Roads Less Travelled

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 & GuestHost: Craig Della PennaREALTOR®, author, nationally recognized rail-trail advocate, and host of Roads Less Travelled.Guests: Yva and Jim RoseFounders 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 LearnWhy 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 AnsweredQ: 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/📸 Instagram: https://www.instagram.com/bikelamoille/📘 Facebook: https://www.facebook.com/bikelamoille/ 🎧 Follow Craig Della Penna🌐 Website: https://www.northamptonrealtor.com/📘 Facebook: https://www.facebook.com/craig.dellapenna/📸 Instagram: https://www.instagram.com/craigdp413/🔗 LinkedIn: 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

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 & GuestHost: Craig Della PennaREALTOR®, author, nationally recognized rail-trail advocate, and host of Roads Less Travelled.Guest: Bonnie LaiFounding partner of 1st Knock Realty and the Luxe Home Team, serving first-time buyers, international clients, and families across Greater Boston.💡 What You’ll LearnHow 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 AnsweredQ: 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📸 Instagram: https://www.instagram.com/your_real_estate_quarterback/?hl=en📘 Facebook: https://www.facebook.com/1stknockrealty🎧 Follow Craig Della Penna🌐 Website: https://www.northamptonrealtor.com/📘 Facebook: https://www.facebook.com/craig.dellapenna/📸 Instagram: https://www.instagram.com/craigdp413/🔗 LinkedIn: 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

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 rail trails can influence real estate decisions.Host: Craig Della PennaRealtor, author, nationally recognized rail-trail advocate, and the first U.S. Realtor to specialize in homes near rail trails.Guest: Bill SkerryBill brings 40+ years of Greater Boston real estate experience, with 640+ transactions and more than $210M in career sales. He works with first-time buyers, longtime homeowners, and sellers across the Greater Boston suburbs through Keller Williams Realty.Price a home for today’s market instead of relying on COVID-era expectations.Plan where to move before listing a home for downsizing.Understand why lower mortgage rates can create more buyer competition.Protect seller equity through stronger pricing and negotiation.Compete with large real estate teams through relationships and local expertise.Evaluate parks, recreation, transportation, and outdoor amenities when choosing a neighborhood.Q: Should buyers wait for mortgage rates to drop before buying a home?A: Lower mortgage rates can bring more buyers into the market, increasing competition and reducing negotiating leverage.Q: What is the biggest mistake downsizing sellers make?A: Listing before deciding where to move next can leave sellers scrambling for housing if their home sells quickly.Q: Why do sellers overprice homes in today’s market?A: Many sellers still base their expectations on COVID-era prices and sales speed even though the market has changed.Q: How can a real estate agent protect a seller’s home equity?A: Strong pricing and negotiation discipline help protect a seller’s hard-earned equity throughout the transaction.Q: What neighborhood features matter to today’s homebuyers?A: Buyers increasingly consider transportation, parks, recreation, outdoor amenities, and proximity to work when choosing where to live.(00:00) - Intro(00:23) - Meet Bill Skerry(04:56) - How Greater Boston Has Changed(07:34) - Creating a Low-Stress Transaction(10:01) - Biggest Downsizing Mistakes(12:13) - Should Buyers Wait for Lower Rates?(14:29) - Housing Affordability Today(19:35) - Why Sellers Still Price Like COVID(21:05) - Local Agents vs. Big Teams(27:23) - Rail Trails & Buyer Demand(30:38) - Pricing, Valuation & Home Equity(39:05) - Future of Greater Boston Housing(41:13) - Building Long-Term Real Estate Equity 🌐 Website → https://billskerry.com/📘 Facebook → https://facebook.com/billskerryrealestate/📸 Instagram → https://instagram.com/bill_skerry/🔗 LinkedIn → https://linkedin.com/in/bill-skerry-9929b0b🎧 Connect Craig Della Penna: 🌐 Website → https://www.northamptonrealtor.com/📘 Facebook → https://www.facebook.com/craig.dellapenna/📸 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don't Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!#GreaterBostonRealEstate #RealEstateMarket #MortgageRates #HomeSellingTips #HomePricing #RealEstateNegotiation #Downsizing🎙️ Host & Guest💡 What You’ll Learn❓ Key Questions Answered⏱️ Chapters💼 Connect with Bill Skerry:

