Anna Reishus/Little Village

The route for RAGBRAI LI stretches from Glenwood on the Missouri River to Burlington on the Mississippi. At 424 miles, this year’s route is fairly short, but it will be the “hilliest ever RAGBRAI,” according to organizers.

It’s not the first time Glenwood and Burlington have been connected. In 1869, the Burlington and Missouri River Railroad reached Glenwood, its final stop in Iowa before heading to Omaha.

Between the start and finish, riders will spend the night in six other southern Iowa cities. Read on for some background on the burgs about to be bombarded by bicycles.

Glenwood

Named after Presbyterian minister Glenn Wood in 1852, this burg is nestled among the Loess Hills, and a quick climb up Old Slaughterhouse Hill gives you a lovely view of the area.

The hills come alive every year as the wildflowers bloom, which inspired the name for the annual Glenwood Superbloom, a gravel cycling race for women. This year’s Glenwood Superbloom is scheduled for Sept. 21, giving any interested RAGBRAI rider two months to rest and recuperate before the race.

From Glenwood, riders will pedal 44 miles, climbing 2,955 feet, to…

Red Oak

Red Oak is home to the impressive Montgomery County Courthouse, described in the National Register of Historic Places as “[p]erhaps the best of Iowa’s Victorian Romanesque courthouses.” Construction on the stately edifice began in 1891.

In a very Iowa moment, it was decided that the old courthouse in Frankfort, the original county seat, would be salvaged to try to save a little dough. Locals voted to drag the two-story building from Frankfort to Red Oak.

“The courthouse was raised up and put upon huge sleds which were yoked to thirty oxen,” according to an early history of Montgomery County. In another very Iowa moment, the movers were overtaken by a surprise blizzard about halfway through the eight-mile journey. They “lost control of the sleds as they were going down an incline… and the courthouse [was] allowed to wander on its own across the prairie” once the oxen were unyoked.

It disappeared from sight.

“It wasn’t until well after the storm that it was located on a farmstead two miles northeast of Red Oak,” the history continued. The oxen were yoked up again, and it was dragged to town square.

Every summer, Red Oak celebrates its history with a festival, Junction Days. (The town’s original name was Red Oak Junction before being shortened in 1901.)

From Red Oak, it’s 40 miles and 1,699 feet of elevation to…

Atlantic

According to local lore, the founders of Atlantic decided to give the town an oceanic name because it was approximately halfway between the Atlantic and the Pacific. A coin was tossed, and the Atlantic won. Whether or not that’s true, Atlantic is connected to both oceans via the American Discovery Trail (ADT), the only continent-spanning trail system just for hikers and cyclists.

Atlantic sits on the northern route called the T-Bone Trail, which follows an old spur line the Rock Island Railroad built to speed up the shipment of Cass County cattle to Chicago’s meatpacking plants. Twenty-five miles up the ADT to Audubon sits Albert, the world’s largest bull statue. Erected in 1964, the 28-foot tall, 45-ton Albert is made of steel and concrete and overlooks the trailhead.

From Atlantic, riders will pedal 79 miles, climbing 4,384 feet, to…

A RAGBRAI rider stops for a drink in downtown Des Moines on Wednesday, July 26, 2023. The week of RAGBRAI was plagued by extreme high temperatures. — Courtney Guein/Little Village

Winterset

Named on an unseasonably cold day in July 1849, Winterset is also appropriately home to the cozy Iowa Quilt Museum.

The city is probably best known as the birthplace of Marion Morrison, known as the actor John Wayne. It’s hard to explain to anyone under 40 what a towering figure Wayne was — in part because most of his 175 movies haven’t aged well, culturally or cinematically — but the John Wayne Birthplace Museum can give visitors a sense of his celebrity.

Winterset’s city park is also home to one of Madison County’s six celebrated covered bridges, as well as Clark Tower, a 25-foot-tall, castle-like limestone structure built in 1926.

Back on the bike, and 74 miles and 3,039 feet of climb later, you’re in…

Knoxville

Knoxville is famous for dirt track racing at the Knoxville Raceway, and its National Sprint Car Hall of Fame & Museum brings in visitors all year long. But RAGBRAI isn’t about internal combustion engines, so let’s honor Knoxville as the birthplace of the Iowa flag instead.

State flags seem like a normal part of life, but the idea didn’t catch on until after the Civil War. By 1917, there were only three states that didn’t have a flag and Iowa was one of them. That year, Dixie Cornell Gebhardt, a lifelong resident of Knoxville, rose to the challenge and created the flag still flying today. Gov. William Harding called Gebhardt “Iowa’s Betsy Ross.”

Sixty miles and 2,441 feet in elevation later is…

Ottumwa

One of America’s must-try diners, Canteen Lunch in the Alley has been serving its version of a loose meat sandwich for the better part of a century. Local boy turned semi-star Tom Arnold introduced Rosanne Barr to the sandwich, who incorporated it into her show, Rosanne.

The spot only has 16 stools, so it can be hard to get a seat. But there are plenty of other options outside the alley, and every year Ottumwa’s food, music and growing diversity is celebrated in the VIVA Ottumwa International Festival.

Cyclists face their longest day, because it’s 82 miles and 3124 feet in elevation to…

RAGBRAI riders camp in Iowa City, their overnight stop on Friday, July 27, 2018. — Zak Neumann/Little Village

Mount Pleasant

Mount Pleasant is accustomed to welcoming thousands of visitors. Every summer since 1950, it’s hosted the Midwest Old Threshers Reunion, a five-day celebration of the era when farm equipment was steam-powered.

Old threshers and other parts of the Midwest’s agricultural heritage are preserved in the Richard E. Oetkens Heritage Museums in Mount Pleasant. At the Hazel Grace Pierson Carousel Pavilion, visitors can ride a restored antique carousel — steam-powered, of course.

The Union Block, built in 1861 and still standing in downtown Mount Pleasant, was a hub for civil rights advocates in the 19th century, its visitors including Frederick Douglass and Sojourner Truth. It also housed the county court offices that awarded Arabella Mansfield her license to practice law in 1869, after she became the first woman in the U.S. to pass the bar exam and be recognized as an attorney.

The final leg of 45 miles and just 1,099 feet of elevation change brings riders to…

Burlington

Burlington is where RAGBRAI LI ends, but it’s where Iowa as part of the United States began. The first raising of the American flag in what became Iowa happened in 1805 in what’s now Burlington’s Crapo Park. In 1838, Burlington became the first capital of the newly created Iowa Territory.

The 85-acre Crapo Park next to the Mississippi is an ideal space to relax and celebrate on July 27. The park has an arboretum, a botanical garden and, as if being adjacent to one of the world’s great rivers wasn’t enough, a lake.

Cyclists looking for a bonus challenge can’t miss Snake Alley, which has a decent claim on the title “Crookedest Street in the World.” The snaking shape of the one-way street was designed to help horses keep their footing as they descended the sharp incline of Heritage Hill in 1894. Now it’s a tourist attraction, and inspired the Snake Alley Criterium, an annual bike race every May with a course that forces riders to try to navigate Snake Alley going uphill.

This article was originally published in Little Village’s April 2024 issue.