The Chainlink

Five Classic Chicagoland Bike Adventures

By Brett Ratner

I don't think I'm alone in the opinion that this spring kinda sucked, weather-wise. Happily, if the forecasts are correct, we are finally in for some premium cycling weather this weekend.

So, we thought it fitting to kick things off right by assembling some of our favorite day trips. We tried to mix it up in hopes to provide a little something for most interests (and mileage goals).

Needless to say, these are just a few of the hundreds of possible trips in the area. So we invite you to share your favorite day trips, overnight trips, restaurants, and riding destinations in the comments below!

North Branch Trail to Chicago Botanic Garden

This one is kinda obvious, but it's definitely a classic and worth mention. Plus it's great for the navigationally-challenged (such as myself).

How to Get There: Pick up the North Branch Trail at the intersection of Milwaukee and Devon in Chicago, and follow the trail north until it drops you off at the southern end of the Chicago Botanic Garden. From there, ride through the park to the visitor's center. Park your bike, grab some food, walk around and enjoy the spectacular scenery. To head back to the city, simply back track on the trail, or take the bike path that follows Lake Cook Road east to pick up the Green Bay Trail, Sheridan Road, or Green Bay Road and head south. Depending on where you're coming from, figure on 40-55 miles round trip.

Tips: Bring a bike lock (and maybe walking shoes) so you can explore the gardens. If the weather is nice, be prepared for lots of bike and pedestrian traffic in some spots. And grab some food at Superdawg when you get back.

Short on Time?: Throw your bikes in the car, park at the North Branch trail head, ride north as long as you like, turn around, and ride back to your car or skip the car and ride to the recently reopened Northerly Island with bike paths through the park, concessions, and a beach to enjoy the sun.

Mountain Biking at Palos

One doesn't generally equate the Chicago-area with mountain biking, but we actually have a really nice trail system a short drive from the city.

How to Get There: It's certainly possible to ride your bike to the Palos Trail System, or take a train most of the way (like Marcelo did). But for convenience, this one might be best by car, since that will afford you the most time to enjoy riding on dirt.

Regardless, for most riders it will require a proper mountain bike, plenty of water (CamelBaks are popular), some snacks, a helmet, eye protection (from wayward branches), and the expectation that trail riding will be more difficult than street riding (and you might fall occasionally). Once you set those expectations, be prepared to have an amazing amount of fun, and a changed perspective on what Chicago-area cycling has to offer. Depending on your goals, you can do a short, 30-minute loop, or be out there all day. 

Tips: Visit for information on all Chicago-area trails, including maps, trail etiquette, directions, parking, volunteering, and trail conditions. Only ride on trails when they are marked as dry. If possible, try to ride with an experienced mountain biker your first few times out. Definitely print out a trail map to take with you. Also, be aware that the trails are two-way. As such, lots of mountain bikers recommend ringing a bell or calling it out when approaching blind corners.

Not Ready for Mountain Biking?: Palos has a nice network of crushed limestone and gravel double track trails, suitable for most hybrids, touring bikes, cyclocross bikes, etc. You can also check out nearby Waterfall Glen.

Des Plaines River Trail

Since it takes a while to dry out in the spring, it might be premature to mention "DPRT." But once it's dry, the Des Plaines River Trail is a local favorite, and for good reason. Imagine gliding along in a quiet, serene forest beside a calm, gentle river.

How to Get There: Much of the trail south of Northwest Highway is dirt (and prone to mud). North of Northwest Highway, the trail is mostly crushed limestone. As such, this time of year, your best bet is to pick up the trail in the city of Des Plaines (where the Des Plaines River crosses Northwest Highway) and head north.

Depending on your level of ambition, you can ride a few miles up and turn around, or take it all the way to the Wisconsin border.

DPRT caters to riders of all ability levels and bike types (though skinny tire road bikes aren't ideal), and if you're looking for a little extra challenge, there are occasional single track offshoots that let you get you get your mountain bike fix on.

