The Lake Wobegon trail runs on the MN/DOT rail corridor formerly owned by Burlington Northern Railroad Company, now Burlington Northern Santa Fe, successor to the original Great Northern Railroad founded by James J. Hill

Turning this abandoned railroad corridor into a trail was the idea of the Albany Jaycees, who spent many hours raising money and support for the trail.
When they approached Garrison Keillor, he graciously agreed that the proposed trail could be called the Lake Wobegon Trail and in the fall of 1998 he participated on the grand opening celebration.

Planning for the trail began in the fall of 1994, and fundraising began in the fall of 1995. Construction costs were a joint effort between the Federal Intermodal Surface Transportation Efficiency Act (ISTEA), Minnesota DNR Regional Trail Initiatives Grant, Albany Jaycees Fundraisers, Central Minnesota Initiative Fund (McKnight Foundation) and Stearns County.

Following the grand opening Keillor composed a poem about the Lake Wobegon Trail for his radio show.

In the December 2000 issue of National GeographicMagazine he wrote that “Holdingford is the town that looks most Wobegonic to me.”

The final section of the Lake Wobegon trail connecting Saint Joseph to Waite Park was competed in the summer of 2018.