Islands    •   8 min read

An Under-The-Radar Oklahoma Town Boasts A Historic Trail, Local Eateries, And Mercantile Shops

WHAT'S THE STORY?

An empty street in Hennessey, Oklahoma

Situated about 70 miles from Oklahoma City, you'll find a hidden gem of a town called Hennessey. While Oklahoma is home to many charming sites, from the mountainous scenic byway of the Wichita Mountains

 to the live music capital that is Yukon, Hennessey is a perfect getaway for travelers wanting to experience small-town charm. With a population of just over 2,000 people, this under-the-radar Oklahoma town might be small, but it's not short on attractions. 

Take, for instance, the Chisholm Trail. Likely

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named after the 19th-century trader Jesse Chisholm, this path played an important role in Hennessey's cowboy history, acting as a trade route that made it easier for Oklahomans to sell cattle in nearby states such as Texas and Kansas. In addition to having a historic trail, the town is also loaded with great shopping attractions. Hennessey Mercantile on Main Street sells everything from clothing to pillows to hemp oil. It also acts as a cafe, selling various coffee and food items. Meanwhile, Prairie Quilt on Main Street is the largest privately-owned quilt store in the state.

If you're looking to explore this unique American village with all its frontier history and folksy charm, then your best bet is to take a flight to OKC Will Rogers International Airport, which is about 65 miles away from the town. Or, if you're able to drive, even better. While in Hennessey, it would be wise to have a car, as this makes it easier to see all the sites as well as travel to neighboring towns. 

Read more: The Most Charming Cobblestone Streets In America That Will Take You Back In Time

Discover The History Of The Chisholm Trail

Trail marker for the Chisholm Trail, Oklahoma

The Sooner State is rich with history, and nowhere is this better on display than in the town of Hennessey. Grab your camera and some hiking boots as you follow along the Chisholm Trail, following in the footsteps of generations of Civil War veterans, cattle drivers, and more. This trade route, which passes through the tiny town of Hennessey, began just after the Civil War. 

When returning Texan soldiers realized their farms held an excess amount of cattle, they began to carve out the 800-mile trail that would allow them to sell their cattle in livestock markets out east. Running up from southern Texas to the town of Abilene, Kansas, livestock passed through some of the region's most gorgeous plains and farmlands. 

Visitors to Hennessey can imagine what they saw when they visit Bull Foot Park. This site once acted as a supply stop for cattle drivers along the trail and was especially treasured for its water well. Today, the park features a half-mile trail loop that is perfect for cycling, running, or walking. For visitors wanting to learn more, the Chisholm Trail Heritage Center is located in Duncan, a city about 120 miles away from Hennessey, and offers education on the history, art, and bygone culture of the Chisholm Trail.

Where To Stay And What To Eat In Hennessey

Shop front and street lamp in  Hennessey, Oklahoma

Oklahoma has some great eats. Places like the delectable restaurants in Krebs, also called Oklahoma's "Little Italy,"  or the sweet treats at the roadside gem of Pops are perfect spots for travelers to satisfy their hunger. Hennessey is no exception, as this little town has some local eateries that would make any visitor's mouth water. Eat It Up on Main Street is a local favorite that offers breakfast, brunch, lunch, and dinner options, including breakfast quesadillas, barbecue, paninis, burgers, and more. 

If you want some great fried chicken, then Rooster's is your spot. Located on the east side of US Highway 81, the restaurant has everything from its specialty fried chicken to ribeye steak, pork chops, burgers, fried pickles, okra, and corn nuggets -- just to name a few. Regardless of the restaurant you choose, though, you'll be delighting in the best of Wild West cuisine with this hearty, Oklahoma fare. 

Lodging in Hennessey might be tricky, as there are not many places to stay in the town, but you can travel to the nearby town of Enid for places like GLō Best Western Enid OK Downtown/ Convention Center Hotel. This complex is only about 20 miles away and offers a variety of rooms at relatively low rates. There's also the Hampton Inn & Suites Enid, located 22 miles away from Hennessey. This spot has great options for accessible rooms and suites, and offers a free hot breakfast, a fitness center, and an indoor pool for guests. 

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