Celebrate Highwood is proud to announce its 2025 series of family-friendly festivals and events which includes:

• Highwood’s Weekly Wednesday Evening Gourmet Market

June 4–August 27 4:30–9 PM (no market July 2)

Everts Park (111 North Ave.)

A weekly outdoor market of this caliber is hard to find. With its ‘Live Evening Concert Series ’‘Ravinia Festival-like’ atmosphere and over 60 vendors each week this Evening Market brings community together to enjoy delicious food and drinks local wares live music and the great outdoors in a family festival setting.

• Inferno Fest

Wednesday June 25 4:30 – 9 PM Everts Park (111 North Ave.)

Celebrate Highwood is fired up to bring you summer’s hottest event Inferno Fest back with spicy food and beverages to test the taste buds of the most fearless food enthusiasts!

• Margarita Night

Wednesday July 16 4:30–9 PM Everts Park (111 North Ave.)

This festive theme night invites attendees to dress in their favorite Jimmy Buffet-style Parrothead and Hawaiian gear to party to the sounds of a Jimmy Buffet tribute band. There will be beach balls flamingos margaritas Mexican food key lime pie and more!

• Highwood Days with NEW Taste of Highwood Thursday July 17- Sunday July 20

Highwood Days Carnival Downtown Highwood Metra Station Parking Lot

Taste of Highwood (location TBA)

Recognized as the City’s oldest festival Highwood Days features one of the area’s largest carnivals with rides games live music and more! The addition of the Taste of Highwood brings together the City’s numerous restaurants and specialty food operations to offer a wide range of mouth-watering creations along with full booze tents. Attendees will enjoy casting their vote for the People's Choice Award for the Best Taste of Highwood.

• Highwood 5K Run Walk & Stroll

Saturday July 19 9 AM Downtown Highwood

The public is invited to put on their sneakers and grab their family friends strollers and pets to join this fun run walk and stroll. The course starts in Downtown Highwood and guides you along the beautiful lake front trail and through historic Fort Sheridan and then back again. 

• Garlic Fest

Wednesday August 13 4:30–9 PM Everts Park (111 North Ave.)

The smell of garlic brings people from near and far to this festive food-filled fest that showcases a plethora of dishes with the ever-popular taste (and scent) of garlic with live music and plenty of family-friendly activities to entertain all evening long. Attendees come to sample a variety of sweet and savory garlic creations from out-of-the-ordinary garlic-infused chocolate cookies ice cream cupcakes and cocktails to the classic savory options like pastas sandwiches sauces and spreads. The Fest features a Taste of Garlic Competition for the best Savory and Sweet creations and the innovative dishes never disappoint!

• Bloody Mary Fest

Sunday August 17 10 AM-5 PM Everts Park (111 North Ave.)

Celebrate Highwood is once again putting a spin on this fan favorite event inviting all types of bloody mixologists to tempt taste buds with various types of tomato-based beverages combined with a variety of spirits beer or other ingredients. From Micheladas to Red Snappers (gin) Bloody Marias (tequila) and more this event is perfect for fest goers with adventurous palates to sample their favorite spirit in a bloody-based cocktail. Vendors will compete for the Proud Mary Award.

• Nashwood

Labor Day Weekend August 29-31 Downtown Highwood

Watch Highwood transform into Nashville over Labor Day weekend. Highwood restaurants and bars will feature 100 free live country southern blues classic and contemporary rock from beginning Friday happy hour and running all day and evening Saturday and Sunday. 

• The Annual Great Highwood Pumpkin Festival & Skeletons on Display

October 3–5 Downtown Highwood (Community Night & Opening Carnival Oct. 2)

The Great Highwood Pumpkin Festival and Skeletons on Display is the biggest outdoor celebration on Chicago’s North Shore featuring all-you-can-carve pumpkins nightly lightings of pumpkin-filled walls carnival rides costume contests trick or treating two stages with live music and entertainment hundreds of skeleton displays food and beverage vendors and so much more!

• Elf Invasion Pub Crawl

Saturday December 6 5:30 PM-Bar Close

Calling all elves to come out and get “Elfed Up’ at the Annual "Elf Invasion Pub Crawl." The public is invited to channel their inner elf dress the part and join a troupe of elves as they visit the City of Highwood’s most popular establishments to enjoy live music food and drink specials and raffle prizes.