I’ve written briefly before about riding Bike the Drive, the Active Transportation Alliance’s chief fundraiser in Chicago. It’s almost always a glorious event, with DuSable Lake Shore Drive cleared of cars for four hours and stunning views of Lake Michigan as the sun rises.
The 2025 edition may have been one of the most glorious I’ve ridden, because there was no wind.
A lack of breeze going one direction or another along the flat Lake Shore Drive is almost unheard of. In 2024, we faced a fierce north wind, so we had to push all the way in one direction but were flying going back south. Usually we face at least a little breeze one way or the other.
But not this year. We had a beautiful day and could cruise freely in each direction.
That made my desire to do my usual two or more laps easier.
You can start Bike the Drive from its base in Grant Park and head either north to Bryn Mawr Avenue or south to 57th Street and the Museum of Science & Industry rest stop, or you can start on either end. I started at 57th Street again this year.
Wherever you start, you can ride for as long as Lake Shore Drive is open. That’s 15 miles each direction for a 30-mile loop. You have from 6:30 to 10:30 a.m. — and even then, you often can get extra time before the sweepers kick you off. Then you get wherever you need to go by riding the Lakefront Trail or on city streets.
After Bike the Drive was canceled in 2020 due to the pandemic and organizers weren’t ready to resume it over Memorial Day weekend 2021, the event was moved to Labor Day weekend, where it has stayed since.
The start time was shifted to 6:30 a.m. in 2022, after the dark first hour we experienced in 2021.
Finishing a quest this year
Bike the Drive fell on Aug. 31 this year. For me, that meant the ride was the conclusion of my quest to ride every day of August.
After amassing more than 1,300 miles in the month, my legs were tired. Still, I was pumped up as always for Bike the Drive, and I aimed to ride at least a metric century, meaning two laps of LSD and change.
Not only was there little to no wind — maybe a tiny south breeze toward the end — but it was sunny and the temperature quickly rose from the 60s into the 70s.
Starting from the South Side, I was even more fortunate when about 20 members of the Major Taylor Cycling Club of Chicago passed me, then allowed me to hang on to their wheels at the back of the train.
The Major Taylor train
With the Major Taylor club — which is quite a, um, major club based in the South Side and south Cook County suburbs — I had a peloton to ride with for 12 miles at just under 20 mph. And that was on a Lake Shore Drive that hadn’t filled up with other bicyclists yet — especially on the South Side, when Bike the Drive riders tend to go or come from the north first.
The Major Taylor train cruised nicely at an 18 or 19 mph pace. And it’s a disciplined group. They rode in two pacelines, and each rider had a partner to their side. A leader regularly called out, “Who’s your partner?” to make sure everyone maintained their side-by-side formation and looked out for each other.
Still, these weren’t hammering riders, either, and occasionally riders would break formation or zip around taking pictures and video.
The Major Taylor riders decided to hit the rest stop near Bryn Mawr before I wanted to, so I moved on to my second 15 miles with an eye on maintaining the moving average the club had kind of set for me.
Cruising solo
That moving average was shaping up to be 17 mph. That’s a fast day for me anymore, as I’m usually in the 15’s. Despite my riding every day in August, I did taper a little in the week leading up to Bike the Drive, knowing how tempting it is to fly on Lake Shore Drive.
Heading back south now, it was still easy to cruise as no wind had picked up at all. I did take the opportunity to simply enjoy the views: the sparkling lake on the left, the city buildings on the right.
Also, Bike the Drive has its own brand of people watching. All types join the event: serious cyclists, casual bicyclists on road or hybrid bikes, and families with children of all ages. I saw three girls with bright pink cruiser-style bikes. Some riders don costumes, though I seemed to see fewer of those this year. Some adorn their bikes with little dolls or decorations.
As we approached the center of the city again, the Gold Coast shined and the towering John Hancock building ahead drew closer. The lake views got even better passing the North Avenue and Oak Street beaches.
Then we rode past Navy Pier, the Ferris wheel in the distance, and traversed Lake Shore Drive’s famous S-curve (the latest incarnation, of course) back to Grant Park. I did finally stop quickly for fruit and snacks at the main rest stop behind Grant Park before carrying on.
It’s actually riding the S-curve north that provides a spectacular view of the lake, especially in the morning when the sun’s still rising. It’s a downhill toward the lake, then the final curve as the mesmerizing Gold Coast buildings emerge on the left.
Second lap
I rode back down the South Side of LSD and took a longer rest on 57th Street for picture-posting. Then I embarked on my second lap.
Still riding solo, the fatigued legs certainly weren’t happy. But it wasn’t too bad keeping up the 17 mph average. There was plenty of room on the drive to weave around other bicyclists if I needed to.
From the South Side, it was odd to see the exit signs to Interstate 55. Then I passed the mighty McCormick Place and Soldier Field, as I had with the Major Taylor club on the first lap.
I zipped past Grant Park to make the north run a nonstop 15-mile effort again. I got to Bryn Mawr and headed back south right away, stopping for snacks again only at the main rest stop at Grant Park.
About 9:30 now, Lake Shore Drive seemed to thin out on the south half. I had plenty of room to ride, though everyone seemed to relax and often disregard the advice, on digital construction signs, of “fast riders left,” “slow riders right,” so some dodging was still required.
Homestretch and the bonus
I got back to 57th Street OK with the 17 mph average intact after 60 miles — and it was only about 10 a.m., so Lake Shore Drive would still be open for at least a half hour. Shut up, legs! Let’s do a little more!
And my legs were really not happy now; I was feeling it in my hamstrings. But I still pushed to keep up the average, and I succeeded when I reached Grant Park again. Finally, Lake Shore Drive was starting to close — they blocked off the turn back south to get back to Hyde Park, so onto the Lakefront Trail I went.
I was actually looking forward to a slower ride on the trail, thinking it’d be crowded, as I felt overall plenty tired now. But it turned out the trail was pretty open, as it tends to be on the South Side vs. the North, and I could still ride at a pretty good pace.
By the time I got back to 57th, I had completed 74 miles with a 17.0 mph average, my Garmin said. Now I felt plenty satisfied, too.
As it often is when Bike the Drive ends, the sun was shining on a warm, gorgeous day. Lake Michigan looked a marvelous blue, and the buildings and skyline glistened. Soon the cars were back on Lake Shore Drive and the city got back to its day.
But with this Bike the Drive, what a way to finish August.
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