A Beginners Guide to Trail Running in Chicago

Chicago’s probably not the first place you think of when it comes to trail running. However, we’d argue that our city is actually quite the hidden gem when it comes to running adventures. 

The Windy City is full of trails worthy of short to long-distance runs – whether you’re on the Lakefront path, in the northwest side neighborhoods on The 606, or southwest of downtown on the rugged trails in Palos Hills.

We’ve put together this post as a resource to help you learn and soak up knowledge on what it takes to jump into trail running. 

From gear to consider to our top-picks for trails, check out our 5-step guide to trail running in and around the city:

Step 1: Get Your Gear

The gear you get can either make or break your running experience. Shoes that are too big, socks that don’t wick away moisture (check out Swiftwick to solve this problem), lack of water and food on the trail (consider carrying these in a Nathan running vest), are just some of the common mistakes new runners make when it comes to gear.

We recommend you check out a local gear shop (see the “Pro Tip” section below) to make sure you get gear that fits your body type and needs depending on the type of trail running you plan to embark on.

Some of the key pieces of gear you’ll need to consider before hitting the trail include:

• Shoes and socks
• Clothing (shorts, pants, shirt, etc.)
• Layers (jacket or pull-over for warmth)
• Running vest or fannie pack
• Hydration (hand-held bottle, hydration pack, etc.)
• Headlamp (or other light source)
• Food
• Sunscreen
• Extras: sun glasses, hat, headphones, cell phone

Pro Tip: Check out local running and outdoor stores in your area. Near downtown Chicago, stores like Fleet Feet, Arc’teryx in Wicker Park, and REI Co-op in Lincoln Park are a great start. Their employees are a great resource to bounce questions and ideas off of and can recommend the best gear, trails, and tips for your specific needs.

Step 2: Train Ahead of Time

Trail runners – no matter their skill level – are only as strong as their preparation and training ahead of a run. It’s super important to make sure you’re healthy pre-run so that you can continue to stay healthy during and after. Otherwise, you risk injury (or burnout).

• Strength Training – Focus on building core and leg strength. Planks, squats, lunges, and crunches are a good place to start. Frequent workouts well before and in-between trail running sessions can give your body the support it needs to stay healthy on-trail.

• Warm-Up – Consider a slow jog for 5 to 10 minutes at the start of your run to warm up “cold” muscles. Jumping into a full-pace run in your first mile (or even less) can lead to injuries if you’re not careful.

• Stretching – It’s extremely important to make sure your muscles are stretched, especially post-run. Because trails tend to be very dynamic (in incline and terrain), which can take a toll on your leg, back, shoulder and core muscles, your body will thank you for giving them a good stretch after your run. Key muscles to hit include: quads, calves, low back, hip flexors, hamstrings, and glutes. 

• Rest Days – If your body is telling you to rest: do it. Doing so can keep you healthy and preserve your energy so you can run even more. Some experts out there suggest running ~3-4 days per week (or less), with ~2 days of non-running workouts, and ~1 day of rest per week.

Also, on your first few runs, it might be helpful to mix some walking sections to your trip. Walking allows your body to get used to the feeling of running while taking short breaks to recover. Try intervals of 1 minute walking to 1 minute running, and build-up to a full-time run from there. 

Pro Tip: This Trail Runner training guide is a great place to start if you’re still feeling unsure of how to begin training for your trail running journey.

Step 3: Take Safety Precautions

Safety should be your #1 priority when it comes to running… and it comes in many forms:

Proper nutrition, making sure your gear fits the right way to avoid injury, and making sure you run with a buddy (or at the very least, communicate with a friend that you’re heading out), are just a few. 

Here are some of our go-to safety measures before and during runs:

As we continue to navigate the pandemic, it’s important to keep in mind the CDC guidelines when participating in outdoor sports like trail running. 

It’s recommended you wear a mask in areas you can’t keep social distance (6ft or more) between other runners and always take your temperature and check how you’re feeling before going out. As an additional safeguard, consider hitting the trail earlier in the morning or late in the evening to avoid crowded trailheads and routes.

Make sure to mark and understand your route well-ahead of your planned run. Check out online trial maps, read forums, or even call the park office ahead of time if you’re unsure about where a specific trailhead starts and ends.

When you set out on your run, stick to running only on the trail. You’ll also want to bring a light (a headlamp or your phone will work), tell at least one person where you’re going and when you plan to return, and make sure that you charge your phone to full-battery in case you get hurt or lost and need to navigate your way home via GPS.

There are tons of guides out there (like this one by REI Co-op and in Trail Runner Magazine) that go into great detail about how to set up a nutrition plan if you’re new (or want to get into) trail running.

At a minimum, make sure you’re very well hydrated (17–20 oz. before, 5–10 oz. every 15–20 minutes while running, and at least 17–20 oz within the first 30 minute after your run) and have a solid meal full of carbs and proteins before your run. 

For runs an hour or shorter, you can get away with a small snack and some water ahead of time. For longer runs, you’ll want a full meal or two before your trip. While on the trail, pack some energy chews or fresh fruit to supplement any feelings of fatigue. And within 1-2 hours of making it back home, help your body recover with lots of proteins like lean meats, eggs and fresh veggies.

Pro Tip: If food irritates your stomach on longer runs, try liquid nutrition. Sports drinks can give you the extra calories and energy boost you need to keep your body healthy when you’re going for long-distance.

Step 4: Choose Your Route

When it comes to trail running, there’s a trail for every runner. And luckily for Chicagoans who are looking to hit the dirt (or gravel or concrete) there are tons of options to choose from.

Are you looking for a rugged experience that requires you to jump over root-filled trails and zigzag in between trees? Do you want an urban trail experience near the heart of the city? Do you want to share the trail with local wildlife?

Here are some of our favorite, local trails:

• Paved: The 606 – A reclaimed, 2.7-mile rail trail on the Northwest side that features paved and rubber path options, a 5K and 8K route, and a few gravel spurs that zigzag through foliage.

• Gravel: Waterfall Glen Forest Preserve – 11-miles of crushed limestone gravel path that wind through the heavily-wooded, 2,503-acre Waterfall Glen Forest Preserve just 25 minutes southwest of Downtown Chicago.
• Dirt: Des Plaines River Trail – This off-road, gravel running (biking and hiking) trail spans 31 miles and winds through 12 Chicago forest preserves.
• Rugged: Palos Trail System – Arguably the hilliest section of trials in the city, Palos spans over 26 miles of looped trails just 30 minutes southwest of Downtown Chicago.

Pro Tip: Running and trail map apps – like AllTrails, Strava and Map My Run – are great tools for planning and tracking routes before, during, and after your runs. 

Step 5: Hit the Trail

There’s nothing quite like escaping into nature for a break from the city – especially when you’re able to blaze down trails on a run. 

As you embark on your trail running journey, we hope this guide has been helpful for you as you hit the best trails that the city has to offer.

Pro Tip: Use your time running to relax, better your state of mind, and make an effort to connect with nature. Try running without headphones for a chance, to take a break from stimulation and focus on the simplicity of putting one foot in front of the other.

 This post was written by Erica Zazo, a Chicago-based freelance outdoor + travel writer. Follow her adventures and connect online: @onecurioustrvlr on Instagram

  A big thank you goes out to Swiftwick for all of the images used.