What the Hill?: Movies, Markets, Wine, and Fair Week Fun
If you are looking for reasons to get out of the house this July, there are major events coming up that you can attend. From free movies and wine tastings to gardening classes, family activities, and the Cass County Fair 2026, the community calendar is packed, so go get your family and friends and start planning your calendar.
Free Wine
On Thursday evening, July 9, from 4 to 8 p.m., Wing Hill Wine Co. invites residents to slow down and enjoy a complimentary wine tasting at its downtown location at 115 Wyoming Street.
After a relaxing start to the weekend at Wing Hill Wine Co., consider spending more time downtown. This event is not only an opportunity to enjoy wines in a laid-back atmosphere, but also a chance to visit local shops and catch up with friends before the busy weekend begins. Just taking a walk downtown is full of history and relaxation if you stop and sit at the comfy seating on Gray’s Lot.
Remember Sandlot? Well, Experience this Blockbuster Again! It Returns to the Big Screen
On Friday, July 10, at 7 p.m., People’s Theater continues its Summer Movies series with The Sandlot, a film that highlights baseball, friendship, and summer adventures.
Few films capture the spirit of childhood summers quite like this beloved classic. Generations have grown up quoting lines from the movie and cheering on the ragtag group of neighborhood kids who discover that baseball is about much more than winning games.
Admission is free thanks to sponsorship from the Republican Club of Pleasant Hill, making it an affordable family outing and a chance to enjoy a nostalgic favorite in a historic local theater. Be sure to RSVP at https://www.peoplestheatermo.com/.
Saturday Offers Shopping, Charity, and Entertainment
Saturday, July 11, is fully packed with great things to do.
The Pleasant Hill Farmers Market opens on Saturday, July 11, from 9 a.m. to noon at the corner of Second Street and Highway 58. Visitors can browse fresh produce, homemade baked goods, locally produced honey, handcrafted items, plants, and specialty products while supporting area vendors. Remember, the Farmers Market is not open during the Cass County Fair, so get your goods this week.
Farmers’ markets can be more than places to shop. They can be places where friends get together, children enjoy sweet treats, and residents connect directly with the people who grow and make the products they purchase. Gather and help strengthen the local economy while creating a sense of community.
Meanwhile, just down the road, Paula’s Petals will host a free Sansevieria Dividing Class from 9 to 11 a.m. Gardeners of all experience levels can learn how to divide and repot one of the most popular and hardy houseplants around. The class will take place outdoors and offers practical skills participants can take home and use in their own gardens and plant collections. Registration is required. You can text your name to 816-929-0522 or email paulaspetals2022@gmail.com.
Also taking place Saturday morning, July 11, from 9 to 11 a.m., is Grace Place Diaper Day at Pleasant Hill United Methodist Church. Volunteers will provide diaper assistance to local families in need. The monthly outreach program has become an important resource for many area families and demonstrates the community’s commitment to helping neighbors during challenging times.
As the sun sets, families can head to Pleasant Hill First Christian Church for a free outdoor showing of It Takes Two. The movie will begin at dusk on the church lawn at 519 Cedar Street. Guests are encouraged to bring lawn chairs or blankets and settle in for a relaxing summer evening under the stars. Complimentary snacks will be provided, and if the weather becomes an issue, the event will move indoors to the church basement.
Your Guide to the 2026 Cass County Fair: Six Days of Family Fun, Livestock Shows, Rodeos, Music, and More
The 32nd Annual Cass County Fair returns to Pleasant Hill July 14–19, bringing six days of entertainment, agriculture, family activities, exhibits, competitions, and community traditions. While the fair officially opens July 14, youth livestock competitions begin July 10 as 4-H and FFA members from across the region gather to showcase the animals they have spent months raising and preparing.CassCountyFairMO.com
Celebrating Agriculture and Youth Achievement
Agriculture remains at the heart of the Cass County Fair. Livestock events begin July 10 with the Youth Dairy Cattle Show and Youth Beef Cattle Show, followed by dairy goat, meat goat, swine, sheep, rabbit, horse and mule, dog, and poultry competitions throughout the week.
