The best family-friendly hikes and walks around Highland Park
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Family friendly hiking trails around Highland Park, Illinois, are characterized by diverse landscapes, including restored woodlands, native gardens, and scenic lakefront paths along Lake Michigan. The region features expansive preserves with green lawns and wooded ravines, offering a variety of natural environments. Trails often connect neighborhoods and provide opportunities to explore significant forest environments. This area provides a range of hiking experiences suitable for different fitness levels.
Best family friendly hiking trails in Highland Park
- The most popular family friendly hiking route is The Preserve of Highland Park loop, a 2.4 miles (3.9 km) trail that takes 1 hour to complete. This easy loop explores woodlands and native gardens within a large preserve.
- Another top favourite among local hikers is Park Avenue Fishing & Boating Beach loop via Lake Avenue, an easy 4.5 miles (7.3 km) path. This route offers lakefront views and connects to local amenities.
- Local hikers also love the Skokie Valley Trail, a 10.1 miles (16.3 km) trail leading through varied suburban and natural landscapes, often completed in about 4 hours 6 minutes.
- Hiking around Highland Park is defined by restored woodlands, lakefront paths, and green preserves. The network offers options for different ability levels, from easy strolls to more challenging routes.
- The routes in Highland Park are highly rated by the komoot community with an average score of 4.7 stars from over 15 reviews. More than 200 hikers have used komoot to explore Highland Park's varied terrain.
Last updated: July 8, 2026
16.3km
04:06
20m
10m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
3
hikers
3.94km
00:59
0m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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1
hikers
22.4km
05:46
100m
110m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
7.26km
01:53
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.19km
01:05
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Tips from the Community
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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Millard Park and Beach offer a tranquil neighborhood beach experience, where swimming is not permitted. With over 1,000 feet of Lake Michigan shore and bluff, the upper park showcases a historic garden that provides panoramic views of the lake and beach area. Ongoing efforts to restore the ravine contribute to a thriving habitat for trout spawning and enhance the overall ecology, supporting native wildlife.
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Explore Park Avenue Boating & Fishing Beach, equipped with a concrete ramp and sand launching ramp, complemented by two parking lots and three boat storage facilities. Enjoy scenic views, especially during sailing practice.
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Unveiled in June 2022, The Preserve of Highland Park provides a distinctive natural haven for passive recreation. Discover green lawns, nature-inspired play areas, specialized native gardens, restored woodlands, and interwoven walking and biking trails connecting neighborhoods, and regional biking routes. Immerse yourself in the serene beauty and outdoor experiences of nature.
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Experience the allure of Rosewood Beach, a nationally acclaimed destination offering diverse amenities. Discover a nature cove for ecological programs, a guarded swimming beach, and a recreation beach. Nestled against wooded bluffs, the beach boasts a unique Interpretive Center, along with amenities like concessions, restrooms, and a guard building connected by a charming boardwalk.
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Explore the picturesque Green Bay Trail, a delightful 9-mile route paralleling Chicago's Metra commuter rail line north of the city. Winding through North Shore towns like Kenilworth, Winnetka, Highland Park, and Lake Bluff, the trail is adorned with charming homes, community parks, and convenient amenities. Given its proximity to Lake Michigan, you can opt for shorter on-road side trips to savor beachfront views.
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The statue captures Sheridan astride his mount "Rienzi," inspiring his troops during the pivotal Battle of Five Forks in April 1865, a symbol of his leadership and victory. Visit Fort Sheridan to admire this iconic sculpture, commemorating a key figure in American history.
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Discover the enchanting history of Foley's Pond, once a Foley family brickyard, in 1897. Originally a clay mining site, the pond emerged when an underground spring filled the excavated hole. Purchased by the Park District in 1925, the pond became home to bass, perch, and pickerel. In the 1930s and 1940s, wild canaries adorned the trees around Foley's Pond. Situated between Sunset Valley Golf Course's first and second holes, Foley's Pond offers a unique blend of history and natural serenity.
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Frequently Asked Questions
How many family-friendly hiking trails are available around Highland Park?
There are 14 family-friendly hiking trails around Highland Park, with 11 of them rated as easy, making them perfect for outings with children or those new to hiking.
What kind of scenery can we expect on these family-friendly trails?
The trails around Highland Park offer a diverse range of scenery. You can expect to explore restored woodlands, native gardens, and picturesque lakefront paths with views of Lake Michigan. Many routes also feature wooded ravines and expansive green spaces, providing a refreshing natural escape.
Are there any easy circular routes suitable for families?
Yes, there are several easy circular routes perfect for families. A great option is The Preserve of Highland Park loop, which is just under 4 km and takes you through woodlands and gardens. Another lovely choice is the Foley's Pond loop via Green Bay Road, offering a pleasant 4.2 km walk around the pond.
What do other hikers enjoy most about the family-friendly trails in Highland Park?
The komoot community highly rates the family-friendly trails in Highland Park, with an average score of 4.7 out of 5 stars. Reviewers often praise the well-maintained paths, the beautiful natural settings like restored woodlands and lake views, and the accessibility for all ages, making them ideal for family outings.
Are dogs allowed on these family-friendly hiking trails?
Many trails in Highland Park are dog-friendly, but it's always best to check specific park regulations before you go. Generally, dogs are welcome on a leash, allowing your furry family members to join in the adventure.
Are there any specific points of interest or attractions along the trails for kids?
Absolutely! Many trails offer natural points of interest that kids will love. For instance, The Preserve of Highland Park features pond and wetland overlooks, a pollinator garden, and even a nature maze. You might also encounter various lakes like Skokie Lagoon No. 3 or the Des Plaines River bridge, which can be fun for exploration. The area is also known for birdwatching opportunities, especially at places like Fort Sheridan.
When is the best time of year to hike with family in Highland Park?
Highland Park offers enjoyable hiking experiences year-round. Spring brings blooming native gardens and fresh greenery, while autumn showcases vibrant fall foliage. Summer is perfect for enjoying the lakefront paths, and even winter can be beautiful for a crisp walk through the snow-dusted woodlands, though some paths might be icy. Always check local conditions before heading out.
Is parking readily available at the trailheads?
Yes, parking is generally available at or near the trailheads for most family-friendly routes in Highland Park. Many parks and preserves are designed with visitor access in mind, offering designated parking areas. For specific routes, you can find detailed parking information on the individual komoot tour pages.
Can I reach any of these trails using public transport?
Highland Park's trails are well-integrated with the local community, and some routes may be accessible via public transport connections. Trails are designed to connect neighborhoods and downtown Highland Park, which often have public transport stops. We recommend checking local bus or train schedules and routes to plan your journey to specific trailheads.
Are there any trails that offer a good chance for wildlife spotting?
Yes, the diverse habitats around Highland Park provide excellent opportunities for wildlife spotting. The Preserve of Highland Park and Fort Sheridan Forest Preserve, with their woodlands, wetlands, and native gardens, are particularly good for birdwatching. Keep an eye out for various bird species, small mammals, and other local wildlife as you explore the natural areas.
Are there any longer, but still family-friendly, routes for older children or more active families?
For families looking for a longer adventure, the Skokie Valley Trail offers a moderate 16.3 km route. While longer, its relatively flat terrain makes it manageable for older children or those accustomed to longer walks. It's a great way to experience more of the region's natural beauty.
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