Century Rides in the Midwest

Join the American Diabetes Association along with your friends, family, and colleagues as we ride in support of people living with diabetes.

Pedal with purpose on a 28- or 50-mile journey along the beautiful and historic Prairie Path and Fox River Trail to raise funds for Kamwenge Secondary and Vocational School in Uganda.

An annual organized invitational bicycle tour hosted by the Arlington Heights Bicycle Club, featuring scenic road cycling loops through Lake and McHenry counties in northern Illinois.

A 100-mile ride through scenic northeastern Illinois & SE Wisconsin with 4 different loops, fully supported with SAG, rest stops, and breathtaking views.

The Blackhawk Country Roads Invitational features a 64-mile, 45-mile, and 32-mile ride through the rolling hills of northern Illinois and southern Wisconsin, passing through charming villages and along the scenic Sugar River.

An annual organized late-summer invitational bicycle ride hosted by the Blackhawk Bicycle & Ski Club, featuring scenic road cycling routes of varying lengths—including a 100K metric century and a 100-mile full century—through the rolling countryside, farmland, and rural roads of northern Illinois and southern Wisconsin.

Long-standing recreational bike ride with distances ranging from a short family ride to the 100-mile century. Low-trafficked roads, SAG support, well-stocked aid stations and post-ride lunch make for a great day of riding.

Challenging climbs and rugged autumn scenery through the Shawnee National Forest region.

Join Ride Illinois from June 7-12, 2026 for the 23rd annual Grand Illinois Bike Tour – the nonprofit organization’s largest annual fundraiser and one heck of a good time! Our 2026 route will explore the Metro East area in SW Illinois – including scenic views of the mighty Mississippi River.

An annual organized invitational bicycle ride hosted by the Wheeling Wheelmen Bicycle Club, featuring paved, scenic road routes of 25, 50, 64 (metric century), and 100 miles winding through the farmland, horse country, and quiet roads of northern Illinois and southern Wisconsin.

Scenic Peoria County routes, catered lunch, well-stocked food at rest stops, SAG, Trek Bike Store Technician at venue

An annual recreational cycling event organized by the Evanston Bicycle Club, offering scenic routes ranging from 25 to 100 miles starting from Gillson Park in Wilmette and winding along Lake Michigan toward Wisconsin.

A welcoming, non-competitive fall ride for cyclists of different experience levels. Choose a 10-mile beginner group ride, a 40-mile open route, or the full 62.5-mile metric century.

A long-distance cycling route touring through the wide prairies, farmland, and rural county roadways of central Illinois. Formerly held as an organized weekend cycling tour, this course does not have an active public registration or sanctioned event date and can be ridden anytime as an independent route.

Fully supported rides challenging experienced cyclists to ride from one border of Illinois to the other.

Cycle across the entire state of Illinois in one day, challenging experienced cyclists in peak physical condition.

Pedal along historic Route 66 from St. Louis to Joliet and discover a scenic journey through quaint Midwestern towns, open farmland, and classic roadside attractions.

100 miles around the beautiful forest preserve. Accomplish this by riding multiple times around a two different 10 mile loops, providing you with multiple breaks, if desired.

The Swedish Days Ride travels the quiet, scenic and relatively flat paved roads of rural Kane, Kendall and DeKalb counties, meandering through cornfields and through shaded thoroughfares.

A unique long-distance ride that takes cyclists through three states in one unforgettable day, with miles of lakeside views, welcoming communities, and an extensive network of fully paved bike paths and lightly traveled residential roads.

A unique long-distance ride that takes cyclists through three states in one unforgettable day, with miles of lakeside views, welcoming communities, and an extensive network of fully paved bike paths and lightly traveled residential roads.

An exciting annual bicycle ride with fresh and stunning views each year.

A cycling tour through Oak Park, Illinois, showcasing Frank Lloyd Wright and Prairie School architecture before extending into the surrounding western Chicago suburbs and trails. Formerly organized as an annual late-summer invitational by the Oak Park Cycle Club with morning rolling departures, it is not currently operated as an active sanctioned event with public registration and can be ridden anytime as an independent architectural route.

