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Celebrate Chicago’s best bicycling season with Ride Illinois’ family-friendly September event series

Nine of the 15 rides scheduled across Illinois are taking place in Chicagoland, including two within the city of Chicago.

Parents riding with their kids on the Pullman Labor Ride on the South Side of Chicago and northwest Indiana. Photo: Eric Allix Rogers

This post is sponsored by The Bike Lane.

While Labor Day Weekend, punctuated by Bike the Drive, is the unofficial end of summer in our city, I'd argue that it's the start of the peak Chicagoland cycling season.

Sure, many Chicago area residents, including a large percentage of sustainable transportation advocates (myself included), keep pedaling year-road. After all, if you have fenders and dress for the weather, even during the winter biking is still one of the cheapest, most efficient, and fun ways to get around our city.

But arguably from now until the cold November rain hits is the easiest, most user-friendly time of year to cycle here. On most days you can bike in your favorite clothing without worrying about showing up sweaty, but there's usually no need to put on rain gear or bundle up.

So tomorrow is a great time for the statewide bike advocacy organization Ride Illinois to roll out its 2023 Let’s Ride, Illinois festival, "a celebration of the freedom and benefits that riding a bike offers." The series takes place from September 8 through 17 with free, ten-miles-or-fewer, generally kid-friendly group rides scheduled across the Prairie State.

"This event encourages adults and children from Rockford to Cairo (and all places in between) to enjoy a casual bike ride with their neighbors and to experience their community by bike," the group stated.

Unsurprisingly, since roughly three quarters of Illinoisans live in Chicagoland, nine of the 15 scheduled rides are taking place here, including two within the city of Chicago. Here's a quick rundown of the local events. Click on the pins in the interactive map above for full details.

Locations of the scheduled Chicagoland rides. Image: Ride Illinois

Libertyville Community Bike Ride Sunday 9/10, 9 a.m. at Adler Memorial Park, 1500 N. Milwaukee Ave., Libertyville. "2.5 mile out-and-back and five-mile loop are planned, but you can keep riding when we're done. Mixed-surface bike ride on paved and crushed limestone trails."

Back to School Bike Bonanza Tuesday 9/12, 3 p.m. at Lombard Farmer's Market, 20 St Charles Rd., Lombard. "Kids will learn basic bike safety and get a bike check from Retro Glow Cycles. Parents will receive a packet with a passport and map that will guide your family on a small 2-mile loop. Along the way, you will visit various fun stops to receive a stamp for your passport."

Brewery Ride to Old Irving Brewing Thursday 9/14, 6 p.m. at Earth Rider Cycling, 1873 N Milwaukee Ave., Chicago. "Join other beer-loving cyclists [obviously this is a Let's Ride event that's geared towards adults] on a casual bicycle group ride from Earth Rider Cycling in Bucktown to one of the 60+ micro breweries in the Chicago area. This week we will ride to Old Irving Brewing at 4419 W. Montrose Ave."

Thursday 11 X 11 Thursday 9/14, 6 p.m. at Lake Bluff Metra Train Station, 600 Sheridan Rd., Lake Bluff. "This is a 'no drop' 11 mile ride at an 11 mile per hour pace. We will ride from the Metra Train Station in Lake Bluff and ride on a mix of paved trails and back streets through Lake Bluff and Lake Forest."

OktoberFest Family Day Bike Ride Saturday 9/16, 10:30 a.m. at Towne Square, Smith and Slade streets, Palatine. "Bike Palatine Club leads 2 free community rides at a casual pace either 8- or 15-mile routes around Palatine as part of the Palatine Rotary OktoberFest Family Day celebration."

Famous Women of Wheaton History Bike Tour Saturday 9/16, 2 p.m. at Wheaton Public Library, west side, 225 N. Cross St., Wheaton. "Ride and learn about the great women in Wheaton history with Bob Goldsborough, longtime Wheaton resident, amateur historian, and current writer for the Chicago Tribune."

Let’s Ride Illinois, Saint Charles Saturday 9/16, 2 p.m. at Norton Creek Elementary School, 2033 Smith Rd., West Chicago. "This is a short loop for families and beginner cyclists. It starts from the parking lot of Norton Creek School, meanders through Hunter's Fields and Fox Chase subdivisions, then circles north through historic Wayne village."

• Lakefront Trail Bike Ride Saturday 9/16, 5 p.m. at the Lakefront Trail north trailhead, 900 W. Ardmore Ave., Chicago. "This scenic trail [segment] is about 9.4 miles. You'll start on the North Side and ride along the trail until you reach the Field Museum."

Bicycles, Ice Cream and Fun Ride Sunday 9/24, 2 p.m. at Fishel Park, 1036 Grove St., Downers Grove. "A short ride on low-stress Downers Grove streets. Destination: Every Day's A Sundae."

Are you hosting a low stakes, low-mileage bike event this month that you'd like to include in Let's Ride, Illinois? Click here to register your event. Read more about how to plan and publicize the ride on the 2023 Let's Ride, Illinois website.

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