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Lincolnshire: Happy Times Pumpkin Fest at Didier Farms (Free)
Date: Runs Sept 16 – Oct 31.
Venue: Didier Farms, 16678 W. Aptakisic Road, Lincolnshire, IL 60069
This Chicagoland fall tradition offers amusement rides, shows, fall merchandise, pumpkins, and treats like apple cider donuts and fudge.
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Itasca: Pumpkin Patch Family Carving Fest ($40/family)
Date: Thursday, October 8, 2026 (5 PM - 7 PM)
Venue:Itasca Recreation Center, 350 E. Irving Park Road, Itasca, IL 60143
Families gather for an evening of pumpkin carving with the Itasca Park District. Pumpkins and carving tools are provided, along with a light snack and water, and a prize goes to the most creative pumpkin at the end of the night. Pre-registration is required.
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Des Plaines: Oakton Guitar Festival ($12 General Admission / $10 Students & Seniors; Workshops Free)
Date: Friday, October 9 – Saturday, October 10, 2026 (Friday workshops 1:00 PM – 4:00 PM, concert at 8:00 PM; Saturday workshops 11:00 AM – 4:00 PM, concert at 8:00 PM)
Venue: Oakton College, 1600 E. Golf Rd, Des Plaines, IL 60016
Oakton College’s seventh annual celebration of guitar virtuosity features acclaimed guitarists Randy Roos, Sheryl Bailey, Joe Lo Piccolo and Richard Gilewitz. Students and community members can bring their guitars and participate in free workshops led by the featured performers and Oakton music faculty before each evening concert. Concert admission is free for workshop attendees.
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Norridge: Fall Fest Carnival (Free Admission; Ride Wristbands $30 – $35)
Date: Friday, October 9 – Sunday, October 11, 2026 (Friday 5 PM – 10 PM, Saturday 1 PM – 10 PM, Sunday 1 PM – 6 PM)
Venue: Carnival Grounds, 7740 W. Montrose Ave, Norridge, IL 60706
Enjoy classic festival entertainment at this annual neighborhood fall carnival hosted by Windy City Amusements, Inc.. The community gathering features thrilling amusement rides, carnival skill games, traditional festival food vendors, and ongoing family-friendly entertainment. Unlimited ride specials and pay-one-price wristbands are sold on-site during designated afternoon and evening block windows.
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Hawthorn Woods: Party in the Park & Fireworks Show (Free)
Date: Friday, October 9, 2026 (5 PM; fireworks at 8 PM)
Venue: Community Park, Hawthorn Woods, IL
Originally scheduled earlier in the season and officially rescheduled to October 9, this large community celebration features food vendors, live music from 5–7 PM, a DJ beginning at 7 PM and a fireworks finale at 8 PM. Free parking is available at the designated off-site location.
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Barrington: Grove Ave Food Fest (Free)
Date: Friday, October 9, 2026 (5 PM – 8 PM)
Venue: Grove Avenue School, 900 S. Grove Ave, Barrington, IL 60010
Celebrate the first-ever Grove Ave Food Fest, hosted by the Grove PTO and bringing together families from Grove Avenue School, neighboring schools, and the Barrington community. Enjoy live music from School of Rock, face painting, and a variety of food vendors. A portion of food sales benefits Grove Avenue School, with the ELC and Sunny Hill PTOs hosting fundraising tables and the Barrington Transition Program also participating.
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East Dundee: Santa's Village Pumpkin Patch & Fall Festival ($42+)
Date: Saturday, October 10 – Monday, October 12, 2026 (11 AM–6 PM)
Venue: Santa's Village Amusement & Water Park, 601 Dundee Avenue, East Dundee, IL 60118
Santa's Village receives a full fall makeover with its amusement park and petting zoo plus pumpkin patches, a corn play pit, mini straw maze, seasonal attractions and a harvest-themed menu. The festival operates on weekends during its fall season; admission is included for qualifying season-pass holders, while other guests require park admission.
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Arlington Heights: Autumn Harvest (Free)
Date: Saturday, October 10, 2026 (11 AM–2 PM)
Venue: North School Park, 307 N. Evergreen Avenue, Arlington Heights, IL 60004
Family-friendly fall festival organized by the Village and Arlington Heights Park District featuring hayrides, a petting zoo, children's crafts, pumpkin decorating, face painting, balloon artists, live music, food vendors and the popular Scarecrow Decorating Contest. No admission or registration is required to attend.
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Buffalo Grove: Arts & Crafts Fair (Free)
Date: Saturday, October 10, 2026 (10 AM–3 PM)
Venue: Scott Jacobson Community Arts Center, 225 McHenry Road, Buffalo Grove, IL 60089
Shop a variety of handmade and specialty items from local crafters and small businesses, including seasonal and holiday gift options. The event is organized through the Buffalo Grove Park District's Community Arts Center.
