πŸ‡ΊπŸ‡Έ Midwest Region → β€’ WI

Century Rides in Wisconsin

The comprehensive 2026 directory of 100-mile centuries, metric centuries (62 miles), and endurance cycling tours across Wisconsin.

15 Verified Rides
WI State Code
May through October Prime Riding Window

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.

Explore All Midwest Region Century Rides →

πŸ“ Wisconsin Century Rides Map

15 Plotted Events
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Wisconsin Century Ride Schedule

Showing 15 organized cycling events

Badger Challenge

πŸ“… Sep 27, 2026 (7:00 AM – 12:00 PM)
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
πŸ“ UW Health Eastpark Medical Center β€’ Madison, WI

This 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.

🏷️ $130AlpineMetric Available100M
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Sep 27, 2026 (7:00 AM – 12:00 PM)
RWGPS TelemetryInteractive Route Map (1) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
End Date2026-09-27T12:00:00
Starting VenueUW Health Eastpark Medical Center
Street Address4621 Eastpark Blvd
LocationMadison, WI 53718
GPS Coordinates43.073, -89.3817 (Google Maps β†—)
OrganizerBadger Challenge β†—
Entry Fee$130
RegistrationDirect Registration Link β†—
🏒 Hosted by: Badger ChallengeπŸ“ 4621 Eastpark Blvd, 53718

BayCare Clinic Century

πŸ“… Jun 01, 2026
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
πŸ“ BayCare Clinic headquarters, 1035 Kepler Drive β€’ Green Bay, WI

Ride from Green Bay to Lake Michigan and back. The BayCare Clinic Century bicycle tour is one of the most popular cycling events in Northeast Wisconsin, with more than 500 registered riders in 2026.

🏷️ $0AlpineMetric Available100M
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jun 01, 2026
RWGPS TelemetryInteractive Route Map (1) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
Starting VenueBayCare Clinic headquarters, 1035 Kepler Drive
Street Address1035 Kepler Drive
LocationGreen Bay, WI
GPS Coordinates44.485313, -88.016868 (Google Maps β†—)
OrganizerBayCare Clinic Foundation β†—
Organizer Contact[email protected]
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: BayCare Clinic FoundationπŸ“ 1035 Kepler Driveβœ‰οΈ [email protected]

Bike Northwoods Tour

πŸ“… Jul 04 – 10, 2026
πŸ”οΈ Imperial Century (100 mi)πŸ”₯ Double Century (200K+)
πŸ“ Manitowish Waters β€’ Manitowish Waters, WI

Cycling between 150 to 300 miles on serene, lightly traveled roads surrounded by nature.

🏷️ $0Metric6-dayLoopNo Transportation
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)πŸ”₯ Double Century (200K+)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jul 04 – 10, 2026
End Date2026-07-10
Starting VenueManitowish Waters
LocationManitowish Waters, WI
GPS Coordinates46.123909, -89.830767 (Google Maps β†—)
OrganizerBike Wisconsin β†—
Organizer ContactE-Mail Us
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Bike Wisconsinβœ‰οΈ E-Mail Us

Chippewa Valley Century Ride

πŸ“… May 23 – 24, 2026
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map (2)
πŸ“ Northern Wisconsin State Fairgrounds β€’ Chippewa Falls, WI

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.

🏷️ $65AlpineMetric Available100M
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ—ΊοΈ RWGPS Map (2)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… May 23 – 24, 2026
RWGPS TelemetryInteractive Route Map (2) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
End Date2026-05-24T10:00:00
Starting VenueNorthern Wisconsin State Fairgrounds
Street Address225 Edward St
LocationChippewa Falls, WI 54729
GPS Coordinates44.932202, -91.384376 (Google Maps β†—)
OrganizerChippewa Valley Century Ride Foundation β†—
Entry Fee$65
RegistrationDirect Registration Link β†—
🏒 Hosted by: Chippewa Valley Century Ride FoundationπŸ“ 225 Edward St, 54729

Dairyland Dare

πŸ“… Jul 31, 2027 (6:15 AM – 6:00 PM)
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ”₯ Double Century (200K+)
πŸ“ Dodgeville, WI β€’ Dodgeville, WI, WI

Experience 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.

🏷️ $110Gran FondoMetric Available100M150M
⚑ Event Details & Specifications ›
Dataset Population2027 Forward Calendar
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ”₯ Double Century (200K+)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jul 31, 2027 (6:15 AM – 6:00 PM)
End Date2027-07-31T18:00:00
Starting VenueDodgeville, WI
Street Address53533
LocationDodgeville, WI, WI 53533
GPS Coordinates42.969779, -90.140433 (Google Maps β†—)
OrganizerIncredible Bank β†—
Entry Fee$110
RegistrationDirect Registration Link β†—
🏒 Hosted by: Incredible BankπŸ“ 53533, 53533

Door County Century

πŸ“… Sep 12, 2027
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)⚑ Half Century (50 mi)πŸ—ΊοΈ RWGPS Map (2)
πŸ“ Door County β€’ Door County peninsula, WI

The Door County Century is a scenic cycling event welcoming 3,000 riders each year to the Door County peninsula. Choose from four course lengths: 30, 50, 70 or 100 miles.

