Best Chicagoland Trails to Explore This Winter, According to Nature Experts

By Allison Yates

“We can enjoy the riches of life in one of the world’s great metropolises and still connect ourselves to the natural world.”

— Jerry Sullivan in Hunting for Frogs on Elston

Where are the best trails to explore this winter?

The Chicagoland area has many, many opportunities to explore nature—even more than you’d expect from the country’s third largest city. As Jerry Sullivan’s quote from the book Hunting for Frogs on Elston proves, Chicago is one place you can enjoy both nature and an incredibly diverse city with food, arts and culture, and world-class architecture.

Sullivan’s book, along with Lindsay Welbers’ Chicago Transit Hikes, prove there are countless trails and forests to explore within and just outside of the city limits. You just have to know where to look.

One Chicagoan, nature educator, writer, and Read & Run Chicago speaker Bonnie Tawse, decided to inspire others to get outside in the winter. During the height of the pandemic, she asked her her wide network of “naturalists, nature educators, outdoor enthusiasts, trailfinding fiends, birders, volunteer stewards, urban foresters and more,” to share their recommendations of favorite nature spots in the area. She then shared these weekly on Facebook.

The criteria was broad: Trails should be less than one hour from the city or in the city itself, and recommenders should also provide suggestions for “a "treat" whether that's a donut or a cup of hot cocoa or bag of fried shrimp.”

“Having a recommendation of where to go can be quite helpful in getting us out of the house on the cold, dreary days in the dead of winter,” she wrote. Before you read on, let me set the record straight: Anything Bonnie suggests about nature or the city is always impactful. And knowing that, anything Bonnie’s network suggests must also be. These people rock. You’ll undoubtedly walk away more curious and more connected to Chicago—and learn so much along the way.

With her permission, I’ve condensed a few of the posts and copied them below so you can start to explore the best Chicagoland trails this winter.

Bonnie Tawse (right) with Erin Faulkner, co-steward of Bunker Hill Savanna, during Read & Run Chicago’s Hunting for Frogs on Elston-inspired trail run with Forest Preserves of Cook County in October 2022.

Country Lane Woods

Palos Preserve System
Suggestion from: Cheryl Main McGarry, the woman who taught Bonnie “how to spot a Nuthatch and a Brown Creeper (and how to tell the difference).”

Country Lane Woods is a great introduction to the “extraordinatry and extensive” Palos Preserve System. Take the beige trail or yellow trail from 95th Street east of Willow Springs Road/Flavin Road. You can get around five miles on the east yellow trail.

FOOD: After the trails, stop for ice cream (year round!) from Plush Horse.

Here’s the original post.

Cowles Bog Trail

Indiana Dunes National Park
Suggestion from: Drew Hart, Chicago Region Urban Forestry Specialist with the US Forest Service

Cowles Bog Trail is a 4.7-mile trail in Indiana Dunes National Park. Drew told Bonnie that it’s a “beautiful trail that meanders through several distinct and unique habitats within the Indiana Dunes. I try to explore Cowles Bog in each season to see the beautiful transformation that happens in this special landscape."

FOOD: After the trail, Drew says to eat at The Lemon Tree Grill in Chesterton, Indiana. He loves their Falafel Bowl and Jasmine Rice.

Bonnie challenges people to also do a quick search to see who Cowles Bog was named after and why this person was significant to the Indiana Dunes. Did you do it?

Here’s the original post.

Harms Woods: The Glenview Woods Trail

North Branch Trail
Suggestion from: Irene Flebbe, Assistant Director of the Trailside Museum of Natural History in River Forest

At Harms Woods, Irene recommends you head to the Glenview Woods Trail to take the organge trail from the Glenview Woods picnic/parking area. She continues with specific instructions: “You cross the bridge to the orange walking trail. There is an un-named trail that is almost directly west of the orange trail at the bridge (see photo in the comments) that trail takes you to some maginificent oak savanna, and eventually brings you back to the Orange trail, which you can then follow back north to where you parked your car. This way you see the best stuff on a 45 minute loop.”

FOOD: After the trail, eat burgers at Hackney's on Harms Road.

Here’s the original post.

Middlefork Savanna

Lake County Forest Preserves
Suggestion from: Rob Carmichael, Wildlife Discovery Center in Lake County

Just forty minutes from downtown Chicago, Middlefork Savanna has the highest quality oak savannah in the US and features many trails to walk [OR RUN!] and ride bikes. You can get at least around four miles.

FOOD: Gerhard’s in downtown Lake Forest. According to Rob this French bakery is the “coolest place ever!!!" and the owner is the “coolest lady on earth" and "100% Greek -- reminds me of the mother in My Big Fat Greek Wedding."

Here’s the original post.

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PS: Jerry Sullivan wrote for the Field & Street column for the Chicago Reader and after he passed away in 2000, some of the essays were compiled into the book Hunting for Frogs on Elston. (The book is now out of print but you can purchase the ebook from Univeristy of Chicago Press. Thanks to the generous Forest Preserves of Cook County funding for an October 2022 event inspired by this book, readers and runners received a free, gently used copy.) He taught urban dwellers about Native American history, birds, wildflowers, and as the title of the book reveals, even where to hunt for frogs on Elston Avenue.

PPS: Bonnie Tawse is too humble to admit she’s a nature expert, but she certainly is in my eyes. Having spent over two decades teaching Chicagoans about nature, she’s not only amassed an enormous amount of information about Midwest landscapes, but loves to generously share it with others and help connect everyday people to the magic of our natural environment. (She’s also written a cookie cookbook, among numerous other talents!)

I first met Bonnie while preparing for a Chicago Transit Hikes-inspired trail run on the Bloomingdale Trail in May 2022. She manages volunteers of the Bloomingdale Trail’s Environmental Sentinel citizen science project, which collects data to analyze whether the lake effect impacts the life cycle of serviceberry trees differently on the east and west ends of the trail, which conveniently runs ~2.75 miles east to west. (I believe that they do, based on my own observations!) Later, we worked together again for the Jerry Sullivan-inspired event in October 2022 with the Forest Preserves of Cook County. Sullivan was a geologist and nature educator that Bonnie had met early on in her nature education days.