The best running trails around Highwood
291
runners
48
runs
Jogging around Highwood, Illinois, offers diverse terrain for runners, characterized by its location on a ridge 100 feet above Lake Michigan. The region features local parks with well-maintained pathways, extensive forest preserves, and scenic bluffs overlooking the lake. Access to broader trail networks further enhances the running experience, providing options through grasslands, woodlands, and along the shoreline.
Best jogging routes around Highwood
- The most popular jogging route is Fort Sheridan and Green Bay Trail Loop, a 14.0 miles (22.6 km) trail that takes 2 hours 20 minutes to complete. This route features varied terrain through the Fort Sheridan Forest Preserve and along the Green Bay Trail.
- Another top favourite among local runners is Fort Sheridan Birding Trail Loop, an easy 2.1 miles (3.4 km) path. This trail winds through woodlands and savannas, offering views towards the lake bluff.
- Local runners also love the Foley's Pond loop via Green Bay Road, a 2.5 miles (4.0 km) trail leading through natural areas, often completed in about 25 minutes.
- Jogging around Highwood is defined by lakefront access, diverse forest preserve trails, and connections to regional paths. The network offers options for different ability levels, from easy loops to more challenging long-distance routes.
- The guide includes highly-rated routes that showcase the best of the region's landscape. More than 200 runners have used komoot to explore Highwood's varied terrain.
Last updated: July 2, 2026
34
runners
22.6km
02:20
110m
110m
The Fort Sheridan and Green Bay Trail Loop offers a fantastic jogging experience, blending diverse terrain with stunning Lake Michigan views and historical sites. You'll navigate a mix of paved sections, crushed limestone, and natural paths, including a memorable 0.75-mile stretch of sandy shoreline. The route takes you through savannas, woodlands, and prairies, with awe-inspiring lake overlooks from 70-foot bluffs, making it a visually engaging run.
This difficult 14.0-mile (22.6 km) loop features 351 feet (107 metres) of elevation gain and typically takes about 2 hours and 20 minutes to complete. While the Green Bay Trail sections are generally flatter, the Fort Sheridan trails include rolling terrain, ravines, and some steep grades, so be prepared for a varied workout. Restrooms and picnic areas are available at Fort Sheridan, and the Green Bay Trail offers access to amenities like shops and restaurants.
Beyond the workout, this route is rich in history and biodiversity. You'll jog past historical architecture from the former U.S. Army Post and along parts of the ancient Green Bay Trail. Fort Sheridan is also a haven for birdwatching, lying along a busy migratory flyway, with over 236 species observed. It's a great option for joggers who appreciate a blend of natural beauty, historical context, and a good challenge.
2
runners
3.41km
00:23
20m
20m
The Fort Sheridan Birding Trail Loop offers a unique blend of natural beauty and historical intrigue, making it a fantastic choice for a quick outdoor escape. You'll jog through diverse ecosystems, from woodlands to savanna, and enjoy awe-inspiring views of Lake Michigan from a 70-foot-high bluff. Keep an eye out for the historic Fort Sheridan Water Tower and the tranquil Patton Pond as you navigate the varied terrain of grass, packed dirt, and some asphalt sections.
This easy 2.1-mile (3.4 km) jogging route, with just 58 feet (18 metres) of elevation gain, can be completed in about 22 minutes, making it ideal for a refreshing run. The trail is generally considered easy, though the ravine portions may require more careful footing due to roots and uneven ground. It's a great option for beginner joggers or anyone seeking a scenic, low-impact workout.
What truly sets this trail apart is its exceptional birdwatching opportunities, being located on one of North America's busiest flyways with over 236 species observed. It also provides rare public access to Lake Michigan in Lake County and features historical remnants of the former military base, complete with interpretive signs. This blend of nature, history, and wildlife makes it a standout choice among local jogging routes.
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3.97km
00:25
20m
20m
Jog the easy 2.5-mile Foley's Pond loop via Green Bay Road in Highland Park, offering scenic views around a historic pond.
16
runners
45.9km
04:45
110m
110m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
15
runners
5.37km
00:33
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Highwood
Tips from the Community
The trail is generally flat, making it easy for walking, running, and biking for people of all ages and fitness levels. As you travel along the trail, you'll experience a beautiful mix of habitats.
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This bronze sculpture is a tribute to General Sheridan, a Civil War general. It depicts him on a horse during Battle of Five Forks in April 1865.
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The Lake at Independence Grove is a must-visit stop along the Des Plaines River Trail, offering cyclists a scenic and easy ride through a 115-acre retreat. Once a gravel quarry, this reclaimed space now features smooth paths, gentle terrain, and beautiful lake views—perfect for beginners and family-friendly outings. Visit in the spring, and you might spot colorful wildflowers adding even more charm to this peaceful ride.
