Residential Real Estate and Rail-Trails

An On-the-Ground Reality

In this session you’ll learn about the on the ground reality of getting places, neighborhoods, and communities to “YES” on the idea of a trail. AND you’ll learn the conversations and experiences of house sales near to rail trails.

Presented by:

Event Details

** This event has passed **

April 28, 2022

10:00 AM to 11:30 AM (Pacific Time) {more time zones}

11:00 AM to 12:30 PM (Mountain Time)
12:00 PM to 01:30 PM (Central Time)
01:00 PM to 02:30 PM (Eastern Time)


FREE for members
FREE for nonmembers

Learning Credit Cost: FREE


Closed Captioning is available for this webinar.
Learning Credits
are available for this webinar.


This webinar is free. Would you consider a donation to support this webinar?


Webinar Outline

One of the key things about developing a rail trail is the outreach to trail neighbors. In this session you’ll learn about the on-the-ground reality of getting places, neighborhoods, and communities to “YES” on the idea of a trail. AND you’ll learn the conversations and experiences of house sales near to rail trails. You’ll learn about the minutia details of 21st century real estate in a sellers’ market. How decisions are made and how savvy buyers prevail in a multiple offer situation.

Learning Objectives:

  • Exploring the Historic Context Lens: In many communities, the right of way of the former RR is a treasure trove of history and memories. At one time the upwards of 12%-15% of the workforce was employed by the railroads. Every RR Historical Society or Association has treasure troves of history. When NYSDOT built 400 miles of rail trails in 4 years, to complete the Empire State Trail, they didn’t just roll out the asphalt or stone dust pathway, they actually built the nation’s most compelling series of historic callouts and kiosks. It is being noticed by the press in various realms. History shouldn’t be forgotten. Just the opposite. It will drive traffic and make the linear park, the best loved place in town.
  • Exploring the Community Development Lens: Leveraging the relatively small expenditure of public dollars in constructing the trail will bring forward much more private sector investments. See what is going-on in the Gateway Cities of Massachusetts.
  • Exploring the Trail Neighbor/Abutter Lens: Most times when the idea of a trail comes forward, the ones most concerned/opposed will be the ones who live the closest to the proposed trail. See examples of former opponents who saw the trail as a positive idea after it was built.
  • Exploring the Real Estate Lens: Learn from the first Realtor in the US specializing in the sale of residential property near to a former RR now a linear park. Learn how properties near a trail are so desirable now that we see multiple offers often. Learn what a winning offer will usually have as a part of the packet.


This webinar qualifies as a Health, Safety, and Welfare (HSW) course (via LA CES).

Questions & Answers

Webinar Resources

  • Related Links (pdf)

    Webinar Partners


    Craig Della Penna, Associate Broker, The Murphys Realtors, Trailside Team
    Northampton, Massachusetts

    Craig Della Penna is the Executive Director with Norwottuck Network, an Associate Broker with The Murphys Realtors, Trailside Team, as well as the Owner of Sugar Maple Trailside Inn in Florence, MA.

    For 12 years, Craig marketed rail freight and operated New England’s largest and most successful railroad-owned, transloading facility—Railroad Distribution Services, Inc. For seven years, he worked for Rails to Trails Conservancy as their New England Field Representative focusing on the policy end of building rail trails as well as public outreach. Today he is a successful Realtor, the fist realtor in the US specializing in the sale of property near to rail trails.

    Having given well over 1,200 lectures in 21 states and Canadian provinces, Craig is one of the countries most sought after motivational speakers on the economic development, tourism, and community development aspect of rail-trails, and their leveraging small amounts of public dollars to redevelop forgotten or derelict lands into treasured places. He is also the author of five books and numerous op-ed/guest editorials on the value of smart growth development, and rail-trails. In their 10th anniversary issue, THE RIDE MAGAZINE named him as the most effective advocate for rail-to-trail conversions on the eastern seaboard. He has also written the forward to three other books on rail trails and has been featured as a case-study in five books for, creative marketing, 21st century branding, etc.

    He and his wife Kathleen, operate an award-winning bed & breakfast in a restored, Civil War era house where the restoration was so extreme, it was featured on HGTV. The house sits 8 feet from one of the earliest muni-built rail trails in New England. And within 150 miles of his house sits the densest network of former steam RR corridor in the US. He also is reassembling the longest rail trail in the Northeast. The Mass Central Rail Trail, which runs 100+ miles from Boston to Northampton, Mass. This directly connects with 17 other trails over the 104+ miles. And he publishes the most widely read, free monthly eNewsletter about trails.


    Closed Captioning

    We are offering closed captioning for our webinars, thanks to a partnership with VZP Digital. If you are in need of this service, please email us prior to the webinar. An unedited transcript will be sent to all attendees following the webinar.

    Learning Credits and CEUs

    American Trails is proud to be a certified provider of the following learning credits and continuing education opportunities:

    • American Institute of Certified Planners Continuing Maintenance (AICP CM)
    • Landscape Architecture Continuing Education System (LA CES PDH) (most HSW approved)
    • National Recreation and Park Association (NRPA) CEU equivalency petition
    • CEU/PDH equivalency petition for other accepting organizations

    Learning credits are free for attendees for American Trails webinars and the International Trails Symposium, as well as for other conferences, webinars, and workshops we offer credits for. Learn more here.


    While we may individually agree (or disagree) in whole or in part with any or all of the participants, the views expressed in these webinars are not necessarily representative of the views of American Trails as an organization or its board and staff. Unless specific situations are noted by presenters, nothing in American Trails webinars should be considered to be interpreted as a standard.

    Terms and Privacy Policy

    By registering for our webinars, you submit your information to the webinar organizer and associated presenters and sponsors, who may use it to communicate with you regarding this event and their other services. Your organization may also be added to the American Trails Business Directory. You can easily cancel your registration at any time.

    4,399 views • posted 12/16/2021