Things To Do This Weekend September 25-27, 2026

By: Stephanie Wylie 09/22/2026

With a cold stein in one hand, a pretzel around your neck, and an axe at the ready, autumn is officially making its grand entrance across Lake County. Whether you are looking to test your strength in a traditional stein-holding contest, sip your way through 50 wines or indulge in fresh, warm apple donuts, this weekend offers no shortage of ways to celebrate the season. From lively Bavarian fests and family-friendly beer gardens to high-end architectural galas, here are five can't-miss local events to kick off fall.

Here are the top things to do this weekend September 25-27, 2026 in the land of lakes.

1. Oktoberfest in Highland Park

Stein in hand, pretzel around the neck, axe at the ready. Highland Park's Oktoberfest celebration returns to the heart of the Ravinia District. The entertainment kicks off with a Bavarian dance performance, followed by Alpine Thunder, a stein-holding contest and Icons of Country closes out the evening. In the park, a full bier hall tent anchors the grounds alongside hammerschlagen, a high striker, axe throwing, fowling, cornhole and ring-o-ring. Pretzel necklaces, photo opportunities and meet-and-greets with Disney's characters are all part of the family-friendly programming. Lynfred Winery and Steep Ravine Brewing Company handle the beverages, while a variety of vendors take care of any kind of craving. Details are at EnjoyHighlandPark.com.

Saturday, September 26; 4 to 8 p.m. Free admission. Jens Jensen Park, 540 Roger Williams Ave., Highland Park.

2. Oktoberfest presented by Mainstreet Libertyville and GLMV Chamber

MainStreet Libertyville and the GLMV Chamber of Commerce host the fifth annual Oktoberfest at the Mickey Finn's Brewery back lot. Saturday afternoon from noon to 5 p.m., the Lake County Libation Trail partner becomes Familygarten, a family-friendly window designed for parents who want to enjoy a seasonal sip while the kids take part in their own activities. The full weekend features live music, a selection of seasonal brews, food and traditional Bavarian bier sports including hammerschlagen and masskrugstemmen. Dirndls, lederhosen and other German attire are strongly encouraged. For more information, visit MainStreetLibertyville.org.

Friday-Saturday, September 25-26; Fri.: 5 to 10 p.m. and Sat.: Noon to 10 p.m. Tickets start at $25 and comes with a commemorative stein and one beer ticket. Mickey Finn’s Brewery, 345 N. Milwaukee Ave., Libertyville. 

3. Dance 830 12th Annual Gala at Citadel Theatre Co.

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Not every gala gets to happen inside a work of architecture. Citadel Theatre's 12th annual Dance 830 Gala takes place Saturday, Sept. 26 at a property designed by renowned architect David Adler serving as one of the North Shore's most distinguished private event settings. The evening features a tour of the select rooms of the Adler Estate, cocktails, culinary stations, passed hors d'oeuvres and a live and silent auction. The Lake Forest events is also highlighted by the gala's signature dance, entertainment and a paddle race. The Gentlemen of Leisure Band takes over for dancing, accompanied by a dessert buffet. Tickets are available at CitadelTheatre.org.

Saturday, September 26; 5 to 11 p.m. Tickets start at $275. Adler Estate, 830 N. Green Bay Rd., Lake Forest. 

4. Fall Wine Walk in Antioch

Fifty wines, more than 30 stops, one commemorative glass and a free bottle at the end. The Fall Wine Walk takes over downtown Antioch on Saturday, Sept. 26. The self-guided event winds through more than 30 participating restaurants, retailers and businesses, with wine samples available at each stop. Tickets include a celebratory wine glass, a keepsake tote bag, a raffle entry and a bonus bottle of wine to take home. Tickets are available at Antioch.IL.gov.

Saturday, September 26; Noon to 4 p.m. Tickets start at $49. Sequoit Creek Park, 845 Main St., Antioch. 

5. Apple Fest in Historic Downtown Long Grove

Fresh. Baked. Caramel-dipped. Candied. Wine. Sangria. Long Grove’s Apple Fest has mastered every possible way to enjoy the fruit. The annual Apple Fest fills three days with apple-forward food, local artisans, live music and a charming downtown autumn atmosphere. Apple pies, donuts, caramel and candied apples, apple wine and apple sangria anchor the food offerings, supplemented by the menus of Long Grove's local restaurants operating throughout the festival. Live acts include 7th Heaven, American English, Kashmir and more. Artisans from across the area set up to showcase handmade goods. Updates are available at LongGrove.org.

Friday-Sunday, September 25-27; Fri.: Noon to 11 p.m., Sat.: 10 a.m. to 11 p.m. and Sun.: 10 a.m. to 6 p.m. Admission starts at $7 and children under 12 are free. Historic Downtown Long Grove, various locations on Old McHenry and Robert Parker Coffin Roads, Long Grove. 

For more things to do this weekend September 25-27, continue here. To see all of the top happenings in September, click here.