A two-day bike tour of the Amish countryside and lakes of northeast Indiana, with routes ranging from 22 to 100 miles.

The 34th Annual B&O Bicycle Tour will showcase portions of the B&O Trail as well as scenic countryside. You may choose from 11-, 15-, 25-, 45- and 62-mile loops.

A 100K (~62miles) and a 25-mile ride through the scenic, open roads of Boone County, Indiana, with live music, food, and a beer garden.

A weekend built around bikes, trails, community, and raising funds for trail work. Join us for a full weekend of pristine singletrack, live music, great food, and camping as we celebrate the awesome trails of Brown County.

The Buffalo Bicycle Stampede features five route lengths all coursing in and around the Tippecanoe River valley in the Indiana counties of White, Pulaski, and Cass. The Century ride will also visit Starke County.

Paved, vehicle-free rail-trail route along the Cardinal Greenway.

A 10-day, 1000-mile cycling event across Indiana, with daily departures from various locations.

Rolling, scenic roads through Kosciusko County and northern Indiana lake country.

A tour of Wabash County, not a race, so feel free to modify your route along the way. Supplies and gear (SAG) stops will be available along the routes and clothing can we dropped off at each SAG stop and will be delivered to you back at the YMCA at the end of your ride!

Dave, Rich, and Friends are embarking on a 100-mile ride on the Indiana Cardinal Greenway Rail Trail to raise funds for Dayspring Center.

Riders compete in this unique self-supported bicycle race. The goal is to reach a select list of historical cemeteries in and around Hoosier National Forest.

The Dust Bowl 100 presented by Zipp is a century ride that celebrates Indiana's backroads on two wheels, with three distances available (100M, 100K, & 44M).

A premier 100-mile endurance road cycling route through southeastern Indiana (Jefferson, Ripley, Jennings, and Decatur counties) that crosses five historic 1880s covered bridges: Busching, Otter Creek, Westport, Scipio, and James.

Distances of 10 (family fun ride), 17, 34, 50, 62, & 100 miles

An annual late-fall endurance gravel bicycle race and ride traversing the rugged gravel, dirt roads, and fire trails through the Hoosier National Forest in southern Indiana.

The 44th Annual Great Pumpkin Metric is a century ride on Sunday, October 4, 2026.

A community bicycle ride and festival event with 50 and 25 mile routes for cyclists of every skill level, followed by an after party with food, craft beer, and live music.

The Harvest 50 Gravel Race is a hard, fast, and exhilarating ride through the scenic countryside of Boone County, Indiana. Known for its top-notch organization, outstanding SAG stops, and a challenging yet rewarding course, this race is a favorite among gravel enthusiasts.

Challenging climbs and ridge views across Southern Indiana.

Join us for the Hilly Hundred Weekend, a three-day cycling event in October. Ride through the rolling hills of Indiana with us!

A 100-mile ride to celebrate the life and legacy of Marshall 'Major' Taylor, a world champion and the world's first African-American sports superstar.

A popular, long-running charitable cycling event hosted in the historic town square of Hope, Indiana, offering riders scenic, well-marked countryside routes across Bartholomew and Shelby counties.

Central Indiana's premier endurance cycling event featuring 25-Mile, 62-Mile (100km), and 100-Mile Century routes across signature greenways and open country roads.

Join us for the first ride of the season, the Teays River 100K in celebration of International Women’s Day: We Ride Together. This is a 100% paved route taking cyclists through farmlands and creek valleys in Warren, Fountain, and Tippecanoe counties along the Wabash River.

Mostly flat route held alongside the annual Blueberry Festival.

The Orchard Country Bicycle Tour offers three routes for riders to choose from, ranging from 16 to 63 miles, with the option to combine routes.

A celebration of cycling with a metric century, 40 mile, and 15 mile route, featuring beautiful country roads, challenging hills, and stunning lake views.

