Attractions and places to see around Highwood offer a blend of natural areas and cultural sites. The city is situated at the top of the Skokie ravine, marking the highest point between Chicago and Milwaukee. Visitors can explore various forest preserves, rivers, and lagoons, alongside a vibrant dining scene and frequent community festivals. Highwood provides diverse points of interest for outdoor recreation and cultural engagement.
Last updated: May 4, 2026
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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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From this grassy spot you get a lovely view of Skokie Lagoon No. 3. This lagoon is part of the Skokie Lagoons nature preserve, located in Glencoe and Winnetka, Illinois. This lagoon is one of seven interconnected lagoons spanning 190 acres, managed by the Forest Preserve District of Cook County. The lagoons were created by the Civilian Conservation Corps between 1933 and 1940, transforming a marshy area into the artificial lagoons seen today. On hot days you might see folks fishing, and kayaking. This is a great spot to rest and relax before continuing on your ride.
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This is a paved 21.3 mi (34 km) trail from Highland Park to Chicago. It's shared use, so look out for other pedestrians and watch your speed. Enjoy the smooth, traffic-free riding!
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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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This bridge crosses the Des Plaines River, which flows through Wisconsin and Illinois. This part of the Des Plaines River Trail is used to connect the two nearby nature centers and their miles of trails. You get a pretty good view from the middle of the bridge, too.
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The North Branch Trail is a 20-mile paved trail that follows the North Branch of the Chicago River. The trail winds through forests and fields, so keep your eye out for wildlife, especially deer.
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Skokie Lagoons are a series of lagoons in this nature preserve managed by the Forest Preserve District of Cook County. Though bordered by roads, it's a nice little nature escape with kayaking, boating, fishing, bird watching, and paddling options. The lagoons are all connected and together measure about 190 acres. The water enters from Chicago Botanic Garden through the lagoons to the Skokie River, and the low dams keep the water levels below the inner islands.
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This is a paved 21.3 mi (34 km) trail from Highland Park to Chicago. It's shared use so look out for other pedestrians and watch your speed. Enjoy the smooth, traffic-free riding!
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Highwood is surrounded by diverse natural areas. You can visit the Skokie Lagoons for kayaking, boating, fishing, and bird watching. The MacArthur Woods Forest Preserve offers a preserved forest with a rich variety of plants and a significant habitat for breeding birds. Additionally, the Half Day Forest Preserve Ponds feature scenic gravel trails and opportunities for bird watching.
Yes, several attractions around Highwood are suitable for families. The Skokie Lagoons offer recreational activities like kayaking and bird watching that families can enjoy together. The MacArthur Woods Forest Preserve and Half Day Forest Preserve Ponds provide easy trails and natural beauty for family walks and picnics. Highwood also hosts numerous community festivals and events throughout the year, often centered around Everts Park, which are great for all ages.
Highwood has a rich historical context. You can explore **Fort Sheridan**, a former military base that significantly shaped the area's development. For local heritage, the Highwood Historical Society, located in City Hall, preserves and shares the community's past through exhibits and walking tours. You can learn more about their work at highwoodhistoricalsociety.com.
Highwood offers excellent opportunities for outdoor activities. You can cycle along the North Branch Trail, a 20-mile paved path following the Chicago River, or explore the trails alongside the Des Plaines River. For more specific routes, check out the Running Trails around Highwood or Hiking around Highwood guides for detailed options.
Yes, there are several easy hiking options. The Half Day Forest Preserve Ponds feature flat, crushed gravel trails perfect for leisurely walks. The MacArthur Woods Forest Preserve also offers accessible paths through its preserved forest. For a curated list of gentle routes, refer to the Easy hikes around Highwood guide.
Highwood is known as a premier dining destination on the North Shore. You'll find a variety of acclaimed restaurants, including Froggy's French Cafe, La Casa de Isaac & Moishe for Mexican cuisine, The Del Rio Restaurant for Italian fare, and Miramar Bistro, which offers French dishes with Cuban accents. There's also Tala Coffee Roasters and the 28 Mile Distilling Co. with a tasting room.
Highwood fosters a vibrant cultural arts scene. The Midwest Young Artists Conservatory and The Performer's School offer arts education and serve as public recreation facilities. The Fine Art Studio of ROTBLATT-AMRANY, located in the old village of Fort Sheridan, also contributes to the local art landscape.
Highwood's attractions can be enjoyed year-round, but the spring, summer, and fall months are particularly pleasant for outdoor activities in the forest preserves and along the trails. These seasons also coincide with many of Highwood's frequent festivals and events, such as 'Celebrate Highwood' and 'Highwood Days', which offer a lively atmosphere.
Yes, in the vicinity of Highwood, you can find architecturally significant homes designed by Frank Lloyd Wright. These include the Millard House (1906) and Mary Adams House (1905), both notable Prairie School designs listed on the National Register of Historic Places.
Visitors particularly appreciate the tranquility and diverse recreational opportunities. For instance, at Skokie Lagoon No. 3, people enjoy the peaceful nature escape with options for kayaking, fishing, and bird watching. The MacArthur Woods Forest Preserve is valued for its preserved forest landscape and rich bird habitats, offering a beautiful natural setting within the area.
Absolutely. The North Branch Trail is a popular 20-mile paved cycle way that follows the North Branch of the Chicago River, winding through forests and fields. Additionally, the Des Plaines River features accompanying trails that are excellent for cycling. Many forest preserves, like Half Day Forest Preserve Ponds, connect to larger trail networks, including the Des Plaines River Trail, which is suitable for biking.


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