Bike the Drive

From August 31 to September 6, 2026, Chicago’s iconic Lake Shore Drive transforms into a haven for cyclists of all ages and skill levels during the annual Bike the Drive event. This cherished tradition invites families, friends, and solo riders to experience the city’s stunning lakefront in a unique, car-free environment. The route stretches nearly 30 miles, offering breathtaking views of Lake Michigan and the Chicago skyline, with rest stops providing water and snacks to keep everyone refreshed. Whether you’re a seasoned cyclist or a first-timer, this event promises a memorable journey through the heart of the city.

The festivities kick off on Sunday, August 31, 2026, with the main event taking place from 5 AM to 9 AM. Participants can choose to ride the entire 30-mile loop or opt for shorter distances, making it accessible for all. After the ride, the celebration continues with a vibrant festival in Grant Park’s Butler Field, featuring live music, a beer garden, and activities for children. Local vendors and exhibitors will be on hand, offering a variety of goods and services to enhance your experience. Notably, Chis Cakes Pancakes will serve an all-you-can-eat breakfast, complete with fluffy pancakes and sausages, adding a delicious touch to the day’s events.

This event is perfect for families seeking a fun and active way to spend time together, pet owners looking for dog-friendly activities, couples desiring a scenic and romantic outing, and large groups aiming to create lasting memories. The sense of community and connection to nature make Bike the Drive a standout experience. To participate, registration is free but required online, and limited bike rentals are available at Speedway concession stands.

For those traveling from out of town, consider booking accommodations at the Fairmont Chicago, which offers special rates and amenities for event participants. Ready to make some lakeside memories? Start planning your stay now on Lake.com.