Windsor Harvest Festival

Early on the Sunday morning of the 2026 Windsor Harvest Festival, word went out from the organizers: “Confirmed! We are setting up for launch this morning.” The launch was the hot-air balloons at Eastman Park, which go up on festival mornings when the weather allows. The same notice told people to bring their coffee and donuts and “drag your crew out of bed.” The donuts that morning came by way of Mr. Yo’s Donut, which the festival thanked by name.

The festival runs over Labor Day weekend, Saturday through Monday, and bills itself as Windsor’s largest celebration. It spreads across three town parks. Eastman Park has the balloons, Boardwalk Park has the Saturday night fireworks, and Main Park has the vendor rows. The Town of Windsor Parks, Recreation & Culture department lists the festival among its special events. A 2017 Greeley Tribune account described it as a collaboration between town departments and the Windsor Harvest Festival Committee, which is mostly run by volunteers. The festival’s own page calls it a non-profit. The 2026 edition opened on Saturday, September 5, and was billed as the 104th annual.

Balloons, pancakes, and pie without forks

On the Saturday night of 2026, the fireworks over Boardwalk Park were joined by a drone show, which the festival credited Chevron with helping to make possible. Boardwalk Park is also the site of the Windsor History Museum. It holds five old buildings moved there from around town, among them the 1882 train depot, a schoolhouse, a beet shack and a chapel.

On Sunday, the balloons were followed by breakfast. Community groups host a pancake breakfast at the Rec Center; in 2026 it was Colorado Impact Gold. The festival steered diners from there to the Windsor Cruise-In Car Show, where classic, custom and muscle cars park in the Windsor High School lot at 1100 Main Street. The parks department’s notice for the show listed breakfast burritos from Luna’s Tacos and Tequila, drinks from Espresso on the Move and gelato from Puciugo Gelato.

Main Park holds more than 200 vendor booths on Saturday and Sunday, with arts and crafts among the commercial stalls. The park also has a farmers market, live music, games for children and a beer garden. Kelsey Jo and the Wildcards played Main Park on the Sunday of 2026. There was a chalk-on-the-walk contest, and a pie-eating contest with strict rules: no forks, no spoons, no hands. Afterward the organizers admitted they were not sure who had won, “but we are pretty sure everyone left with pie in places pie was never meant to be.”

Parade morning on the final day

Monday belongs to the parade, which starts at 9:00 a.m. “Grab your family, friends, coffee and breakfast and come find a seat,” the festival posted on the morning of September 7, 2026. That year the parade was led by its grand marshals, Debbi and Don, who were honored for helping handle the festival’s hot-air balloons for the previous 20 years.

Entries are judged by class. In 2026 the commercial float prize went to Mood Ease Massage, with Fritzler’s Farm Park second. Severance High School Performing Arts Booster and Windsor Baptist Church placed in the religious and non-profit class. Windsor High School Football and A Dance Place placed among youth groups, and the Colorado Eagles and Corvettes West Car Club among the cars, trucks, boats and motorcycles. The Pride of Windsor Marching Band took the large-school band prize, and Nelson Nutrition Minis won the adult horse class. The tractor class went to an entry listed simply as “Tractors.” After the last float, the afternoon went on with food, rides, games, bingo, the beer garden and live entertainment.

The boy at 1st and Sunflower

The festival’s chairman, Casey Johnson, first saw the parade when he was 8. He told the Greeley Tribune in 2017 that the floats lined up at the corner of 1st and Sunflower streets near his home, and he remembered the colorful floats and a lot of candy. At 10 he rode in the parade as a Boy Scout, and in eighth grade he began helping with the festival for community service. More than 20 years later, in 2017, he was its chairman. On October 2, 2026, the Windsor Area Chamber of Commerce named the festival its non-profit of the year. The festival’s thanks went first to Johnson, “for his tireless work bringing this community together every year.”

Johnson’s 2017 festival added a little train and inflatable slides to the kids’ zone at Main Park. That year the home and garden show became a garden show only, because the home side had drawn little interest the year before. Residents brought the best things from their gardens, from the biggest pumpkin to the best-looking flowers, and the public chose a winner, who received a $50 gift card. The country singer Carly Pearce was booked for the free Saturday night concert, and the Tribune expected a crowd of thousands.

Luke Bolinger, then the town’s recreation supervisor, described the festival this way: “It celebrates Windsor as a community in the fact that everything is centered around how Windsor has grown and what we’ve seen develop here in Windsor.” On the work it takes, he said: “There’s just so much history with those three days, it takes a lot of folks.”

Two paved blocks in 1921

That history begins with a road. Caitlin Heusser, museum curator for the Town of Windsor, wrote in the Greeley Tribune in 2016 that Windsor became the first town in Weld County to have a paved street in 1921, when two blocks of Main Street were completed. The town celebrated with a Carnival of Progress, a full day of events held on the new pavement. There was a decorated auto parade and a grand masked ball, an airplane exhibition and airplane rides, egg and balloon races, a tug of war, and bronco busting. Johnson’s version, as he gave it to the Tribune in 2017, is that the festival began as a celebration of the first paved stretch of road into Windsor, where Main Street is now.

From 1922 to 1941 the celebration continued each year as the Labor Day Carnival. Heusser wrote that it was suspended for seven years during the Second World War, and when it returned it was dubbed the Harvest Festival.