Middletown Days

Middletown Days opens on a Friday evening in June with ropes in the air. At 6 p.m. the “Buckles & Spurs” team roping starts in the Main Arena of Middletown Central Park, a quarter mile off Highway 29 on Central Park Road. For 2026, Lake County Features reported two roping categories, one for ages 7 and under and one for 7 and over. The celebration falls on the third full weekend in June, usually Father’s Day weekend. Its host, the Middletown Central Park Association, holds it “to raise money to build, develop and maintain the park for the people of Middletown.” The 2026 edition, the 65th, ran June 19 to 21 under the theme “Celebrating 250 Years of the Red, White & Blue.” The association gives the 2027 dates as June 18, 19 and 20.

Mutton bustin’ and a dance until one

On Saturday the whole park is in use. Vendors and stage acts fill the park area all day, and a silent auction runs in the Lions Building. After the parade the association serves its barbecue, billed on the schedule as “MCPA’s Famous BBQ,” at the Bob Greenwade BBQ area. The Middletown Lions Club keeps an outside bar open all day. On the Obie Sanders Stage there are free line-dancing lessons through the day and a Cutest Cowgirl/Cowboy Contest, and at 3:30 Middletown High School students perform Baile Folklórico.

In the arena, the children’s playday costs $5 to enter, pays out in ribbons and trophies, and is sponsored by Hardester’s Market & Hardware. Children compete in three age groups: 6 and under, 7 to 10, and 11 to 13. The events are a watermelon-eating contest, a stick-horse race for the smallest, an egg race, a boot race, a three-legged race and a sack race. The finale is a water-balloon toss and what the program calls the “water blaster brigade.” A tug-of-war follows. Breakaway roping and barrel racing start at 2 p.m. At 4 comes mutton bustin’, open to the first 20 entered.

At 8 p.m. the Dance Under the Stars begins on the Obie Sanders Stage, and the schedule runs it to 1 a.m. Tickets are $15 a person or $25 a couple, and children 10 and under get in free. Lake County News gave the 2026 band as The Happy Axedents, while the association’s schedule lists “The Happy Accidents.”

Sunday starts with the Lions Father’s Day Breakfast, 8 to 11 a.m. in the Lions Building, and Cowboy Church at 9 by the stage. Later in the day there is the Bloody Mary Horseshoe Tourney at the Youth Football horseshoe pits, a gymkhana in the Main Arena, and the Queen and Princess Raffle. The Hide Ride & Rescue Race runs at dusk. The money goes to the park and to the Lions Club. According to Lake County Features, the club gave five $1,000 scholarships to Middletown graduates in 2026, and it works with the association to maintain the children’s playground behind the Lions Building.

The parade on Highway 29

The parade steps off at 10 a.m. Saturday, after an 8 a.m. line-up. Entries gather in the dirt lot at Perry’s Deli at the south end of town. They travel north on Highway 29 to Young Street at the Tri Counties Bank, then return by Bush Street. Floats bound straight for the park may have to wait on Pine Street until the highway reopens. The 2026 rules capped the parade at 100 entries and limited skits to a minute and a half. Entry categories included Junior Horseman, Fireman’s Entry, Farm Equipment, Antique Car, Charro/Charra Costume, Mounted Person/Group and Pooper Scooper.

Kathleen Scavone of Lake County Features described horses, floats and classic cars on the route, with clowns blowing bubbles and tossing candy. The 2026 rules forbid throwing candy, trinkets or any other object from an entry, and entries that do so can be disqualified from awards. The announcer names the grand marshals as they pass. Trophies and ribbons are handed out at 1:30 p.m. on the park stage.

A park built one structure at a time

The park was given to the people of Middletown by the Stewart family. The association’s history page records that the first Middletown Days was held in 1961 “to start building ‘THE PARK.’” The association still describes the park as privately owned and kept up by volunteers, sponsors and donors. Its undated list of early work reads like a site plan filled in over years:

• a dance floor and bandstand, then the arena
• the Park Club Building, then a lease of land to the Lions Club and the Lions building on it
• Mona Buttle’s Snack Shack and a barbecue overhang
• a new stage and a children’s park
• two of the arena’s four bucking chutes, donated by Clay Emerson
• a new well, drilled by Larry Herman Drilling
• materials for a new snack shack, given by Mike Browning
• a facelift for the arena

In 2011 the celebration marked “50 Years of Fun.” That year’s parade ran on Saturday, June 18. In May 2012 two Middletown High School students, Justin Skinner and Devin Manson, helped install the overhang on the Obie Sanders Stage. That December the seniors who had used the Central Park clubhouse moved to their own new building. Work on a new announcing stand began in October 2012, and the stand went up in 2013. In 2016 Hope City took down the old main building and began building a new one; the group was later named a Middletown Days grand marshal itself. A new Silver Spur Saloon opened in 2017.

On May 18, 2020, association president Charles Egger wrote to the community that the June 19–21 celebration was cancelled. The history page heads his letter “HEAR YEE, HEAR YEE...First time ever. No Middletown Days 2020.” Lake County News later announced the winners of the 2021 Queen and Princess competition.

The same history page keeps photographs of a 1968 Rancheria float, a 1980s drill team of Lisa Comstock and Wendy Johnson, the 1998 parade, and an unnamed Pony Color Guard. It credits Nona Perez and Craig Eve as the park’s “unofficial/official” picture-historians. Nona Perez has also served as a grand marshal.

Grand marshals and pioneers

Each year the celebration names grand marshals for the parade and gives a Pioneer Award. At the 54th annual Middletown Days, the grand marshals were Jim and Carol Bolander, married 55 years after falling in love on one date. Jim had worked 23 years as a machinist and could handle a team of as many as eight horses. The Pioneer Award that year went to Harry and Rilla Krall, who had owned Noble’s Bar on Main Street and restored order there. A biography prepared for the celebration recalled the bar’s earlier days. A rowdy had jumped behind the bar and bitten off half a bartender’s ear. One customer had hit another with a hatchet. Cowboys had ridden into the bar on horseback. Just before the Kralls took over, a customer fired a pistol at the tavern. The same weekend, Selena Weatherwax won the annual Dolly Parton look-alike contest.

The 2026 grand marshals were brothers Grant and Ross Hardester of Hardester’s Markets. Their family chain has stores in Middletown, Cobb and Hidden Valley and began selling groceries and hardware in 1943. Grant started working in the business as a child in the early 1970s, and Ross a few years later. Both remember earning about 50 cents an hour. Their parents had held the grand marshal title before them. Ross remembered watching Grant ride horses in the parade. “What I like about Middletown Days is you see people that have moved away, come back to visit,” Grant said.

The 2026 Pioneer Award went to 96-year-old Hal Webber of Perry’s Deli; the association’s write-up spells the name Weber. Webber moved to Lake County in 1992 after a 27-year career in Fairfax and retired at 59. He opened Perry’s that same year and kept it open from 5 a.m. to 11 p.m., seven days a week. Lake County Features reports that he has owned about 20 Perry’s Delicatessens, including stores in Napa, Sonoma and the Sierra Nevada. The Middletown deli passed from Webber to his son Tim and then to Tim’s son Derek, and its dirt lot is where the parade lines up. “When I think about it, they did all of the hard work,” Derek said. “Perry’s has become an institution because of what they built.”

Grant Hardester put the weekend this way: “You see the grandparents show up, the great-grandparents show up, and the next generation show up.”