Highwood enjoys the good life with a thriving dining scene, festivals, and nightlife that attracts visitors from across the North Shore. Aptly named for its high elevation relative to Lake Michigan and its wooded setting, Highwood is located just north of Highland Park. 

The city is known for its award-winning restaurants, offering everything from Italian to French cuisine. In the summertime, residents enjoy Highwood’s popular Evening Markets, recognized among the best on the North Shore. The city’s oldest festivals, the annual Holiday Lighting Ceremony and Highwood Days, are always a favorite of the residents. But it has become most well-known for its Pumpkin Festival with a record setting number of carved pumpkins on display each year.

Real estate varies from duplexes and ranches to luxury apartments, condominiums, and single-family homes. The community also includes part of Fort Sheridan, a master-planned residential community and national historic landmark that was originally a U.S. military base.