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East Dundee: Art of the Fox Launch & Art Walk (Free)
Date: Saturday, October 10, 2026 (2 PM–5 PM)
Venue: Dundee Depot South Lawn, 319 N. River Street, East Dundee, IL 60118
Community arts celebration launching East Dundee's participation in the Art of the Fox initiative. Visitors can explore a self-guided public-art walk, meet participating artists, browse local art vendors and take part in family-friendly eco-focused activities.
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Elk Grove Village: Pumpkin Fest (Free)
Date: Saturday, October 10, 2026 (10 AM–3 PM)
Venue: Prince of Peace United Methodist Church, 1400 S. Arlington Heights Road, Elk Grove Village, IL 60007
Family- and pet-friendly fall festival with a pumpkin patch, pumpkin decorating, build-your-own scarecrows, hay maze, games, pumpkin-pie eating contest, live music, food trucks and a fall marketplace featuring artists, crafters, jewelry makers, baked goods and other local vendors.
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Algonquin: Barktober Ocktober Fest (Free)
Date: Saturday, October 10, 2026 (11 AM - 3 PM)
Venue: Keller Williams Inspire, 115 W. Main Street, Algonquin, IL
Community fall festival benefiting local animal rescue efforts with food trucks, community vendors, adoptable dogs, face painting, raffle prizes, family activities, and pet-friendly fun.
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Mount Prospect: Knight of Champions Marching Band Festival ($15+)
Date: Saturday, October 10, 2026 (Afternoon - Evening)
Venue: Prospect High School, Mount Prospect, IL
The 30th Annual Knight of Champions Marching Band Festival brings more than a dozen Chicagoland high-school marching bands together for competition in Class A, AA and AAA divisions, with awards for music, visual performance, percussion, auxiliary and overall effect.
Park Ridge: Olson's Ace Hardware Harvest Fest (Free Admission; Kids Zone Wristband $10)
Date: Saturday, October 10, 2026 (3:00 PM – 7:00 PM)
Venue: Olson’s Ace Hardware, 700 N. Northwest Hwy, Park Ridge, IL 60068
Enjoy a family-friendly autumn celebration featuring a DJ, BBQ food truck, Artisan Alley with local vendors, raffles benefiting Advocate Children’s Hospital, and seasonal activities. A $10 Kids Zone wristband includes inflatables, a petting zoo, face painting, crafts, glitter tattoos, a pumpkin patch, pony rides, caricatures, balloon art, wall climbing, and more.
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Palatine: Downtown Palatine Grand Re-Opening Celebration (Free)
Date: Saturday, October 10, 2026 (3 PM - 9 PM)
Venue: Firefighters Memorial Parking Lot / Downtown Palatine, Brockway & Slade Streets, Palatine, IL 60067
Large downtown community celebration marking completion of Palatine's street and infrastructure improvements. The event includes live music throughout the afternoon and evening, downtown restaurant participation, food and drinks, and a designated outdoor event area.
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Huntley: Fall Harvest Fest & Trunk-or-Treat (Free)
Date: Saturday, October 10, 2026 (2:30 PM–5:30 PM)
Venue: Springbrook Community Church, 10115 Algonquin Road, Huntley, IL 60142
Family fall festival featuring trunk-or-treating, a decorated-vehicle contest, chili cook-off, food, bounce house, bonfire and s'mores, pumpkin painting and other seasonal activities.
Lincolnshire: Fall Festival & Craft Fair (Free)
Date: Saturday, October 10, 2026 (10 AM–1 PM)
Venue: Lincolnshire Swim Club, Lincolnshire, IL
The second annual community Fall Festival & Craft Fair combines local vendors and makers with outdoor fall activities, food and a neighborhood gathering.
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Long Grove: Brothers' Field Fall Fest (Free Admission; Donations Accepted)
Date: Saturday, October 10, 2026 (1:00 PM – 9:00 PM)
Venue: Brothers' Field, 340 Old McHenry Rd, Long Grove, IL 60047
Celebrate autumn with an open-air community festival featuring a DIY scarecrow contest, tractor rides, games and seasonal activities, food vendors, drinks at the Tiki Bar, and live music on the lawn. Wendy Lynn Markus performs from 1:00 PM – 3:00 PM, followed by Social Pariah from 6:00 PM – 9:00 PM. Admission is free, with donations accepted.
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McHenry: Holiday House Artisan & Vintage Harvest & Hallow Market : Free
Date: Saturday, October 10, 2026 (10 AM–3 PM)
Venue: Holiday House, 1404 N. Chapel Hill Road, McHenry, IL 60050
Seasonal artisan and vintage market featuring 25+ local vendors with handmade goods, vintage finds, gifts and antiques, along with food vendors, music, games and family-friendly seasonal activities. Admission and parking are both free.
