4.3
(68)
8,275
runners
515
runs
Jogging around Highwood offers diverse landscapes, from urban green spaces to expansive natural preserves. The region provides well-maintained pathways in local parks and scenic lakefront access along Lake Michigan. Key features include the Fort Sheridan Forest Preserve, known for its ravine-bluff habitats and varied trails, and the Green Bay Trail, which connects several North Shore towns. These areas combine to create a varied terrain suitable for different running preferences.
Last updated: June 24, 2026
10
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
runners
8.30km
00:54
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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8
runners
4.50km
00:28
30m
30m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
10
runners
5.48km
00:36
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
runners
9.96km
01:02
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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The Lordship Tea Room in Writtle closed to the public on 30 August 2024 [1]. For a similar experience, consider visiting other Tiptree Tea Rooms in Essex, such as the Tiptree Tea Room at Bond Street in Chelmsford. [1] https://www.bbc.com/news/articles/czrj3ykkrp3o [2] https://www.tea-and-coffee.com/afternoon-tea/tiptree-tea-room-at-the-college
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Alternative route to Stonehill Rd when going through Roxwell. Take Greenhill Lane, which leads onto this short, flat segment of gravel path.
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Rode through this with road bike, no issues on an October ride.
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Can be beautiful but bit of a dead end if you are on a road bike and skinny tyres
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As you walk towards this tunnel it seems strange to have two entrances! Once you have dropped down the spiral steps all becomes apparent.
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Added this little road blindly as part of an extended loop. It was perfectly passable on my road bike (25mm tyres) but could get trickier if itβs wet.
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Highwood offers a wide selection of running routes, with over 500 options available. These range from easy park loops to more challenging trails through forest preserves.
Yes, Highwood has many easy running routes perfect for beginners. For example, the Everts Park Loop is an easy 2.8-mile trail through local green spaces, ideal for a gentle run.
Running in Highwood offers diverse scenery, from the tranquil green spaces of local parks like Everts Park to the scenic Lake Michigan shoreline. You can also explore the unique ravine-bluff habitats of the Fort Sheridan Forest Preserve and the charming views along the Green Bay Trail.
Absolutely. Many of Highwood's parks and trails are suitable for families. The well-maintained pathways in Everts Park and Highwood Softball Park offer pleasant, safe environments. The Fort Sheridan Forest Preserve also has trails that are great for family outings, combining nature with interpretive art installations.
Many trails in Highwood, particularly within the Fort Sheridan Forest Preserve, are dog-friendly. However, it's always best to check specific trail regulations regarding leashes and waste disposal to ensure a pleasant experience for everyone.
Yes, Highwood features several circular running routes. The Everts Park Loop is a popular easy option. The Fort Sheridan Forest Preserve also offers various loop trails, such as the Fort Sheridan Birding Trail Loop, allowing you to experience diverse habitats and lake views.
While running in Highwood, you can encounter several interesting sights. The Lakefront Trail passes through the historic Fort Sheridan. Within the Fort Sheridan Forest Preserve, you'll find unique ravine-bluff habitats and interpretive art installations. You might also spot Hanningfield Reservoir Causeway or Writtle Village Green and Duck Pond if you explore routes further afield.
The running routes in Highwood are highly rated by the komoot community, with an average score of 4.3 stars from over 60 reviews. Runners often praise the diverse terrain, from scenic lakefront paths to peaceful forest preserves, and the well-maintained trails that cater to various fitness levels.
Yes, Highwood is known for its beautiful lakefront access. The Lakefront Trail, which is part of the annual Highwood 5K Run course, guides runners along the scenic Lake Michigan shoreline. The Fort Sheridan Forest Preserve also offers approximately 0.75 miles of Lake Michigan shoreline with stunning views.
Yes, the Green Bay Trail is easily accessible from Highwood and offers a 9-mile route that parallels Chicago's Metra commuter rail line. This trail winds through several North Shore towns, providing a great option for longer runs and exploring beyond Highwood.
The Lakefront Trail is a significant route that takes runners through the historic Fort Sheridan. This area combines natural beauty with a sense of history, offering a unique backdrop for your run.
Highwood's moderate climate allows for year-round enjoyment of its parks and trails. While spring and fall offer pleasant temperatures and vibrant scenery, the trails are generally accessible throughout the year, with winter runs providing a different, often serene, experience.


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