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.

A 100-mile ride through scenic northeastern Illinois and southeast Wisconsin, with 4 different loops and SAG support.

The ride features a delightful route, starting at the Greater Rockton Centre on Main Street in Rockton, Illinois. Plenty of parking, restrooms and food are included to ensure you enjoy the beauty of this spring ride in the country.

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.

The Grand Illinois Bike Tour is a fully supported bike tour that includes overnight stays at hotels, ride navigation, SAG support, refreshment and water stops, and more. The tour explores the Metro East area in SW Illinois, including scenic views of the Mississippi River.

The 52nd Annual “No Baloney Bicycle Ride” on Saturday, August 22, 2026 at a new location! Scenic Peoria County routes, catered lunch, well-stocked food at rest stops, SAG, and Trek Bike Store Technician at venue.

The North Shore Century is a 100-mile ride that takes place on the scenic roads of the North Shore of Lake Michigan. The ride starts and finishes at Fort Sheridan in Lake Forest, Illinois.

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.

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

Cycle across the entire state of Illinois in one day! The RAIL South ride will be approximately 165 miles and travel from St. Louis, MO to Vincennes, IN.

The River to Rail Ride bicycling event is back this year on September 12, 2026. Hosted by the Vermilion County Conservation District, the event will have four routes starting at Kennekuk County Park with all proceeds benefiting the continued development of the Kickapoo Rail Trail.

Experience the Mother Road on Two Wheels 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-mile bike ride around the beautiful forest preserve, with multiple breaks and a community atmosphere.

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 a smooth, safe, and enjoyable ride from start to finish.

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

The B&O Bicycle Tour is a 100-mile ride on the B&O Trail.

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

A weekend built around bikes, trails, community, and raising funds so we can continue to build this place together.

The Buffalo 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.

A 10-day, 1,000-mile cycling event across Indiana, with daily departures and routes.

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

A 100-mile bike ride through Wabash County, with support stops and a free commemorative shirt.

Dave, Rich, and Friends are embarking on a 100-mile ride on the Indiana Cardinal Greenway Rail Trail on September 19 to raise funds for Dayspring.

Riders compete in this unique self-supported bicycle race 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, offering three distances (100M, 100K, & 44M) through picturesque landscapes and historic terrain.

The Five Covered Bridges Century is a 100-mile ride that takes you through the rolling hills and scenic countryside of Indiana, featuring five historic covered bridges.

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

The original gravel road race in Indiana, with a 100k course featuring a mix of gravel and pavement with challenging climbs.

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.

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 century ride to celebrate the life and indomitable spirit of Marshall 'Major' Taylor, an Indianapolis native, a world champion, and the world's first African-American sports superstar.

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.

A 100-mile ride designed for those 'warming-up' for the bicycling season, with routes for 16, 32, and 63 miles, and assistance provided for riders with breakdowns.

A celebration of cycling and the growing cycling-scene in Putnam County, including beautiful country roads, challenging hills, stunning lake views, and murals galore!

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.

A one-day one-way ride across Indiana in its 37th year, with a 168-mile course from Terre Haute to Richmond, and a 205-mile extended route.

Cycling Around Kosciusko County Lakes   Since 2011, the Rotary Tour des Lakes has brought together cyclists, families, volunteers, nonprofits, and community organizations for one of Northern Indiana’s most scenic summer traditions.

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

Come tour north-central Indiana on your bicycle! Over 40 years and still rolling, 2027 marks the 42nd annual Sizzling ride! Setting out from Kokomo, multiple bike event routes (approximately 40, 60 & 80 mile routes) are available including a 100-mile century bicycle tour.

Cycle your way into Spring with various tour options, including a 100K Metric Century.

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.

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.

Event proceeds benefit the Whitewater Canal Trail and the Cincinnati Cycle Club Philanthropy Foundation.

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

A 100-mile cycling event to benefit Wabash Valley Race For The Cure, with a group ride, police escorts, and 4 scheduled stops to refuel.

Tour de La Porte is more than a walking, running, and cycling event—it’s a powerful weekend of movement with purpose.

This can be a beautiful, pleasant bike ride around Lake Monroe, or, by a series of poor decisions, you can visit each of the 10 boat ramps to create a very challenging ride.

