EnjoyHP Events
Get excited for a new season of alfresco dining and live, family-friendly entertainment in the heart of downtown Highland Park and beyond.
A dynamic lineup of special events and festivals returns to Downtown Highland Park AND the Ravinia District beginning this June! New this year, the City is bringing back the popular Oktoberfest event, in a new location in the Ravinia District. You can also expect to see extended hours on our most popular events, expanded event footprints, even more intergenerational programming (including special children-focused hours), and enhanced seating & dining areas. 2026 is the year to discover unique local dining, family-friendly entertainment, and weekend concerts through an exciting lineup of FREE events.
Check back soon for event details, music lineup and more!
For more information on how to be a part of the 2026 Downtown Highland Park event season as a participating vendor, entertainer, or sponsor, please contact the City’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
2026 Event Lineup
Taste of Highland Park
🍴🍸🎸
Taste of Highland Park 🍴🍸🎸
Friday, June 19 | 5 PM - 10 PM
Saturday, June 20 | 3 PM - 10 PM
Port Clinton Square (600 Central Ave.) & Central Ave. between First St. and Second St.
Highland Park’s premiere food and music festival returns in 2026 with more music, more food, and more fun! Savor the taste of summer with delicious dishes and select beverages specially curated from over one dozen local Highland Park restaurants, all while jamming out to exceptional live entertainment. Get a taste of what sets Highland Park’s restaurant scene apart on Chicago’s North Shore.
New for 2026: Enhance your experience with additional covered seating, misting fans, and a photography exhibit. Plus, families will enjoy special children-focused programming from 3 PM - 5 PM on Saturday.
Downtown Concerts at Port Clinton
🎵
Downtown Concerts at Port Clinton 🎵
Fridays, July 10 - September 25 | 6 PM - 8 PM*
Port Clinton Square (600 Central Ave.)
Spend your Friday evenings at Port Clinton with great food and great music. Enjoy 10 Friday evening concerts featuring performances from a variety of artists and genres (including special performances by Highland Park performing arts groups) and on-site food and beverage vendors. The extended finale concert will take place September 25 (from 4 PM - 8 PM) and will feature the return of the ever-popular Scarecrow Trail.
New for 2026: Take a trip around the world without ever leaving Highland Park this summer. Each week, partake in global cuisine from an onsite local Highland Park restaurant while enjoying accompanying world music. No passport neccesary.
*Concerts will not take place on July 24 or August 21. The kickoff concert will take place from 5 PM - 7 PM. The finale concert will take place from 4 PM - 8 PM.
Vintage Car Show
🚗
Vintage Car Show 🚗
Saturday, August 22 | 12 PM - 4 PM
St. Johns North Lot (525 Central Ave.)
Step back in time and experience the elegance, craftsmanship, and the nostalgia of a bygone era. Relive the golden age of automobiles at the Vintage Car Show on Saturday, August 22. Head to the St. John’s North Lot (525 Central Ave.) and peruse a fabulous array of over 200 vintage, classic, and antique vehicles, hot rods, muscle cars, and pop culture icons all while enjoying a live radio broadcast, kid-friendly activities, delicious food, and ice cold beverages.
New for 2026: Attention car lovers! The Vintage Car Show will expand onto St. Johns Ave. between Central Ave. & Park Ave. That means more cars, more nostalgia, and more fun.
Oktoberfest
🍻
Oktoberfest 🍻
Saturday, September 26 | 4 PM - 8 PM
Jens Jensen Park (540 Roger Williams Ave.)
Back by popular demand! Oktoberfest returns as a City-produced event in 2026. Enjoy classic Oktoberfest fare, entertainment, a bier hall, and games (like axe throwing, a high striker, and hammerschlagen), plus special children’s programming.
New for 2026: Oktoberfest has a new venue: Jens Jensen Park in the Ravinia District. Enjoy a lush, park-like setting while participating in all your favorite Oktoberfest activities.
📷: The Bitter Jester Foundation for the Arts provided the stage for the City of Highland Park’s 2023 Oktoberfest event.
Stews & Brews
🍲
Stews & Brews 🍲
Saturday, October 10 | 4 PM - 9 PM
Port Clinton Square (600 Central Ave.) & Central Ave. between First St. and Second St.
Stews & Brews returns to Downtown Highland Park for a fifth season! This HP-exclusive event combines two Midwestern favorites: comfort foods and beverages. Stay cozy with fire pits, heaters, hearty food, and great live music. The evening culminates with a People's Choice competition for the favorite Stew and Brew. This event is sure to warm the hearts and souls of all who attend!
New for 2026: Ramp up the cozy with even more fire pits and heat towers! Plus, enjoy extended event hours with special children-focused programming from 4 PM - 6 PM
Getting to EnjoyHP Events & Parking
Ample parking can be found throughout downtown Highland Park, including a parking garage underneath Port Clinton Square, nearby surface lots, a parking lot along St. Johns Ave., and a two-level parking deck south of Central on First St. and St. Johns. The City encourages guests to use non-motorized transportation where available. Bike racks are available at the St. Johns parking lot (525 Central Ave.) and in the immediate vicinity. Metra trains and Pace busses are other viable options.
More information about parking in the City of Highland Park is available here.
Downtown Highland Park is easily accessible via public and non-motorized transport.
Metra - take UP-N to the Highland Park station, located a 4 minute walk from The Lot.
Pace Bus - take Highland Park/Highwood Route 472 to the St. Johns/Central stop, across the street from The Lot.
Bike/Walk - from the north, take the Robert McClory Bike Trail south to Vine Ave. Head east on Vine, turning south onto St. Johns Ave. From the south, take the Robert McClory Bike Trail north along St. Johns Ave. Bike racks are available at The Lot and in the immediate vicinity.
For events in the Ravinia District, such as Oktoberfest, the public is likewise encouraged to walk or bike along the enhanced Green Bay Trail - Robert McLory Bike Trail , ride the Metra north or south to Ravinia Station at Roger Williams in the Ravinia Business District, or take a Pace Bus. If traveling by car, Highland Park is easily accessible via north Lake Shore Drive to Sheridan Road, US 41 and 294. Exit Clavey Road east to Green Bay Road and east on Roger Williams Avenue. Free parking is available.
Taste of Highland Park, Downtown Concerts, and Stews & Brews
600 Central Ave.
Vintage Car Show
525 Central Ave.
Oktoberfest
540 Roger Williams Ave.
Thank You to Our 2026 Sponsors
For sponsorship opportunities and packages, please contact Ripple Public Relations - info@ripplepublicrelations.com / 847.432.6000