15 Best Things to Do in Highland Park (IL)

Furnished with beautiful architecture and long known as a creative hotbed, the wealthy lakeside city of Highland Park sits on the North Shore in the Chicago suburbs.

One of the many great things about Highland Park is just how accessible the Lake Michigan shore is here, with a series of lakefront parks and a Lake County Preserve in the city’s boundaries.

You’re also a matter of minutes from the Chicago Botanic Garden and the Skokie Lagoons, which are two huge Chicagoland attractions, while for three months in summer Highland Park stages the historic Ravinia Festival, which always has a star-studded bill.

Two long-distance bike paths slice through Highland Park, and the city’s downtown is everything you could want from a central commercial district.

1. Chicago Botanic Garden

Highland Park’s south end borders one of the top visitor attractions in the Chicago Area. On nine islands and covering almost 400 acres, the Chicago Botanic Garden boasts 27 different display gardens growing some 2.5 million plants.

These can be found in four different habitats recreating the natural landscapes of northeastern Illinois, with woods, prairie, wetlands (Skokie River Corridor) and lakes and shores.

A garden on this scale might be a little daunting, but you can download an app that will direct you to the plants in bloom at the time of your visit.

Alongside the dazzling horticultural displays are exhibitions of botanically-themed photography and fine art at the impressive Regenstein Center and the Plant Conservation Science Center.

2. Ravinia Festival

Where many towns have summer concert series, Highland Park’s Ravinia neighborhood has the world-famous Ravinia Festival.

This summer-long event is the oldest outdoor music festival in the country, first taking place in 1905 as entertainment at the amusement park on this site. Since 1936 the festival has been the summer residency for the Chicago Symphony Orchestra.

Involving some 150 individual performances, the festival takes place on the idyllic grounds of Ravinia Park at venues like the Pavilion (3,350 seats), the Martin Theatre (850) and Bennett Gordon Hall (450), while the sprawling lawn has a sound system so you can enjoy the performances over a picnic.

The Ravinia Festival spans all genres, and in the prestigious roll call of recent performers are Aretha Franklin, Dolly Parton, Bob Dylan, Diana Ross, Stevie Nicks, Brian Wilson, Lady Gaga, Herbie Hancock, Smokey Robinson and Blondie.

3. Rosewood Beach

At the foot of wooded bluffs and connected by a boardwalk is a fabulous place to relax by Lake Michigan in summer. The pride of the Park District of Highland Park.

Rosewood Beach is made up of a guarded swimming beach, a recreation beach and an educational “nature cove”.

This is accompanied by a unique and modern interpretive center, serving as an anchor for all kinds of programs for people of all ages.

Able to accommodate up to 50 people, this space is also rented out for birthday parties and other events. To access Rosewood Beach you’ll need a beach pass, free for Highland Park residents and available for the day or season for non-residents.

4. Architecture Tours

Developed steadily from the 1880s onwards, Highland Park is blessed with a staggering variety of significant architecture.

Frank Lloyd Wright contributed several buildings, along with luminaries like 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 famous building here by Wright is the Willits House (1901), which can be viewed from the outside at 1445 Sheridan Rd, and is held as one of the first great Prairie School projects.

The Chicago Architecture Center organizes regular guided walks through the city, and these last for two hours.

Alternatively you can head to the Historic Preservation Commission page on the City Hall website for a choice of self-guided tours, with themed walks for works by Seyfarth and Van Bergen in particular.

5. Downtown Highland Park

A few blocks in from the lakeshore, and right next to the Metra station, Highland Park has a downtown commercial district that is full of life and teeming with shops and restaurants.

These can be found on both sides of the tracks, on pedestrian-friendly streets, dotted with trees and endowed with several places to take a seat and watch the world go by.

Shoppers will find fashion boutiques, furniture shops, antiques and collectibles stores, jewelers, a gift shop, shoe shop and much more.

These are complemented by an amazing diversity of tea rooms, cafes, bakeries, pancake houses, ice cream parlors, sandwich shops and restaurants for everything from hot dogs, deep-dish, Thai, pan-Asian, contemporary American, sushi and tamales.

6. Skokie Lagoons

In the 1930s the Civilian Conservations Corps (CCC) took part in a massive project dredging the wetlands south of the present Chicago Botanic Garden to create a sequence of seven artificial lagoons on the Skokie River.

In almost 900 acres these remain a big draw for visitors, whether you want to hike or ride a bike on land or hit the water, renting a craft from Chicago River Canoe and Kayak.

Fringed by woods, picnic areas and lots of safe places to go ashore, the lagoons are a joy to explore, and are popular with anglers for their high quantities of crappie, channel catfish, largemouth bass and many more species.