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Mundelein: Grand Dominion Annual Craft Show (Free)
Date: Saturday, October 10, 2026 (10 AM–3 PM)
Venue: Grand Dominion by Del Webb, 3555 Grand Dominion Circle, Mundelein, IL 60060
Large annual craft show with handmade jewelry, original paintings, personalized gifts, toys, embroidery, beadwork, apparel, seasonal décor, greeting cards, bath products, candles, crochet and knitted goods, woodcrafts, quilts, pet accessories and other locally made items. Free admission and free parking.
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Rolling Meadows: Bird Show ($5.45)
Date: Saturday, October 10, 2026 (10 AM - 3PM)
Venue: Rolling Meadows Community Center, Rolling Meadows, IL
Midwest Bird Shows brings together bird breeders, enthusiasts and vendors for a specialty bird show featuring companion birds and bird-related products and information.
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Rosemont: Collect-A-Con Chicago ($30+)
Date: Saturday, October 10 – Sunday, October 11, 2026 (Saturday 10 AM–6 PM; Sunday 10 AM–5 PM)
Venue: Donald E. Stephens Convention Center – Hall A, 5555 N. River Road, Rosemont, IL 60018
Massive trading-card, collectibles, anime and pop-culture convention featuring 900+ vendor tables, Pokémon and other trading cards, comics, vintage toys, video games, collectibles, celebrity and voice-actor guests, exclusives and live entertainment. Children age 7 and younger receive free admission according to the organizer.
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Vernon Hills: Witches Night Out (Free)
Date: Saturday, October 10, 2026 (3 PM–7 PM)
Venue: Hawthorn, 122 Hawthorn Center, Vernon Hills, IL 60061
Fall-themed vendor event with a marketplace, live music, crafts, giveaways, seasonal activities and shopping throughout Hawthorn.
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Barrington Hills: Fall Festival (Free)
Date: Sunday, October 11, 2026 (12 PM–4 PM)
Venue: Barrington Hills Park District Riding Center, 361 Bateman Road, Barrington Hills, IL 60010
Signature community fall festival featuring live music, festival food, pony rides, face painting, a traveling zoo, K9 demonstration, mechanical bull, Living Horse Museum, fall crafts and other all-day family activities.
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Barrington: Motobert Fest at Cycle Werks (Free)
Date: Saturday, October 10, 2026 (11:00 AM – 4:00 PM)
Venue: Cycle Werks, 126 N. Cook St, Barrington, IL
Enjoy a community event at Cycle Werks featuring motorcycle-themed activities and a festive fall atmosphere.
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Lake Zurich: U.S. National Championship Pumpkin Weigh-Off
Date: Saturday, October 10, 2026 (3 PM - 5:30 PM; pumpkin unloading 1 PM - 2:45 PM)
Venue: Paulus Park, 200 S. Rand Road, Lake Zurich, IL 60047
National giant-pumpkin competition presented through the Great Pumpkin Commonwealth, with growers competing for the U.S. championship and cash prizes based on pumpkin weight.
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Lake Zurich: Howl-O-Ween Dog Parade & Expo (Free)
Date: Sunday, October 11, 2026 (10 AM–1 PM)
Venue: Staples Park, 501 Red Bridge Road, Lake Zurich, IL 60047
Family-friendly pet expo featuring a trick-or-treat dog parade at 11 AM, costume contest, photo booth, pet-product vendors, food trucks, music, pet-health talks and animal adoption organizations.
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Schaumburg: Chicago Vintage Guitar Expo ($10)
Date: Sunday, October 11, 2026 (9 AM–3 PM)
Venue: Chicago Marriott Schaumburg, 50 N. Martingale Road, Schaumburg, IL 60173
Long-running Chicagoland guitar and music-collectibles expo with Midwest dealers buying, selling and trading guitars, amplifiers, parts, accessories, rock memorabilia, banjos, ukuleles, mandolins, basses and other music-related collectibles.
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Barrington - BStrong Together Community Wellness Walk & Family Health Fair : Free
Date: Sunday, October 11, 2026 (12 PM - 2 PM)
Venue: Citizens Park, 511 N. Lake Zurich Road, Barrington, IL 60010
This free family event pairs a community walk with games, crafts, and resources supporting youth and family mental and physical wellness. Past years included a DJ, a bubble performer, animal therapy teams, a library Story Walk, a scavenger hunt, and booths from local organizations.
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Prospect Heights: Golden Years Wellness Expo (Free Admission)
Date: Monday, October 12, 2026 (10:00 AM – 2:00 PM)
Venue: Recreation Building, 110 W. Camp McDonald Road, Prospect Heights, IL 60070
Join fellow active adults for a free wellness-focused community event featuring health screenings, bingo, door prizes, refreshments, and resources from local organizations. No registration is required.
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