Tips: A good day trip is taking the trail up to Libertyville, and then pedaling over to Mickey Finn's for lunch. Or, head east on the North Shore Bike Path into Lake Bluff and take the Robert McClory Bike Path back south to Highland Park, where you can pick up the Green Bay Trail.

Trail Still Wet?: If you're riding on DPRT and it's mushy in spots, turn around, hop on Busse Highway and head back toward the city via Park Ridge. Then continue on Northwest Highway and grab lunch and/or drinks in Edison Park, which has lots of bars and restaurants.  

Barrington Hills

This is an amazing area we recently enjoyed for the first time. While we did have an unpleasant run-in with a couple of cyclists, it was otherwise a stellar experience. 

To recap, Barrington Hills offers a lot of rolling terrain, scenic horse farms, natural prairie restorations, and smooth roads. It's possibly some of the best road cycling in the Chicago area.

How to Get There: To access these fine roads, take your bike on Metra's Northwest Line and get off at the Barrington stop. Some suggested routes can be found here and here. And when you get hungry and thirsty, you can swing by The Onion Pub & Brewery for refreshments.

Tips: This area has a history of friction between cyclists and motorists, so obey all traffic laws and watch for signs instructing you to ride single file. Be courteous to car traffic and try to represent cyclists in a positive light. 

Want to Stay Closer to the City?: Sheridan Road up to Highland Park and back is always a good choice to get your road bike fix, and have you back in time for lunch.

Photo by Chainlinker Rob Nathan

Illinois Prairie Path to Two Brothers Roundhouse

A perennially-popular ride among Chainlink members is the trek to Two Brothers Roundhouse in Aurora.

How to Get There: Pick up the Illinois Prairie Path in the town on Maywood, and ride it until it literally delivers you to the Roundhouse's front door. Just be careful to go south when the Prairie Path splits near Wheaton. When you are done eating and/or tasting Two Brothers beer, take Metra's BNSF Line back to the city, which is literally across the parking lot from the Roundhouse. You honestly couldn't ask for more convenience.

Tips: It's crushed limestone the whole way, so bikes with slightly fatter tires work better, and the trail can be wet and sloppy if there's recently been rain. On the plus side, the trail passes through several towns, offering several opportunities for coffee stops.

Want Less Pedaling and More Sipping?: We love the Temperance Tap Room in Evanston, easily accessible from the North Channel Trail. If that's too far, Half Acre Tap Room is a can't lose choice, too!

About the author:

Brett Ratner ( has been a professional journalist for more than 25 years. He has contributed to dozens of publications, including The Chicago TribuneThe Nashville TennesseanThe Nashville SceneGuitar Player, and Musician. Brett began commuting by bike in 2005. Shortly thereafter, his interest in cycling expanded to century rides, bike camping, and trail riding. The competition bug bit in 2012 and nowadays he occasionally races cyclocross, track, mountain bikes, criteriums, and gravel for The Bonebell.


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Comment by dav on June 6, 2016 at 8:41pm

Thank you for this article. It gave me a bunch of summer ideas.

Comment by Jonathan Quist on April 21, 2016 at 3:00pm
The Fox River Grove Metra station gets even closer to Barrington Hills.
"Friction" between cyclists and motorists is one thing, but some cyclists have given local residents legitimate reasons for anger.
(Hint: the Algonquin Rd Elementary School in Fox River Grove and adjacent to Barrington Hills has a pair of porta potties available year round. Hiding behind a resident's stone wall a mile from there and defecating in view of their security cameras does not make the village bike friendly.)
Comment by Jared on April 14, 2016 at 4:39pm

Another good trip is Metra to Crystal Lake then south via the Fox River Trail to Aurora, though Metra is also available in Elgin and Geneva.  One of the more scenic long distance trails in the area with many diversions along the way.

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