Roads Less Travelled

Craig Della Pena

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.

  1. 1d ago

    The Real Cost of Pricing Like It’s 2021 | Bill Skerry

    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:

    The Real Cost of Pricing Like It’s 2021 | Bill Skerry

  2. Oct 9

    Bike Tourism and the Business of a Trail Town | Alison Leathers

    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 & Guest Host: Craig Della Penna Craig 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 Leathers Alison 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 Learn How 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 Answered Q: 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

    Bike Tourism and the Business of a Trail Town | Alison Leathers

  3. Sep 25

    How Rail Trail Cyclists Drive 25% of This Inn’s Revenue | Pecco Beaufays

    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 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 Learn How cyclists generate about 25% of the inn’s revenue What bike tourists need from cyclist-friendly lodging How luggage shipping improves long-distance rides Why weather can change cancellation policies How rail-trail partnerships support local tourism What to consider before buying a B&B ❓ Key Questions Answered Q: 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. 🔗 Resources Full 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

    How Rail Trail Cyclists Drive 25% of This Inn’s Revenue | Pecco Beaufays

  4. Sep 18

    Bike Tourism: The Service Behind the Stay | Pecco Beaufays

    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 serving Northern Rail Trail visitors. Learn how bike tourism shapes guest services, premium hospitality, and the daily demands of running an inn along New England rail trails. 🎙️ Host / Guest Host: 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 Learn Assess bike tourism’s business potential: Pecco says cyclists generate 25% of Highland Lake Inn’s revenue. Make one-way cycling trips easier with trailhead transport and access to guests’ cars. Support premium rates with quality bedding, breakfast ingredients, and personal service. Prepare for guest emergencies through Pecco’s account of four EMS calls in two days. Build trail awareness through collaboration with New Hampshire’s tourism office. Decide whether running a B&B fits your life and willingness to care for guests. ❓ Key Questions Answered Q: How does bike tourism differ from resort tourism? A: Craig Della Penna describes bicycle touring as journey tourism, with visitors traveling along a route. Resort tourism centers on one destination. Q: How does Highland Lake Inn handle e-bike charging? A: Pecco describes an outdoor charging area away from the building, following local fire department advice, and discussing battery condition with guests. 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. ⏱️ Chapters (00:00) - Intro (01:39) - From Luxury Hotels to Highland Lake Inn (06:20) - Alex Bernhard and the Northern Rail Trail (13:05) - What Cyclists Need From an Inn (18:52) - Bike Tourism and Local Economies (23:14) - Guest Services and E-Bike Charging (27:49) - Before You Buy a Bed and Breakfast (30:56) - Premium Rates and Personal Service (34:22) - Four EMS Calls in Two Days (36:06) - Cyclists and 25% of Inn Revenue (37:54) - Working With Tourism Partners (40:27) - Addressing Rail-Trail Opposition (43:21) - What Makes Innkeeping Rewarding (48:36) - 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 #CraigDellaPenna #RailTrailRealEstate #NorthamptonRealtor #PioneerValley #BikeTrailHomes #GreenwaySolutions #NewEnglandRealEstate #RailTrails #SugarMapleInn

    Bike Tourism: The Service Behind the Stay | Pecco Beaufays

  5. Sep 11

    Affordable Housing Starts with Cooperative Living | Craig Della Penna

    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 co-founded Petal People Cooperative (founded 2002), hauling trash and recycling by bicycle in Northampton, MA every day since 2007, and serves as President of the Northampton City Council. 🏡 Daniel Trenner - Professional Dancer & Co-Liv Daniel Trenner is a professional dancer who converted his Florence, MA home into an intentional, intergenerational household that has hosted more than 100 residents over 17 years. ing Pioneer💡 What You'll Learn: ✔️ How Petal People hauls trash and recycling entirely by bicycle ✔️ Why Daniel converted a five-bedroom house into a nine-bedroom intentional household ✔️ Cooperative living vs. co-housing vs. co-living, explained ✔️ Why insurance and lending are still unsolved problems for co-living ✔️ How group living reshaped the pandemic experience for both guests 🎧 Listen now for a fresh, practical look at alternative ways to live and build community. 💼 Connect with Alex Jarrett: 📘 Facebook → https://www.facebook.com/pedalpeople (company) 📸 Instagram → https://www.instagram.com/pedal_people_coop/ (company) 💼 Connect with Daniel Trenner: 🔗 Website → https://www.alexjarrett.com/campaign/ 🏢 Company → https://www.pedalpeople.coop/ 📘 Facebook → https://www.facebook.com/DanielTrennerTango/ 📸 Instagram → https://www.instagram.com/trennerstangoarchive/ 🔗 Website → https://danieltrenner.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/ #CoLiving #Cooperative #Sustainability #RealEstate #Northampton #IntentionalCommunity #RoadsLessTraveled

