Top 15 Activities in Highland Park, Illinois You Can’t Miss

Showcasing stunning architecture and long recognized as a center of creativity, the affluent lakeside community of Highland Park is situated on the North Shore in the Chicago suburbs.

One of the most appealing aspects of Highland Park is its easy access to the shores of Lake Michigan, featuring a series of lakefront parks and a Lake County Preserve within the city limits.

You are also just minutes away from the Chicago Botanic Garden and the Skokie Lagoons, both major attractions in the Chicagoland area. Additionally, for three months during summer, Highland Park hosts the historic Ravinia Festival, featuring a lineup of notable performers.

Two long-distance bike paths traverse Highland Park, and the city’s downtown area offers an exemplary commercial district with ample amenities.

1. Chicago Botanic Garden

At the southern edge of Highland Park lies one of the premier visitor attractions in the Chicago area. Spanning nearly 400 acres across nine islands, the Chicago Botanic Garden features 27 distinct display gardens that are home to approximately 2.5 million plants.

These gardens encompass four diverse habitats that replicate the natural environments of northeastern Illinois, including woodlands, prairies, wetlands (Skokie River Corridor), and lakeshores.

A garden of this size may seem overwhelming, but an app is available for download to assist you in locating which plants are in bloom during your visit.

In addition to the breathtaking horticultural displays, exhibitions of botanically-themed photography and fine art can be found at the outstanding Regenstein Center and the Plant Conservation Science Center.

2. Ravinia Festival

While numerous towns host summer concert series, Highland Park’s Ravinia neighborhood is home to the internationally acclaimed Ravinia Festival.

This summer-long event is the oldest outdoor music festival in the United States, originally established in 1905 as entertainment at the amusement park located on the site. Since 1936, the festival has served as the summer residency for the Chicago Symphony Orchestra.

Featuring around 150 individual performances, the event unfolds on the picturesque grounds of Ravinia Park, utilizing venues such as the Pavilion (3,350 seats), the Martin Theatre (850), and Bennett Gordon Hall (450). The expansive lawn features a sound system that allows attendees to enjoy performances while picnicking.

The Ravinia Festival showcases an array of music genres, and recent performers include esteemed artists such as Aretha Franklin, Dolly Parton, Bob Dylan, Diana Ross, Stevie Nicks, Brian Wilson, Lady Gaga, Herbie Hancock, Smokey Robinson, and Blondie.

3. Rosewood Beach

Situated at the base of wooded bluffs and connected by a boardwalk, Rosewood Beach offers a wonderful location for relaxation by Lake Michigan during the summer. It is a pride of the Park District of Highland Park.

This beach includes a lifeguarded swimming area, a recreation beach, and an educational “nature cove.”

Also featured is a contemporary interpretive center that serves as a hub for various programs catering to individuals of all ages.

This facility can accommodate up to 50 individuals and is available for rental for private events. Access to Rosewood Beach requires a beach pass, provided free of charge for Highland Park residents, while non-residents may acquire a daily or seasonal pass.

4. Architecture Tours

Development began steadily in Highland Park from the 1880s onward, leading to a remarkable array of significant architectural works.

Frank Lloyd Wright contributed several structures, along with other notable architects such as W.W. Boyington, Howard Van Doren Shaw, John S. Van Bergen, David Adler, Robert E. Seyfarth, and Prairie School landscape architect Jens Jensen.

The most renowned building in the area by Wright is the Willits House (1901), visible from the exterior at 1445 Sheridan Rd, recognized as one of the pioneering examples of the Prairie School movement.

The Chicago Architecture Center coordinates guided walking tours of the city, typically lasting two hours.

Alternatively, self-guided tours featuring thematic walks centered on the works of Seyfarth and Van Bergen can be found on the Historic Preservation Commission page of the City Hall website.

5. Downtown Highland Park

Located just a few blocks from the lakeshore and adjacent to the Metra station, Highland Park features a vibrant downtown commercial district bustling with shops and dining establishments.

These amenities can be found on both sides of the tracks, along pedestrian-friendly streets, adorned with trees and equipped with multiple seating areas for relaxation and people-watching.

Shoppers can explore a variety of fashion boutiques, furniture stores, antique shops, jewelers, gift shops, shoe stores, and more.

This is complemented by a remarkable diversity of cafes, tea rooms, bakeries, pancake houses, ice cream parlors, sandwich shops, and restaurants offering everything from hot dogs and deep-dish pizza to Thai, pan-Asian, contemporary American, sushi, and tamales.

6. Skokie Lagoons

In the 1930s, the Civilian Conservation Corps (CCC) undertook a substantial project to dredge the wetlands south of the present Chicago Botanic Garden, creating a series of seven artificial lagoons along the Skokie River.

These lagoons, spanning nearly 900 acres, continue to attract visitors, offering opportunities for hiking, biking, or water-based activities while renting kayaks or canoes from Chicago River Canoe and Kayak.

