Back in the late 1800s and early 1900s, Pendleton was famously known as the entertainment capital of Eastern Oregon. The rough-and-tumble town had been a vital stop for pioneers on the Oregon Trail, serving as a railroad hub for connecting to nearby communities and hosting a whopping 32 bars and 18 brothels in the downtown core.

Today, the city of nearly 17,000 has sanded down those rough edges but retains a strong sense of history. From the Pendleton Bronze Trail to the various museums in and around town, you are never far from Pendleton’s storied history: the good, the bad, and the ugly.

So as the sun sets on back-to-school season, give yourself a crash course on the city’s claims to fame (and, at times, infamy) with visits to these intriguing, family-friendly museums and historical sites. Pendleton History 101 is now in session.

Go Beneath the Surface: Pendleton Underground Tours

If you want to get a feel for what those early days were like, there’s no better place to start than with Pendleton Underground Tours.

Offered year-round, the tour takes roughly 90 minutes and heads under the city’s sidewalks to deliver an immersive look at Pendleton’s historical underground economy (literally). Visitors pass through a replica bar, an old cardroom, underground bunks, and more–all lurking below the modern-day downtown. “It sets the stage for Pendleton,” says Brooke Armstrong, executive director of Pendleton Underground Tours. “It gives you an idea of what Pendleton was about and what it was like.”

The various rooms are decorated to look as they did in the late 1800s, and each tour guide offers historical information and context for how the underground thrived.

Of course, Pendleton’s seedier side gets its due. The tours don’t shy away from discussing prostitution (one aboveground stop is an old brothel), opium dens, bootlegging, and other crimes. “That always draws people’s interest,” Armstrong says.

Note: Children under 6 and pets are not allowed on the Pendleton Underground Tour, and reservations are required.

Only in Pendleton: Round-Up and Happy Canyon Hall of Fame Museum

With a stadium large enough to host a professional sports team, it only makes sense that Pendleton’s historic Round-Up rodeo gets its due with a hall a fame that celebrates more than a century of bull riding, barrel racing, bareback riding, and more.

The Round-up and Happy Canyon Hall of Fame Museum opened in 1969 and has since expanded to tell the story of the people and participants who’ve made the Round-Up and Happy Canyon such legendary events. Exhibits and displays show Native American and cowboy artifacts, historical information on past Round-Ups, Happy Canyon, and more.

10,000 Years of History: Tamástslikt Cultural Institute

Native Americans have 10,000 years of history on the Columbia Plateau, and that story is told in exacting detail at the Tamástslikt Cultural Institute, located on the Confederated Tribes of the Umatilla Indian Reservation located behind Wildhorse Resort and Casino.

The museum celebrates the Cayuse, Umatilla and Walla Walla tribes with rotating exhibits, film, multimedia displays, artwork, and authentic artifacts.

That history can be seen in the Coyote Theater–where a 10-minute presentation blends playfulness and tradition to tell the story of how the world came to be–and throughout the main exhibit hall, where hundreds of artifacts line the walls. In a more somber setting, the museum unflinchingly shows how tribes were chased off their land and forced onto reservations as European-Americans ventured west in the 1800s.

Ready for Takeoff: Pendleton Air Museum

One of the region’s newest museums, the Pendleton Air Museum opened in downtown Pendleton in the summer of 2017.

The museum was originally established in 1989 and had searched for years for a home to showcase its displays on 20th century history and aviation. And, as it turns out, Pendleton had a close connection to that era: The city’s airport was turned into an air base during World War II, and it housed members of the 555^th Parachute Infantry  an all-black smoke jumping unit known as the Triple Nickles that fought forest fires across the country. Pendleton’s air base was also home for a time to the Doolittle Raiders.

Exhibits change every few months, but visitors can generally expect to encounter historical artwork, old military uniforms, and wartime artifacts–including helmets and canteens.

For the Kids: Children’s Museum of Eastern Oregon

Adults shouldn’t have all the fun, so the Children’s Museum of Eastern Oregon promises an enjoyable day for your little ones.

The aspiring chef in your family can play in Big John’s Pizza Kitchen; budding artists can get creative in the Art Studio; your future firefighters can hang out in the Fire Station; tomorrow’s rock stars can practice in the Music Wall; and so forth. The museum offers exhibits for toddlers and children of all ages, and the various play areas are designed to help a child learn, grow, and develop in fun and engaging ways.

Local Insight: Heritage Station Museum

Tucked into Pendleton’s 1909 train depot, the Heritage Station Museum documents more than 150 years of Umatilla County history.

It does so through a variety of artifacts and immersive exhibits that don’t stop at telling visitors about life in Umatilla County. Rather, the museum shows what life was like with a 1942 caboose (which is open for viewing), a converted gallery that documents the region’s history; a barn and homestead re-creation, complete with authentic farm tools; a one-room schoolhouse that closed in 1940; and more.

It’s tough to fit all of Pendleton’s museums into a one-day visit. Check out our accommodations in and around Pendleton for overnight stays at  historic hotels, B&Bs, resorts, and lodges.