Pumpkin Hallow
October 1-18
Deanna Rose Children's Farmstead
13800 Switzer Road, Overland Park, KS
Take a horse-drawn hayride to Pumpkin Hollow at Deanna Rose Children’s Farmstead, then enjoy a spider web maze, pedal cars, old-fashioned games and other fall activities before choosing a pumpkin to take home. Select dates through Oct. 18 are currently listed.
https://artsandrec-op.org/farmstead/pumpkin-hollow/
KC Oktoberfest
Oct. 2: 5-11 p.m.; Oct. 3: 11 a.m.-11 p.m.
Crown Center Square, 2450 Grand Blvd.
A traditional Oktoberfest featuring KC Bier Co. beer, German food, Bavarian entertainment, games and family activities at Crown Center.
https://kcoktoberfest.com/festival-info/
Hawkfest
October 10
1:00 PM- 4:00 PM
7951 W 160th St. Overland Park,
This sixth annual community event features live band, food trucks, fire performances, inflatables, hayrides, and so much more.
https://www.bluhawk.com/events/hawktoberfest/
Oktoberfest at Prairiefire
October 10
10 AM-2 PM
Join us for a day packed with fall fun for the whole family! Enjoy bouncy houses, yummy food, local vendors, pumpkin decorating, cake walk, DIY friendship bracelets, face painting, a magician and so much more.
https://www.prairiefireop.com/happenings
Brew at the Zoo
October 10
6:30 pm - 11 pm
The Kansas City Zoo
Enjoy an adults-only (ages 21+) evening of live music, free samples from more than 30 local breweries and wineries, and delicious food truck fare at Brew at the Zoo. Your ticket also includes admission to GloWild: Hidden Treasure, Kansas City Zoo and Aquarium’s immersive lantern festival.
https://kansascityzoo.org/brew-at-the-zoo
Taps & Tastes
October 17
Early Admission at 1 pm; General Admission at 2 pm.
Boulevard Beer Hall, 2534 Madison Ave., Kansas City
General Admission includes access to Taps & Tastes festival experience, including unlimited beer/beverage tastings from local brewers and distilleries, curated bites from KC restaurants, a souvenir tasting glass, and live entertainment throughout the event.
https://www.boulevard.com/tapsandtastes/
Boozy Book Exchange
Sunday, October 11
12:00 PM-3:00 PM
KC Wine Co. 13875 South Gardner Road Olathe
Bring a book (or a few!) you’ve enjoyed but are ready to share. Sip on your favorite wines while exploring the literary gems brought by others. Exchange your books and leave with fresh reads to enjoy, all in the relaxing ambiance of the winery. Grab your friends and your favorite reads for an afternoon of wine, words, and wonderful company.
https://www.kcwineco.com/events/upcoming-events/boozy-book-exchange-2-4389r
Night at the Living Farm
October 16-17 & 23-24, 2026 | 5:30-9pm
Deanna Rose Children's Farmstead 13800 Switzer Road, Overland Park
Dress in your best costume and get ready for a night of Halloween fun for all ages. From spooky thrills to not-so-scary chills, there’s something for everyone. Activities Included: scary and non-scary hayrides, line dancing in the dairy barn, Ruby's carnival games, rubber duck races at the mining shack, spooky experiments with mad science, flashlight pumpkin walk, dancing with Princesses, scarecrow maze, and marshmallow roast. Food will be available for additional purchase.