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Highland Park|Local Event

Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

Celebrate Highwood Announces 2026 Series of Family-Friendly Festivals and Events

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111 North Ave

Celebrate Highwood is excited to announce its 2026 season of festivals and community events. The year begins with the Evening Gourmet Market (June 3–August 26), bringing weekly Wednesday nights of food, music, and more than 60 vendors to Everts Park. Summer officially kicks off with the Kick-off to Summer Carnival (June 5–7), followed by the fiery fun of Inferno Fest (June 24). July features Highwood Days & the 2nd Annual Taste of Highwood (July 17–19), along with the community‑favorite Highwood 5K Run, Walk & Stroll (July 18). Later in the month, Margarita Night (July 29) brings tropical energy and Jimmy Buffet–style entertainment. August highlights include Garlic Fest (August 12), celebrating creative sweet and savory garlic dishes, and Bloody Mary Fest (August 16), where mixologists showcase inventive tomato‑based cocktails. Over Labor Day weekend, Nashwood (September 4–6) transforms Downtown Highwood into a Nashville‑inspired music takeover. Fall brings the iconic Great Highwood Pumpkin Festival (October 2–4), the North Shore’s largest autumn celebration, and the year wraps up with the festive Elf Invasion Pub Crawl (December 5).

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