Nature and cycling trails
Several hiking trails and cycling routes wind through the city of Highland Park, which lies roughly 40km (25 miles) north of Chicago.
The origins of the Green Bay Trail, which runs parallel to the city’s Metra North commuter rail line, are believed to date back to the Ice Age, when woolly mammoths used it as a migration route.
Today the trail is bordered by restaurants, shops and parks, where monarch butterflies hover among the milkweed.
Architecturally designed houses
Property in Highland Park is substantial and the city’s generous, wood-framed homes complement its sprawling woodland setting. Several esteemed 20th-century architects built in here, including WW Boyington, Howard Van Doren Shaw and Frank Lloyd Wright.
The latter’s Willits House is deemed one of America’s first important prairie houses, which typically feature low-rise buildings with large, overhanging eaves.
There are four public beaches in Highland Park with access to Lake Michigan, including the newly renovated Rosewood Beach with its sheltered swimming cove.
The nearby North Shore Yacht Club on Park Avenue attracts a flotilla of kayakers and sailors each weekend.
Conceived as an amusement park and later run as an artists’ colony, Ravinia today is famous for its annual open-air music festival. The summer home of the Chicago Symphony Orchestra since 1936, the festival also hosts pop and jazz concerts. Over the years picnic-goers have sprawled across the lawns, listening to artists including Louis Armstrong, who played here in the 1950s. More recently, the festival’s highlights have ranged from performances by cellist Yo-Yo Ma to works by Stephen Sondheim, the composer.
Highland Park has been home to some illustrious residents: Jill Stein, the Green Party’s 2016 nominee for US president, grew up here, as did astronaut John Grunsfeld and internet activist Aaron Swartz.
Basketball star Michael Jordan built a seven-acre estate in Highland Park, which features a regulation-sized basketball gymnasium and a cigar room. His jersey number, 23, is emblazoned on the front gates.
Photographs: Scott Olson/Getty Images; Mark McMahon/Corbis via Getty Images; Wayne Cable; PhotoStock-Israel/Alamy; Steve Bly/Alamy
Related article: Michael Jordan claims victory in China trademark dispute
Related article: A taste of Highland Park
Related article: Five reasons to live in Oud-Zuid, Amsterdam