4.5
(79)
6,823
runners
232
runs
Jogging around High Wood offers access to diverse natural landscapes, including wooded areas and trails along water features. The region features a network of paths, with many routes winding through preserves and alongside rivers. These trails provide varied terrain suitable for different fitness levels, from flat crushed gravel paths to routes with gentle elevation changes.
Last updated: June 25, 2026
5.0
(1)
27
runners
5.61km
00:38
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
13
runners
6.19km
00:46
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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16
runners
5.69km
00:37
70m
70m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
17
runners
6.21km
00:44
40m
40m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
14
runners
7.25km
00:49
90m
90m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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In St Mary's Well, near Culloden Battlefield, the injured soldiers bathed their wounds. You can spend some time here and leave a piece of fabric today to fulfill a wish.
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Nice to chill out on easy tracks, a few bits to see in the woods as you go round.
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Typical forest tracks through the trees, easy to cycle beautiful smells after it's has been raining.
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Good place to see, lots of history around this area. Around the well could do with a wee clean up.
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Can be easily missed as its not on the main track but well worth seeing & looking up the history of these woods close to Culloden Battle Field.
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Nice place to see but getting a bit tatty looking with all the old ribbon & bits people are tying up in trees. Ruin is still good to look at through.
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A 'Clootie' well. This was the place of Pagan tradition where a piece of cloth was left to make a wish. A clootie is the word for 'rag', and it was also believed that the well had healing powers.
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There are over 240 running routes around Highwood, offering a wide variety of options for different preferences and fitness levels. These include routes through natural preserves, along riverbanks, and near Lake Michigan.
Yes, Highwood offers a good selection of easy jogging trails. There are 28 routes specifically rated as easy, often featuring flat, crushed gravel paths, such as those found in the Half Day Forest Preserve Ponds area, which are perfect for a gentle run.
Jogging in Highwood provides access to diverse natural landscapes. You can run alongside the serene Skokie Lagoons, follow the scenic Des Plaines River Trail, or explore the wooded areas of MacArthur Woods Forest Preserve. Many routes also offer views of Lake Michigan, particularly in the Fort Sheridan Forest Preserve.
Many of Highwood's natural preserves and trails are dog-friendly, though it's always best to check specific preserve rules regarding leashes. Areas like the Des Plaines River Trail and various forest preserves generally welcome leashed dogs, making them great options for running with your canine companion.
For breathtaking views, consider routes that pass through Fort Sheridan Forest Preserve, where the Fort Sheridan Beach lookout offers stunning vistas of Lake Michigan. Patton Pond also provides a unique perspective with views of both the pond and Lake Michigan.
Yes, many of the trails in Highwood's forest preserves and natural areas are designed as loops, making them ideal for circular running routes. For example, High Wood loop from Balloch offers a scenic circular path, and The Preserve of Highland Park features a 2.4-mile loop.
The running routes in Highwood are highly regarded by the komoot community, with an average rating of 4.5 stars from over 70 reviews. Runners often praise the varied terrain, the peaceful natural settings, and the well-maintained paths that offer a refreshing outdoor experience.
Yes, several areas offer family-friendly running options. The flat, well-maintained trails around Half Day Forest Preserve Ponds and The Preserve of Highland Park are generally suitable for families, providing easy surfaces and scenic surroundings for a leisurely jog or walk.
While specific public transport access points vary by trail, Highwood and its surrounding areas have some public transportation options. It's advisable to check local bus or train schedules and routes to determine the best way to reach your desired trailhead, especially for preserves further from the town center.
Absolutely. The interconnected network of trails, such as the Des Plaines River Trail, allows for extended runs by combining different sections and preserves. You can easily link various paths to create longer routes, offering ample opportunities for endurance training.
While many routes are moderate, advanced runners can find challenges by combining longer sections of trails or exploring routes with more varied terrain and elevation changes within the larger forest preserves. There are 33 routes rated as difficult, providing more rigorous options for experienced runners.
Highwood itself offers various cafes and eateries. While not directly on every trail, many preserves are a short drive from town amenities. For example, the Lochandinty Wood – Hillhead Café loop from Inverness Airport (note: this route is not in Highwood, Illinois, but the question is about cafes) suggests that some routes might have nearby facilities, but generally, you'll find options in Highwood's downtown area.
Highwood offers great running conditions throughout much of the year. Spring and fall provide pleasant temperatures and beautiful scenery with changing foliage. Summer mornings and evenings are also popular, while winter running is possible, though trails may be snowy or icy, requiring appropriate gear.


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