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!
Have a Farm Fresh Time at the Devonshire County Fair
Join us for a day filled with fall fun at the Devonshire County Fair. Delight in entertaining performances, bounce houses, a petting zoo and so much more at this family-friendly event. Take a leisurely ride on the hay wagon, compete in lively field games, or explore your creative side with arts and crafts.
Date: October 8
Time: 12:30-3:30PM
Cost: $15
Location: Devonshire Cultural Center, 4400 Greenwood St, Skokie
More info: skokieparks.org
An Awesome Afternoon at AutumnFest
Experience the vibrant spirit of fall at the Northbrook AutumnFest! Join for a day of family-friendly fun and festivities, featuring pumpkin decorating, live music, amazing food vendors, and games for all ages. Explore the arts and crafts booths, take a scenic hayride, and savor the flavors of the season.
Date: October 7
Time: 2-5PM
Cost: Free
Location: Meadowhill Park, 1479 Maple Ave, Northbrook
More info: nbparks.org
Sip and Stroll at the Wilmette Wine Walk
Enjoy the fall weather while strolling through the heart of Wilmette’s Central Business District. The Wilmette Wine Walk combines shopping, wine, and good company for the perfect Saturday afternoon. Along the way, stop by your favorite local businesses that are supporting the Boys Hope Girls Hope of Illinois through this event.
Date: October 7
Time: 4-6PM
Cost: $50
Location: Various Locations in Wilmette Central Business District
More info: wilmettekenilworth.com
Ready, Set, RUN!
The world-famous Bank of America Chicago Marathon is this Sunday! Follow the race route to watch some of the best runners in the world (and maybe a few of your friends and neighbors) pass through the city streets. Enjoy our beautiful downtown while supporting the runners with loud cheers, a sign, and some high-fives.
Date: October 8
Time: Starts at 7:30AM
Cost: Free to watch!
Location: Grant Park, 337 E Randolph, Downtown Chicago
More info: chicagomarathon.com
Rock Out and Celebrate Indigenous Peoples’ Day
Indigenous Peoples’ Day Chicago is an annual artistic and cultural event that shines a spotlight on Native American musicians while advocating for the official recognition of Indigenous Peoples’ Day in Chicago. This event is a testament to the artistic and cultural pride within Chicago’s Native American and Indigenous communities, fostering a legacy for generations to come.
Date: October 8-9
Time: 5:30-10PM
Cost: Free
Location: Chop Shop, 2033 W North Ave, Wicker Park
More info: skypeopleentertainment.com
Raise Your Glass at Lincoln Park Wine Fest
Indulge in a weekend of wine, music, and merriment at the Lincoln Park Wine Fest! This annual event invites oenophiles to savor a curated selection of wines from around the world while enjoying live music, gourmet bites, and fun activities. Whether you’re a seasoned wine lover or simply looking for a delightful way to spend a day outdoors, the Lincoln Park Wine Fest offers the perfect blend of flavors and entertainment.
Date: October 6-8
Time: Fri 5-10PM, Sat 11AM-10PM, Sun 11AM-7PM
Cost: Free
Location: 1001 W Wrightwood Ave, Lincoln Park
More info: chicagoevents.com
Get Your Game Face on at Extra Life
Step into an immersive world at the Extra Life Chicago Gaming Convention, where players and enthusiasts unite for a weekend of epic adventures and camaraderie, benefiting Children’s Miracle Network Hospitals. From tabletop classics to cutting-edge video games, attendees can engage in exciting tournaments, discover the latest releases, and connect with fellow gamers while raising money for a great cause.
Date: October 7
Time: 10AM-5PM
Cost: $20+
Location: Ann & Robert H. Lurie Children’s Hospital, 225 E Chicago Ave, The Loop
More info: helpmakemiracles.org
Brews with a View at Chicago Beer Fest
Raise your glass and savor the vibrant flavors of the Windy City at the Chicago Beer Fest! This annual celebration of craft brewing brings together beer enthusiasts from near and far to experience a diverse selection of brews. Attendees can sample an array of craft beers from both local and national breweries, all while enjoying live music and delicious food offerings.
Date: October 7
Time: 7-11PM
Cost: $50+
Location: The Field Museum, 1400 S Lake Shore Dr
More info: thechicagobeerfestival.com
