The Katy Trail State Park has many distinctive features, one of which is that it’s the longest rails-to-trails park in the United States. Imagine an historic railroad, the MKT, otherwise known as the Katy, running for 264 miles through the state of Missouri, then remove the tracks—and that’s the park. It’s a long, crushed limestone, skinny path that more or less follows the Missouri River.

I was lucky enough to join a group of cyclists hosted by Missouri Tourism to explore the trail in June. While I stayed with the support vehicle since I don’t cycle, I hiked a lot of the trail and explored many of the communities along its path. As I told my cyclist friends, it felt like every day lasted a week with all of the discoveries I made!

Here are some of my favorite stops on the Katy Trail.

St. Charles

I flew into St. Louis, MO, situated right next to St. Charles and the start of the Katy Trail State Park at the Machens Trail Head. St. Charles, the original seat of Missouri’s state capitol in the 1800s, is an historic city. In fact, the old Capitol building is just a stone’s throw from the Katy Trail.

You don’t even have to leave the trail to see the 15’ statue of Lewis & Clark, and Seaman (Lewis’s Newfoundland dog) in Frontier Park. In fact, the Katy Trail between St. Charles and Boonville is an official segment of the Lewis and Clark National Historic Trail.

Between my strawberry shortcake at Boone’s Colonial Inn for lunch, and a cold one at the Bike Stop Café, I spent the afternoon soaking up the history of St. Charles.

Augusta

Augusta is a B&B paradise with a dozen, mostly historic, properties. After an early morning walk, I ate breakfast at Kate’s Coffee House Café to the ringing of 160 year-old church bells, then sipped wine from vineyards established in 1859 at Mount Pleasant Winery for coffee break. The Augusta area, I discovered, was the first federally approved American Viticultural Area in the U.S. The reason—the Hayne Silt-Loam soils in the area.

Today, there are a dozen wineries with amazing tours like the ones at Montelle Winery and Noboleis Vineyards. The vineyards I didn’t visit, I sampled during dinner at the Silly Goose Restaurant in Augusta.

Hermann

I have to confess that Hermann was my favorite stop along the Katy Trail. My visit started at the Stone Hill Winery, and its Vintage 1847 Restaurant built in an old barn with even the stalls still preserved.

One of the great things about Hermann, especially for visitors on bicycles, is that they have a low cost ($10 for the day) trolley that takes you out to all nine wineries for tastings as well as through the historic town. After a day of wine tasting, it’s also great to find many B&Bs to stay in. Mine was the Captain Wohlt Inn (circa 1840) with a room that was historic—cool—and comfy!

For insights into the past of this historic community, the Old German School Museum is a must-see. Likewise with the Tin Mill Brewing Company, where you’ll find their brewed beer or cider along with pizza, and a completely intact mill that’s ready to grind grain.

Cyclists ready to fill their coolers and move on will find the Wurst Haus, with all of its homemade brats and sausages (they recently won 10 first place prizes out of 10 entries in the Best of the Wurst German competition!), the perfect place to have breakfast and stock up.

Jefferson City

Jefferson City is the Missouri State Capitol, so a free guided tour of the Capitol Building is great for a hot afternoon’s activity. While the elegant Ozark gray marble interior is stunning, my favorite room was the House Lounge with the colorful Thomas Hart Benton Murals and their playful look at the state’s history.

For a totally different experience of Missouri, visit the Missouri State Penitentiary (built 1831), which looks exactly the way it did when the last prisoner was moved to the new facility in 2004. You can even sit in the gas chamber if you dare! Afterwards, chill out at everyone’s favorite local ice cream spot, Central Dairy Ice Cream Parlor, or sip some cool Go to Jail Ale, or Deathrow Oatmeal Stout, at Prison Brews Brewpub.

Rocheport

Katy Trail cyclists find the old 243’ train tunnel at Rocheport a great place to get out of the sun. The tunnel, built in 1892, has a naturalistic cut through the native stone on the eastern end, and the western end has a Romanesque arch, with the soil above supported by brick and rustic stones.

The town has a number of beautiful historic brick properties to see as you pedal through, plus some antique shops to stop in. My most amazing find though, was a jukebox store/museum, with all kinds of musical collectibles from a 1948 Trashcan juke box to vintage albums.

Boonville

Boonville is a great stop, with the Boonville Visitor Center & Museum situated right on the Katy Trail. Next to it, you’ll also find the restored mission style station and caboose, along with the Lewis Miller’s Mitchell Collection of vintage cars, wagons, cycles and motorcycles. It has 400 sites and structures on the National Register of Historic places, one of which is Hotel Frederick—I can highly recommend it for lunch or a place to spend the night.

 Sedalia

The old west is still alive and kicking in Sedalia, which for a few decades back in the 1800s was the trail’s end for cattle drives. In fact, an iconic bronze sculpture of a cowboy driving cattle, created by J. Michael Wilson, fills the Trail’s End Starline Brass Plaza. Marked by an historic arch, the downtown has about 112 properties on the National Historic Register. The Sedalia Katy Depot which is part of the trail, was built in 1896, has been fully restored, and contains an excellent museum of the area history.

And for a great dining experience as the end of the Katy Trail nears, check out Kedhe’s BBQ, aboard a vintage rail car.

Clinton Trail Head

I’m sure you’ll agree, when you reach the Clinton Trail Head, mile marker 264, that the Katy Trail has been a grand adventure!