The Complete Chicago Trail Running Guide 2025

Discover the best Chicago trail running routes, nearby forest preserves, races, clubs, and training tips to get off the lakefront path and into nature.

If you only know Chicago running as the Lakefront Trail and the marathon, you’re missing the best part: how much dirt we actually have within an hour of the city.

Trail running in Chicago is a bit of a magic trick. You hop off the Red Line or out of your west loop condo, drive 20 to 40 minutes, and suddenly you’re dodging roots, splashing through creeks, and hearing more woodpeckers than sirens. This guide walks you through exactly where to go, how to train, and how to plug into the local trail scene, whether you’re sneaking in weekday miles or planning a race weekend around the forest preserves.

Use this as your complete Chicago trail running guide for 2025, especially if you’re:

• A city runner who’s sick of concrete and wants softer surfaces
• A visiting runner here for a race who wants a “real” trail day
• A marathoner dabbling in trail and ultra training
• Someone who just wants a quiet, green place to run without getting lost

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1. Trail running in Chicago: what it’s actually like

Chicago trail running is defined by three things: forest preserves, crushed limestone, and surprise hills.

You won’t find long alpine climbs here. What you do get is endless networks of dirt and limestone paths that are perfect for building volume without pounding your legs. A lot of people start on the wide, groomed Des Plaines River Trail or Salt Creek Trail, then work up to the more technical singletrack at places like Palos.

Typical Chicago trail running features:

• Soft limestone “bike paths” that are great for long runs and marathon training
• Singletrack loops with roots, rocks, and short punchy climbs
• Loop systems inside forest preserves that are safe, mapped, and usually well marked
• Real seasons: frozen, rutted ground in winter, mud in spring, humid shade in summer, and perfect leaf-covered paths in fall

If you’re training for a trail ultra, you can absolutely do it here. Palos, Swallow Cliff, and some of the longer forest preserve systems will give you enough elevation and technical practice if you string them together smartly.

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2. The best trail running routes in and around Chicago

I’ll break this into three tiers: “intro to dirt,” “real trails close to the city,” and “destination long run” spots. All of these are places Chicago runners actually use every week.

2.1 Palos / Sag Valley – the crown jewel

If you ask a local “where should I trail run in Chicago,” they’ll say Palos before you finish the sentence.

Where it is Southwest of the city around Palos Park and Palos Hills, inside the Cook County Forest Preserves. The two main systems are the Palos Trail System and Sag Valley.

Why runners love it It’s the most “real” trail we have: rolling hills, proper singletrack, roots, rocks, and enough elevation to actually matter. This is where most Chicago ultrarunners train.

Classic starting points

• Bullfrog Lake lot (Willow Springs Rd, near 95th St) easy access to multiple loops
• Wolf Road Woods (W 95th St & Wolf Rd) access to yellow, green, and brown loops
• Country Lane Woods (La Grange Rd, south of Rt 20) good for longer combinations

What it’s like Mostly dirt singletrack and some doubletrack. Short climbs that stack up over time. A mix of dense woods, small lakes, and some prairies. Cell service is spotty in a few low pockets but usually workable.

Insider tips

• In spring, Palos gets muddy fast. Expect standing water on some lower sections after heavy rain.
• MTB traffic is real on weekends when it’s dry. Most bikers are courteous, but stay alert on blind corners.
• If you’re new, stick to the main color-dotted trails and download an offline map in advance.

2.2 Swallow Cliff Woods – stairs plus rolling singletrack

Where it is Palos Park, just south of McCarthy Rd on La Grange Rd (near the big Swallow Cliff stairs).

Why it’s popular The 125-ish limestone stairs are legendary. Local runners use them for hill repeats, then disappear into the wooded singletrack loops.

What it’s like One big central hill with the staircase, surrounded by rolling forest trails. You can piece together 3 to 10 miles without repeating too much, especially if you cross under La Grange Rd to Swallow Cliff South.

Insider tips

• Weekends midmorning are packed with walkers on the stairs. For smoother repeats, go early or on a weekday.
• The parking lot fills on nice spring and fall days. The south lot often has more space.
• This is a great place to practice power hiking and downhill control for hilly races.

2.3 Des Plaines River Trail – long, flat, and forgiving

Where it is Runs north-south through Lake County and into Cook County, loosely following the Des Plaines River. One of the best access points from the city is near the Old School Forest Preserve or Independence Grove up in Libertyville.

Why runners love it You can run forever without a traffic light. It’s mostly crushed limestone and very flat, so it’s perfect for long runs, marathon training, and first forays off the pavement.

What it’s like Wide path, mostly shaded, paralleling the river. You pass through multiple forest preserves so the scenery changes enough to keep the miles interesting.

