In September, the streets of Evanston and its surrounding areas come alive with the rhythmic hum of bicycle tires at the North Shore Century 2026, one of the Chicago region’s most popular cycling events. This year marks the 38th annual event and this ride offers an unparalleled journey through scenic neighborhoods, a glimpse of architectural marvels, tranquil tree-lined streets, and the invigorating breezes of Lake Michigan. The countryside unfurls its beauty, oscillating between the flat to rolling terrain on its route between the Chicago area and Wisconsin. Chosen as one of our Best Road Cycling Events in the Midwest, the event is produced by Evanston Bicycle Club.

The heart and soul of the event lies in its community, as club members showcase their famous culinary prowess by crafting homemade treats for the aid stations, and more than 150 volunteers come together to handle the complexities of the event, from registration logistics to real-time route support. The strict limit of 2400 participants offers an exclusive experience, and the event stands as a beacon of charity, with partner organizations raising nearly $100,000 annually.

There is a diverse range of routes at the North Shore Century tailored for both seasoned cyclists and those looking for a leisurely ride with 4 ride lengths starting with the century, the metric century (62 miles), the half Century, and finally the quarter century.

All rides commence and conclude at Dawes Park in Evanston, close to the Arrington Lakefront Lagoon at Church Street and Sheridan Road. With gates opening at 6 am, participants should take note of the recommended start times for each ride to ensure they finish before the rest stops close.

The Classic Century (100 Miles) starts before 8 am and the journey encompasses a vast loop to Pleasant Prairie in Wisconsin. Cyclists traverse through Glenview, Northbrook, Highland Park, and Lake Forest, primarily on residential streets. The latter part of the route promises coastal views, traveling from Lake Bluff back to Evanston and there are 5 aid stations on course.

The Metric Century (62 Miles) begins before 10 am, and in addition to the 50-mile route, this incorporates a scenic loop through western Lake Forest. There are two aid stations on this course.

The Half Century (50 Miles) starts before 11 am with a route that riders pedal to Lake Bluff to relish the views, traveling primarily via quiet residential streets and featuring two aid stations.

Finally, the Quarter Century (25 Miles) also starts before 11 am and features a route perfect for families and novices, showcasing the architectural beauty of Wilmette, Winnetka, Glencoe, and Kenilworth and has one aid station.

Cyclists can pedal with peace of mind, knowing that local bike shops are providing mechanical support at each stop and SAG vehicles are readily available along the way.