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 mass-participation cycling event combining Hawkeye pride with fitness and excellence, featuring 25, 60, and 100-mile distance options starting and finishing in the Iowa City / North Liberty area.

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

A two-day cycling adventure through the glacier-carved Mississippi River Valley.

Iconic eight-day cross-state tour across Kansas featuring optional century and metric stages.

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.

The World’s premier Gravel event in the Flint Hills of Kansas.

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.

A recreational and social fun bicycle ride through the farmland and villages of mid-Michigan.

BFK's Fall Bike Celebration offers a cycling experience unlike any other, featuring routes through the beautiful Southwest Michigan and the Amish-Indiana countryside, with a delicious meal at the finish.

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

Race the setting sun as you cross the mighty Mitten on bicycle – from coast to stunning freshwater coast.

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

Michigan's annual, fully supported, epic end-of-summer bicycle camping tour.

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.

Experience the stunning landscapes of the West Michigan Lakeshore with the 51st Annual Holland 100 bike tour! This exciting event offers cyclists of all levels the chance to explore the Lakeshore’s charming towns and its beautiful surroundings from the breathtaking lakes to picturesque countryside routes.

Features the scenic and varied roads and landscapes of Kalamazoo County. All routes start in the picturesque village of Schoolcraft in southern Kalamazoo County.

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

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

Pedal through Scenic Leelanau County, enjoy stunning Grand Traverse Bay and Lake Michigan views, and savor a picnic provided by the VI Grill.

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.

Join us for our 40th Anniversary Tour! A one-day recreational bicycle tour with 4 scenic routes that follow the shoreline of the legendary Torch Lake.

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

The Savage Century gravel course is simply amazing. Open farmland, pristine woods and secluded roads are just a few of the sights you will see on this 100-mile gravel adventure.

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.

One of the most spectacular gravel courses in the United States, with 6000 ft of climbing and a decidedly remote feel.

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

Big BAM is Missouri’s Annual Bike Ride across the State of Missouri held twice annually on the KATY Trail with additional road rides based upon special events like this year’s 100th Anniversary of Route-66.

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.

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

A 5-day bicycle tour through scenic rural Nebraska, with daily mileage ranging from 45-70 miles.

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 a 100K (62 miles) cycling event hosted by Toledo Area Bicyclists (TAB) to raise funds for bikes for kids.

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.

Feel the extraordinary support and excitement throughout your journey as we come together to reach our goal — a world free of MS.

Bike MS: Oxford is a 25, 50, 75-mile ride with fully stocked rest stops, supplied with hydration and nutritious snacks, every 8 to 18 miles.

Bike to the Bridge is an annual fundraiser benefiting Cancer Assistance of Williams County, whose mission is to bridge the need for local cancer patients.

Choose from 15K, 30K, 60K, or go big with the 100K challenge. A shotgun start at 8 AM—let’s roll! Along the way, you’ll find awesome rest stops stocked with snacks, drinks, and smiling volunteers cheering you on.

A 38-mile cycling event through wine country.

The Hancock Horizontal Hundred is a cycling event that takes place in Findlay, Ohio, with routes ranging from 15 to 100 miles. The event features quiet Hancock County roads and a variety of routes for different skill levels.

A beautiful, relatively flat ride on quiet farm roads near Waldo, Ohio.

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.

Jerry's Jeromesville Journey has been a traditional club century ride (100 miles) for over 30 years. The northern half (in Lorain County) is mostly flat. The terrain starts to give way to some rollers as you get into Ashland County, and a tough one comes just outside Hayesville. The ride home gets easier (if that's possible in a century) as you get farther north. The route loses altitude as you make your way toward Oberlin.

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

Cleveland to Cincinnati, Ohio

The 52nd annual Red Flannel Metric Century, half metric, and 25 miles Flatlander Routes.

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.

A fun, healthy, and family-oriented day of cycling for people of all ages through picturesque areas of the Northern Miami Valley.

Join us for the Annual Young’s Charity Bike Tour. The two-day main ride mile options are 51 miles, 82 miles or (for those who are really ambitious) a 100 mile option.