The history of Oshkosh flows throughout the city, and with it are the many features and activities it offers.

Oshkosh was once home to the Ho-Chunk Indians, who surrendered their land to the United States government in 1836. Webster Stanley, one of the area’s first white settlers, built his home in the area, followed by a trading post, a tavern and an inn. Settlers began flocking to the area, and soon enough, the first sawmills — for which Oshkosh became famous — started operating.

The Civil War and the expansion of railroads boosted Oshkosh’s lumber trade, giving it the nickname “Sawdust City.” The town continued to flourish, but fires in 1874 and 1875 ravaged and destroyed the original downtown. Still, many of the reconstructed buildings are standing today.

Much of Oshkosh’s unique Native American history is on display at the Oshkosh Public Museum, located near the campus on Algoma Boulevard. “With almost 300,000 objects in our collections,” the museum’s site says, “you are sure to discover some awesome artifacts on view.”

“The museum is the ideal place to connect with the community and its past … [with] over 70,000 historic photographs, along with film, letters and diaries.” The museum also features a wide array of programs and presentations throughout the year, the calendar for which is located on their website.

For those looking to learn more about Oshkosh’s history, the Paine Art Center and Gardens, 1410 Algoma Blvd., sits at the heart of the city’s lore. Also located near the UWO campus, construction of the historic estate began in the 1920s as Oshkosh’s lumber businesses continued to expand. The Paines didn’t build the house for themselves; rather, they wanted the house to serve as a museum showcasing exquisite architecture, furnishings and art.

Construction of the house halted during the Great Depression and didn’t resume until the mid-1940s. Nathan Paine died before the house was completed, but his wife, Jesse Paine, oversaw the house’s completion, opening it to the public in 1948. 

The Paine’s website describes the estate’s style as a variety of “interior and exterior architectural features, such as arches, doorways, columns, window panes and chimney stacks, [giving] it the appearance of being built over three centuries in evolving English styles. Much of the estate’s architecture, décor, artworks, and landscaping derives from English country houses while utilizing and accentuating the natural resources and beauty of Wisconsin.”

Get active outdoors

Though the temperature is dropping, fall is the perfect season to get outdoors and connect with nature, and the Wiouwash Trail is the ideal place to do so. Its name is a combination of Winnebago, Outagamie, Waupaca and Shawano — the four counties through which the trail runs. Starting in downtown Oshkosh and going through the UWO campus, the trail extends for nearly 22 miles and borders Lake Butte des Morts, the Fox River, multiple grassland prairies, farmland and tons of distinctive wildlife scenes.

A little farther away, High Cliff State Park in Sherwood features massive cliffs and picturesque views of Lake Winnebago. The park was given its name due to the limestone cliff of the Niagara Escarpment, which extends north to Niagara Falls, New York.

Additionally, it’s located on land held sacred by Native Americans whose effigy mounds are scattered throughout the park. Estimates suggest that these mounds were built between 1,000 and 1,500 years ago, though their exact purposes are unclear. The park features numerous trails, various historic sites, a campground, picnic areas, a beach and great views of unique wildlife species.

EAA Aviation Museum

Back indoors and in the city, the EAA Aviation Museum is an aeronautic enthusiast’s best friend. The museum features aircraft and memorabilia from World War II, the Korean War and Cold War, and much more.

“Inside the museum is the entire story of personal flight, from the Wright Brothers to spaceflight, with nearly 100 aircraft on display,” said Dick Knapinski, EAA’s director of communications. “Among the unique exhibits are a full-size reproduction of SpaceShipOne, the world’s first successful civilian spacecraft, and a Vietnam War-veteran Huey helicopter.”

EAA also features a variety of special events throughout the year, including seminars, virtual flight simulations, and a myriad of flight-related activities. EAA is best known for its annual airshow in July, which sports interactive venues, over 10,000 personal, historical and military aircraft, and dazzling aeronautic shows.

Memorable dining spots

A hallmark of vintage dining, Ardy & Ed’s Drive In, 2413 S. Main St., feels like a 1950s diner. Open since 1948, carhops on roller skates serve you food while classic tunes play in the

background. Ardy & Ed’s serves everything from ice cream and desserts to fish and french fries.

Another great food stop is Caramel Crisp and Cafe, at 200 City Center, a 90-year-old shop located near the UWO campus that sells homemade cookies, pies, popcorn and other snacks. The shop also includes a bookstore, ice cream shop, gift shop and a café serving deli-style sandwiches, smoothies, coffee and more.

Other opportunities

Oshkosh’s unique history is on full display in its museums and frozen-in-time shops, but its downtown also hosts a range of uniquely vintage experiences. For instance, The Time Community Theater at 445 N. Main St., shows older movies barred from the modern screen — often for free. An upcoming show is the Rocky Horror Picture Show, complete with a costume contest, on Sept. 17.

In addition to a myriad of local businesses, Downtown Oshkosh features seasonal farmers markets, craft fairs and various other community events listed on downtown Oshkosh’s website at downtownoshkosh.com, all of which bring together the vivacious spirit of a historical city.