Things To Do This Weekend September 19-21, 2025

By: Stephanie Wylie 09/18/2025

Get ready for a jam-packed weekend as communities across Lake County celebrate the change in seasons with festivals, food and fun. Downtown Deerfield will host its annual Harvest Fest while downtown Waukegan bursts with color for the 5th Annual Fiesta Sin Frontera. You can also celebrate Oktoberfest in Libertyville or enjoy the last Summer Market in Vernon Hills. No matter what you choose, there’s an event for everyone to enjoy this weekend.

Here are the top five things to do this weekend September 19-21, 2025.

1. Deerfield Harvest Fest

As the summer sun fades and the first crisp evenings of fall arrive, downtown Deerfield is preparing to transform into a hub of food, music and celebration. The Village of Deerfield and the DBR Chamber of Commerce will host the annual Harvest Fest. The day begins with the weekly Farmers Market, a staple in downtown Deerfield as well as the Touch a Truck event. In the afternoon, vintage and specialty vehicles will take center stage during the Cruise into Harvest Fest Car Show. When the sun sets, Harvest Fest comes alive with live music featuring Roger That, Delta Pines, Blooze Brothers and Sixteen Candles, a variety of restaurant offerings and a beer and wine tent. From food tents serving local favorites to the soundtrack of live bands echoing through downtown, the evening promises something for everyone. More details are available at Deerfield.IL.US. 

Saturday, September 20; Farmers Market and Touch a Truck: 7 a.m.-12:30 p.m. Deerfield Harvest Festival: 2:30-10 p.m. Free admission. Parking available in Downtown Deerfield Metra, Lindemann and the Village of Deerfield Parking Lots. Downtown Deerfield, Robert York and Park Avenues, Deerfield. 

2. 5th Annual Fiesta Sin Frontera in Waukegan 

Downtown Waukegan will burst into color, sound and flavor as the city hosts the 5th Annual Fiesta Sin Frontera, a daylong celebration of Mexican heritage and community pride. The festival features a packed schedule of live entertainment, traditional performances and family activities. The centerpiece of the evening, the Grito de Independencia, will take place at 6:30 p.m., honoring Mexico’s historic call for freedom. Festivalgoers can expect the lively energy of folklórico dancers representing traditions from multiple countries, the vibrant sounds of live music and the playful spirit of chinelos — masked dancers rooted in Mexican Carnival. Fiesta Sin Frontera delivers with a wide selection of Mexican street food. It reflects not only the city’s large Latino population but also the spirit of inclusion and celebration that resonates across the community. More information can be found at WaukeganIL.Gov. 

Saturday, September 20; 11 a.m.- 11 p.m. Free admission. City of Waukegan, 32 N. Genesee St., Waukegan. 

3. Oktoberfest Presented by MainStreet Libertyville

Downtown Libertyville is gearing up for a weekend filled with music, beer and Bavarian tradition as MainStreet Libertyville and the GLMV Chamber of Commerce present Oktoberfest at Lake County Libation Trail partner Mickey Finn’s Brewery. The festival kicks off Friday evening and continues Saturday with a family-friendly session before closing with an adults-only celebration that night. Don your lederhosen or dirndl and join neighbors in raising a glass to tradition. Oktoberfest will feature live music, seasonal brews, hearty Bavarian-inspired food and traditional bier sports, including Hammerschlagen and Masskrugstemmen, designed to bring a touch of Munich to Lake County. Tickets and additional information are available at MainStreetLibertyville.org.

Friday-Saturday, September 19-20; Fri.: 5-10 p.m. and Sat.: 1-4 p.m. Tickets start at $28. Mickey Finn’s Brewery, 345 N. Milwaukee Ave., Libertyville. 

4. Hawthorn Summer Market in Vernon Hills

Shoppers and families will gather one last time this season for the Summer Market at Hawthorn Row, bringing a mix of local goods, food and community activities to the heart of Vernon Hills. Visitors can sip coffee while browsing artisan booths, discovering handcrafted goods and sampling bites from food vendors and trucks. In addition to shopping, the event will feature family-friendly activities, including a children’s storytime and community games on The Row. This weekend’s Hawthorn Summer Market is the final date in a seasonal series that kicked off in July. More information can be found at VisitHawthorn.com.

Saturday, September 20; 10 a.m.-1 p.m. Free admission. Hawthorn Row, 750 Hawthorn Row, Vernon Hills. 

5. Woman, Life, Freedom Film Festival at Wayfarer Theater

Independent cinema will take center stage in Highland Park this week as the Woman, Life, Freedom Film Festival at Wayfarer Theaters. The celebration is hosted by the Association of Iranian Film and Theatre Artists Abroad and aims to spotlight women’s resilience and creativity through powerful storytelling on screen. The annual event presents films that confront themes of gender equality, freedom of expression and the fight for liberation. By creating a platform for marginalized artists, the festival seeks to inspire both filmmakers and audiences to connect with narratives of courage and change. Tickets and a full schedule of screenings can be found at WayfarerTheaters.com. 

Sunday, September 21; 4 p.m. Adults: $15 and Children: $12. Wayfarer Theaters, 1850 Second St., Highland Park. 

For more things to do this weekend, September 19-21, 2025, click here.