Spooky Season in Highland Park

Written By City of Highland Park

Pumpkins, treats, gatherings, decor, and more… Let our guide to Spooky Season raise your spirits. Click on a calendar date below to learn more about each event. Check back often as new entries are added!

 
Calendar
Scarecrow Trail
Sep 25
Halloween Fun
Scarecrow Trail
Halloween Fun
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Halloween Fun
Witches Brine Workshop
Oct 8
Halloween Fun
Witches Brine Workshop
Halloween Fun
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Halloween Fun
Boo Bash
Oct 17
Halloween Fun
Boo Bash
Halloween Fun
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Halloween Fun
Kids Night Out: The Great Pumpkin
Oct 17
Halloween Fun
Kids Night Out: The Great Pumpkin
Halloween Fun
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Halloween Fun
Not-So-Spooky Spider Party
Oct 21
Halloween Fun
Not-So-Spooky Spider Party
Halloween Fun
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Halloween Fun
Paws & Candy Adoption Event
Oct 23
Halloween Fun
Paws & Candy Adoption Event
Halloween Fun
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Halloween Fun
Halloween Open Play Pickleball
Oct 23
Halloween Fun
Halloween Open Play Pickleball
Halloween Fun
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Halloween Fun
Scary Skate
Oct 23
Halloween Fun
Scary Skate
Halloween Fun
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Halloween Fun
Bubbleween
Oct 24
Halloween Fun
Bubbleween
Halloween Fun
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Halloween Fun
Pumpkin Pool Splash
Oct 24
Halloween Fun
Pumpkin Pool Splash
Halloween Fun
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Halloween Fun
Halloween Boo Bash
Oct 29
Halloween Fun
Halloween Boo Bash
Halloween Fun
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Halloween Fun
Halloween Bash
Oct 29
Halloween Fun
Halloween Bash
Halloween Fun
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Halloween Fun
Candy Stroll at Port Clinton
Oct 29
Halloween Fun
Candy Stroll at Port Clinton
Halloween Fun
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Halloween Fun
Ravinia District Candy Stroll
Oct 30
Halloween Fun
Ravinia District Candy Stroll
Halloween Fun
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Halloween Fun
 

Plus, check out Lynfred Winery and Steep Ravine Brewing Company! These two Highland Park establishments are participating in the 2026 Visit Lake County Spooks & Spirits Libation Trail.

Dining
Lynfred Winery
Downtown Highland Park, Taste of Highland Park, Stews & Brews, Lake County Flavor Fest 2025, 2025 Outdoor Dining, Date Night, Lake County Spooks & Spirits 2025, 2026 Flavor Festival, 2026 Outdoor Dining, Oktoberfest, Lake County Spooks & Spirits 2026
Lynfred Winery
Downtown Highland Park, Taste of Highland Park, Stews & Brews, Lake County Flavor Fest 2025, 2025 Outdoor Dining, Date Night, Lake County Spooks & Spirits 2025, 2026 Flavor Festival, 2026 Outdoor Dining, Oktoberfest, Lake County Spooks & Spirits 2026

1823 St. Johns Ave. | 847.780.3853
lynfredwinery.com/highland-park

Illinois' oldest and largest continually-operating family winery

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Downtown Highland Park, Taste of Highland Park, Stews & Brews, Lake County Flavor Fest 2025, 2025 Outdoor Dining, Date Night, Lake County Spooks & Spirits 2025, 2026 Flavor Festival, 2026 Outdoor Dining, Oktoberfest, Lake County Spooks & Spirits 2026
Steep Ravine Brewing Company
Ravinia District, Taste of Highland Park, World Food & Music Fest, Oktoberfest, Decades, Stews & Brews, Lake County Flavor Fest 2025, Ravinia Fest Dining 2025, 2025 Outdoor Dining, Vintage Car Show, Margarita Era, Date Night, Lake County Spooks & Spirits 2025, 2026 Outdoor Dining, FIFA World Cup 2026, Lake County Spooks & Spirits 2026
Steep Ravine Brewing Company
Ravinia District, Taste of Highland Park, World Food & Music Fest, Oktoberfest, Decades, Stews & Brews, Lake County Flavor Fest 2025, Ravinia Fest Dining 2025, 2025 Outdoor Dining, Vintage Car Show, Margarita Era, Date Night, Lake County Spooks & Spirits 2025, 2026 Outdoor Dining, FIFA World Cup 2026, Lake County Spooks & Spirits 2026

582 Roger Williams Ave. | 773.362.5553
steepravinebrewingcompany.com

Brewery & restaurant

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Ravinia District, Taste of Highland Park, World Food & Music Fest, Oktoberfest, Decades, Stews & Brews, Lake County Flavor Fest 2025, Ravinia Fest Dining 2025, 2025 Outdoor Dining, Vintage Car Show, Margarita Era, Date Night, Lake County Spooks & Spirits 2025, 2026 Outdoor Dining, FIFA World Cup 2026, Lake County Spooks & Spirits 2026
Learn more about the Libation Trail
 

Contact Marketing Coordinator, Diane Larson, to have your Halloween event, menu, or decor featured.

City of Highland Park
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