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Sometimes, it can be hard for anyone who lives and works in the city to find great running trails. Chicago, however, is surrounded by great trail runs, including the Palos/Sag Valley Trail System, which made Runner’s World list of 25 best trail runs in America. The magazine says that the Chicago area itself is so nice for running because of its miles of flat, crushed gravel rail trails.

The only problem, then, becomes which trail to choose. Once Google maps launched a decade ago, locating trails became easier, and a new generation of apps has made the area’s best running spots even more accessible.

Below are 21 great resources for trail runners in Chicagoland, which includes several of those apps plus audiobooks, running sites, blogs, forums and local running clubs.




Maplets is an iOS and Android app with more than 10,000 continually updated offline maps for the US and the globe. Use the it for easy access to offline maps from Paris to Yosemite. The maps track your precise locations, and because they’re downloadable you can use the maps even when you don’t have service.



For anyone who travels frequently, Localeikki crowdsources locally recommended and publicly accessible recreation locations. When you’re looking for a place to run while on the road, just input your location to get recommendations. You’ll get pictures and a list of amenities, as well, including bathrooms, drinking water and parking. If it’s a group run you’re looking to join, Localeikki includes regularly scheduled runs in its database.



This iOS and Android app isn’t new — Runkeeper launched in 2008 to get runners to stick with their routines, and it now has some 45 million users across the globe. The app shows progression made (in terms of fitness, distances run, and so on), and it makes scheduling workouts and runs simple.



You can track your runs on your iPhone, Android or GPS device with this Strava, which will analyze your performance and keep up with your personal records. It’s the app’s social experience, though, that will kick your competitive nature into high gear. When you compare times and distances with friends, it not only provides added motivation, but also camaraderie even when you’re running alone.


Map My Run

The creators of MapMyFitness developed this iPhone, Android and Blackberry app specifically for runners. Whether it’s tracking your elevation, duration, pace or distance, you can record and analyze every aspect of your run. Then, chart your route on the interactive map and share your results with friends on Facebook or Twitter (but no boasting).




Many distance runners find they need extra stimulation for their minds while on a long run, and sometimes a playlist just doesn’t keep the mind engaged. Some runners have found audiobooks to be the perfect companions while on the trail. Two or three long runs might be enough to get through a single book.


The Age of Wonder: How the Romantic Generation Discovered the Beauty and Terror of Science

As Books@Works’ Cecily Hill, a runner who prefers books to podcasts or music, wrote in a recent blog post:

“I listen to audiobooks while running, and their texture bleeds into my experience on the trail or the road in a way podcasts and music fail to. I spent an entire summer listening to Richard Holmes’s The Age of Wonder: How the Romantic Generation Discovered the Beauty and Terror of Science; I remember it as blue and green and wondrous, and, once, during a lightning storm, terrifying.”


Trailhead — The Dirt on All Things Trail Running

Veteran trail runner Lisa Jhung told RootsRated that she wrote her new book, Trailhead — The Dirt on All Things Trail Running, so people would stop being intimidated by trail running.

A co-founder at Adventure Sports magazine, Jhung added: “People think ultra trail running and trail running are the same thing, and I wanted to make it clear that they’re not. Anyone can enjoy running on a trail. I wanted to break down the intimidation factor and demystify it. I also wanted to write something that was fun and visual and engaging and creative.”


Fat Man to Green Man: From Unfit to Ultramarathon

Ira Rainey, who calls himself a “desperately average runner, mildly entertaining writer, and highly enthusiastic beer-drinker,” is also the author of the book Fat Man to Green Man: From Unfit to Ultramarathon. If you’re looking for something to listen to while you’re trail running, this humorous account of how “an overweight and unfit slacker who felt a bit sorry for himself because he had sore feet” took on the challenge of becoming an ultramarathon runner might be just the thing.


A Short History of Nearly Everything

The American bestselling author of humorous books on travel, Bill Bryson is also the author of A Short History of Nearly Everything, a breezy overview of science from its inception. A number of runners have cited Bryson’s Short History as being perfect for long runs.



