Century Rides in Wisconsin
The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Wisconsin.
Cycling in Wisconsin: Terrain & Route Overview
Wisconsin is a heartland cycling paradise, renowned for pristine dairy farmland, scenic glacial geology, and an enthusiastic cycling culture. In southwestern Wisconsin, the famous Driftless Area escaped the smoothing effects of ancient glaciers, creating a dramatic labyrinth of steep limestone bluffs, twisting river valleys, and quiet rural backroads with severe, punchy climbs. To the northeast, Door County offers a tranquil peninsula ride along Lake Michigan and Green Bay shorelines, passing cherry orchards, lighthouses, and seaside villages. Events like the Dairyland Dare challenge riders with massive elevation gains, while centuries across the northwoods wind through pine forests and past glacial lakes. With smooth country roads, cheese-and-beer-fueled finish line festivities, and fantastic volunteer crews, Wisconsin is a premier century state.
Terrain Characteristics: Driftless Area unglaciated bluffs, Door County coastal peninsula, and northwoods lake country.
Riding Season & Weather: May through October.
📍 Wisconsin Century Rides Map
15 Plotted EventsBadger Challenge
SeptemberThis scenic century ride is the perfect challenge for cycling enthusiasts. You'll experience a breadth of quintessentially Wisconsin settings, including farmsteads with grazing cattle, charming lake views, shady woodlands and rolling fields.
BayCare Clinic Century
JuneRide from Green Bay to Lake Michigan and back, going Bayshore to Lakeshore. Century riders will bike from the waters of Green Bay to Lake Michigan and back, going Bayshore to Lakeshore.
Bike Northwoods Tour
JulyThe Bike Northwoods Tour is an annual 6-day ride in and around Wisconsin's rustic Northwoods, cycling between 150 to 300 miles on serene, lightly traveled roads surrounded by nature.
Chippewa Valley Century Ride
MayThe Chippewa Valley Century Ride is a non-profit cycling event that showcases the stunning scenery of Chippewa County. Choose your challenge with 35, 50, 75, or 100-mile routes winding through picturesque farmland, along the Chippewa and Flambeau Rivers, past Lakes Wissota and Holcombe, and through the unique kettle moraine topography of the Chippewa County Forest.
Dairyland Dare
AugustExperience the thrill of the Dairyland Dare Bike Ride in the breathtaking hills of southwest Wisconsin. Set in terrain untouched by glacial flattening, the Dairyland Dare delivers some of the most challenging riding in the Midwest, steep forested ridges, deep river valleys, and unforgettable climbs.
Door County Century
SeptemberThe Door County Century is the original century distance cycling event welcoming 3,000 riders each year to the scenic Door County peninsula. Choose from four course lengths: 30, 50, 70 or 100 miles.
Horribly Hilly Hundreds
JuneOne of the Midwest's toughest challenges for serious cyclists with up to 10,000 feet of elevation gain, serving as an important fundraiser for Friends of Blue Mound State Park.
Peninsula Century Spring Classic
JunePedal up, down, and across the Door County Peninsula for 36 years, the Spring Classic has been showcasing the natural beauty of Door County in the best way possible, from the saddle of a bicycle.
Ride Across Wisconsin
JulyA century ride that attracts cyclists from around the country and the world, with various route options, including an epic, hard, and worth it route.
Scenic Shore Bike Tour
JulyJoin the Scenic Shore Bike Tour along the picturesque shoreline of Lake Michigan in Wisconsin, with distance options of 25, 75, 100, or 150 miles, and know that every pedal helps advance the mission to cure blood cancer.
Spectacular Annual Great Bike Ride Around Wisconsin
AugustAn annual 6-day cycling tradition featuring riding between 150 to 300 miles in and around central and southern Wisconsin.
Sugar River & Military Ridge Century Trail Loop
AnytimeCombines the scenic Sugar River and Badger State rail-trails with quiet paved backroads through Swiss heritage country.
The Sadistic Century
AugustA fun and challenging road bicycle ride on hilly, smooth, quiet roads in Western Wisconsin with routes including 200 km, 100 mile, 100 km, 60 km, and 50 km lengths.
Will to Ben
OctoberBike Wisconsin's newest week long tour from the Will B. Rolling statue in Port Byron, IL to the Ben Bikin' statue in Sparta, WI.
Wright Stuff Century Ride
SeptemberEnjoy beautiful views of Wisconsin's Driftless region including Frank Lloyd Wright’s Taliesin and Unity Chapel. We have three challenging routes, all starting at Brigham Park in Blue Mounds.