An annual scenic autumn cycling event touring northern Indiana's Pumpkinvine Nature Trail, MapleHeart Trail, and surrounding rural Amish country, offering both multi-use paved trail and road routes ranging from family rides to century options.

The Ride Across Indiana (RAIN) is a 100-mile ride that takes you through the rolling hills of Indiana. The ride starts in Indianapolis and takes you to the Ohio River, then back to the city.

A community experience with scenic routes, SAG stops, and proceeds supporting local community projects and nonprofit partners.

Two distance options, 25 and 50 miles, with a post-ride meal, music, and a complimentary beer.

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Come tour north-central Indiana on your bicycle! The ride covers gently rolling Indiana “hills” along lightly traveled roads and wooded creeks, between farmland, and through some of the small towns of Howard County, Indiana.

The Spring Cycle Weekend features various cycling tours of different distances, including a 100K and 48-mile tour, as well as shorter routes for families and casual riders.

Celebrate 2026 with a bicycling odyssey across the rolling hills of Dubois County. The annual Strassenfest Bicycle Ride offers FOUR routes of approx. (12, 20, 50, and 65 mi) to challenge riders of all experience levels.

Hosting a 5k Run/Walk and 10, 40, 60 and 100 mile bike rides to raise funds for Mental Health and Substance Abuse Treatment for those in Northwest Indiana that are in need and cannot afford the treatment

The Subaru CASA Cycling Challenge is an extreme cycling event that allows individuals and teams to test their endurance over a 24-hour period while raising funds for children in need.

A flat to gently rolling course that will take you past or through several north central Indiana landmarks.

A 100-km ride through the beautiful countryside of Indiana.

Northeast Indiana rural roads hosted by the 3RVS cycling club.

A 100-mile group ride through Fishers, Carmel, Zionsville, Brownsburg, Avon, Plainfield, Greencastle, Brazil, and Terre Haute, with 4 scheduled stops to refuel.

An annual charity cycling and running event held in Northwest Indiana benefiting healthy living and youth programs at the La Porte County Family YMCA, offering road cycling distances of 15, 25, 40, 60, and 100 miles.

A signature hill-climbing cycling tour around Lake Monroe organized by the Bloomington Bicycle Club, challenging riders to descend and climb out of up to 10 public DNR boat ramps around the reservoir.

Loops exploring the People Trail network and rural Bartholomew County roads.

An annual cycling event exploring the scenic Wabash River and Big Pine Creek watersheds across Tippecanoe, Fountain, and Warren counties with paved and gravel route options ranging from 16 to 101 miles.

A multi-day bicycle tour across Iowa, a festival on wheels, and a showcase of Iowa's hospitality.

The Stiff Ride is a 38-mile (44 miles with the Shueyville Loop) cycling event that takes place in Cedar Rapids, Iowa, and is known for its beer and party atmosphere.

Scenic autumn tour visiting the historic covered bridges and limestone ridge roads made famous across Madison County.

The ride now begins and ends from Council Grove High School (129 Hockaday Street), with different route choices available to riders on Saturday, Sunday, and Monday of Memorial Day weekend. Riders can choose to ride all three days or select one or two. There will be long and short routes and both gravel and paved road options–so bring all your bikes! E-bikes are welcome too on all of our routes.

Gravel event- family style! Cool temps and time to stretch the legs with a bicycle or without! Cycling and running in a small town atmosphere.

Hosted near Pittsburg State University, tracing quiet rural blacktop roads through southeast Kansas farmland.

Scenic late-summer ride through rolling oak-lined ridges, Kaw River bottomlands, and historic farm roads.

The iconic 4-day adventure in the Flint Hills.

Join the American Diabetes Association along with your friends, family, and colleagues as we ride in support of people living with diabetes.

Join our annual, one-day bicycle tour held on the last Sunday of September, which takes you through the orchards, forests, and wine country in and around Three Oaks, Michigan. Cyclists can choose from routes of 15, 25, 37, 50, 62, 75, or 100 miles, making it accessible for riders of all ages and skill levels.

