planning Your Ride (21:52) – Lamoille Valley Route Tips (23:53) – Scenic Stops and Local Food (28:18) – Starting a Trail Business (32:17) – Patience and Partnerships 💼 Connect with Yva and Jim Rose 🔗 Website:https://www.lamoillevalleybiketours.com/ (https://www.lamoillevalleybiketours.com/) 📸 Instagram: https://www.instagram.com/bikelamoille/ (https://www.instagram.com/bikelamoille/) 📘 Facebook: https://www.facebook.com/bikelamoille/ (https://www.facebook.com/bikelamoille/) 🎧 Follow Craig Della Penna 🌐 Website: https://www.northamptonrealtor.com/ (https://www.northamptonrealtor.com/) 📘 Facebook: https://www.facebook.com/craig.dellapenna/ (https://www.facebook.com/craig.dellapenna/) 📸 Instagram: https://www.instagram.com/craigdp413/ (https://www.instagram.com/craigdp413/) 🔗 LinkedIn: https://www.linkedin.com/in/craigdp/ (https://www.linkedin.com/in/craigdp/) 📌 Like, follow, and share Roads Less Travelled for more conversations about real estate, communities, and the places people call home. #RoadsLessTravelled #CraigDellaPenna #YvaAndJimRose #LamoilleValleyRailTrail #VermontEbikeTours #VermontRailTrails #EbikeRentals #VermontTourism #TrailTowns #RailTrailBusiness #VermontCycling #RealEstatePodcast
23 Oct 2026
Buying a Home in Greater Boston: Costs & Challenges | Bonnie Lai
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® to specialize in homes near rail trails, Craig connects real estate with community development and the places people call home. Discover how buyers can explore assistance programs, evaluate condo ownership costs, understand housing affordability, and consider how public MLS listings support transparency and fair housing. 🎙️ Host & Guest Host: Craig Della Penna REALTOR®, author, nationally recognized rail-trail advocate, and host of Roads Less Travelled. Guest: Bonnie Lai Founding partner of 1st Knock Realty and the Luxe Home Team, serving first-time buyers, international clients, and families across Greater Boston. 💡 What You’ll Learn How to explore Massachusetts homebuyer assistance programs. How condo fees, special assessments, insurance, and financing affect ownership costs. Challenges facing buyers in Greater Boston’s real estate market. Considerations for international buyers and relocating families. How ADUs and multigenerational living relate to housing affordability. Challenges of converting commercial buildings into housing. Why private listings, public MLS access, and fair housing matter. ❓ Key Questions Answered Q: How can first-time homebuyers find financial assistance in Massachusetts? A: Buyers can explore homebuyer education classes and local programs that may offer grants or mortgage benefits. Eligibility and availability vary. Q: What challenges are homebuyers facing in Greater Boston? A: Conditions vary by location and property type. Some homes attract strong competition, while parts of the condo market face affordability and financing pressures. Q: What hidden costs should condo buyers consider? A: Condo fees, special assessments, building repairs, insurance, and lender requirements can affect the total cost of ownership. Q: Why do public MLS listings matter for transparency and fair housing? A: Public MLS listings can broaden access to property information. Bonnie Lai discusses transparency concerns surrounding private listings and their implications for fair housing. ⏱️ Chapters (00:00) – Introducing Bonnie Lai (01:00) – First-Time Homebuyer Programs: ACDC and MAHA (02:19) – Building a Real Estate Career and Team (05:25) – Serving Greater Boston’s Diverse Buyers (07:03) – Navigating a Competitive Market (11:46) – International Buyers and Relocation (13:18) – Condo Financing, Fees, and Insurance (16:22) – Can Commercial Buildings Become Housing? (17:33) – Affordability, Family Housing, and ADUs (19:34) – Grants and Local Homebuyer Resources (21:30) – Private Listings, MLS Access, and Fair Housing (29:14) – Closing Thoughts 💼 Connect with Bonnie Lai 🔗 LinkedIn: https://linkedin.com/in/bonnie-lai-54039513 (https://linkedin.com/in/bonnie-lai-54039513) 📸 Instagram: https://www.instagram.com/your_real_estate_quarterback/?hl=en (https://www.instagram.com/your_real_estate_quarterback/?hl=en) 📘 Facebook: https://www.facebook.com/1stknockrealty (https://www.facebook.com/1stknockrealty) 🎧 Follow Craig Della Penna 🌐 Website: https://www.northamptonrealtor.com/ (https://www.northamptonrealtor.com/) 📘 Facebook: https://www.facebook.com/craig.dellapenna/ (https://www.facebook.com/craig.dellapenna/) 📸 Instagram: https://www.instagram.com/craigdp413/ (https://www.instagram.com/craigdp413/) 🔗 LinkedIn: https://www.linkedin.com/in/craigdp/ (https://www.linkedin.com/in/craigdp/) 📌 Like, follow, and share Roads Less Travelled for more conversations about real estate, communities, and the places people call home. #RoadsLessTravelled #BonnieLai #GreaterBostonRealEstate #FirstTimeHomeBuyer #AffordableHousing #MassachusettsRealEstate #CondoMarket #HomebuyerPrograms #FairHousing #MLS #RealEstatePodcast
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