October Brings Festivals, Authors, Ribbon Cuttings and Fall Fun to Pleasant Hill
(Check all hosts for changes or cancellations)
October is arriving with a busy calendar in Pleasant Hill, bringing everything from barbecue and live music to a bestselling author, ribbon cuttings, classic cars and plenty of opportunities to support local organizations.
The first weekend of the month is especially packed, with several events happening Friday and Saturday, Oct. 2–3.
Friday, Oct. 2, begins with a welcome for one of Pleasant Hill’s newest businesses. The Pleasant Hill Chamber of Commerce will hold a ribbon cutting for Dream Vacations at 10 a.m. at the Chamber office, 100 Wyoming St. The community is invited to help welcome Sheila and Jeff Bryan and celebrate their business.
Later that afternoon, readers will have an opportunity to hear from New York Times bestselling author Lisa Wingate as part of the Cass County Public Library Author Series. Wingate will talk about her life and work as an author and take questions from the audience beginning at 3 p.m. at the Pleasant Hill Branch of the Cass County Public Library. Registration is required. For additional information, contact Teresa Schaefer at 816-987-2231.
Meanwhile, one of Pleasant Hill’s biggest fall weekends will be getting underway with the Big Creek Fall Festival Oct. 2–3.
Friday evening, Oct. 2, festival activities include more than 20 vendors from 5 to 9 p.m., along with food, drinks and live entertainment. A beer tent featuring wine slushies and other selections will be open from 5 to 11 p.m., while Taste the Que and VIP barbecue dinners will be offered from 6 to 8 p.m. A whiskey and spirits tasting follows from 8 to 11 p.m., and Mudflap Mafia will provide live music from 7 to 11 p.m.
The festival continues Saturday morning, Oct. 3, with a Boy Scout pancake breakfast from 8 to 10 a.m. From there, the day fills up with Kids Que and Junior Que barbecue competitions, a cornhole tournament, more than 20 vendors, food trucks, a silent auction, bounce house, home brew competition, Boy Scout demonstrations, whiskey and spirits tasting and the Dammit Don Dunk Tank.
Saturday evening, Oct. 3, will put local talent in the spotlight. The Pleasant Hill Talent Show will be held at the Cass County Fairgrounds, with singers, dancers, musicians, comedians, magicians and other performers invited to take the stage. Five judges will select the winners, with cash prizes of $100 for first place, $75 for second and $50 for third. Those interested in competing can register through Downtown Pleasant Hill under the Fall Festival information.
Admission to the Big Creek Fall Festival and pavilion entertainment is free, although some food, tasting and competition activities require tickets or advance registration.
Saturday, Oct. 3, also brings a celebration along the Rock Island Trail. Missouri State Parks will hold a ribbon-cutting ceremony for the Ted and Pat Jones Bridge at 10 a.m. at the Pleasant Hill trailhead. The community event is free and marks the official opening of the bridge.
The following week shifts from festivals to regional business and economic development. The Pleasant Hill Chamber will host the Cass County Coalition of Chambers Luncheon from noon to 1 p.m. Thursday, Oct. 8, at the Pleasant Hill Police Department Training Center. Guest speakers from the Missouri Department of Economic Development are scheduled to speak. The luncheon costs $20 per person, with RSVPs requested by Oct. 2 at phillmochamber@gmail.com.
By mid-month, another Pleasant Hill tradition will wrap up its season. Pleasant Hill Cruise Nights will hold its final cruise of 2026 from 5 to 9 p.m. Friday, Oct. 16, in downtown Pleasant Hill. Classic cars, trucks and automotive enthusiasts will gather for one last evening of chrome, horsepower and conversation. The event is sponsored by the Pleasant Hill Historic District and Steve & Anthony’s TLC Auto.
Also on Friday, Oct. 16, Rainbow Kingdom Preschool and Parent’s Day Out will host its Chili Supper and Silent Auction Fundraiser from 5:30 to 7:30 p.m. at the United Methodist Church Community Life Center Gym, 1300 Lexington Road. Dinner includes chili, hot dogs, cake, lemonade and tea, while the silent auction will feature themed baskets, baked goods, gift cards and certificates, home décor and other items.
The silent auction closes at 7 p.m., and dinner will be served while supplies last. Tickets are $10 for adults and $5 for children ages 3 to 10, with children 2 and younger admitted free. No ticket is necessary to participate in the silent auction. Proceeds will help Rainbow Kingdom with school supplies and playground needs.
Fall shopping will also be on the calendar Friday–Saturday, Oct. 16–17, as Paula’s Petals Greenhouse & Floral hosts its second annual Fall Vendor Event. Visitors can browse local vendors, shop the greenhouse and stop by the floral bar from 10 a.m. to 4 p.m. at 33607 E. 199th St. Admission is free.
From a major festival weekend to authors, ribbon cuttings, cars, fundraisers and fall shopping, October is starting with plenty of reasons to get out and spend some time around Pleasant Hill.
And there’s still plenty of October left.