Websites, Blogs and Forums

Trail Runner Nation

A community of like-minded people, Trail Runner Nation defines itself as a “share point for information” rather than a website. Using social media and podcasts, trail runners connect and share advice on pacing, race nutrition, running shoes and other gear.

Created by Kyle Redelinghuys from Johannesburg, South Africa, this blog promotes “the beauty that comes with trail running.” Redelinghuys’ own surroundings do a good job of promoting that beauty, as well. Here, you’ll find pictures, routes and insights alongside descriptions of hikes and running trails. There are also interviews with athletes such as Johardt Van Heerden, who won the South African Trail Championships earlier this year.


My Chicago Athlete

This Chicago-centric magazine is written by runners for runners. You’ll find reports on speaking appearances by top athletes in the area, interviews with triathletes such as Lionel Sanders, and when you can next join an elite runner on a fun run.


The /r/Running Subreddit

The /r/running subreddit is a forum where you can find discussions about everything running. There’s a thread about using running as a stress-related coping mechanism, and one about the steady pace of those who run 40plus miles a week. There’s even a story-turn-discussion when, on a rural run, a Canadian runner paused to round up a herd of cows who had escaped their pasture through a hole in the fence.


A Trail Runner’s Blog

Technology entrepreneur Scott Dunlap writes that he “took up trail running and triathloning in 2001 to get off the work treadmill and see a bit more of the outdoors.” He adds that he also loves to eat, and the running helps “justify those extra helpings.” His blog is about all types of running (trail, ultra and triathlons). For a good overview, read his look back at 2014 in a post called A Year of Gratitude.



Running Clubs in Chicagoland


This Chicago-area group of ultra and trail runners has a Facebook club, and the Strava feed on the website displays the club’s latest runs. You don’t have to be an experienced runner to join; the group consists of those who want to try ultra and trail running. You do, however, have to be committed to crew or pace another member and volunteer at one ultra every year.


Alpine Runners

With some 600 members, this running club in Lake Zurich claims it’s the largest in the Chicagoland area. The most popular run is bright and early every Saturday morning, with mileage varying from 4 miles around the lake to 22 miles just before the Chicago marathon. You can also check out the 5.5-mile training run on Tuesdays at 6:30 p.m., which starts at Paulus Park. There is also a Sunday morning marathon training run at Busse Woods at 7 a.m.


Fox River Trail Runners

The Fox River Trail Runners club was founded in 1995 to promote running and currently claims more than 600 members from all over the western suburbs of Chicago. In addition to supporting local youth running groups, it provides group and training fun runs and hosts three races a year: the Great Western Half Marathon, the Summer Sunset 5K, and the four-mile Fox and Turkey.


Frontrunners Frontwalkers

This club meets twice a week, on Tuesdays and Saturdays, for a run/walk along Chicago’s lakefront. With approximately 150 members, the club is for the LGBT community and friends. After each run, the group gathers at a nearby restaurant.


Evanston Running

Competitive, recreational and new runners looking to get fit will find partners to run and train with in the Evanston Running Club, where the motto is “nobody runs alone.” There are 400 members who regularly meet for group runs, with at least one run almost every day during the summer. These include early morning lakefront runs as well as some at Lighthouse Beach Park.


Libertyville Running

One of Chicagoland’s newest running clubs was formed in 2014 and includes runners who are experienced, training for a race or just there to have a casual run with friends. Membership is free, and the summer schedule includes weekly speed workouts as well as short fun runs (2-8 miles) and longer run (3-20 miles), both of which start at Cook Memorial Park.


Lisle Windrunners

The Lisle Windrunners Club celebrates its 30th birthday this year. There are currently more than 50 members, ranging in age from mid-20s to older than 80. Group training runs during through November are held three times a week, with the Saturday morning 5–10 mile run at Herrick Lake on fine grain limestone trails.


Images by:
Robin McConnell
David Mark
Jori Samonen

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