🏷️ $0AlpineMetric Available100M
⚑ Event Details & Specifications ›
Dataset Population2027 Forward Calendar
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)⚑ Half Century (50 mi)πŸ—ΊοΈ RWGPS Map (2)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Sep 12, 2027
RWGPS TelemetryInteractive Route Map (2) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
Starting VenueDoor County
LocationDoor County peninsula, WI
GPS Coordinates44.84384, -87.375311 (Google Maps β†—)
OrganizerBay Shore Bicycle Club β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Bay Shore Bicycle Club

Gordon Pine Barrens 50

πŸ“… Jun 05, 2027
⚑ Half Century (50 mi)
πŸ“ Gordon, WI

The Gordon Pine Barrens 50 (GPB50) 2nd year went very well. We saw 200 riders from 10 States and 80+ different communities. The feedback for our riders gave the overall feeling of success. Many positive comments about the rustic, challenging, and motor vehicle free roadways and trails. The event saw a high level of competition and at the sametime provided a high quality β€œlaid back feel.” As the GPB plans on...

🏷️ $45🚡 GravelHalf CenturyGravel
⚑ Event Details & Specifications ›
Dataset Population2027 Forward Calendar
Qualified Distances
⚑ Half Century (50 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jun 05, 2027
Street Address9730 Ball Park Dr
LocationGordon, WI 54838
GPS Coordinates46.239359, -91.792307 (Google Maps β†—)
OrganizerGordon Pine Barrens 50 β†—
Entry Fee$45
RegistrationDirect Registration Link β†—
🏒 Hosted by: Gordon Pine Barrens 50πŸ“ 9730 Ball Park Dr, 54838

Horribly Hilly Hundreds

πŸ“… Jun 13, 2026
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
πŸ“ Blue Mound State Park β€’ Blue Mound State Park, WI

One of the Midwest's toughest challenges for the serious cyclist, with up to 10,000 feet of elevation gain.

🏷️ $0AlpineMetric Available100M
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jun 13, 2026
Starting VenueBlue Mound State Park
LocationBlue Mound State Park, WI
GPS Coordinates43.0174, -89.832 (Google Maps β†—)
OrganizerFriends of Blue Mound State Park β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Friends of Blue Mound State Park

Hungry Bear Gravel

πŸ“… May 08, 2027
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
πŸ“ Cable, WI

We will have minimal course markings with route arrows on the pavement and arrow cards along the course. Please use GPS navigation. The 2027 routes will be similar to those in 2026, but check back before race day for final directions. All courses are open to traffic, and ATV and snowmobile trails are shared. Obey the rules of the road and watch for other users. Make sure to download the routes to your phone or...

🏷️ $49🚡 Gravel100MMetric AvailableGravel
⚑ Event Details & Specifications ›
Dataset Population2027 Forward Calendar
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… May 08, 2027
LocationCable, WI 54821
GPS Coordinates46.207944, -91.293257 (Google Maps β†—)
OrganizerChequamegon Area Mountain Bike Association (CAMBA) β†—
Entry Fee$49
RegistrationDirect Registration Link β†—
🏒 Hosted by: Chequamegon Area Mountain Bike Association (CAMBA)

Peninsula Century Spring Classic

πŸ“… Jun 19, 2027
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)⚑ Half Century (50 mi)πŸ—ΊοΈ RWGPS Map (3)
πŸ“ Horseshoe Bay Farms β€’ Door County, WI

The ride features four routes: a 30-mile, 50-mile, Metric Century, and Century that weave along Northern Door County’s beautiful back roads, along the shoreline, and past iconic landmarks.

🏷️ $0Metric CenturyCentury100M
⚑ Event Details & Specifications ›
Dataset Population2027 Forward Calendar
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)⚑ Half Century (50 mi)πŸ—ΊοΈ RWGPS Map (3)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jun 19, 2027
RWGPS TelemetryInteractive Route Map (3) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
Starting VenueHorseshoe Bay Farms
Street Address8142 HWY 57
LocationDoor County, WI 54202
GPS Coordinates45.0503, -87.2792 (Google Maps β†—)
OrganizerPeninsula Century Spring Classic β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Peninsula Century Spring ClassicπŸ“ 8142 HWY 57, 54202

Ride Across Wisconsin

πŸ“… Jul 11, 2026
πŸ”οΈ Imperial Century (100 mi)πŸ—ΊοΈ RWGPS Map (2)
πŸ“ Phoenix Park β€’ Eau Claire, WI

Ride Across Wisconsin attracts cyclists from around the country and the world.

