Best events in
Highwood

Looking for events or things to do in Highwood, IL? Known as a dining and nightlife destination on the North Shore, its walkable downtown is packed with independent venues. The local scene is fueled by a mix of weekly community markets and distinctive annual food and music festivals.

Downtown Highwood's pedestrian-friendly layout makes it easy to build an evening by visiting a distillery like 28 Mile Distilling Company before catching a set at The Toadstool Pub.
Live music is a local staple, with venues ranging from the vinyl-focused Mojo's Vinyl Bar to craft breweries and cocktail lounges.
Everts Park serves as a central hub for community gatherings, including the weekly Highwood Evening Gourmet Market and The Great Highwood Pumpkin Fest.

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Christian Heritage Academy

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11/15- Wheeling, IL- Friendsgiving in Wine Country

Sun, Nov 15 • 5:00 PM

583 N Milwaukee Ave

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November 28, 2026 TCG Tradezone Chicago O'Hare Marriott

Sat, Nov 28 • 11:00 AM

Marriott Chicago O’Hare

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MBA Brasil 2026

Friday • 2:00 PM

Kellogg Global Hub

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Chicago | Премʼєра фільму "КІЛЛХАУС " | “KILLHOUSE”

Thu, Nov 12 • 7:00 PM

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Check ticket price on event

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Fri, Nov 13 • 9:00 AM

Glenview Park District - Park Center

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Sat, Nov 14 • 12:00 PM

Hatty's Club

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Chicago Speed Dating for Singles Age 55+ ♥ Mt Prospect, IL

Sun, Nov 15 • 2:00 PM

Mount Prospect Public House

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ОЛЕКСАНДР ПОНОМАРЬОВ CHICAGO благодійний концерт Revived Soldiers Ukraine

Sun, Nov 15 • 6:00 PM

Christian Heritage Academy

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11/15- Wheeling, IL- Friendsgiving in Wine Country

Sun, Nov 15 • 5:00 PM

583 N Milwaukee Ave

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November 28, 2026 TCG Tradezone Chicago O'Hare Marriott

Sat, Nov 28 • 11:00 AM

Marriott Chicago O’Hare

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Today • 1:00 PM GMT

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The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

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This Little World: a New History of Tudor and Stuart England

Wed, Nov 11 • 7:30 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Thu, Nov 12 • 7:00 PM EST

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Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Today • 1:00 PM GMT

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Wed, Nov 11 • 7:30 PM GMT

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Thu, Nov 12 • 7:00 PM EST

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Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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Wed, Nov 18 • 10:00 AM CST

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Highwood

Where can I find live music events in Highwood?

Look for performances at local pubs, bars, and distilleries. The Toadstool Pub frequently has live acts, and 28 Mile Distilling Company hosts artists in its cocktail lounge. Highwood also hosts the annual Nashwood music festival across multiple venues.

What are some popular food and drink events in Highwood?

Highwood is known for its unique food and drink festivals. The city hosts annual events focused on specific themes, including Garlic Fest and Bloody Mary Fest. The weekly Highwood Evening Gourmet Market is also a major draw in warmer months.

How can I experience nightlife in downtown Highwood?

Explore the dense collection of bars along Green Bay and Sheridan Roads. Enjoy craft beer at Broken Tee Brewing Co., sample wine at Pazzo di Vino, or visit a unique spot like Mojo's Vinyl Bar for a lively night out with great music.

Are there popular outdoor events in the area?

Yes, Everts Park is the center for many outdoor community events. It hosts the Highwood Evening Gourmet Market weekly from June through August, along with large annual celebrations like The Great Highwood Pumpkin Fest.

What's a good idea for a date night in Highwood?

A great date night could involve wine tasting or craft cocktails. Pazzo di Vino offers a tasting room and patio seating, while 28 Mile Distilling Company provides a unique atmosphere with its 1920s-style lounge and courtyard.

What kind of annual festivals does Highwood host?

Highwood hosts several creative annual festivals and pub crawls. Beyond food-centric events, the city puts on the Nashwood music festival and the themed Elf Invasion Pub Crawl, which draws crowds to various downtown establishments.

Which neighborhood in Highwood is best for finding things to do?

Downtown Highwood is the main hub for entertainment and events. Its walkable layout is packed with restaurants, bars, and venues, making it easy to enjoy an entire evening of activities without needing to drive between spots.

Where are some unique bars to check out in Highwood?

Mojo's Vinyl Bar offers a distinct experience with over 5,000 records. For a different vibe, Pazzo di Vino is a local winery with a tasting room, and 28 Mile Distilling Company features a 1920s-meets-modern aesthetic.

Events near Highwood

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Nearby cities

Chicago

Aurora

Evanston

Rolling Meadows

Naperville

Oak Park

Lisle

Kenosha

Lombard

Mokena

Wheaton

Woodridge

Barrington

Oak Brook

Tinley Park

Crystal Lake

Elgin

Oak Lawn

Skokie

Frankfort

Elmhurst

Joliet

Gurnee

St. Charles

Harvey

Highland Park

Woodstock

Plainfield

Northbrook

Orland Park

Chicago

Aurora

Evanston

Rolling Meadows

Naperville

Oak Park

Lisle

Kenosha

Lombard

Mokena

Wheaton

Woodridge

Barrington

Oak Brook

Tinley Park

Crystal Lake

Elgin

Oak Lawn

Skokie

Frankfort

Elmhurst

Joliet

Gurnee

St. Charles

Harvey