The Assenmacher 100 is a recreational and social fun bicycle ride through the farmland and villages of mid-Michigan.

The Fall Bike Celebration Weekend offers a cycling experience unlike any other, featuring routes through the beautiful Southwest Michigan and the Amish-Indiana countryside, starting and finishing in the charming Vicksburg Historic Village.

A one day road bike ride throughout scenic Manistee and Benzie Counties.

A scenic cycling route across the MacArthur Bridge and around the perimeter and interior pathways of Belle Isle Park in the Detroit River, offering views of the Detroit and Windsor skylines. Without an active sanctioned event date or public registration, this course can be ridden anytime as an independent route.

Ride 204 miles from Lake Huron to Lake Michigan or 100 miles through the Manistee National Forest and back.

The Cornerstone 100 Lake Erie Bicycle Tour is the signature ride for Monroe County Cornerstone 100. The ride will take place, rain or shine, on September 12, 2026.

Fully supported ride over Labor Day weekend. Seven routes from Lansing to Mackinaw City.

The Dirty Donut is the first event of its kind to be held on dirt roads. This event has 6 different distances of 4, 16, 26, 42, 62, and 100 miles.

Cycle through West Michigan’s beautiful countryside and small towns. Explore the beauty of Michigan’s Lakeshore from scenic lakes to wooded trails.

Features the scenic and varied roads and landscapes of Kalamazoo County. All routes start in the picturesque village of Schoolcraft and travel on low-traffic rolling back roads, passing orchards, vineyards, farm fields, wetlands, and wooded hills.

The Lakeshore Harvest Ride glides you through the rolling countryside of Southwest Michigan. You can visit wineries, cider mills, family farms, orchards and art studios along the way.

2-day, 100 mile bicycle touring event from Chicago to New Buffalo, Michigan.

Pedal through Scenic Leelanau County, taking you on a one-day journey through the countryside with stunning Grand Traverse Bay and Lake Michigan views.

The event will take place at the Delta Hotels Kalamazoo Conference Center, where participants will enjoy the Vendor area, Dessert Social, and various Seminars.

Join us for a day of scenic bicycle touring over tree-lined roads or beautiful gravel trails. The routes wind through rural and recreation areas and vary enough to appeal to a broad range of cyclists.

Scenic, low traffic paved and gravel routes with post-ride meal provided by Albion Malleable Brewing Company.

Four distances. One destination. Choose your suffering — 22 to 100 miles of pure Michigan gravel adventure.

A self-supported 100-mile gravel bike endurance race featuring open farmland, pristine woods, secluded roads, and Ivan the Terrible. Designated as the MGRS (Michigan Gravel Race Series) Ultra course.

The Freebike is a cycling event that aims to get more kids on bikes, with a 100-mile century ride and other distances, followed by a post-ride block party in Minneapolis.

Heck of the North Productions will produce the highest quality adventure cycling events by providing beautiful and challenging courses, fostering passion for cycling culture via artistic and philanthropic endeavors and promoting strong community and business partnerships.

Le Grand du Nord is one of the most spectacular gravel courses in the United States. Beginning in downtown Grand Marais, riders will quickly leave the shores of Lake Superior as they head into the Sawtooth Range.

Scenic ride connecting the paved Root River State Trail network with rolling Driftless country backroads.

Ride Historic Route-66 Paved Backroads along meandering trout streams and beaver ponds and past relics of yesteryear.

Pedal the Cause is a charity bike ride that funds cancer research in St. Louis. 100% of participant-raised donations seed, speed and lead cutting-edge cancer research at Siteman Cancer Center & Siteman Kids at St. Louis Children’s Hospital.

A long-distance cycling route tracing scenic riverways, bottoms, and countryside roadways along regional river corridors. Without an active public registration or sanctioned organized event date, this course can be ridden anytime as an independent route.

Long-standing recreational bike ride with distances ranging from a short family ride to the 100-mile century. Low-trafficked roads, SAG support, well-stocked aid stations and post-ride lunch make for a great day of riding.

