Highwood Days, the city’s oldest festival, returns from July 17–19, 2026, offering a weekend of classic summer entertainment. The event features one of the region’s most popular carnivals in the Downtown Highwood Metra Station parking lot, complete with rides, games, and a live music lineup.Running concurrently at Everts Park, the second annual Taste of Highwood showcases the community's renowned culinary scene. Visitors can sample creations from local restaurants and specialty food vendors while casting their votes for the "People's Choice Award." The festivities also include a 5K Run, Walk & Stroll on Saturday morning, making it a comprehensive weekend of community celebration and North Shore dining.

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