The Cheshire brought a taste of British-inspired architecture to our St. Louis overnight stop. Photo: Lenses & Latitudes.
Unique Places to Stay on a Midwest Road Trip: 3 Historic Hotels We Loved
Some of my favorite road trip memories happen after the sightseeing ends.
There is something special about checking into a hotel that has a story of its own—a place where the architecture, décor and atmosphere feel like another stop on the itinerary rather than just somewhere to sleep.
During our eight-day Midwest road trip in June 2026, my brother Craig and I stayed in three very different historic properties: The Cheshire in St. Louis, Hotel at Old Town in Wichita and The Empress of Little Rock.
When the Hotel Becomes Part of the Road Trip
Each property gave us a memorable experience, but for different reasons.
One felt like an escape to England, another brought a former warehouse to life and the third placed us inside a dramatic Victorian mansion.
If you’re searching for unique places to stay on a Midwest road trip, here’s how these three accommodations compare—and which kind of traveler I think would enjoy each most.
Disclosure: Our stays at The Cheshire, Hotel at Old Town and The Empress of Little Rock were hosted as part of travel collaborations. All observations, comparisons and opinions are my own. There are no booking prices listed here because rates and inclusions can change.
Three Unique Historic Hotels at a Glance
| Hotel | Location | Signature Experience | Best For |
|---|---|---|---|
| The Cheshire | St. Louis, Missouri | British-inspired interiors and literary-themed rooms | Travelers seeking a playful, atmospheric stay |
| Hotel at Old Town | Wichita, Kansas | Historic warehouse details and walkable Old Town setting | Travelers balancing character with convenience |
| The Empress of Little Rock | Little Rock, Arkansas | Elaborate Victorian mansion architecture | History lovers, architecture fans and special-occasion travelers |
The Cheshire: A British-Inspired Stay
After a long first day filled with Route 66 roadside attractions, murals and memorable detours, checking into The Cheshire felt like we had briefly left Missouri behind.
The property leans into its English country-inn character with dark wood, comfortable common spaces and details that encourage guests to look around instead of immediately heading to their rooms.
What makes The Cheshire different from a standard chain hotel is the way its theme extends beyond the front entrance.
Its guest rooms celebrate British writers and literature, and our James Bond Suite added a fun, distinctive element to the experience.
Instead of feeling like a generic place to spend the night, the hotel became one of the stories we brought home from the trip.
Who Should Stay at The Cheshire?
I would recommend The Cheshire to travelers who enjoy themed boutique hotels, unusual interiors, literary touches and a sense of escape.
It’s particularly appealing if your St. Louis plans include Forest Park or nearby attractions.
The hotel’s official website lists amenities such as breakfast, Wi-Fi, dining and a seasonal pool; confirm what’s currently included and available when you reserve.
Road-trip placement: This was our first overnight hotel on the trip, after driving through Illinois and reaching St. Louis on June 13. Its atmosphere gave the journey a memorable beginning.
Read more: Our full review of The Cheshire in St. Louis →
For accommodations and current hotel information, see The Cheshire’s official website →
Hotel at Old Town: Industrial History Meets Convenience
Hotel at Old Town offered a completely different style of historic stay.
Instead of a literary-inspired retreat, this Wichita hotel occupies the former Keen Kutter warehouse, with exposed brick and architectural details that reflect its industrial past.
The soaring interior atrium immediately caught my attention—and my camera’s.
For our trip, its strongest feature was the balance between history and practical comfort.
We were spending two days visiting Tanganyika Wildlife Park and exploring Wichita, so having a convenient place to return to mattered.
We appreciated our Double Queen Studio Suite, the covered parking available during our stay and the ability to enjoy restaurants in the surrounding Old Town district without continually moving the car.
It’s the kind of accommodation that works especially well when your days are busy.
We could enjoy the architecture and neighborhood without giving up a practical home base between activities.
The hotel’s connection to Wichita history made it more memorable than a typical overnight stop.
Who Should Stay at Hotel at Old Town?
This would be my choice for travelers who want historic character but place a high value on convenience.
It makes sense for a Wichita city break, a trip built around nearby attractions or a road-trip stop where restaurants and evening entertainment are an important part of the plan.
The hotel currently highlights its Old Town location, suite options and parking on its official site; double-check the details for your travel dates.
Road-trip placement: We used Hotel at Old Town as our Wichita base for the June 16–17 portion of the trip, giving us two days for Tanganyika Wildlife Park and time in Old Town.