Insider tips

• After heavy rain, low sections near the river flood. Check local conditions or be ready to turn around.
• Mid-summer can be buggy. If you’re a mosquito magnet, wear long socks or use spray.
• Many local ultras (like DPRT) use this path, so it’s ideal for course-specific training.

2.4 Salt Creek Trail – west side workhorse

Where it is Runs through the western suburbs, roughly from Brookfield to Wood Dale, with good access near Bemis Woods, Fullersburg Woods, and near Brookfield Zoo.

Why it’s great Easy access if you live or stay on the west side. Great combination of crushed limestone, short wooded sections, and little road crossings.

Insider tips

• Park at Bemis Woods South off Ogden Ave for quick access to longer stretches of trail.
• You can run from near the zoo and feel “out of the city” in about ten minutes.
• Limited lighting, so bring a headlamp if you’re running pre-dawn in fall or winter.

2.5 Busse Woods – loops and wildlife

Where it is Elk Grove Village, northeast of O’Hare.

Why runners go One main 7.3-mile paved loop plus interior paths and some dirt side trails. It’s technically more multi-use path than pure trail, but the forest setting and easy mileage make it a staple.

What it’s like You circle lakes, cross small bridges, and often see elk in the enclosure near the east side. Great for tempo efforts or long easy runs.

Insider tips

• If you’re doing speed work, go early before cyclists traffic gets heavy.
• Snow is often compacted enough for winter running, but icy spots linger in shaded areas.

2.6 Waterfall Glen – rolling limestone loop

Where it is Near Darien and Lemont in DuPage County. Main parking at the Waterfall Glen Forest Preserve trailheads off Lemont Rd or Bluff Rd.

Why runners love it A ~9.5-mile limestone loop with legit rolling hills by Chicago standards. Popular with both road and trail runners.

What it’s like Mostly wide crushed limestone with some steeper rollers in the southwest section. You’ll see everyone from ultras in training to families walking.

Insider tips

• Great place to practice steady-state or marathon-pace efforts on softer surface.
• Minimal shade on some stretches, so mid-summer can feel hot.
• The small waterfall area is pretty but crowded. Don’t plan speed work right there.

2.7 Kettle Moraine (Wisconsin) – true destination trails

If you’re serious about a trail ultra or you just want a “big day” on real hills, locals head north.

Where it is Southern Kettle Moraine (near La Grange / Eagle, WI) and Northern Kettle Moraine farther north. From downtown Chicago, think 1.5 to 2 hours by car.

Why it’s worth the drive Real climbs, technical rooty stretches, and long sections of singletrack. Many Midwest trail races use Kettle Moraine as their home base.

Insider tips

• Start at the Nordic Trailhead or Emma Carlin for easy-to-follow loop options.
• Cell service can be spotty. Download maps and tell someone your plan.
• Treat this as a true long-run day, not just “a quick drive for a few miles.”

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3. Chicago-area trail races you should know

Chicago’s race calendar is full of 5Ks and road marathons, but the trail and ultra scene is strong and growing. The exact dates shift year to year, so use RaceThere to search by distance and month, then cross-check with the race websites. Here are race types and series to look up when planning your season.

3.1 Palos and Swallow Cliff trail races

A lot of local trail races use Palos and Swallow Cliff as their playground, usually with options from 5K up to 50K. Expect looped courses with repeated climbs and rooty sections. These are ideal “first trail race” venues if you’re comfortable on hilly terrain.

What to expect:

• Early-season mud in March and April races
• Warmer, humid conditions by June and July
• Generous cutoffs for longer distances, but you do need to stay moving on the hills

3.2 Des Plaines River Trail ultras and marathons

The Des Plaines River Trail is home to several classic ultra and marathon events that draw runners from all over the Midwest. Courses here are usually point-to-point or out-and-back on the limestone path, so they’re flatter and faster than Palos but still surrounded by trees.

Good for:

• First-time 50K or 50 mile runners who want minimal technical terrain
• Marathoners testing ultra waters without adding a ton of climbing
• Pacing practice because the terrain stays consistent

3.3 Illinois and Wisconsin trail series

Once you’re hooked, you’ll find that a lot of Chicago runners hop state lines for races. Southern Kettle Moraine, Ice Age area races, and various Wisconsin and northern Illinois trail series are all within 2 to 3 hours. Use RaceThere’s filters to look at:

• Trail half marathons in spring in northern Illinois great tune-up events
• Summer 50Ks and 50 milers in Kettle Moraine
• Late fall ultras that line up nicely after Chicago Marathon training cycles

When planning, think about your home base. If you’re in the city and don’t own a car, pick races you can reach via Metra plus rideshare or by coordinating with local club carpools. This is common and pretty accepted in the community.

