Welcome to Highwood. Highwood is the North Shore’s destination for festivals, food & family fun! The beautiful Everts Park, in the heart of downtown Highwood, hosts many of Highwood’s festivals including the weekly Evening Market, Garlic Fest, Bloody Mary Fest & more! The city is a small, family-oriented town that draws people from of all the surrounding suburbs to dine, drink, shop and be entertained. Highwood is on the Metra line, offers wonderful restaurants and bars, bike trails and parks (some right on Lake Michigan), great Highland Park schools, and a long tradition of community spirit.