“People have been riding mountain bikes in the woods since before they were called mountain bikes. In the free ride movement of the late 90s, early 2000s, there was a lot of road building in the south end [of the park]. A lot of wooden features that were 12 feet, 16 feet high at some points, were constructed just by locals. That was causing an issue for Monroe County - not to say that a lot of people were getting injured but it just increased the risk and increased their liability and you know that's something that they don't want. GROC - in 2005, I think - had lobbied to get Tryon Park as well as Bay Park West open and legal use for mountain bikes. In doing so they also partnered with Monroe County to steward the land.”
- Alex Parsons, GROC

Although much of the history is not readily available, it can be confirmed that much of Tryon Park was once farmland. Because of this, there are many relics of the early-to-mid-1900s such as cars, tires, and old dumping grounds where only glass, metal, and porcelain objects remain. Monroe County Parks formally allowed mountain biking in the park in May of 2011.