Drive / Drive / Hiawatha-plus-transfer to Waukesha / Cottage Grove
Glacial Drumlin State Trail
Long Wisconsin limestone rail-trail between Waukesha and Cottage Grove.
Field Trip Needs recheck 2h 10m to good stuff 52 mi 2/5 intervals
Decision
Field Trip dry trail, low wind, want a long uncomplicated surface
Avoid soft trail after rain, strong headwind, no shuttle plan
Workout gravel endurance / rail-trail day
Surface Mixed: Mostly limestone rail-trail with some paved segments.
Access
Chicago to Waukesha / Cottage Grove 2h typical drive time
10 min roll to the useful riding
Drive is simplest. Hiawatha gets to Milwaukee, not cleanly to the trailhead.
Confidence
Geometry Generated
Surface Known
Access Link only
Last checked 2026-05-28
Scouting card: verify trail status, access, and route shape before treating the GPX as ride-ready.
Hazards
- Long point-to-point · medium Plan a turn-around, shuttle, or partial segment.
Effort Windows
- Long limestone corridor · 45-120 min Steady aerobic blocks are the point.
A big surface-time option. It is not technical, but it absolutely belongs in an off-road planner because it gives a lot of unpaved mileage.
Planning note: this entry was added as an off-road possibility. Treat the GPX and map line as scouting geometry until replaced with a ridden or sourced route file.
Ride Sheet
Drive Chicago to Waukesha / Cottage Grove
Access 2h 10m to good stuff
Workout gravel endurance, rail-trail day, steady tempo, big mileage
Bailouts Trail towns along the corridor
Water Waukesha, Dousman, Lake Mills, Cottage Grove
Bathrooms Trailheads and towns when open
Best When dry trail, low wind, want a long uncomplicated surface
Avoid soft trail after rain, strong headwind, no shuttle plan