According to fair organizers, exhibitors spend hundreds of hours raising, feeding, caring for, and preparing their animals for competition. The livestock shows offer the public a chance to learn more about agriculture while supporting local youth involved in 4-H and FFA programs.
Additional youth-focused events include the 4-H Public Speaking Contest on July 14, exhibit judging, and the annual Cass County Youth Livestock Sale on July 15.
Grandstand Action Every Night
The fair’s evening entertainment schedule features something different nearly every night.
The action begins Tuesday, July 14, with Motocross Races at the fairgrounds. ATV and UTV races follow on Wednesday, July 15, giving spectators a chance to watch riders compete for top honors.
Thursday, July 16, brings one of the fair’s most popular attractions—the Demolition Derby.
Rodeo fans can enjoy MRCA/URA Adult Rodeo performances on both Friday and Saturday evenings, July 17 and 18. Mutton Busting sign-ups will be held before each rodeo, giving young cowboys and cowgirls a chance to participate in one of the fair’s favorite traditions.
The fair concludes Sunday, July 19, with the MSTPA Truck and Tractor Pull, featuring powerful machines competing in a test of strength and horsepower.
Music Throughout Fair Week
Music will be featured at both the fairgrounds and downtown Pleasant Hill.
On Thursday, July 16, Mudflap Mafia performs at the Miller Entertainment Pavilion from 9 to 11:30 p.m.
Friday evening begins with a Gospel Music Show featuring Reunion Gospel Band at Depot Park from 6:30 to 8 p.m. Later that night, Trevon Dawson takes the stage at the Miller Entertainment Pavilion from 10 p.m. until 1 a.m.
Saturday includes a Variety Music Show at Depot Park from 10 a.m. to 2:30 p.m., followed by an evening performance from Jordan Isackson at the Miller Entertainment Pavilion.
Exhibits Showcase Local Talent
Visitors looking for a quieter fair experience can explore exhibits featuring the work of local residents and 4-H members.
The 4-H Exhibit Hall will be located in the downstairs level of the Memorial Building, while the Quilt Show will be displayed upstairs. The Train Depot will host the Art and Photo Show, Home Economics Show, and Horticulture Show.
Exhibits will be open Friday, July 17, from 1 to 8 p.m. and Saturday, July 18, from 9 a.m. to 6 p.m.
Together, the exhibits showcase the creativity, craftsmanship, and talents of people throughout Cass County.
Family Fun for All Ages
Families will find activities throughout fair week.
Opening Ceremonies take place July 14 at 6:30 p.m. at the fairgrounds. Other events include the Power Wheels Race, Bingo, and a new Hot Dog Eating Contest.
Saturday, July 18, is expected to be one of the busiest days of the fair. The day begins with the Knights of Columbus Pancake and Sausage Breakfast at the downtown gazebo from 8 to 10 a.m.
The annual Cass County Fair Parade follows at 9 a.m., along with the Bike Rodeo, Car Show, 4-H Square Dance demonstration, Pet Show, and Super Farmer Competition.
Downtown Pleasant Hill and the fairgrounds will both be buzzing with activity throughout the day.
Carnival Returns
Evans Midland Empire Shows will once again bring its carnival midway to the Cass County Fair.
The carnival will operate Tuesday through Thursday from 6 to 11 p.m. and Friday and Saturday from 5 to 11 p.m. The midway will not operate on Sunday.
Guests can purchase ride tickets individually or buy unlimited ride wristbands for $30. Attractions range from family favorites such as the Carousel, Super Slide, Dizzy Dragons, Tea Time, and Ferris Wheel to thrill rides including the Zero Gravity, Cliff Hanger, Downdraft, Ring of Fire, Rock Star, and Scrambler.
With rides, games, lights, food, and entertainment, the carnival remains one of the fair’s most popular attractions.
A Pleasant Hill Tradition
For generations, the Cass County Fair has brought together agriculture, entertainment, and community spirit. Whether visitors come to cheer on livestock exhibitors, enjoy live music, browse exhibits, ride carnival attractions, watch the rodeo, or line the streets for the parade, the fair offers something for every age.
From July 14 through July 19, Pleasant Hill will once again serve as the gathering place for one of Cass County’s most anticipated summer traditions.