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4. Local trail running clubs and group runs

Chicago’s club scene is deep, and more road groups are adding trail days to their weekly schedules. Two big names you’ll see often are the Chicago Area Runners Association (CARA) and the local trail and ultra crews.

4.1 Chicago Area Runners Association (CARA)

CARA isn’t purely trail focused, but they organize training programs that use softer surfaces like the Des Plaines River Trail and Waterfall Glen for long runs. If you’re marathon training and want one trailish long run a week, CARA’s groups are an easy starting point.

Look for:

• Summer and fall training cycles that include forest preserve long-run options
• Occasional Palos or trail-focused special events

4.2 Trail and ultra crews

There are a few Chicago-based trail and ultra communities that organize informal group runs, race carpools, and social events. The exact names and meetups evolve, but you can usually find:

• Weekend Palos group runs from common trailheads like Bullfrog Lake
• Long runs on the Des Plaines River Trail in Libertyville and surrounding preserves
• Informal stair sessions at Swallow Cliff when someone has a mountainous race coming

Finding these groups:

• Search for “Chicago trail running” or “Chicago ultrarunners” on Facebook and Strava clubs
• Check notice boards in local running shops, especially in the city and near the western and northern suburbs
• Ask at packet pickup for local trail races runners are quick to invite you along

4.3 How welcoming are they to visitors and beginners?

Very. Chicago runners are used to people popping in for a few weeks during marathon season or while in town for work. If you show up on time, introduce yourself at the trailhead, and are honest about your pace and distance, you’ll almost always find someone to run with.

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5. Where to buy trail gear and get local advice

Most Chicago running stores are road focused, but quite a few carry legit trail shoes and packs now that more people are racing trails and ultras.

5.1 What to look for in a Chicago trail shoe

Because our terrain is mixed limestone, dirt, and a bit of mud, most locals use a versatile shoe more than a super aggressive mud claw.

You’ll want:

• Moderate lugs that grip soft dirt but still feel okay on short pavement sections
• Good drainage for wet spring runs and humid summer days
• Enough cushioning to handle packed limestone for 20 plus miles

Ask the staff where they personally trail run. If they say “Palos” and “Kettle,” you’re talking to the right person.

5.2 Hydration and weather-specific gear

Chicago trail runs can swing from icy in January to 90 plus degrees and humid in July. Plan your gear around the extremes.

• Winter: Microspikes or grippy trail shoes, thermal tights, mittens, and a light traction-friendly gaiter are helpful on icy limestone.
• Spring: Waterproof socks or quick-drying socks help when low spots flood.
• Summer: Handheld bottle or vest, light sun sleeves, and a hat. Shade helps but it’s still humid.
• Fall: Layers you can stash easily when you warm up think light gloves and a packable shell.

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6. Seasonal trail running tips for Chicagoland

Running in Chicago is all about adapting to the season. The trails change character every few months.

6.1 Winter: frozen trails and short daylight

From December through February, expect cold, wind, and snow that melts and refreezes.

• Trails like Palos can get rutted from footprints that freeze overnight. Slower running and shorter strides help.
• Busse Woods and Des Plaines River Trail often get packed down by walkers and runners, making them more runnable.
• Start later in the day if you can. Midday sun is your friend.
• Some forest preserve parking lots close at sunset. Check closing times on the Cook County Forest Preserves site before planning evening runs.

6.2 Spring: mud season and flooding

March and April are muddy, especially after snowmelt.

• Assume low spots near rivers will be wet. Have a Plan B route that stays on higher ground.
• Don’t be the person who creates huge go-around tracks to avoid puddles. Run straight through the water when it’s safe. It preserves the trail.
• Bring dry socks and a towel for the car. Your future self will thank you.

6.3 Summer: humidity and bugs

June through August can be deceptively hard. The shade helps with sun exposure, but the humidity in the trees can feel like a sauna.

• Start early to avoid peak heat, especially for long runs.
• Hydrate more than you would on the Lakefront. You can go a long way between fountains or parking lots.
• Bug spray is not optional near the river trails.
• Thunderstorms roll through quickly. If the radar looks dicey, stay close to the trailhead.

6.4 Fall: prime trail season

September through early November is peak Chicago trail running.

• Cool temperatures, dry trails, and color in the trees.
• Trails are busier with hikers on nice weekends. Be courteous and call out when passing.
• Many trail and ultra races cluster in this window, so it’s a great time to plan a goal race.

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7. How to train for trail races while living in the city

You can absolutely train for a trail marathon or 50K while living in a high-rise near the Loop. You just need one or two trail days a week plus smart use of city terrain.

7.1 Use the Lakefront and city paths for volume and speed

Do most of your easy mileage and workouts where it’s convenient.

