OWENSVILLE — Route 66 is celebrating its Centennial year in 2026, which has already brought many travelers through Cuba and the surrounding areas. For those who are attracted to historic landmarks, gems like the Wagon Wheel and Shamrock motels, murals, monuments and large rocking chairs, welcome to Cuba.

While Route 66 travels cross-country from Chicago, Ill., to California there are many sights to see within the city limits of Cuba and the surrounding areas. With the Route  66 Centennial Kickoff event in Springfield on April 30-May 2, Cuba Free Press hit the Mother Road, and we can 100 percent say the Sullivan, Cuba, Fanning stretch has the action.

Bright and early on April 30, the sun was just hitting the yard at the Shamrock Court in Sullivan, as a motorcycle and a Chevrolet pulled up, ready to begin a three-day road trip adventure. The group of six headed for the main office. Employees were busily cleaning the newly remodeled rooms when the motel extraordinaire, Sadie Borrini, greeted eager visitors.

The Shamrock, which is not expected to open until late May, is owned by (Roamin) Rich Dinkela and his wife, Christina Dinkela, who also recently acquired the Wagon Wheel Motel in Cuba. Despite not being open for overnight stays, Borrini was happy to provide a walk-through.

“I just talked to a man from Japan,” Borrini said when asked about visitors she’s encountered as she pointed out stone work with shamrocks, sunbursts and diamond shapes. “Every room will be themed and decorated differently.”

From the neon room with a lit-up 1930s rocket ship, glass walls and rope lights, to the Ozark display that connects to a nature scene complete with a waterfall, this 10-bedroom motel will require multiple stays to see it all.

Rich Dinkela, former president of the Route 66 Association of Missouri and enthusiastic historic preservationist of the road, arrived during the tour.

“We’ll be open in the next couple of weeks,” he said. “We are doing everything we can to be done, and there’s nothing in here we haven’t touched.”

Dinkela said the Shamrock was in a state of disrepair when he first purchased it and began restoring it to glory with new features, from new electric and plumbing to walls and decor.

“Fifty years from now, we don’t want to regret anything we’ve done,” Dinkela said. “People will come here to experience the past with modern conveniences.”

There have been a lot of ups and downs for the Dinkelas, with the Shamrock property and now the Wagon Wheel Motel, but he said it’s worth it.

“This place is a jewel,” Dinkela said. “I think we will have a lot of people stop along the way.”

Dinkela works hard to ensure the survival of Missouri’s history along the road. His trademark name, “Roamin” Rich,” is etched in steel at the Devil’s Elbow Bridge site, and he, along with the Association, owns a 1920s Route 66 Bridge in Laclede County that they hope to restore.

“We want to be one of the most popular stops on Route 66,” Rich said. “Everyone who comes here feels the energy from this place. It was never in any books.”

Dinkela stumbled on the 1948 Shamrock Motel in 2016 and initially began helping the owners to clean it up. Eventually, in April 2021, he purchased it. He has found several Easter eggs along the way in his journey to restore it, including leftover rock that they are using to build the front courtyard, and two exterior rooms that were roughed out to be restrooms for a campground.

“We discovered two exterior bathrooms out back that were never finished,” Rich said.

One room now has a shower, and a second room has a restroom. He plans to add a camper hookup and possibly cabins.

Traveling west into Cuba, a new Route 66 photo opportunity greets visitors on the left-hand side, just across the highway from Missouri Hick Barbecue. The restaurant’s owner, Ryan Meiser, took the initiative to have the family-friendly photo opportunity installed. Next door to the restaurant, the Wagon Wheel Motel’s main office has one of the best memorabilia stores between Sullivan and Springfield, as does its nearest rival, the Fanning Outpost. Visit with the hotel’s front desk attendant and concierge, Laney Highley, about local sightseeing and eateries.

Pick up Route 66 shirts, hats, stickers and maps while checking on availability to stay over. The service is wonderful, and the soda selection is an 8-year-old’s fascination. For the average soda connoisseur, both the Wagon Wheel and Fanning Outpost offer a variety.

Cuba is full of sightseeing selections for everyone, but especially for classic car enthusiasts looking for that perfect backdrop to take a picture along the famous road. The city boasts more than 14 murals, in all sizes. Whether for a group event or a one-kid show, there’s a mural for that.

For single-person pictures or selfies, visit Viva Cuba Gardens at the intersection of Highway 19 and Washington Street, located conveniently across from Rich’s Famous Burgers (102 West Washington Blvd. To visit all the local sights would take a full day at least.

Cuba and the surrounding areas are also top-notch when it comes to the hidden gems, from historic cemeteries located between Route 66 and Interstate 44 to original road curbing. Travelers may someday soon choose to stay at the Shamrock in Sullivan, only to travel a few miles to stay at the Wagon Wheel, the oldest continuously operated motel on Route 66, and visit all Cuba has to offer before hitting the road to the Fanning Outpost and the world’s second largest rocking chair.

Ryan and Jennifer Thompson own the Fanning Outpost, with its large array of Route 66 memorabilia, from clothing to postcards to stickers. The Cuba Free Press group was sure to grab a stack of it all at both of Cuba’s retailers, because the road offers plenty of locations to leave stickers.

