How to Have a Grand Ol’ Time at Leavenworth, the Oldest City in Kansas

Leavenworth, Kansas

As the first city in Kansas, Leavenworth knows a thing or two about frontier life. The still-active Fort Leavenworth trained Buffalo Soldiers and mapped the Santa Fe Trail, while downtown holds onto its riverboat-era charm.

You’ll find military history buffs, Army families, and locals mixing it up in this Missouri River town. Add it to your weekend getaway bucket list, and here’s the best things to do during your visit.

It’s the Oldest and First City in Kansas

Founded in 1854, Leavenworth is Kansas’s first incorporated city. A group of settlers from Weston, Missouri started the town near Fort Leavenworth, and it quickly became a hub for folks heading west.

Its spot on the Missouri River made it great for transportation, while the nearby fort helped the city grow fast. During the territorial days, Leavenworth played a big part in the “Bleeding Kansas” conflicts, with both pro-slavery and anti-slavery groups leaving their mark on the city’s early days.

Historic Leavenworth Main Street

Downtown Leavenworth mixes old-school architecture with modern shopping. Walking down Delaware Street, you’ll spot beautiful Victorian buildings housing cool boutiques, antique shops, and local eateries.

More than 275 independent businesses call this area home, selling everything from handmade crafts to vintage treasures. Don’t miss local favorites like Queen’s Pantry British Foods, Artistic Works by Lu, and The Pot Rack. The whole area really comes alive during the Holiday Open House and Summer Sidewalk Sale.

Follow the 5K History Walk

The 5K History Walk lets you get some steps in while soaking up local history. This self-guided tour takes you past about 130 locations that tell Leavenworth’s story while you stroll through downtown and nearby neighborhoods.

The 5K walk begins at Haymarket Square, located at the intersection of 7th and Cherokee Streets. Participants head east along the south side of Cherokee Street towards the Missouri River, then follow Esplanade Street to Delaware and Shawnee Streets before returning to the starting point.

Check Out the Carousel Museum

Charles Parker (the “Amusement King”) set up his factory in Leavenworth back in 1892, making hand-carved wooden carousels that shipped all over the world.

The C.W. Parker Carousel Museum, also known as the Leavenworth Carousel Museum, is one of several museums sponsored by the Leavenworth Historical Museum Association.

Opened in 2005, the building houses carousels that are historically registered, as well as a C.W. Parker cylinder piano, an Artizan A-X-1 band organ, and a Wurlitzer 153 Band Organ. It also has several reproduced or repaired carousel horses.

Visit America’s Oldest Active Military Base

As the oldest active military base west of the Mississippi, Fort Leavenworth is a must-see. Built in 1827, this place was key to America’s westward expansion. You can visit several cool spots here, like the Frontier Army Museum with its military artifacts and the impressive Buffalo Soldier Monument.

The latter commemorates the service and sacrifices of the 9th and 10th Cavalry Regiments. They were also known as the “Buffalo Soldiers,” who were African American soldiers who served in the U.S. Army during the late 19th and early 20th centuries.

Drive The Glacial Hills Scenic Byway

The Glacial Hills Scenic Byway offers 63 miles of rolling hills shaped by ancient glaciers thousands of years ago. The route winds through Leavenworth, Atchison, and Doniphan counties with amazing views of bluffs and the Missouri River.

Fall is hands-down the best time to go, when the hills explode with red and gold leaves. Keep your eyes peeled for deer, wild turkeys, and all kinds of birds along the way.

See Rare Lincoln Artifacts at Saint Mary University

The University of Saint Mary has one of the coolest Lincoln collections you’ll find anywhere. Thanks to the donation of Bernard H. Hall. The hall contains more than 10,000 items, including rare items such as one of Lincoln’s last messages to his wife.

The Abraham Lincoln collection, known as the Bernard H. Hall Abraham Lincoln Collection, is housed within the LeBeau Special Collections at the University of Saint Mary, located on the second floor of the Keleher Learning Commons.

Spend Time at Rustic Rural Farms

Leavenworth’s farm scene is booming with cool spots to visit. Swing by Crescent Moon Winery to sample local wines in their tasting room surrounded by vineyards. At Manna Meadows, you can hang out with fuzzy alpacas and shop for super-soft alpaca products.

Don’t miss Grinter Farms in September when their massive 40-acre sunflower field blooms – it’s an Instagram goldmine! Hillside Honey Apiary sells amazing local honey, while Lazy B Ranch offers tours featuring heritage livestock. Most places are seasonal and might need reservations, so call ahead.

Hunt for Colorful Street Art Throughout Town

Grab your camera and go on an art hunt around town! Leavenworth has a number of awesome murals painted on buildings downtown. Check out the “First City of Kansas” mural on406 Shawnee Street, or the “Explore Leavenworth Mural” at 416 Cherokee Street, a Buffalo Bill Cody mural.

The statues are cool too, such as the Buffalo Soldier Monument and the 6888th Central Postal Directory Battalion Monument, as well as an Abraham Lincoln statue in the city’s downtown area.

Explore the First City Museum

The First City Museum tells the story of Leavenworth’s unique history as Kansas’s oldest city. Before becoming a museum, it housed the home of four prominent families.

The museum today is much like it appeared after a major renovation in the mid 1880s. The First City Museum houses collections of early Leavenworth frontier railroad artifacts including buggies, cutters, Great Western Stoves, and even a large bank safe where Buffalo Bill Cody’s father, Isaac, stored his gold dust.

Drop by the Leavenworth Farmers Market

Nothing beats farm-fresh produce! Head to the Leavenworth Farmers Market on Saturday mornings held at Haymarket Square on Cherokee Street, open from May 4th through August 31st, 7 AM–12 PM, and from September 7th through October 26th, 8 AM–12 PM.

You’ll also find specialty items like fresh vegetables and fruits, handmade soaps, and berry jams. The farmers are super friendly and happy to chat about growing tips or recipe ideas.

Go on a Melissa Etheridge Hometown Tour

Rock star Melissa Etheridge grew up right here in Leavenworth before hitting it big. Music fans can follow a self-guided tour of spots important to the Grammy winner’s early years.

You’ll see her childhood home and Leavenworth High School where she studied and performed in talent shows. The Hometown Tour takes you through key spots in Melissa’s life, starting with the guitar-shaped sign at 4th St. and Muncie Rd., honoring her hometown.

It then moves to the Leavenworth VA Medical Center, 4th Street, and The Tune Shop, where she took music lessons. Other highlights include the C.W. Parker Carousel Museum, the Missouri River, and the United States Penitentiary, all featured in her songs.

How to Get to Leavenworth, Kansas

Leavenworth is just 30 minutes northwest of Kansas City. Flying in? Kansas City International Airport (MCI) is only 25 miles away.

Highways I-70, I-29, and US-73 all provide good access to town though not directly. If you’re not renting a car, there are shuttle services from the airport, but you’ll need to book ahead.

Once you’re in Leavenworth, downtown is totally walkable, though you’ll need wheels to check out Fort Leavenworth and the farm attractions. Parking is plentiful and free throughout town.