Have some extra time in Chelsea?  Here's a few attractions you won't want to miss

Chelsea, Oklahoma is more than a historic Route 66 stop — it’s a gateway to unique attractions, outdoor adventures, and small-town experiences throughout Rogers County and Northeast Oklahoma. Whether you're planning a full Route 66 road trip or a relaxing day trip from Tulsa, you’ll find antique shops, local restaurants, scenic countryside drives, and nearby historic landmarks just minutes from downtown Chelsea. Extend your stay and discover why travelers exploring Route 66 in Oklahoma often choose Chelsea as a base for experiencing the charm, history, and hidden gems of the surrounding area.

The Hogue House

​The Hogue House, built in 1912, is on the National Register of Historic Places, and was the first Sears & Roebuck home to be constructed in Oklahoma. 
In 1912, local rancher and businessman Mr. Hogue was in Chicago on a cattle-marketing trip when he discovered something remarkable. Sears, Roebuck and Company was showcasing fully constructed display homes to promote its “Modern Homes” mail-order catalogs. Customers could choose a design, purchase the materials and plans, and have everything shipped by rail to their hometown.
The Hogues selected a two-story, seven-room house priced at $1,660 — a significant investment at the time. Encouraged by his wife, Mr. Hogue placed the order, and their future home was shipped to Chelsea by the Frisco Railroad, where it was assembled and still stands today as a testament to early 20th-century innovation and small-town ambition

The Hogue House is located at: 
​1001 Olive St
Chelsea, OK 74016

Route 66 Pedestrian Underpass

Believed to be the only surviving pedestrian underpass along Route 66, Chelsea’s historic underpass was originally constructed to provide a safe alternative to crossing busy Highway 66. For decades, it quietly served the community before being revitalized in 2016 by local leaders committed to preserving the town’s Route 66 heritage.
As part of the restoration, artist Kenneth Hollingshead was commissioned to transform the tunnel’s walls with painted scenes depicting Chelsea’s past. Today, the Route 66 Pedestrian Underpass and Mural offers visitors more than a passageway — it provides a walk through history, immersing travelers in the stories that shaped this Oklahoma town.

Pryor Creek Bridge

One of the earliest major improvements along Route 66 in Oklahoma was the construction of a Modified Pratt Through-Truss bridge over Pryor Creek on the edge of Chelsea in 1926. Stretching 123 feet long and 19 feet wide, the steel structure features six panels reinforced with distinctive X-shaped bracing — a design that provided both strength and durability for the growing traffic along the Mother Road.
The bridge still stands on the original Route 66 alignment, offering visitors a rare opportunity to experience an authentic piece of early highway engineering. Local lore recalls that the massive structure was moved into place using teams of horses and mules — a testament to the determination and ingenuity of the era.

Maplewood 

At just ten years old, Will Rogers experienced the loss of his mother and came to Chelsea to live with his two older sisters, Sallie McSpadden and Maud Lane. In their homes, he found stability, guidance, and the support of an extended family that helped shape his early years.
As Rogers’ fame grew across the nation, Chelsea remained a place of refuge — a quiet sanctuary away from the demands of public life. In 1892, Tom and Sallie McSpadden built a large country home known as Maplewood, where young Will lived for a time and attended an Indian school a few miles outside of town.
Today, both the McSpadden and Lane homes still stand in Chelsea, offering a tangible connection to the early life of one of Oklahoma’s most beloved figures.

Jesse Bartley Milam Home