Unique Fall / Halloween Activities in Chicagoland


There is still plenty of time to explore the nearby apple orchards and pumpkin patches. Those are usually the first two categories we think of when we talk about the onset of fall in the midwest. And of course, Halloween!



But, here are some other ideas, to explore this October!


No need to drive up the East Coast, enjoy the changing of the leaves in your own state by biking, walking, or driving through the below locations!



Pumpkin Spice Lattes may be all the rage, but a trip to the city for a fall dessert at one of these amazing bakeries is more my speed!


  • Bang Bang Pie & Biscuits
    • Both locations are closed due to the pandemic except for preorder through their online pantry for contactless pickup in Logan Square
    • I’ve been eyeing the Frankenpie. A mash-up of three different pies: Pumpkin-Cheesecake, Apple Cider Custard, and Salted Miso Caramel Apple Pie. 2 slices of each makes the whole Franken-Pie!
  • Firecakes Donuts
    • Seasonal donuts include: Apple Cider & Pumpkin Crème Brûlée
    • No one will judge you if you make it a Donut Ice Cream Sandwich either. Consider it a prescription for 2020
  • First Slice Pie Cafe
    • Did you know that Food & Wine voted First Slice as one of America’s BEST apple pies?!
    • In addition, First Slice served more than 37,000 meals in 2007, and currently serves close to 4,000 meals each month to Chicago’s hungry, every month.
  • Floriole
    • Their thanksgiving menu is up and running for orders!
    • The Pumpkin Baby cake is to DIE for! It’s a pumpkin loaf dipped in Valrhona Orely’s blonde chocolate. You’ll thank me later.
  • Beatrix 
    • The Oh My! Caramel Pie will have your mouth watering and you ordering seconds.
  • Blue Sky Bakery & Cafe
    • “Blue Sky does more than create sweet and savory pastries made with the freshest, highest quality ingredients. As a nonprofit organization, we also raise the edible consciousness of our community by providing transitional employment to homeless and at-risk youth.”
    • Pumpkin pecan scone with a side of social justice please!
  • BomboBar
    • You are just going to drool over BomboBar’s fall menu! If the salted caramel hot chocolate and caramel apple cider wasn’t enough already, there’s the pumpkin pie marshmallow and apple caramel gelato to sweep you off your feet.
  • Brown Sugar Bakery
    • The most famous and tastiest caramel cake in Chicago! Don’t sleep on this amazing bakery.
  • Do-Rite Donuts
    • I’ll take my pumpkin spice in donut form thank you very much. With a Michigan apple fritter on the side. :p
  • DMK Burger Bar
    • Skip the campfire and head straight to DMK for a toasted marshmallow shake. Hard day monitoring the e-learning? Make it a boozy shake! 😉
  • Eli’s Ark
    • These adorable ice cream, creature creations will have you going “batty!”
    • Check out their halloween and thanksgiving themed characters!
  • Glazed And Confused
    • Filled caramel candy apple, pumpkin maple streussel… or preorder a spooky Halloween themed donut box, this eclectic donut shop has every fall flavor you need!
  • Goddess And The Baker
    • Trick or Treat yourself to a Pumpkin Apple Butter Latte before exploring the rest of their delicious menu!
  • Hoosier Mama Pie Company
    • The pie of the month is the Sour Cream Dutch Apple Pumpkin (does it get more fall than that?)
    • Make sure to order online for your Thanksgiving pie pick up orders!
  • Jeni’s Splendid Ice Creams
    • Known for the unique ice cream flavors you can be guaranteed for some fall-tastic picks here!
    • Be the most popular guest at your Friendsgiving by bringing a quart of the pumpkin cake roll & salty caramel.
  • Jo-Jo’s Shake Bar
    • Until November 1st, JoJo’s outdoor patio is converted into an adorable pumpkin patch! Pick out pumpkins, enjoy fall themed shakes and biggie hot chocolates, as well as their normal menu!
    • Don’t leave without the Pumpkin Patch Shake! Topped with a slice of pumpkin pie, taffy apple, roasted marshmallow, and reese’s pretzel.
    • Their pumpkin shaped domes are are available on a first come, first serve basis!
  • Katherine Anne Confections
    • Upgrade from your regular old chocolate with a creamy cup of Katherine Anne’s drinking chocolate!
    • The salted caramel will definitely be the right flavor for the season
  • Kilwins
    • There are multiple locations around Chicagoland but the Hyde Park location is African American owned and operated, so we like to support them whenever we can!
    • You will find yourself drooling over the caramel apples and chocolate confections but my absolute favorite flavor of ice cream from Kilwins is their Perfect Apple Pie flavor. I look forward to this returning to their menu every single fall!
  • Mindy’s Bakery
    • The famous Mindy Segal will be selling to go hot chocolate on the weekends!
    • Forget fall, I would drink this delectable cocoa in the heat of the summer if I could!
  • Molly’s Cupcakes
    • The fall / winter cupcake flavors are back in season and I am here for it!
    • Don’t miss out on the pumpkin spice, apple pie, pecan pie, and chocolate peppermint!
  • Pie, Pie My Darling
    • 100% Vegan sweets baked from scratch!
    • You can find their cakes by the slice (while supplies last) for delivery and pickup at Uptons Breakroom in West Town & The Handlebar in Wicker Park. The flavor changes every other week, so check their menus/ instagram for this week’s flavor.
    • E-mail to inquire about ordering a whole cake!
  • Pretty Cool Ice Cream
    • “Available a la carte, or as a boxed set, our Fall Harvest flavors are perfect for these blustery days. Whether this season brings out the pumpkin spice cravings, or finds you popping fistfuls of kettle corn we have a pop for you! Apple makes two appearances- spiced cider frozen into an ice pop is refreshing and comforting. But the star of the show is the Apple Cider Donut pop- made by blending real donuts into our ice cream before it gets a cinnamon sugar coating just like the pumpkin patch favorite!”
  • Sweet Mandy B’s
    • Their Pumpkin Whoopie Pies are BACK and we are so excited! If you can’t decide between these or the Apple Streussel pop tart, I would recommend just getting both. 🙂
  • XO Marshmallow
    • The World’s FIRST Marshmallow Café is right here in Chicago!
    • Their s’mores menu is fantastic! Plus, hot chocolate, marshmallow latte, pumpkin spice marshmallows, and more!
  • Xurro
    • The yummiest Churros with a creative spin!
    • I’ll take one S’more milkshake please! But just to hold me over until the Peppermint Christmas milkshake returns! 🙂

