This study aims to develop a detailed understanding of the success factors required in the development of a multi-municipal regional trail network. It has been prepared with the view of generating a trail planning framework that integrates community wellness and active transportation considerations, along with tourism and economic development opportunities. In doing so, this study will add to the growing body of research into the benefits and impacts of regional trail networks to local communities while advancing our understanding of the unique challenges to be faced in the planning shared infrastructure projects across multiple jurisdictions. Key informant interviews were conducted with representatives from regional trail groups and local trail associations along with municipal and provincial governments throughout the months of November 2014 to February 2015. The interviews explored the participants' experience, and knowledge of the development, management and governance aspects of regional trail initiatives in Ontario. Themes were created and organized to capture the connections and interrelations of the data collected. The history of trails development in North America dates back to the first nations. Their trails were established for early trade and helped lay the framework for future settlement patterns across the country. Just like the historical long-distance trails of the First Nations, modern regional trail infrastructure must be established to connect communities with regional points of interest. Some regional walking trails can be hundreds of kilometres long and in some cases even thousands of kilometres long. There is a growing interest in regional trails that also serve as long-distance cycling routes. The province of Ontario has a long and rich history with the development of long-distance and regional trail systems. In the early part of 2003, the Ontario government began development of The Ontario Trails Strategy. It offered a vision of achieving 'a world-class system of diversified trails which enhance the health and prosperity of all Ontarians'. Several key themes have been identified in the trails literature. Generally trails are perceived to provide a broad range of community benefits including recreation, quality of life, health and wellness, alternative transportation, and economic development. Trails are also recognized as a source of economic activity, particularly with regard to tourism, and are seen to have a generally positive impact on adjacent property values. As a 'Quality of Life' community asset, trails are seen to play an important role in attracting new residents as well as the attraction, retention and expansion of businesses in a community. The literature appears to indicate that local trails organized together to make a long distance regional trail may provide a reasonable return on investment in the form of enhanced tourism to the region. The literature indicates that the ultimate success of a regional trail is likely to depend upon the ability to connect existing tourist and business attractions within the area together with a trail that offers a natural scenic urban getaway experience. Four regional trails in Ontario were selected for in-depth review; the Bruce Trail, the Waterfront Trail, the Niagara Circle Route, and the Trans Canada Trail. Representatives from each of these organizations participated in an in-depth interview. The interviews focused on general themes and trends within trails in Ontario and explored specific background information for each group. Particular attention was paid to the vision of the organization, as well as their governance and operational details. The case study area included the single-tier municipality of Guelph, the upper tier municipalities of Wellington County and Waterloo Region, and several lower tier townships and cities. General demographic information was reviewed as well as key attributes of each municipality and township. A comprehensive inventory of existing trail infrastructure was assembled, and particular attention was paid to existing regional trails within each jurisdiction. Specific guidelines for the development of regional trail networks within each community also was compiled based upon a review of each community's Official Plan, along with supporting documents such as Trails Master plans, Cycling Master Plans and Active Transportation Studies. Each community within the case study has made significant investments in local pedestrian trail infrastructure to promote community wellness, tourism, and economic development. This research indicates that a regional trail linking the Tri-Cities of Guelph, Cambridge and Kitchener/Waterloo would provide an opportunity to leverage investments in trail infrastructure and provide additional opportunities and benefits for that entire region. The development of a Regional Trail Steering Committee is recommended to coordinate the planning and implementation process. One of the first priorities would be the development of a clear and well articulated vision to help establish the purpose and branding of the regional trail and provide insight into the stakeholders, supporters, and grassroots groups that will be vital in the planning process. While any number of groups or organizations could spearhead the development of a regional trail steering committee, at this time the Grand River Conservation Authority seems to be in the best position to champion the cause.