    Affordable Housing Starts with Cooperative Living | Craig Della Penna

  6. Sep 4

    Rail Trail Adventures & Cycling Tourism in New Hampshire with Marianne Borowski

    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 Trail. How combining rail trails with dirt back roads creates multi-day cycling journeys. The importance of community collaboration with local chambers and businesses. Managing multi-use trails alongside snowmobiles, ATVs, and walkers. Technical insights on trail surfacing, crushed stone mixes, and maintenance. Why cycle tourism drives sustainable economic growth in small mountain towns. 🎧 HOSTED BY: Craig Della Penna 👤 GUEST: Marianne Borowski – Trail Developer & Outdoor Recreation Advocate Marianne Borowski is the President and Founder of the Cross New Hampshire Adventure Trail and Vice President of the New Hampshire Rail Trails Coalition. A former protein biochemist during the early years of biotech, she shifted careers after moving to Mt. Washington Valley in 2003, becoming a cross-country ski instructor, later director of the Jackson Ski Touring Foundation ski school, and now a member of its Board of Directors. Today, she focuses on restoring, maintaining, and connecting rail trails across New Hampshire. An avid cyclist, Marianne has also biked across the U.S. 👉🏻 CONNECT WITH MARIANNE BOROWSKI Facebook: https://facebook.com/crossnewhampshire  Instagram: https://instagram.com/crossnewhampshire  👉🏻 CONNECT WITH CRAIG DELLA PENNA – ROADS LESS TRAVELLED Website: https://www.greenwaysolutions.org/ Website: https://www.northamptonrealtor.com/ Website: https://www.sugar-maple-inn.com/  Instagram: https://www.instagram.com/craigdp413/  LinkedIn: https://www.linkedin.com/in/craigdp/

    Rail Trail Adventures & Cycling Tourism in New Hampshire with Marianne Borowski

  7. Aug 28

    Sustainable Farming and Trail Access with Kristen Sykes

    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 essential for aging populations and car-free commuters. The intersection of local farm markets and small business support. How historical right-of-way conversions transformed travel routes in Massachusetts. The mental and physical health benefits of everyday access to nature. 🎧 HOSTED BY: Craig Della Penna  👤 GUEST: Kristen Sykes – Conservationist, organic farmer, and advocate for sustainable land use and active mobility. Kristen Sykes is a conservationist, organic farmer, and advocate for biking and pedestrian infrastructure. She has been actively involved in advancing sustainable land use, active transportation, and community-based environmental initiatives. Through her work in conservation and agriculture, Kristen promotes healthier ecosystems and resilient local communities, while championing safe, accessible mobility options for all. 💼 Connect with Steven Hawk:🌐 Website → https://www.facebook.com/kristen.sykes2/ 📷 Instagram → https://www.instagram.com/super.syked 🔗 LinkedIn → https://www.linkedin.com/in/kristen-m-sykes/ 🎧 Follow Craig Della Penna: 🌐 Website → https://www.greenwaysolutions.org/ 🌐 Website → https://www.northamptonrealtor.com/ 🌐 Website →https://www.sugar-maple-inn.com/ 📷 Instagram → https://www.instagram.com/craigdp413/ 🔗 LinkedIn → https://www.linkedin.com/in/craigdp/ ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/ Don’t forget to LIKE 👍 SUBSCRIBE 🔔 COMMENT 💬 below!

    Sustainable Farming and Trail Access with Kristen Sykes

  8. Aug 7

    How One Advocate is Transforming Rail Trails for Wheelchair Access

    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 town officials, the economic potential of accessible outdoor spaces, and the future of integrating local history into community paths. 🎧 Hosted by: Craig 🎤 Featuring: Steven Hawk Steven Hawk is a resident of Ware, Massachusetts, and an active user of the local Rail Trail. As a wheelchair user, Steven relies on the trail several times a week for transportation, grocery shopping, visiting family and friends, and enjoying time outdoors. His experience highlights the importance of accessible community spaces that support independence, connection, and mobility for people of all abilities. 💡 What You’ll Learn in This Episode: ✔ Transforming personal physical limitations into community-wide accessibility improvements ✔ Educating local officials on the real-world impact of ADA compliance ✔ Building productive relationships with town managers to fix safety hazards ✔ Utilizing the third place concept to revitalize small-town economies ✔ Securing fast infrastructure updates by speaking directly to land developers ✔ Implementing QR codes to share local history and community wayfinding resources ✔ Encouraging outdoor exploration and independence for residents of all abilities 💼 Connect with Steven Hawk:🌐 Email → stevenhawk813@yahoo.com 🎧 Follow Craig Della Penna: 🌐 Website → https://www.greenwaysolutions.org/ 🌐 Website → https://www.northamptonrealtor.com/ 🌐 Website →https://www.sugar-maple-inn.com/ 📷 Instagram → https://www.instagram.com/craigdp413/ 🔗 LinkedIn → https://www.linkedin.com/in/craigdp/ ⭐ Produced by Icons of Real Estate - https://iconsofrealestate.com/ 🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below! #RailTrail #Accessibility #ADACompliance #CommunityDevelopment #OutdoorRecreation #InclusiveDesign #SmallTowns #WheelchairAccess

    How One Advocate is Transforming Rail Trails for Wheelchair Access
See All (48)

Trailer

About

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.

Information

  • Creator
    Craig Della Pena
  • Years Active
    2025 - 2026
  • Episodes
    48
  • Rating
    Clean
  • Copyright
    © Craig Della Pena
  • Show Website
    Roads Less Travelled

You Might Also Like