• Tempo and interval work on the Lakefront Trail or 606 Bloomingdale Trail flat, predictable surface so you can focus on effort.
• Hill work on city bridges, parking garage ramps (off-peak), or treadmill incline if you’re training for hilly events.
• Easy weekday runs from home so you can save commute time for weekend trail trips.

7.2 Make your long run a trail day

Pick one weekend day as your “forest preserve long run.” Rotate between Palos, Waterfall Glen, Des Plaines River Trail, and Salt Creek.

• For flatter trail races, emphasize long, steady efforts on DPRT or Salt Creek.
• For hilly races, plug in Palos and Swallow Cliff more often. Include hiking up the steeper climbs to practice realistic race strategy.
• If you’re prepping for a mountain race and stuck in Chicago, focus on repeat climbs and descents at Swallow Cliff stairs or Palos hills to get your legs used to constant elevation change.

7.3 Practice race nutrition on the trail

Don’t wait until race day to see what your stomach does on dirt.

• Use your long trail runs to test the same gels, chews, or real food you’ll use on race day.
• Chicago humidity can mask how much you’re sweating. Weigh yourself pre- and post-run occasionally to see how much fluid you tend to lose.
• Carry salt or electrolyte mixes when it’s above 70°F and humid.

If you need help dialing this in, combine this guide with a dedicated running nutrition and fueling resource, then test your plan on back-to-back long trail weekends.

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8. Getting to the trails: transit, driving, and logistics

One of the biggest barriers for city runners isn’t fitness, it’s cars. The good news is you have options.

8.1 If you have a car

You’re set. From most city neighborhoods:

• Palos and Swallow Cliff are about 30 to 45 minutes southwest, depending on traffic.
• Waterfall Glen is roughly the same southwest window.
• Des Plaines River Trail trailheads in Lake County are often 40 to 60 minutes north.
• Busse Woods is about 30 to 45 minutes northwest.

Plan around rush hour. Saturday early mornings are ideal, especially if you want guaranteed parking at popular trailheads.

8.2 If you don’t have a car

You can still trail run regularly if you’re a little creative.

• Metra: Take a north or northwest line toward trailheads near the Des Plaines River Trail or forest preserves, then run from the station. The schedules change, so check weekend timetables.
• Ride share: Split an Uber or Lyft with a friend or group to Palos or Swallow Cliff. It’s common for groups to carpool this way.
• Club carpools: Many local trail groups coordinate rides from city neighborhoods. Introduce yourself in group chats and offer gas money.

8.3 Safety and etiquette in the forest preserves

Chicago’s forest preserves are generally safe during daylight hours, but a few basic habits help.

• Run with at least one other person on more remote singletrack, especially at Palos.
• Tell someone where you’re starting, your planned loop, and when you expect to finish.
• Download an offline map or take a photo of the trail map at the trailhead.
• Stay alert around bikes on multi-use sections and yield appropriately on narrow trails.

And a simple but important one: pack out your gel wrappers and trash. The preserves are strict about litter, and the trail community takes it personally.

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9. Planning your Chicago trail running trip with RaceThere

If you’re visiting Chicago and want to build a mini trail camp or plan races around your stay, RaceThere is your best planning tool.

Here’s how to use it for Chicago trail running:

1. Search by location and set Chicago, IL or nearby suburbs as your base.
2. Filter for trail races, ultras, or off-road events in the 50 to 100 mile radius window.
3. Adjust by month to match your travel window, then start building your calendar.
4. Click into each event to check terrain notes, elevation gain, and surface type so you can match them to the routes in this guide.
5. Use the list of preserves and parks here to set up your pre-race shakeout and post-race recovery runs.

If you’re local, consider mapping your entire trail season around RaceThere’s filters. You can:

• Do a spring trail half at Palos as a test race.
• Target a summer or early fall 50K on DPRT.
• Add a late fall ultra in Wisconsin to close out the year when Chicago weather is still reasonable.

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10. Next steps: get off the Lakefront and onto dirt

Trail running in Chicago isn’t about huge mountains. It’s about discovering how much green space we actually have once you step outside the grid and follow the paths under the trees.

Pick one concrete step from this guide and do it in the next week:

• Block off a Saturday morning and drive to Palos or Swallow Cliff.
• Swap one long road run for a limestone loop at Waterfall Glen or Des Plaines River Trail.
• Join a local group run heading to the forest preserves.
• Jump on RaceThere and line up a trail race that scares you just enough.

Once you’ve taken a few turns on real dirt, it changes how you think about running in Chicago. The city energy is still there when you want it, but you’ll know that deep in the preserves, the only traffic you’ll hit is a line of runners quietly climbing a hill together.

Use this guide to find your routes, and use RaceThere to find your races. The rest is just lacing up and heading for the trees.