Surrounded by woods and picnic areas, with numerous safe spots to land, these lagoons are a delight to explore and are favored by anglers seeking high catches of crappie, channel catfish, largemouth bass, and various other species.

7. Sunset Woods Park

Acquired in phases from 1920 to 1949, this beloved 34-acre park adjacent to downtown Highland Park encompasses substantial nature reserves, including Mesic Closed Savanna and ephemeral wetlands.

The park also features a variety of recreational facilities, including a tennis court, basketball court, baseball diamond, multi-use field, picnic area, and a shelter.

One of the park’s standout features is its children’s playground, which has been updated to include separate areas designed for children under and over five years old. The playground retains the iconic Rocket Ship that has captured the imaginations of generations.

8. Fort Sheridan Forest Preserve

A few stops on the Metra will land you at a breathtaking natural site offering complimentary public access to the lakeshore.

As suggested by its name, Fort Sheridan Forest Preserve occupies the grounds of a former military base, conceived by distinguished landscape designer O.C. Simonds (1855–1931) to seamlessly integrate with the bluffs, ravines, savanna, and lakeshore of the landscape.

More than a century later, the preserve stands as a notable destination for birdwatching, with a recorded 236 different species observed within the area.

The preserve features almost four miles of trails, and a highlight is the stunning lakeside overlook positioned atop a 70-foot bluff.

9. Skokie Valley Bike Trail

One of two bike paths traveling north and south through Highland Park, the Skokie Valley Bike Trail spans approximately ten miles and is paved with asphalt, providing a smooth riding experience.

The trail follows the Skokie Valley, with railroad tracks situated to the west and I-41 to the east for most of its length.

The southern trailhead is located at the very southern end of Highland Park, accessible via Lake Cook Road, near the Chicago Botanic Garden.

This peaceful green corridor allows for minimal interaction with road traffic and passes through tranquil linear parks such as Buckthorn Park.

10. Robert McClory Bike Path

This picturesque 25-mile bike path connects a series of charming North Shore communities. It begins just south of Highland Park at the Braeside Metra station and stretches through Lake County, reaching all the way to the Wisconsin border.

Much of the path runs along the former right-of-way of the Chicago North Shore and Milwaukee Railroad, which operated from the 1910s until 1963.

The trail requires a few brief detours within Highland Park but traverses residential neighborhoods and a series of linear parks, while also bordering the lovely Fort Sheridan Forest Preserve on its western edge.

11. Hidden Creek Aquapark

The Park District of Highland Park manages this exceptional waterpark, which is ideal for family outings while also catering to adults who may wish to swim laps. The main pool features a large wading area with sandy beach entry and a six-lane lap pool.

Among the park’s attractions are two significant water slides (73 feet and 160 feet), a drop slide, a kiddie slide, a splash pad, and a diving section.

Families can enjoy the Bayou Backyard, an expansive grassy area with plenty of space for gatherings, complemented by a concessions area at Creekside Cafe.

12. Moraine Beach

This lakeside neighborhood park is an ideal location for passive recreation, featuring an upper section with lawns and mature trees, as well as a lower section directly on the lake.

The upper area invites nature walks, picnics, and exploration of a sculpture garden, with a path leading down through a ravine to the Lake Michigan shore, where a beach typically lies during summer months.

This area often serves as Highland Park’s dog beach, available from April through November.

13. Park Avenue Boat Ramp

Home to the North Shore Yacht Club, this Park District of Highland Park facility offers another access point to the lakeshore.

Individuals with a season pass may launch their boats using the concrete ramp or via the beach.

Moreover, this is a lovely place for a beach stroll, especially during the early morning hours as the sun rises over the lake.

Just behind the ramp lies Central Park, a densely wooded area featuring a playground, splash pad, and picnic grove adjacent to the parking area.

14. Heller Nature Center

Managed by the local park district, Heller Nature Center provides nature-focused programs for visitors of all ages and features an interpretive center with a live nature exhibit showcasing bees and various bird species.

It remains a popular destination within a 100-acre preserve boasting oak-hickory forests, tallgrass prairies, and natural wetlands.

During the winter, the trails are ideal for cross-country skiing, with ski rentals available at the center.

15. Prairie Wolf Forest Preserve

Located just west of Highland Park, this 435-acre Lake County forest preserve was gradually acquired in segments throughout the 1970s.

In the 1990s, a remarkable community initiative took place to restore the expansive wetlands, planting over 61,000 vegetation to foster a habitat for birds, amphibians, and reptiles.

The preserve features primarily wet prairies and calming oak woodlands, which can be explored via a 1.75-mile multi-use trail and a 1-mile nature trail equipped with interpretive signage.

For dog owners with a permit, a dedicated off-leash dog park is located a short distance north, encompassing 44 acres of fields and open water, providing ample play space for pets.