🏷️ $0MetricCentury
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)πŸ—ΊοΈ RWGPS Map (2)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jul 11, 2026
RWGPS TelemetryInteractive Route Map (2) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
Starting VenuePhoenix Park
Street Address330 Riverfront Terrace
LocationEau Claire, WI
GPS Coordinates44.783972, -91.487686 (Google Maps β†—)
OrganizerBike Fed β†—
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Bike FedπŸ“ 330 Riverfront Terrace

Scenic Shore Bike Tour

πŸ“… Jul 25 – 26, 2026
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ”₯ Double Century (200K+)πŸ—ΊοΈ RWGPS Map
πŸ“ Concordia University β€’ Concordia University in Mequon, WI

Join the Scenic Shore Bike Tour along the picturesque shoreline of Lake Michigan in Wisconsin. Choose your distance - 25, 75, 100, or 150 miles - and know that every pedal helps advance our mission to cure blood cancer.

🏷️ $100Metric Available100M
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)πŸ”₯ Double Century (200K+)πŸ—ΊοΈ RWGPS Map
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Jul 25 – 26, 2026
RWGPS TelemetryInteractive Route Map (1) → β€’ Send to Wahoo/Garmin β†— β€’ GPX ⬇ β€’ TCX ⬇
End Date2026-07-26T00:00:00
Starting VenueConcordia University
Street AddressConcordia University in Mequon
LocationConcordia University in Mequon, WI
GPS Coordinates43.236389, -87.984444 (Google Maps β†—)
OrganizerBlood Cancer United β†—
Entry Fee$100
RegistrationDirect Registration Link β†—
🏒 Hosted by: Blood Cancer UnitedπŸ“ Concordia University in Mequon

The Bear 100

πŸ“… May 01, 2027
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
πŸ“ Laona, WI

'Explore the Hidden Gravel' of the Nicolet National Forest! Routes: 103 miles, 61 miles, and 31 miles...an adventure for everyone from gravel curious first timers to seasoned veterans. Chip timing for all distances, soup and breadsticks included at the finish. Youth ride free! All youth riders 16 and under must present a signed parental release form and participate with an adult or be part of an established...

🏷️ $59 - $69🚡 Gravel100MMetric AvailableGravel
⚑ Event Details & Specifications ›
Dataset Population2027 Forward Calendar
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… May 01, 2027
Street Address4863 Elm Street
LocationLaona, WI 54541
GPS Coordinates45.556617, -88.673404 (Google Maps β†—)
OrganizerThe Bear 100 and Laona Rescue β†—
Entry Fee$59 - $69
RegistrationDirect Registration Link β†—
🏒 Hosted by: The Bear 100 and Laona RescueπŸ“ 4863 Elm Street, 54541

The Sadistic Century

πŸ“… Aug 15, 2026
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
πŸ“ Dunn County Recreation Park β€’ Menomonie, WI

A fun and challenging road bicycle ride on hilly, smooth, quiet roads in Western Wisconsin. Routes include 200 km, 100 mile, 100 km, 60 km and 50 km lengths with three distinct rest stops mainly in Dunn County, Wisconsin.

🏷️ $0AlpineMetric Available100M200K
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)⏱️ Metric Century (62 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Aug 15, 2026
Starting VenueDunn County Recreation Park
Street Address620 17th St
LocationMenomonie, WI 54751
GPS Coordinates44.87182, -91.92651 (Google Maps β†—)
OrganizerThe Sadistic Century Organizing Committee β†—
Organizer Contact[email protected]
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: The Sadistic Century Organizing CommitteeπŸ“ 620 17th St, 54751βœ‰οΈ [email protected]

Will to Ben

πŸ“… Oct 03 – 09, 2026
πŸ”οΈ Imperial Century (100 mi)
πŸ“ Port Byron β€’ Port Byron, WI

Bike Wisconsin's newest week long tour from the Will B. Rolling statue in Port Byron, IL to the Ben Bikin' statue in Sparta, WI!

🏷️ $0MetricCentury
⚑ Event Details & Specifications ›
Dataset Population2026 Verified Census
Qualified Distances
πŸ”οΈ Imperial Century (100 mi)
Event TypeCycling Century
Event StatusScheduled
Attendance ModeIn-Person (Offline)
DateπŸ“… Oct 03 – 09, 2026
End Date2026-10-09
Starting VenuePort Byron
LocationPort Byron, WI
GPS Coordinates43.78444, -88.787868 (Google Maps β†—)
OrganizerBike Wisconsin β†—
Organizer ContactE-Mail Us
Entry Fee$0
RegistrationDirect Registration Link β†—
🏒 Hosted by: Bike Wisconsinβœ‰οΈ E-Mail Us