Read more: Our full review of Hotel at Old Town in Wichita →
Check Hotel at Old Town’s official website → for current accommodation information.
The Empress of Little Rock: Stay Inside a Victorian Mansion
There are places where you notice the building before anything else, and The Empress of Little Rock is one of them.
Housed in the historic Hornibrook Mansion, completed in 1888, this property delivers the sort of dramatic Victorian architecture that makes me want to stop and photograph every detail.
From the mansion’s striking exterior to its richly decorated interiors, The Empress felt less like an ordinary hotel and more like stepping into another period.
This was not a historic theme added to a newer building. The architecture itself is the experience.
We arrived during the Little Rock portion of our trip, after spending time at the William J. Clinton Presidential Center and dining in the city.
The contrast between a busy sightseeing day and a quiet evening inside the mansion made our stay especially memorable.
For me, the most compelling aspect was the abundance of architectural details.
Period-style furnishings, woodwork and decorative features offer so much to appreciate, particularly if you enjoy photography, preservation or buildings with a distinctive past.
Who Should Stay at The Empress of Little Rock?
I would recommend The Empress to architecture enthusiasts, history lovers and travelers planning a distinctive couples’ getaway or special occasion.
The rooms in an historic mansion are not necessarily interchangeable, so review the specific room’s layout and amenities before booking.
Anyone with accessibility considerations should ask the property directly about the room and route that best fit their needs.
Road-trip placement: We stayed here during our June 19 Little Rock stop, near the end of the eight-day journey. It was a fitting finale to a trip filled with memorable buildings and experiences.
Read more: Our complete Empress of Little Rock historic bed-and-breakfast feature →
For current rooms and reservation information, visit The Empress of Little Rock’s official website →
Which Historic Hotel Is Right for Your Midwest Road Trip?
After staying at all three, I wouldn’t choose a single universal winner. They serve different kinds of trips and personalities.
One thing these hotels have in common is that each helped shape our experience of its city.
St. Louis gave us a taste of England. Wichita connected our stay to the city’s industrial past. Little Rock wrapped up the journey with remarkable Victorian architecture.
Tips for Booking Unique Historic Hotels on a Road Trip
Frequently Asked Questions About Unique Midwest Road Trip Hotels
What are some unique places to stay on a Midwest road trip?
Three memorable properties from our actual June 2026 road trip were The Cheshire in St. Louis, Hotel at Old Town in Wichita and The Empress of Little Rock. They offer British-inspired style, historic warehouse architecture and a Victorian mansion experience, respectively.
Which hotel is best for travelers who love architecture?
The Empress of Little Rock is especially appealing for elaborate Victorian design. Hotel at Old Town showcases historic industrial architecture, while The Cheshire features British-inspired architectural and interior details.
Which of these hotels is best for a convenient Wichita stop?
Hotel at Old Town worked particularly well for our visit because it placed us near restaurants in Wichita’s Old Town district and served as a base for two days at Tanganyika Wildlife Park.
Did you stay at all three hotels yourself?
Yes. My brother Craig and I stayed at all three during our June 13–20, 2026 road trip. The accommodations hosted our stays, and this comparison reflects our experiences and opinions.
Should I book the same hotels on an eight-day road trip?
Only if they fit your route, interests and budget. We enjoyed all three, but the best choice is the one that makes sense for your travel days and the experiences you hope to have. Use our full itinerary to see where each stop fitted into the journey.
Make Room for a Hotel Worth Remembering
Finding distinctive accommodations was only one part of our journey.
If you’d like to see how these overnight stops fit around Route 66 landmarks, wildlife encounters, public art and sightseeing, start with our complete eight-day Midwest road trip itinerary →
For the bigger story behind the trip, read The Ultimate Midwest Road Trip: Route 66, Tanganyika Wildlife Park & Hidden Gems →
If you’re creating your own version, our Midwest road trip planning guide → covers route planning, hotel choices, budgets and practical travel decisions.
For me, a memorable road trip isn’t only about what we do between breakfast and dinner. Sometimes the place where we spend the night becomes one of the highlights.
These three hotels reminded me to make room on the itinerary for that kind of experience, too.
Have you stayed somewhere unusually memorable on a road trip? I’d love to hear about it in the comments.
About Angela
Angela Addington is the travel photographer and writer behind Lenses & Latitudes. She shares firsthand destination guidance and practical photography advice for independent and solo travelers, women over 50, road-trippers and weekend explorers. Learn more about Angela.