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 helped Lanesboro grow from an extremely quiet town into a thriving visitor destination.The conversation covers B&B cash flow, seasonal hospitality, cyclist-friendly amenities, local collaboration, and why successful trail advocacy often starts at the grassroots level.🎤 Host & GuestHost: Craig Della PennaCraig Della Penna is the host of Roads Less Travelled, a rail-trail advocate, author, and the first U.S. REALTOR to specialize in properties near rail trails.Guest: Alison LeathersAlison Leathers manages her family’s Cottage House Inn in Lanesboro, Minnesota. She is the third generation involved in the family lodging business and also serves on local boards and committees focused on her rural community.💡 What You’ll LearnHow bike tourism can support lodging and small businesses in a trail town.How to evaluate B&B cash flow, seasonality, and room revenue before investing.How secure bike storage, e-bike charging, parking, and flexible check-in improve the cyclist guest experience.How hospitality businesses can plan staffing and cash reserves around peak tourism months.How local innkeepers can share resources and solve guest problems together.How arts, trails, and outdoor recreation give visitors more reasons to stay longer.Why successful trail advocacy often begins with local community demand.❓ Key Questions AnsweredQ: What should you check before buying a B&B in a trail town?A: Alison Leathers recommends reviewing cash flow, seasonal demand, and whether room revenue can cover expenses while still allowing the owner to maintain and reinvest in the property.Q: What amenities are useful for bike tourists staying at an inn?A: Cottage House Inn offers secure bike storage, e-bike charging, off-street parking, shared spaces, and flexible self-check-in with electronic keypad access.Q: How can a small town grow tourism around a rail trail?A: Lanesboro combines rail trails with lodging, arts, outdoor recreation, events, and collaboration among businesses, city government, the chamber, and local organizations.Interested in bike tourism, trail-connected communities, or hospitality near rail trails? Follow Roads Less Travelled for more conversations with the people building stronger communities around great paths.⏱️ Chapters(00:00) - Intro(00:35) - Meet Alison Leathers(01:20) - From Yellowstone to the Family Inn(03:39) - Root River Trails & Local Inns(05:57) - How Rail Trails Revived Lanesboro(08:48) - Creating a Better Guest Experience(12:03) - Amenities for Bike Tourists(13:46) - Investing in a Trail-Town B&B(16:33) - Managing Seasonal Cash Flow(17:42) - Arts Tourism & Commonweal Theatre(19:29) - Small-Town Leadership & Collaboration(23:27) - Trail Tourism & Local Business(25:00) - Arts, Trails & the Rural Economy(26:53) - Why “It Takes a Village”(28:10) - Leadership Lessons from Agriculture(29:21) - Grassroots Trail Expansion 💼 Connect with Alison Leathers:🌐 Website → https://www.cottagehouseinn.com/🎧 Follow Craig Della Penna: 🌐 Website → https://www.northamptonrealtor.com/📘 Facebook → https://www.facebook.com/craig.dellapenna/📸 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don't Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!#RoadsLessTravelled #CraigDellaPenna #RailTrailRealEstate #NorthamptonRealtor #PioneerValley #BikeTrailHomes #GreenwaySolutions #NewEnglandRealEstate #RailTrails #SugarMapleInn

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 / GuestHost: Craig Della Penna — Realtor and rail-trail advocate.Guest: Pecco Beaufays owns Highland Lake Inn and Andover Barn in East Andover, New Hampshire. His hospitality career began with a cooking apprenticeship at Hotel Sacher in Vienna and later included work with Kempinski in North and South America.💡 What You’ll LearnHow cyclists generate about 25% of the inn’s revenueWhat bike tourists need from cyclist-friendly lodgingHow luggage shipping improves long-distance ridesWhy weather can change cancellation policiesHow rail-trail partnerships support local tourismWhat to consider before buying a B&B❓ Key Questions AnsweredQ: How important is bike tourism to Highland Lake Inn?A: Pecco says cyclists using the Northern Rail Trail generate about 25% of the inn’s revenue.Q: What services do touring cyclists need from an inn?A: Pecco highlights flexible cancellations, meal coordination, transportation, luggage shipping, bike support, and other services that make long-distance cycling easier.Q: Why does Pecco make exceptions to his cancellation policy for cyclists?A: Cycling trips depend heavily on weather, so Pecco allows more flexibility when rain makes a planned ride impractical.Buying an inn or investing near a trail? Follow Roads Less Travelled on Spotify for more conversations about trail-connected communities.🎧 Considering a trailside property? Follow Roads Less Travelled for the conversations behind the purchase.🔗 ResourcesFull episode: [YouTube episode URL]Highland Lake Inn and Andover Barn: [Guest website URL]Connect with Craig: [Host website URL]⏱️ Chapters(00:00) - Cold Open: Service Comes First(00:35) - Meet Pecco Beaufays(01:49) - Buying Highland Lake Inn(04:14) - The Barn: 13 Bedrooms, Events for 180, a Meadow for Horses(05:46) - Why He Chose This Inn: Gutted and Rebuilt in the 90s(06:43) - Growing With the Northern Rail Trail(08:24) - Flexible Cancellations for Cyclists(09:30) - Expanding the Rail Trail Network(10:50) - The 100-Mile Trail & Lodging Vision(13:41) - What Touring Cyclists Need(16:39) - The Legacy of Highland Lake Inn(18:11) - Closing Remarks 💼 Connect with Pecco Beaufays:🌐 Website → https://www.highlandlakeinn.com/🌐 Website → https://www.greenwaysolutions.org/nyt-bb-story-1🎧 Follow Craig Della Penna: 🌐 Website → https://www.northamptonrealtor.com/📘 Facebook → https://www.facebook.com/craig.dellapenna/📸 Instagram → https://www.instagram.com/craigdp413/🔗 LinkedIn → https://www.linkedin.com/in/craigdp/📌 Don't Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!#RoadsLessTravelled #PeccoBeaufays #CraigDellaPenna #NorthernRailTrail #BikeTourism #RailTrails #Hospitality #NewHampshire