Spring tradition tackling rolling terrain, country backroads, and river valleys across the Ozarks.

Pedal through Nebraska’s breathtaking rolling plains and discover a side of the state you’ve never seen before.

America's longest rail-to-trail conversion crossing the Niobrara River valley and northern prairie.

A 5-day bicycle tour, pedaling through beautiful, scenic rural Nebraska every year in June.

Come GRIND across 120 miles, and ROLL over 8,600 ft of elevation gain on the fast and rugged red scoria roads that crosshatch the BADLANDS of western North Dakota.

The Maah Daah Hey 100 racecourse takes you across one of the most majestic single-track adventures in the world, with miles of uninterrupted trail through the heart of the rugged Badlands.

The 32nd Annual Maumee River Ride is back—and after last year’s incredible turnout, we’re rolling into 2026 with even more energy, more impact, and yes… more parking.

Join the Dayton Cycling Club for our annual cycling celebration of spring! Enjoy the beautiful quiet scenic roads of western Montgomery, southern Darke and Eastern Preble Counties.

The ABC Ride showcases the rolling hills and quaint villages of Summit, Medina and Wayne Counties. The routes of 25, 50, 62 and 100 miles provide scenic and challenging routes for families, as well as experienced cyclists.

Challenging rollers and climbs through Holmes County farmland and valleys.

Join us on June 13, 2026 for the ride of a lifetime. Dedicated riders like you are fueling life-changing breakthroughs for the nearly 1 million people living with multiple sclerosis in the US.

Bike MS: Oxford is a one-day cycling event with various route options for different skill levels, including a 100-mile route. The event features fully stocked rest stops, support and gear vehicles, and a finish line with local food available.

Ride from Bryan to Lockport Bridge, through Goll Woods, then on to Oxbow Lake in Defiance County—before returning to Bryan.

Choose from 15K, 30K, 60K, or go big with the 100K challenge. Along the way, you’ll find awesome rest stops stocked with snacks, drinks, and smiling volunteers cheering you on.

A 7-8 day cycling tour on paved, low-traffic roads that gives you the chance to discover the scenic and historic attractions along the OH Route 250 corridor, with different choices for distances and challenges.

The Hancock Horizontal Hundred is a 52nd annual century ride that takes place in Findlay, Ohio. The event features four routes of varying distances, including a 15-mile community ride, a 30-mile half-metric distance, a 62-mile metric century, and a 100-mile full century.

A relatively flat ride in north central Ohio with routes ranging from 11 to 62 miles.

Scenic continuous route entirely along the historic Ohio & Erie Canal Towpath.

The 53rd IRISH HILLS TOUR traverses the varied terrain of Northwestern Ohio and Southeastern Michigan. The choice of 10, 31 and 62 miles makes this the ideal tour for both the novice and the experienced rider.

A traditional club century ride (100 miles) with hills and possible wind, passing through Lorain and Ashland counties.

The Metroparks Bicycle Tour offers the opportunity to visit up to four scenic, wooded, Toledo Metroparks and view the historic Maumee River.

Team of 3-5 machines, stick together, cover ~120km in 8 hours.

Experience Ohio from end to end on one of the state’s most iconic cycling adventures. The Ohio to Erie Trail Adventure follows the renowned Ohio to Erie Trail from the banks of the Ohio River in Milford to the shores of Lake Erie in Cleveland.

Cleveland to Cincinnati, Ohio

Ride Weekend welcomes more than 7,500 Riders to central Ohio with routes ranging from 17 to 165 miles, including one- and two-day ride options.

Ride with the Lorain County Bicycle Club at their Red Flannel Metric Century event, taking place in The Lodge of New Russia Township on Sunday, November 2, 2025.

The in-person ride takes cyclists through the Village of Bluffton, Ohio, and the scenic surrounding countryside, with routes passing through Gilboa, Pandora, Ottawa, Rawson, and other nearby towns.