The community of Greenfield, Indiana is home to a rich history and culture that is unique within the state of Indiana. In an effort to spread more cultural awareness to both local residents and visitors, the City of Greenfield and Parks & Recreation Department is working on a new project called the Riley Literary Trail, in partnership with the Indianapolis Metropolitan Planning Organization and the Health and Heritage Stellar Region. The Indiana Stellar Communities Program is a multi-state department investment initiative led by the Indiana Office of Community and Rural Affairs. These state programs work with regions on their vision for community and economic development. Expected to open by 2023, the planning stages have been in process for years and we are excited to see what comes from this new cultural trail. 

The Literary Trail as Part of City Revitalization

The origins of the Riley Literary Trail began when the City of Greenfield first started planning for downtown revitalization by meeting with downtown merchants in 2011. At the time, there was not nearly as much business or retail in the area as today, with most opting for locations as near to the intersection of State Road 9 and US-40 as possible. As Joanie Fitzwater, the city’s Planning Director, explained, “They just didn’t feel like there was visibility or any kind of foot traffic anywhere else in the downtown. We wanted to expand connectivity and the downtown footprint.”

The city hired a group of consultants for a full downtown revitalization plan, and out of that process came a three-pronged approach for preserving our architectural heritage, boosting economic development and creating a sense of place through various public projects. “One of those projects,” said Fitzwater, “was a cultural trail that would connect all of our downtown heritage sites to the Pennsy Trail.” As the Pennsy Trail has grown in popularity and extended into Indianapolis, the hope is that the Riley Literary Trail, as the project has come to be known, will introduce cyclists, visitors and even local Greenfield residents to more of the culture and history that exists in our town. 

A Several Year Downtown Planning Process

As the Greenfield city planners and consultants continued to expand on the downtown revitalization plan, they began the application for a Stellar Communities designation. Being named as a Stellar Community by the State of Indiana provides grant funding for major projects from state agencies, including the Department of Transportation, Office of Community and Rural Affairs, the Indiana Housing & Community Development Authority and the Indiana Department of Health, among others. 

Despite many setbacks during the multi-year application planning process, Greenfield eventually partnered with the Towns of Fortville, Shirley and Hancock County leadership to apply for a regional grant as the Health and Heritage region. In 2018, the region was officially designated as a Stellar Community. Greenfield has also benefited from collaborative partnerships with the Greenfield Main Street organization, the Hancock County Community Foundation, Hancock Health, Greenfield Central Schools, the Greenfield Area Chamber of Commerce, Hancock Economic Development, Hancock Arts Council, and many local sponsors and volunteers. Downtown revitalization has seen many great strides forward over the past several years. 

Fitzwater explained, “Our city engineer was able to also procure a grant from the Indianapolis MPO, and our Stellar dollars were available to match that, so between the two we have leveraged the Riley Literary Trail to be our premier Stellar project, along with Depot Street Park and the historic façade renovations.”

What will the Riley Literary Trail Look Like?

The Riley Literary Trail is planning to hit several historical sites throughout Greenfield, and will also install art and cultural features alongside literary history to bring even more educational components to the trail. It is planned to run from the Pennsy Trail north on Riley Avenue to the James Whitcomb Riley Boyhood Home and Museum, which takes guests back to life in the pioneer era to learn all about our famed “Hoosier Poet” and the trail’s namesake. 

Next, the trail will go along the alley to North Street, passing several historic homes and local businesses to connect to the Memorial Building, which Fitzwater calls a “real hidden gem in our community.” Then it will run along American Legion Place past the Courthouse, and the plaza and connect back to the Pennsy Trail. 

Ellen Kuker, Parks Director with Greenfield Parks and Recreation Department, is extremely excited about this new trail. “That history, if you don’t capture it in something, then the next generation doesn’t know,” said Kuker. “That history can change a mindset and the literary trail will have that educational component that for generations to come can appreciate how Greenfield came to be and where we’re going.”

How Local Residents Can Help Plan the Trail

As the Riley Literary Trail project has started to come to fruition, the city has taken many steps to involve the community in its planning for a launch date in 2023. When a consultant was first hired to design it, they sent letters to local property owners on the trail as well as the general public about what they would like to see featured. Once the nuts and bolts of the utility locations and trail construction are completed, the city will reach out again to the community to help tell the story of Greenfield. 

As Fitzwater said, “We want to know what they want to see, and what they know that we don’t… so that we can showcase our cultural heritage along the trail.” With the potential for rotating arts and cultural installations and cultural features to highlight Greenfield’s rich literary history, the Riley Literary Trail is sure to be a favorite spot for residents and visitors alike. 

“We want to bring out bits of our history that help people remember how Greenfield came to be,” said Fitzwater. “Features that will tell the stories of all of this historic and significant architecture, and the people behind creating our city so that we can remember what happened. Those are all things that help people call a place home.”


The Indiana Stellar Communities Program is a multi-state department investment initiative led by the Indiana Office of Community and Rural Affairs. The Health and Heritage Stellar Region is a collaboration between citizens, non-profit organizations and municipalities that is reshaping the future of Hancock County. The region, comprised of the City of Greenfield, Town of Fortville and Hancock County leadership, is focused on promoting and cultivating the health, heritage and heart of our area. To follow our projects and learn more about us, visit our Facebook page or our website at

James Whitcomb Riley Boyhood Home and Museum Photo Credit: City of Greenfield website and Misty Garrity, Misty Eyed Photography