Art Westport
The 45th annual Art Westport is the city’s oldest local art show, showcasing arts and crafts by the city’s top talent. Whether you’re an art enthusiast, a collector or are simply curious, this community event has something for everyone. In addition to the artist booths, there are hands-on activities for children, music and food.
September 5–7. Westport Road & Pennsylvania Avenue, KCMO.
Plaza Art Fair
The highly anticipated Plaza Art Fair encompasses nine city blocks in the historic Plaza shopping district and welcomes a crowd of more than 250,000 every year. Featuring 240 artists, the fair is a top-ranked national art event, with three live music stages and over 20 featured restaurant booths. It’s an event for serious art collectors as well as those just browsing.
September 19–21. Country Club Plaza.
Overland Park Fall Festival
The Overland Park Fall Festival has plenty of autumn fun for the whole family. With more than 75 local and regional artisans, as well as live music and performers for both adults and children, visitors will have a lot to do. There will also be food trucks and vendors in addition to the nearby restaurants and OP Farmers’ Market at this free event.
September 26–27. 7935 Santa Fe Drive, Overland Park.
KC wine co. Fall Festival and Pumpkin Patch
Roam KC Wine Co.’s 40 acres at this all-ages extravaganza. The price of admission includes over 60 activities like corn pits, skee ball, mega slides and plenty of seasonal photo ops. Plus, the Olathe winery’s signature wine slushes will be available for purchase all day, every day.
September 27–October 26. KC Wine Co.
KC Oktoberfest
The region’s largest Oktoberfest returns to Crown Center for two days of authentic German food, drink and music. Hosted by KC Bier Co., this year’s lineup includes touring Alpine rock band Die Schlauberger and local polka favorites like The Happy Wanderers. The festival’s highlight competition? A Masskrugstemmen, a beer steinholding contest that tests endurance and perfect form.
October 3–4. Crown Center.
Chicano Art Festival
At this celebration of Chicano culture, art isn’t the only thing on display. The event also features folkloric dance performances, traditional cuisine, music and poetry. And if you’re a motorhead, this festival is home to KC’s largest lowrider show.
October 5. Liberty Courtyard, West Bottoms.
Weston Applefest
Take a drive to Weston’s quaint historic square for Applefest. Now in its 35th year, festivities kick off Saturday morning with a parade, and the rest of the weekend offers live music, artisan makers and an abundance of warm apple dumplings.
We recommend taking a quick detour (just a block from Main Street’s festival action) and grabbing a round at O’Malley’s 1847 Pub. The historic underground bar, nearly 60 feet below street level, was formerly home to one of the country’s first breweries.
October 5–6. Main Street, Weston.
Lenexa Chili Challenge
Judges aren’t the only ones to get a taste of the entries at this cook-off. Friday night kicks off with live music and family-friendly activities like face painting, but the festivities heat up on Saturday as more than 200 teams serve up their best chilis, hot wings and salsas. Grab a spoon at the gate and sample your way through a tradition nearly four decades strong.
October 10–11. Old Town Lenexa.
Botanical Brewfest
Enjoy the fall foliage with a beer in hand—and for a good cause. Admission includes samples of craft beers (over a hundred various pours will be available) to support Overland Park Arboretum and Botanical Gardens.
October 18. Noon. Overland Park Arboretum and Botanical Gardens.
Night of the Living Farm
Deanna Rose Children’s Farmstead gets a spooky makeover for this after-dark Halloween celebration. Enjoy performances from StoneLion Puppet Theater, hands-on science fun with Mad Science and seasonal staples like hay rides, mazes and marshmallow roasting. Costumes are welcome for all ages.
October 18, 19, 25 & 26. Deanna Rose Children’s Farmstead.
North Kansas City Fall Festival
This Northland festival prides itself on showcasing some of the region’s best bands and beers. The event features pours from over a dozen KC breweries—including Casual Animal Brewing Co. and Vine Street Brewing—and performances throughout the afternoon, from soulful, nine-piece ensemble The Freedom Affair to indie band Honeybee and more.
November 2. Noon. Swift Street (between 14th Avenue and 15th Avenue).