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This stretch of the Des Plaines River Trail leads you to Minear Lake, a peaceful 72-acre lake perfect for a break. Take in the calm waters surrounded by tall trees, then head just steps away to the sandy beach if you're up for a swim. In the summer, it’s an ideal spot for a refreshing dip, but even if you’re just passing through, the quiet shoreline offers the perfect place to pause and soak in the scenery.
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The Lake at Independence Grove, a highlight along the Des Plaines River Trail, offers hikers a scenic 115-acre retreat within a reclaimed gravel quarry. If you're visiting in the spring, you may be able to spot colorful warblers along the surrounding woodlands!
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This winding dirt trail takes you through the heart of the Middlefork Savanna. You parallel the North Branch Chicago River as the trail meanders through verdant riverlands. This is a great place to see herons, turtles, and a host of other wildlife that call the preserve home.
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MacArthur Woods is a preserved forest that showcases the original landscape of the eastern Des Plaines River Valley. The area features a diverse mix of plants, creating an important habitat for breeding forest birds, including the brown creeper, red-shouldered hawk, broad-winged hawk, veery, pileated woodpecker, and several rare warblers.
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A footbridge over the Des Plaines River connects Half Day to Wright Woods Forest Preserve, providing scenic outdoor recreation. Both preserves feature the Des Plaines River Trail, perfect for hiking, biking, horseback riding, and cross-country skiing on its gravel base.
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Frequently Asked Questions
How many running routes are available around Highwood?
There are over 40 diverse running routes available around Highwood, catering to various fitness levels. These paths range from easy loops through local parks to more challenging, longer trails within the Fort Sheridan Forest Preserve and connecting to regional networks.
Are there easy running routes suitable for beginners or casual joggers?
Yes, Highwood offers several easy running routes perfect for beginners or those seeking a relaxed jog. The Fort Sheridan Birding Trail Loop is an excellent option, an easy 2.1-mile path winding through woodlands and savannas with views towards the lake bluff. Another gentle choice is the Foley's Pond loop via Green Bay Road, a 2.5-mile trail through natural areas.
Where can I find longer or more challenging running trails in Highwood?
For longer or more challenging runs, the region offers extensive options. The Fort Sheridan and Green Bay Trail Loop is a demanding 14.0-mile route that takes you through varied terrain, including the Fort Sheridan Forest Preserve and along the Green Bay Trail. Additionally, trails at Fort Sheridan connect to the 20-mile McClory Trail and the 11-mile North Shore Path, providing opportunities for extended jogs.
Are there any running routes with scenic viewpoints or lake access?
Absolutely. Highwood's location on a ridge above Lake Michigan means many routes offer stunning views. The Fort Sheridan Forest Preserve is a highlight, featuring trails that wind through diverse settings and provide awe-inspiring views of Lake Michigan from a 70-foot-high bluff. You can also find public access to the lake's shoreline within the preserve, offering picturesque water views during your run.
What natural features can I expect to see along the running paths?
Jogging routes around Highwood showcase a variety of natural features. You'll encounter open grasslands, dense woodlands, and scenic bluffs, particularly within the Fort Sheridan Forest Preserve. The area also features ravines, mature trees, and access to Lake Michigan, providing a rich and diverse natural environment for your run.
Are there any family-friendly running routes in Highwood?
Yes, local parks like Highwood Softball Park and Everts Park offer tranquil spaces with lush greenery and well-maintained pathways that are suitable for family jogs. These parks provide peaceful escapes and cater to various fitness levels, making them ideal for families.
Are dogs allowed on the running trails in Highwood?
Many trails in the Highwood area, particularly within the Fort Sheridan Forest Preserve, are dog-friendly. It's always recommended to check specific trail regulations for leash requirements and any restricted areas before heading out with your canine companion.
Are there circular running routes available?
Yes, many of the running paths around Highwood are designed as loops, offering convenient circular routes. For example, the Fort Sheridan Birding Trail Loop and the Foley's Pond loop via Green Bay Road are both excellent circular options for joggers.
What kind of landmarks or attractions can I see near the running routes?
While jogging, you might encounter various natural and historical points of interest. The Fort Sheridan Forest Preserve itself is a significant landmark with historical exhibits along its trails. Nearby attractions include Skokie Lagoon No. 3 and MacArthur Woods Forest Preserve, offering additional natural beauty to explore.
Is parking available near the running trails?
Yes, parking is generally available at key access points for the running trails. For instance, the Fort Sheridan Forest Preserve, a major hub for many routes, provides designated parking areas for visitors. Local parks like Highwood Softball Park and Everts Park also typically have parking facilities.
Can I reach the running trails using public transport?
Highwood has public transport options that can provide access to the general area. For specific trailheads, you may need to combine public transport with a short walk or ride. It's advisable to check local transit schedules and routes to plan your journey to the desired starting point.
What is the best time of year to go running in Highwood?
Highwood's moderate climate makes it suitable for year-round outdoor activities. Spring and fall offer pleasant temperatures and vibrant scenery, while summer provides longer daylight hours. Even winter can be enjoyable for running, though trail conditions may vary, so checking local weather and trail reports is always a good idea.
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