Highwood, IL

Highwood is a lively, compact suburb on Chicago’s North Shore with a population of around 5,000. Located right beside the historic grounds of Fort Sheridan, the town grew alongside the army post in the late 19th century and has kept its distinct, down-to-earth character ever since. Today, it is best known across the region for its walkable downtown, fantastic dining scene, and community celebrations like the annual Great Highwood Pumpkin Fest.

ATTRSpiro Bolos / CC BY-SA 2.0

Sitting just minutes from Lake Michigan, Highwood borders Highland Park and the Fort Sheridan Forest Preserve, giving residents quick access to scenic bluffs, woodlands, and shoreline trails. Families benefit from well-regarded public schools, sharing Highland Park High School with their neighbor to the south. With an easy Metra train commute into Chicago and a rich lineup of local parks, youth arts programs, and neighborhood eateries, Highwood offers a friendly, active setting with a charm all its own.