10/16/2026
WHAT'S HAPPENING IN PLEASANT HILL | OCTOBER 16–25, 2026
There's plenty happening in and around Pleasant Hill over the next several days! From the final Cruise Night of the season to community fundraisers, fall crafts, Halloween movies, and live music, here's what's coming up.
Complete lest on PHMOmag.com?thingstodo
FRIDAY • OCTOBER 16, 2026
- Pleasant Hill Cruise Nights – Final Cruise of the Season
Location: Downtown Pleasant Hill
Time: 5:00 PM–9:00 PM
The final Cruise Night of 2026 brings classic cars, trucks, and automotive enthusiasts together for one last evening of chrome, horsepower, and community fun. Sponsored by the Pleasant Hill Historic District and Steve & Anthony's TLC Auto, this seasonal favorite wraps up another successful year in downtown Pleasant Hill.
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- Rainbow Kingdom Chili Supper & Silent Auction Fundraiser
Location: United Methodist Church Community Life Center Gym, 1300 Lexington Road, Pleasant Hill
Time: 5:30 PM–7:30 PM
Enjoy chili, hot dogs, cake, lemonade, and tea while browsing a silent auction featuring themed baskets, baked goods, gift cards and certificates, home décor, and more. The silent auction ends at 7:00 PM, with dinner served while supplies last. Tickets are $10 for adults, $5 for children ages 3–10, and free for children 2 and under. No ticket is required to participate in the silent auction. Proceeds support Rainbow Kingdom Preschool and Parent's Day Out with school supplies and playground needs.
FRIDAY & SATURDAY • OCTOBER 16–17, 2026
- 2nd Annual Fall Vendor Event
Location: Paula's Petals Greenhouse & Floral, 33607 E. 199th St., Pleasant Hill (2nd entrance off the main road)
Time: 10:00 AM–4:00 PM
Cost: Free Admission
Browse local vendors, shop the greenhouse, and visit the floral bar during this annual fall event. Vendors were required to register by September 13 to participate. For vendor information, contact Paula McCloskey at 816-929-0522.
TUESDAY • OCTOBER 20, 2026
- Monthly Chamber Luncheon
Location: Jewel Lodge #480
Join the Pleasant Hill Chamber of Commerce for its October luncheon, hosted by Jewel Lodge #480 and featuring guest speaker Roger Brenner. Attendees are invited to enjoy lunch while connecting with fellow Chamber members and community leaders.
THURSDAY • OCTOBER 22, 2026
- Doormat Craft & Sip
Location: Fleming Floral Station, 801 Cedar St., Pleasant Hill
Time: 6:00 PM–8:00 PM
Join Fleming Floral Station and A² Designs for a night of painting, crafting, w**e, and all things fall, Christmas, and Chiefs. Choose from featured designs or customize your own doormat. The $40 ticket includes doormat painting and crafting, all supplies, step-by-step instruction, w**e, and snacks. Painting will be taught by Dani and crafting by Justine. Space is limited.
Register Here
- Free Family Halloween Monster Movie Fest
Location: Peoples Theater, Pleasant Hill
Time: See theater website
Celebrate Halloween with a free Universal Monsters Halloween Movie Fest featuring two original horror classics, Dracula (1931) and Frankenstein (1931). The event is free, but reservations are encouraged.
RSVP Here
SATURDAY • OCTOBER 24, 2026
- Flower Arrangement Building Class
Location: Paula's Petals Greenhouse & Floral, 33607 E. 199th St., Pleasant Hill (2nd entrance off the main road)
Time: 10:00 AM (approximately one hour)
Cost: $35
Create your own fresh flower arrangement and take it home after this hands-on class. Advance registration is required. Payment is due upon arrival. Choose either the Saturday or Sunday class. Call Paula McCloskey at 816-929-0522 to reserve your spot.
- 44 Years of Big Creek Country
Location: Peoples Theater, Pleasant Hill
Time: See theater website
Celebrate 44 years of Big Creek Country! For more than four decades, Big Creek Country has kept traditional country music alive on the Peoples Theater stage. Join the celebration of this longtime Pleasant Hill musical tradition.
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- Pleasant Hill Project Grad Golf Classic
Location: Shamrock Hills Golf Club, 3161 SW MO 291, Lee's Summit
Registration: 11:00 AM–12:00 PM
Lunch: 12:00 PM–1:00 PM
Sh***un Start: 1:00 PM
The Pleasant Hill Project Grad Golf Classic is an annual fundraiser benefiting the Pleasant Hill High School Class of 2027 Project Graduation. The four-person scramble includes lunch, on-course contests, prize holes, a putting contest, a party hole, a 50/50 raffle, and awards following play. Registration will open soon. Hole sponsorships are available, and additional information may be obtained by contacting Brett Bush at 816-522-6144.
SUNDAY • OCTOBER 25, 2026
- Flower Arrangement Building Class
Location: Paula's Petals Greenhouse & Floral, 33607 E. 199th St., Pleasant Hill (2nd entrance off the main road)
Time: 10:00 AM (approximately one hour)
Cost: $35
Create your own fresh flower arrangement and take it home after this hands-on class. Advance registration is required. Payment is due upon arrival. Choose either the Saturday or Sunday class. Call Paula McCloskey at 816-929-0522 to reserve your spot.
- St. Bridget Church AutumnFest 2026
Location: St. Bridget Catholic Church, Parish Hall, Lower Level of the Church, 2103 Lexington Rd., Pleasant Hill
Time: 11:30 AM–2:00 PM
St. Bridget Catholic Church will host its annual AutumnFest Dinner and Silent Basket Auction, raising funds for the church and the Pleasant Hill Lay Clergy Council. Twenty-five percent of the event's net profits will benefit the Lay Clergy Council, which helps individuals and families in need throughout the community. Over the past several years, AutumnFest has donated more than $7,500 to the council.
Tickets are $15 for adults, $12 for seniors over 65, $6 for children ages 5–12, or $45 for a family of two parents and up to three children. Pre-sale tickets are available through October 24, and tickets will also be sold at the event. Each adult pre-sale ticket includes one free beef raffle ticket for a chance to win a side of beef valued at approximately $2,000.
For more information, contact the parish office at 816-540-4563.
LOOKING FOR MORE TO DO?
Find additional events, registration information, and updates on our complete Pleasant Hill community calendar:
https://phmomag.com/thingstodo/
Please check with event organizers for changes, cancellations, ticket availability, and updated information before attending.
Have an event you'd like to share with the community? Let PHMOmag know!