Grabbing pictures to prove our visit, and leaving our own sticker on the rocking chair before heading out, we began to notice other travelers on the road. None was more memorable than a couple in a new red Chevrolet Corvette, which we’d been following for most of the day, and finally caught up with them at the Uranus Fudge Factory in St. Robert.

Traveling from Billings, Mont., Tony and Cindy Leenknecht left home on April 22, shortly before spring storms, with hail and tornadoes, hit the Midwest. They began their trip in Chicago, Ill., and made it to Cuba on April 30, with plans to attend the Springfield Centennial Kickoff before traveling cross-country.

Fascinated with the road and willing to explore, Cindy Leenknect said they had visited the Pier in Chicago, Ill., Litchfield, Ill., had a memorable military museum and Springfield, Ill., had a remarkable neon light park; but Cuba was one of their favorites.

“We’ve just come down here,” Cindy Leenknect said. “Then the next favorite one is really in Cuba, actually, with the murals and the Civil War murals on the local past. It was awesome.”

Notable fans of original Route 66 historic places, the couple stayed at the Exquisite Victorian in Springfield, Ill., where they weathered out the spring storms. Tony Leenknect said they met wonderful people on Route 66. He highly recommended the proprietors of the Exquisite Victorian Hotel. The small-town accommodations along the original route, such as the Exquisite Victorian, Wagon Wheel and Shamrock, provide homey services that aren’t available in the cities.

“We were fearful of the tornadoes coming into St Louis,” Tony Leenknect said, adding that they requested to stay another night at the Exquisite Victorian, but it was booked out. The owners made it work. “They actually gave up their bed to host us, and they also allowed us to park our Corvette in their garage.”

They may have lost a day of travel, but Tony Leenknect said they made memories.

“We told each other our life stories,” he said.

Cindy Leenknect added that they also heard the tornado sirens. She added that it’s the people along the route that make the biggest impact. Traveling in a newer Corvette draws attention and makes it easier to pick out fellow travelers.

“We were talking to some people from France and Portugal last night, and they saw our car has number one on it, right. They said ‘that is worth more in our country than the car is,’” Cindy Leenknect said.

The couple planned to attend a drive-in movie in Carthage before heading to Springfield for the events.

Cuba Free Press met several couples like the Leenknects, traveling the road with the hopes of seeing the country. Time moves more slowly along Route 66, especially in a classic car. A couple from Louisiana used their trip’s delays over the last several years to create a longer itinerary.

It’s been six years of saving, preparing her 1966 Pontiac Bonneville soft top convertible, and painstakingly researching every town on Route 66 to complete a bucket list of sites to see, but Regina Adkins and her husband, Michael Adkins, are finally on the road.

The couple left their home in Shreveport, La., on March 30, and headed to California to start Route 66 from the beginning of their line. Regina Adkins, whose name means “queen” in Latin, said she has wanted to ride this road for years. It was a bonus that their trip happened to coincide with the National Route 66 Kickoff event in Springfield.

“It’s been an experience, that’s for sure,” Adkins said, talking about things they saw along the route. “Williams, Arizona, was just an hour from the Grand Canyon. It’s a wonderful trip there.”

Her husband, a hobby photographer, took pictures of her car at Forrest Gump Point in Monument Valley.”

Adkins said traveling the road in the same year as America’s 250th birthday has added to the trip.

Although they had already been traveling for five weeks, they still had a way to go.

“We started in California,” she said. “We’re going the other way, to Chicago. Yeah, we kind of ran out of time because we kept looking at stuff.”

The couple originally planned to see the whole route and be on the return journey from Chicago, Ill., but instead, they were just arriving in Springfield, Mo.

“We planned to go to Chicago and then come back here, but we ran out of time,” Adkins said.

Highlighting places they’ve been, Adkins pulled up a list of towns and sights along Route 66 that she knew she wanted to see.

“I made a list of all the small towns on Route 66,” she said. “Did them by state and from west to east, and then I labeled which ones had the cool stuff. Cuba, I have the Wagon Wheel Motel, the murals, the totem pole and the Trading Post.

The Free Press group added a few more.

“Every state has something beautiful about it,” she said. “Death Valley, the Mojave Desert in California. The cactus was blooming. This is April, so there was a lot there in Arizona.”

She said they met so many people.

“Met a lot of Native Americans, Navajos,” Adkins said. “A lot of them wanted to ride in our car.”

Initially, Adkins said they worried the car would be damaged or broken into during this adventure, but they’ve met really nice people along the way.

Traveling Route 66 in a classic car invites attention and conversation from the select group of travelers who are determined to ride the whole way. Strangers are only strangers for a second before they’re sharing stories like lifelong friends. The Adkinses tell those they encounter who are thinking about making the trip that they shouldn’t wait.

“Life is short,” she said, adding that cancer prevented them from taking the trip sooner. “It makes you realize, time is short. You can’t wait until you’ve got enough money or got enough time.”

A proudly framed plaque of Adkins’ bucklist sat with her powder blue Bonneville, “I want to cruise Route 66 on its 100th anniversary in 2026, in my 1966 Pontiac Bonneville convertible while I am 66 years old!”

It’s at least a day’s worth of sights around Cuba and in the surrounding areas, with great food, historic accommodations, and plenty of gems. Cuba’s where it’s at.