Embrace the crisp fall days with exciting activities that’ll make your autumn glow. From checking out charming boutiques to savoring pumpkin spice treats at seasonal festivals, there is so much to see and enjoy. Venture into fall foliage trails and local landmarks to infuse a dash of adventure into your autumn plans. Don’t miss out on these activities scheduled for this weekend to fully savor the changing leaves!

Rock Out with the Wilmette Block Party

Located in the heart of downtown Wilmette, the 2023 Wilmette Block Party will feature an array of activities and entertainment for all ages. From live music performances by local talents to a diverse selection of food trucks offering culinary delights, the event aims to create an atmosphere of fun, connection, and celebration. 

Date: September 9 
Time: 12PM 
Cost: Free 
Location: Wilmette Village Center, 1101 Lake Ave 
More info: wilmettepark.org

Learn More About Lenny Bruce Onstage at Northlight

I’m Not a Comedian, I’m Lenny Bruce at Northlight Theatre in Skokie is a riveting theatrical experience that delves into the provocative and influential life of legendary comedian Lenny Bruce. This gripping one-man show offers an exploration of Bruce’s groundbreaking comedy and the struggles he faced while pushing the boundaries of free speech.

Date: September 9 
Time: 2PM and 8PM 
Cost: $34+ 
Location: North Shore Center for Performing Arts, 9501 Skokie Blvd 
More info: northshorecenter.org

Vroom Over to the Vintage Car Show

The Vintage Car Show in Highland Park promises a nostalgic journey through automotive history. This event is a true delight for car enthusiasts and history buffs alike: from classic muscle cars to elegant pre-war models, visitors can expect to marvel at the craftsmanship and design of a bygone era.  

Date: September 9 
Time: 12-4PM 
Cost: Free 
Location: The Lot Highland Park, 1707 St Johns Ave 
More info: enjoyhighlandpark.com

Craftsmanship & Community at the Renegade Craft Fair

Get ready for a vibrant showcase of creativity, craftsmanship, and artistic talent at the Renegade Craft Fair. Discover one-of-a-kind treasures, engage with passionate creators, and support the thriving independent maker community. With live music, food vendors, and a lively atmosphere, the Renegade Craft Fair promises an amazing experience celebrating the beauty of handmade goods.

Date: September 9-10 
Time: 11AM-7PM 
Cost: Free 
Location: Wicker Park, between Damen Ave and Ashland Ave 
More info: renegadecraft.com

Celebrate the Arts in Lakeview

The Lakeview Festival of the Arts is a vibrant celebration of creativity that transforms Lakeview into a hub of artistic expression. Attendees can explore a diverse array of unique artworks, interact with talented artists, and savor a medley of culinary delights from local food vendors.

Date: September 9-10 
Time: 11AM-7PM 
Cost: Free 
Location: Lakeview, along Broadway between Belmont and Hawthorne 
More info: lakevieweastfestivalofthearts.com

Savor the World at Dumpling Fest

World Dumpling Fest is a culinary journey that transcends borders and tantalizes taste buds. From steaming, savory potstickers to delicate, sweet dessert dumplings, this festival offers a tantalizing exploration of dumpling diversity. As visitors stroll through Logan Square, they’re treated to a mouthwatering world tour, savoring dumplings from Asia to Europe and beyond. 

Date: September 9 
Time: 12-7PM 
Cost: Free  
Location: Logan Square, 3150 W Logan Blvd 
More info: starevents.com

Come Taste it All at Taste of Chicago

The Taste of Chicago is a delectable summer extravaganza that captures the heart and palate of the Windy City. This iconic food festival, held annually in Grant Park, is a culinary odyssey that brings together the city’s foodies for lots of fun. Beyond the food, live music performances, art installations, and family-friendly activities add to the festive atmosphere.

Date: September 8-10 
Time: 11AM-9PM 
Cost: Free 
Location: Grant Park, 301 S Columbus Dr 
More info: chicago.gov

Raise Your Steins at Oktoberfest

German American Oktoberfest paints a vivid tapestry of German culture with traditional food, music, and beer. From bratwurst and pretzels to the lively oompah bands, Oktoberfest immerses visitors in the rich traditions of Germany. The event’s welcoming atmosphere, complete with traditional Bavarian dance and family-friendly activities, is a cherished Lincoln Square tradition.

Date: September 8-10 
Time: Fri 5-11PM; Sat 12-11PM; Sun 12-10PM 
Cost: Free 
Location: Lincoln Square, between Lincoln Ave and Leland Ave 
More info: germanday.com