Day One of the Woodstock weekend is a beautifully varied 400K that heads north and west into southern Wisconsin before looping back home.
From Woodstock, the adventure begins heading north toward Delavan Lake and Whitewater, before turning west through Milton. Riders are rewarded with rolling hills and classic dairy-country scenery as the route climbs into New Glarus, one of the highlights of the day.
The return leg heads south through the green countryside of Brodhead, east to Darien, then south toward Sharon. From there, the route passes through Capron—before rolling through Marengo and returning to Woodstock, the set of Bill Murray’s Groundhog Day classic.
This is a full-value 400K: varied terrain, steady climbing, and long stretches that reward smart pacing and patience.
Getting to Woodstock
Woodstock is easily accessible from Chicago via the Metra Union Pacific Northwest (UP-NW) Line, which runs directly from Ogilvie Transportation Center to downtown Woodstock. The station is centrally located and a convenient option for riders traveling in from the city for the weekend.
Riders are encouraged to arrive Friday night for a relaxed start to the weekend, with a team dinner and several affordable overnight options available nearby.
Disclaimer: Routes may change after a pre-ride due to road conditions, construction, or safety concerns. Any updates will be shared with registered riders.
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Riders
Day One of the Woodstock weekend is a beautifully varied 400K that heads north and west into southern Wisconsin before looping back home.
From Woodstock, the adventure begins heading north toward Delavan Lake and Whitewater, before turning west through Milton. Riders are rewarded with rolling hills and classic dairy-country scenery as the route climbs into New Glarus, one of the highlights of the day.
The return leg heads south through the green countryside of Brodhead, east to Darien, then south toward Sharon. From there, the route passes through Capron—before rolling through Marengo and returning to Woodstock, the set of Bill Murray’s Groundhog Day classic.
This is a full-value 400K: varied terrain, steady climbing, and long stretches that reward smart pacing and patience.
Getting to Woodstock
Woodstock is easily accessible from Chicago via the Metra Union Pacific Northwest (UP-NW) Line, which runs directly from Ogilvie Transportation Center to downtown Woodstock. The station is centrally located and a convenient option for riders traveling in from the city for the weekend.
Riders are encouraged to arrive Friday night for a relaxed start to the weekend, with a team dinner and several affordable overnight options available nearby.
Disclaimer: Routes may change after a pre-ride due to road conditions, construction, or safety concerns. Any updates will be shared with registered riders.
