This carefully crafted itinerary is designed to guide you through the unique blend of history, culture, and natural beauty that these charming areas offer. Immerse yourself in the rich history at local museums and historic sites, gaining insights into the pioneering spirit of the West. Savor the local flavors at beloved eateries, offering a taste of the region’s culinary delights. Explore the great outdoors, with scenic landscapes and recreational opportunities that showcase Wyoming’s stunning natural environment. Whether you’re a history buff, a foodie, or an outdoor enthusiast, this itinerary promises an unforgettable experience.
This itinerary does not include everything this area has to offer. Be sure to check out the full list of Wyoming listings at Travel Wyoming Events Calendar to avoid missing out on all the fun.
Suggested Time:
2 Days
Douglas, Wyoming
The historic depot in Douglas was built in 1886 and was a staple of the community. Later turned into a museum. It now features eight historic rail cars and a steam locomotive. Guests are invited to climb aboard many of the rail cars and browse the gift shop, which offers local and train-themed items.
Douglas, Wyoming
For a delightful lunch, head to the restaurant housed in the historic Burlington Northern Railroad Depot. Afterward, take a short walk across the street to admire the 100-year-old LaBonte Hotel.
Douglas, Wyoming
Visit Jackalope Square for a fun photo opportunity with the giant jackalope statue. As you stroll through downtown Douglas, explore the historic theater, the bowling alley and various boutique shops.
Douglas, Wyoming
Located on the Wyoming State Fairgrounds, the Wyoming Pioneer Museum showcases a diverse collection focused on westward expansion. Be sure to check out the history of Douglas’ infamous Jackalope. The fairgrounds also host various events throughout the year, from rodeos to community gatherings including the Wyoming State Fair.
Choose from a variety of dining options in Douglas, including Mexican cuisine and other local favorites. You can find a complete list of restaurants in the annual vacation directory available at the Railroad Museum and several area businesses.
Douglas, Wyoming
Walking enthusiast and furry friends will love this walking path. Access the concrete walkway from either Richards or Center streets, and enjoy the scenic views near the Jackalope Bridge.
Douglas, Wyoming
Open from Memorial Day to Labor Day. This former officers’ club from WWII features murals painted by Italian POWs. Pack a picnic lunch or pick up something to eat in Douglas for your next stop.
Douglas, Wyoming
Enjoy a picnic at Ayres Natural Bridge Park, featuring a stunning rock bridge spanning LaPrele Creek, surrounded by red rock walls, green lawns and beautiful trees. Note that dogs are not allowed, but there is a nearby boarding facility if needed.
Glenrock, Wyoming
Explore the Glenrock Paleon Museum and enjoy the new town square with a splash pad, play area and amphitheater. Visit “Rock in the Glen,” etched with the names of pioneer travelers, accessible from the community’s west end.
Glenrock, Wyoming
Glenrock’s walking path follows the route of the historic railroad. The local Main Street group is working to place historic markers along the trail, detailing important aspects of its history. Walkers enjoy crossing a bridge build in 1923. Hotel Higgins, built in 1917, is a great place to spend the night and offers on-site dining.
Esterbrook, Wyoming
A mountain community located south of Douglas. Visiting this area leads to a beautiful scenic drive and multiple hiking areas. The mountain community can be accessed via Esterbrook Road. A portion of this drive is gravel road. Inquire at the visitors center for a map and current conditions. Be prepared as there are no service available.
Douglas, Wyoming
Visit Washington Park, which is beautiful in all seasons. Here, you’ll find a statue of Sir Barton, America’s first Triple Crown winner. Learn more about his story at the Wyoming Pioneer Museum.
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Wyoming’s open roads and beautiful scenery make it an ideal state for a road trip.