Oregon Trail Loop

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Fort Laramie/Register Cliffs/Guernsey State Park/Oregon Trail Ruts/Quebec 01

Roundtrip drive time: 4 hours 15 minutes. Can be split into two days with an overnight at Guernsey State Park if desired.


Broke an axle on your wagon? Need to trade for supplies? Died of Dysentery?  Anyone who has played the classic Oregon Trail or one of its many reboots will enjoy the chance to get a glimpse of the real-life history behind the trail that saw thousands of emigrants in the mid-1800s.

This itinerary hits regional highlights and would be best taken in with an overnight in Guernsey or camping at Guernsey State Park. If you only have one day, we recommend skipping Guernsey State Park and venturing to Quebec 01 on a different day.



What Was the Oregon Trail?


Depiction of travelers on the historic Oregon Trail.


The Oregon Trail is a trail that spans thousands of miles from what is now Missouri and Iowa to Oregon City, Oregon. Finding its inception in the late 1830s, the Oregon Trail predated the railroad by decades, and the highway even more so, as the primary way for travelers in America to cross from the crowded East Coast to the promises of the West.

Fueled by a combination of economic panic and mass propaganda (and offers for free land), the Oregon Trail would become part of the greatest migration in North American history.

Where Is the Oregon Trail Located?


Map showing the Oregon Trail stretching from Missouri to Oregon.


If you’ve played the old Oregon Trail games or given a general Google search into the subject you may think the trail began in Independence, Missouri. Indeed it did, but also didn’t. Independence was the primary starting spot for most folks, but there were several other “beginnings” to the trail known as jumping-off places. Some of these include Kansas City, Missouri, Council Bluffs, and others. 

Can You Still See the Oregon Trail?


You can catch landmarks and evidence of the Oregon Trail throughout the West. Even some jumping-off places, like Saint Joseph, Missouri, are still strongly connected to their trail roots. As you head West there are many more - like Scott’s Bluff, or Chimney Rock.

Wyoming, for its part, has several points, including the historic Fort Laramie, the Wagon Rutts in Guernsey (where you can still see Oregon trail wagon ruts from the original travelers), and Independence Rock outside of Casper.


Things to Do near Oregon Trail


Perhaps one of the most prevalent sites of Oregon Trail history is the small town of Guernsey, Wyoming. While the town may be small, the history here is huge - giving you the chance to transport yourself to the trail’s heydays. Here you can walk the very trails of the pioneers at Register Cliff and the Oregon Trail Wagon Ruts. Nearby you’ll also find the historic Fort Laramie Site.


1. Fort Laramie National Historic Site 


Guests gather outside Fort Laramie National Historic Site, a popular thing to do along the Oregon Trail.


Drive time: 1 hour, 45 minutes

Heading east on Hwy 85 (just north of Cheyenne), head toward Torrington. Take a left on Highway 26. Continuing northwest on Hightway 26, you will find Fort Laramie National Historical Site.

What began as a fur trading fort in 1834, developed into a major military post by 1849 until its abandonment in 1890. Today, the fort is run by the US National Park Service (no entrance fee). Visitors can learn about life at the fort as well as the history surrounding it and its connection to the Oregon Trail, as well as other trails and famous people and events, including the Pony Express. The transcontinental telegraph, the Pony Express, and several stages fed through here. The location was a site for treaty signings, the hub of trading, and a resting place for tens of thousands of people moving west.


2. Register Cliff Monument State Historic Site 


Visitors at the base of the Register Cliff Historic Site.


Drive time: 25 minutes

After digging into frontier life at the fort, plug “Register Cliff Monument State Historic Site” into your GPS or Smartphone and choose a route. What takes roughly 25 minutes by vehicle was a full day’s journey for the wagon- and cart-toting pioneers. Carving a party’s information on the large sandstone cliff was a rite of passage for the travelers and a well-known (literal) landmark along the trail. The human spirit is palpable as you stand at the base of the cliff and hunt for the oldest dates on the wall. The monument is run by Guernsey State Park and has no entry fee.


3. Oregon Trail Ruts State Historic Site


A sweeping prairie with long, winding wagon ruts from the Oregon Trail.


Drive time: 10 minutes

Hop back in the car and search “Oregon Trail Wagong Ruts State Historic Site.” The sandstone in the area lends once again to capturing history. Thousands of wagon wheels passed over this stretch of land and wore down ruts up to five feet deep in the soft stone! Just a short walk from the parking area, visitors can imagine what the pioneers must have been thinking as they maneuvered all their worldly possessions across Wyoming. There are no fees to access the site (also overseen by Guernsey State Park). There are picnic shelters and a restroom available to the public.


4. Guernsey State Park 


Drive time: 15 minutes

Next stop: Guernsey State Park, just to the north of the town of Guernsey. Entrance fees run $6-9 per vehicle, giving you access to the reservoir, seven campgrounds (overnight camping is an additional fee, make reservations here, hiking trails, and a museum.


5. Guernsey Visitor's Center and Museum


The museum, open from May 1 to September 30, was constructed by the Civilian Conservation Corps and is a great example of what Franklin Roosevelt’s New Deal program set about to accomplish during the Great Depression. Part of the hiking trail system, historic picnic shelters, and the “Castle” were also products of this program. A great stop for history buffs and outdoor enthusiasts alike. 

6. Chugwater, Wyoming


The front of the Chugwater Soda Fountain, a historic landmark along the Oregon Trail.


Drive time: 50 minutes

Make your way back to Hwy 26, and head west. You will intersect you with I-25, where Cheyenne is less than an hour and a half drive south. Chugwater might be a great food stop along the way - Buffalo Lodge always has Chugwater’s internationally acclaimed chili on the menu or try the Chugwater Soda Fountain,  the oldest still-operating soda fountain in Wyoming. H3: Quebec 01 Missile Alert Facility State Historic Site


Bonus Stop: Quebec 01 Missile Alert Facility State Historic Site 


Drive time: 20 minutes; Final stretch to Cheyenne: 30 minutes

If you still haven’t gotten your fill of history, you can make a stop at Quebec 01 Missile Alert Facility State Historic Site just off I-25 ($2-6/person, kids 11 and younger are free) to see a decommissioned IBCM launch capsule 60 feet underground and the living facilities where the missileers and support staff stayed during their deployment to the field (Drive time: 20 minutes). Then, it is a quick 30-minute drive back to Cheyenne!


Additional Tips for the Oregon Trail Loop




Regardless of the season you’re in Wyoming, it’s always a good idea to make some practical preparations. Always be ready for driving in a little bit of wind or inclement weather - snow in the winter, thunderstorms in the Summer afternoons, etc. Keep in mind the trails and roads around these areas can be winding and uneven, so take care!

If you want to spend a few days exploring this loop of hidden gems, consider staying overnight at Guernsey. Guernsey State Park offers spots for camping. Keep in mind the park will be $18.25-$32.25 for an overnight stay. Day use at the park is $7-$12. 

The town of Guernsey has a few spots to stay as well, including a few hotels, like the Cobblestone Inn and a Travelodge.  


Experience History and Adventure on the Oregon Trail Loop

Wyoming’s Oregon Trail Loop is truly a hidden gem of sorts in the Equality State, and is a great opportunity for any visitor - from the history buff to the outdoor enthusiast. Nature, history, food and fun - you can find it all on this loop outside the roads most traveled. 


Want some other trip extension ideas? Check out our posts on the Trainiac Tour and the Prehistoric Adventure.

For more ideas planning your Cheyenne itinerary, head over to our Legendary Trips page or our Whirlwind Tour to hit the highlights!