7. Sunset Woods Park

Acquired in stages from 1920 to 1949, this cherished 34-acre park next to downtown Highland Park contains sizable nature reserves comprising Mesic Closed Savanna and ephemeral wetlands.

Elsewhere there’s a wealth of facilities for recreation, with a tennis court, basketball court, baseball diamond, multi-use field, as well as a picnic area and shelter.

Perhaps Sunset Woods Park’s enduring feature is its children’s playground with separate areas for children up to and over five years old. This has recently been updated, retaining the Rocket Ship feature that has caught kids’ imaginations for generations.

8. Fort Sheridan Forest Preserve

A couple of stops on the Metra and you’ll be at a stunning natural location offering free public access to the lakeshore.

As you can tell from the name, Fort Sheridan Forest Preserve is on the site of a former army base, which was conceived by the eminent landscape designer O.C. Simonds (1855–1931) to merge seamlessly with the land’s bluffs, ravines, savanna and lakeshore.

Well over a century later, the preserve is a prime birding destination with 236 different species recorded at this spot.

There are almost four miles of trails scurrying through the preserve, and a must see is the glorious lakeside overlook atop a 70-foot bluff.

9. Skokie Valley Bike Trail

One of a pair of bike paths traveling north to south through Highland Park, the Skokie Valley Bike Trail is around ten miles long and paved with asphalt for a smooth ride.

As the name tells you, the route is along the Skokie Valley, and for much of the trail you’ll be riding with the railroad tracks on the west side and I-41 to the east.

The southern trailhead is at the very southern end of Highland Park, off Lake Cook Road, close to the Chicago Botanic Garden.

In this peaceful strip of greenery you’ll rarely have to contend with road traffic and will pass through quiet linear parks like Buckthorn Park.

10. Robert McClory Bike Path

A long line of picture perfect North Shore communities are linked by this 25-mile bike path. Starting not far south of Highland Park at Braeside Metra station, the Robert McClory Bike Path shoots north through the length of Lake County as far as the Wisconsin line.

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

The path requires a few short detours in Highland Park, but runs through residential areas and a series of linear parks, and also skirts the west flank of the beautiful Fort Sheridan Forest Preserve.

11. Hidden Creek Aquapark

The Park District of Highland Park operates this excellent water park, perfect for family days out but also a decent choice for adults who want to swim some laps. The main pool merges a large wading area with beach entry and a six-lane lap pool.

Among the attractions are two main water slides (73 feet and 160 feet), a drop slide, a kiddie slide, a splash pad and a diving area.

Families can park themselves at Bayou Backyard, a generous grassy space with plenty of room for everyone, and there’s a concessions area at Creekside Cafe.

12. Moraine Beach

This lakeside neighborhood park is perfect for passive recreation, with an upper section that has lawns and mature trees and a lower section right by the lake.

In the upper area you can take nature walks, go for picnics and admire a sculpture area. A path here will lead you down through a ravine to the Lake Michigan Shore, where there’s normally a beach in the summer months.

This is also usually the setting for Highland Park’s dog beach, accessible April through November.

13. Park Avenue Boat Ramp

Home to the North Shore Yacht Club, this Park District of Highland Park facility is another place in the city where you can get onto the lakeshore.

People with a season pass can launch their boats from the concrete ramp, but also from the sand.

And for everyone else, this is somewhere to take a stroll on the beach, with gorgeous views early in the day when the sun is coming up over the lake.

And just behind, you’ve got Central Park, a densely wooded space with a playground, splash pad and picnic grove by the parking area.

14. Heller Nature Center

Run by the local park district, Heller Nature Center offers nature-oriented programs for all ages, and also has an interpretive center and a live nature exhibit with bees and several bird species.

But the center continues to be a popular location, in a 100-acre preserve of oak-hickory forest, tallgrass prairie and natural wetland.

When winter comes around the trails are ideal for cross-country skiing, and you can rent a pair of skis from the center.

15. Prairie Wolf Forest Preserve

Just west of Highland Park is a 435-acre Lake County forest preserve rescued in blocks in the 1970s.

In the 1990s there was a wonderful community effort to restore the sweeping wetlands here, planting over 61,000 plants to create a habitat for birds, amphibians and reptiles.

The other habitats at Prairie Wolf are mainly wet prairie and calming oak woodland that you can discover on a 1.75-mile multi-use trail and via a 1-mile nature trail with interpretive boards.

If you have a four-legged friend and a permit, there’s a separate off-leash dog park a short way north with 44 acres of fields and also open water where puppers will have the time of their lives.