Roads Less Travelled
By Craig Della Pena
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Episodes: 26
Description
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.
| Episode | Date |
|---|---|
|
The Biggest Mistake Killing Trail Development Projects
|
Apr 17, 2026 |
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One Step Closer to a Village: Co-Ops, Co-Living & Relearning Human Connection
|
Apr 10, 2026 |
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Connecting Communities: Hudson Valley's Rail Trail Success - EP 21
|
Apr 03, 2026 |
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An 83-Mile Cycling Route Through New Hampshire You’ve Never Heard Of - EP 20
|
Mar 27, 2026 |
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Transformative Rail Trail Projects Across Massachusetts - EP 19
|
Mar 21, 2026 |
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Innovative Strategies for Bed and Breakfast Success - EP 18
|
Mar 21, 2026 |
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Innovative Strategies for Developing Sustainable Trail Networks - EP 17
|
Mar 13, 2026 |
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The Evolution of Rail Trail Advocacy in Natick - EP 16
|
Mar 08, 2026 |
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Competitive Markets and Mortgage Strategies Unveiled - EP 15
|
Mar 07, 2026 |
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From Railways to Rail Trails: Belchertown's Journey - EP 14
|
Feb 28, 2026 |
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Revitalizing Ware: Community Development and Healthcare Visions - EP 13
|
Feb 27, 2026 |
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Building Massachusetts’ Trail Network: Inside MassDOT’s Vision - EP 12
|
Feb 20, 2026 |
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Cross-Country Cycling and Community Trails Impact - EP 11
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Feb 20, 2026 |
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Innovation on the Move: Videography and Biking Paths - EP 10
|
Feb 13, 2026 |
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Championing Access for All: Rail Trail Innovations - EP 9
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Feb 06, 2026 |
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Exploring Conservation: Farming, Biking, and Community Ties - EP 8
|
Jan 30, 2026 |
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Exploring Community Life in Northampton and Beyond - EP 7
|
Jan 16, 2026 |
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From Railways to Pathways: A Journey in Trails - EP 1 - Part 3
|
Jan 02, 2026 |
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From Railways to Pathways: A Journey in Trails - EP 1 - Part 2
|
Dec 19, 2025 |
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From Railways to Pathways: A Journey in Trails - EP 1 - Part 1
|
Dec 05, 2025 |
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Trailblazing the East Coast: A Journey of Greenways - EP 6
|
Nov 14, 2025 |
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Exploring New England's Trail Magic and Rail History - EP 5
|
Oct 31, 2025 |
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Connecting Communities: The Future of Trail Infrastructure - EP 4
|
Oct 17, 2025 |
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The Impact of Trails on Local Real Estate - EP 3
|
Oct 17, 2025 |
|
Community Partnerships: Building a Thriving Local Economy - EP 2
|
Oct 17, 2025 |
|
Intro
|
Sep 24, 2025 |