Are all the registration required Halloween events filled? Don’t fret! Check out these other Halloween ideas!


  • Fall at Lincoln Park Zoo
    • “Simply make your free reservation to visit the zoo this fall to stroll the one-way trail and cherish the fall ambiance without the crowds. This year, Lincoln Park Zoo will be adorned with carved pumpkins, corn husks, and hay bales—not to mention the crisp autumn breeze rustling orange and yellow leaves and fall temperatures favorable for outdoor animal viewing.Along the way, enjoy two new experiences—the Pumpkin Walk, a beautifully designed path through Pritzker Family Children’s Zoo (one $3 ticket required for entry), and Patch’s Pumpkin Bar & Grill, a fall-themed pop-up located at Bird’s Eye Bar & Grill. Plus, cherish the return of longtime festive favorites: live professional pumpkin carvers (Saturdays only, as part of the Pumpkin Walk), delicious festive snacks, and a pumpkin patch.”
  • Pumpkinpalooza Pumpkin Decorating Contest
    • October 17th – 30th
    • Calling all young creative souls! Decorate a pumpkin as one of your favorite book characters!
      The rules are simple:
      *Contest open to children ages 5-12
      *Pumpkins must be inspired by a book or a character from a book
      *Pumpkins, gourds can be real or fake
      *No carving
      *Paint, glue, or paste items on your pumpkins
      *Pumpkins must be submitted by 5p.m. on October 17, 2020
      *Include the name of the book/character that inspired your pumpkin and name and contact information of the pumpkin’s creator
      *Voting takes place in person at Red Hive Market in Batavia from October 18-October 30th
      *Top three vote getters receive a fabulous Pumpkinpalooza SWAG bag!
  • Chitown Movies Halloween Drive In
    • Oct. 26- Hocus Pocus
    • Oct. 27- Madilda
    • Oct. 28- Monsters, Inc.
    • Oct. 30- Matilda
    • Oct. 31- Monsters, Inc.
  • Replay’s Alley of Darkness Haunted Drive Through
    • Park and enjoy a short movie before 30 minutes of scares in a 360 degree show!
  • Goebbert’s Halloween Trick or Treat On The Farm
    • Pingree Grove
    • Saturday, October 31st 9AM – 6 PM
    • All the farm favorites will be open, wear your costumes!
    • This will be their first ever scavenger hunt, trick or treating day
    • You do need to buy tickets online before arriving but they are not sold out yet! It’s the same process for entering the pumpkin patch any other day / weekend
  • Goebbert’s Fall Light Show
    • You can experience a light show unlike any other. Turn on your radio, and drive thru the light show with your whole family.
    • $5 per person or if you have more that 4 people it is only $20 a car.
    • Cash or card is accepted. You can purchase tickets online or at the light show entrance.
    • Tuesday, Wednesday, Thursday & Sunday:7pm-10pm; Friday & Saturday: 7pm-11pm
  • Buffalo Grove Halloween Light Show
    • 860 Woodhollow Lane
    • Tune your radio to 88.7 FM
    • 6:30 – 9 PM every night!
    • 2 week long nightly event
  • Boo-mingdale Halloween Drive- Through
    • Saturday, October 24th, 9-11:30 AM
    • 259 Springfield Drive, Bloomingdale
    • Drive through the Library, Village, Police and Fire Department parking lots and enjoy:
      – Themed guests, roving entertainment, DJ music
      – Display of the annual Trunk-or-Treat vehicles
      – Police and Fire Department exhibit of emergency and first responder vehicles on display
      – Children receive a small pumpkin gourd and a treat bag during the drive-thru experience (while supplies last)
  • St. Charles Gallery of Ghoulish Homes
    • Best viewed at dusk October 16th – 31st
    • Drive or walk by some of the spookiest houses in St. Charles!
  • Mack Manor Drive Through Display
    • 1066 Algonquin Road, Fox River Grove
    • Monday – Thursday 6-8:30
    • Friday & Saturday, 6-10pm
    • Sunday 4-9 pm, allowing for daylight viewing hours.
    • If you have small children that might be frightened, please turn on flashers to ensure monsters stay away. It is unknown- if and when – any of the undead shall make a visit.
    • Radio station 106.9 FM
    • No charge but accepting donations
  • The Cote’s Haunted Yard
    • 6907 Townsend Blvd, Plainfield, IL
    • Friday & Saturday only from 6 – 10 PM
    • No more appointments being taken but walk ups allowed. (Those with appointments get in first) 6:30 or 8:30 – 10 may be the best bet for walk ups
  • Museum of Science and Industry Boo Fest
