Michigan Porch

How a railroad's initials became the Polly Ann Trail

The Polly Ann Trail runs about 17 miles up northeast Oakland County on a former railroad bed, from Orion Township through Oxford and Leonard toward the county line.

The trail is named after a nickname for a railroad that no longer exists. A line chartered back in 1879 once climbed north out of Pontiac toward the timber country of Michigan’s Thumb, and somewhere along the way locals softened its initials into “the Polly Ann” — the kind of pet name a town gives a railroad it sees every day. The last train ran in 1984, the rails came up, and the affectionate name slid right over onto the path left behind.

That path now runs about 17 miles up the northeast corner of Oakland County, dead flat the whole way because trains never could climb. It stitches together Orion, Oxford, and Addison Townships and the villages of Oxford and Leonard before it reaches the Lapeer County line, where the corridor keeps going north under the same name. Most of the surface is crushed stone, with paved stretches where it slips through the towns.

The easy grade is the whole appeal. Bikes, joggers, dog walkers, and — once the snow lands — cross-country skiers all share it, and nobody has to fight a hill. It threads past kettle lakes, gravel pits left from the glaciers, hay fields, and a few small downtowns where you can lean the bike against a wall and get a sandwich before pedaling on.

Leonard is the stop worth lingering in: a tiny village where the trail runs right through, and the old grain elevator and a 1880s feel still hang in the air. The whole corridor passed into public hands in the 1990s, and a local council of the towns it crosses keeps it mowed, signed, and open — volunteers doing for a footpath what a section gang once did for the rails.

Sources

Last reviewed against the listed sources: June 23, 2026.

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