    • “Two weeks of family-friendly science experiences will let you get into the Halloween spirit. Our limited capacity, timed-entry tickets and other protocols allow for plenty of space and comfort for a scary good time indoors. Explore a specially decorated exhibit with a “Scary Storage” look at the Museum’s curiosities, take part in physically distanced trick-or-treating, and examine the science of Halloween with pumpkin drops, slime, eyeballs and chilling laboratory sessions.”
  • Galewood’s Not So Spooky Halloween Parade
    • Thursday, October 29th
    • 5:15 – 6PM
    • Parade Route: Wabansia to Nashville, Nashville to Armitage, Armitage to Neva, Neva to Wabansia
    • Greet Halloween characters and get some candy
  • Terror In The Timbers
    • Camp Big Timber Elgin
    • “Think you’re safe behind a piece of glass and some metal? Think again. The dead have taken over the once innocent Camp Big Timber and are coming for the living…one car at a time. This one-of-a kind drive-thru scenic Halloween experience allows you to simply put your car in park, sit back and let the Terror begin.”
  • Highwood Skeleton Walk
    • Hundreds of skeletons have descended upon Highwood’s businesses! Go check it out!
  • La Grange Skeletober
    • “La Grange has plenty of spirit this month when dozens of friendly, life-sized skeletons lounge in front of local businesses for the season. This annual display is organized by the La Grange Business Association; each engaging skeleton is sponsored by a local business as a way of inviting visitors to explore La Grange.  Skeletober is sponsored by Chiro One. Get the walking map to all the skeletons.”
  • Glen Ellyn Scarecrow Row
    • Oct 21st – 31st
    • “Follow the Rows and Rows of 100+ Scarecrows lined up in Downtown Glen Ellyn at this FREE Family-Friendly and Socially Distant Outside Event!  Join the fun and see the handmade Scarecrows created by scout troops, community members, local businesses, & non-profits. Explore unique one-of-a-kind storefronts with their decorated windows and dine the fall menu at one of our many restaurants.”
  • Morton Arboretum Scarecrow Trail
    • Oct 1st – Nov 1st
    • Morton Arboretum requires timed entry ticket reservations in advance online
    • “Take a stroll around Meadow Lake to view scarecrows created by local scout troops and school groups. After your walk, vote for your favorite scarecrow online.”
  • Aurora Sugar Skull City
    • October 15th – November 15th
    • “The 30-day celebration honors the beloved Mexican cultural tradition of Day of the Dead, and coincides with events during First Fridays on November 6.”
    • “Downtown storefronts will be decorated with festive displays for the holiday. Local artists Pierre Lucero, Jose Sanchez, and Joseph Gagnepain painted storefronts along Broadway and Stolp Avenue. Sugar skull artwork submitted by two dozen local artists also will be displayed in downtown windows. Patrons will be invited to vote on the artwork and participate in photo contests on Aurora Downtown’s social media pages.”
    • “Patrons also will be encouraged to participate in a scavenger hunt to find two yellow sugar skull screen prints located in downtown windows, fill up at authentic Mexican bakeries and restaurants, and download coloring pages from the website.”
  • Homer Glen Heritage Park Scarecrow Display
    • October 10-31: Walk along Heritage Circle and View the creative scarecrow displays. Vote for your favorite! Three winners will be chosen.
    • Come out to Heritage Park (day or night) for bats, spiders, ghosts, and lights! The park will be decorated with all things spooky the month of October.
  • Fall at Brookfield Zoo
    • The dino’s are still stomping through the zoo as well as halloween decorations to take your fall selfies!
    • A great location to view fall leaves as well!
  • Naperville Halloween Lights Map
    • Utilize this map to go on a driving tour of festive Halloween houses in Naperville!
  • Naperville Halloween Celebrations
    • Sat & Sun, Oct 24th & 25th
    • Sat from 1-4 there will be a pop up pumpkin patch (free)
    • Sunday business trick or treat from 10 – noon
    • Plus much, much, more!
  • Fall Festival at the Promenade (Bolingbrook)
    • October 23rd – 25th
    • Artisans, crafts, fall food
    • Kids scavenger hunt on the 24th only


Did I miss anything? Comment with a unique fall activity you have enjoyed so far!


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