Recently, there was an article in the National Review that declared “American Men are Suffering a Friendship Recession!” Now, at first, I had no idea what they were talking about. But the article showed that the percentage of men with at least six close friends fell by half since 1990, from 55 percent to 27 percent. Now that may seem crazy but it isn’t too far-fetched! The question is, why is this happening? What is going on with guys that our friendships are dropping like flies?

The article gives some ambiguous answers, but perhaps one of the biggest reasons is that we just aren’t putting in the time to connect with each other. So how can we remedy that? How can we find ways to connect more with our old pals & create stronger bonds? Well, the answer may be as simple as the classic guy’s trip to a place like Sheridan, Wyoming!

What Makes a Guys Trip?

Now, I am sure many of you guys are reading this and thinking, “Why on earth would I want to take a guys trip to Sheridan, Wyoming? Isn’t that just a big old cowboy town with cows and horses?” Well, to be fair, Sheridan is historically known for its ranchers, pioneers, and definitely its cowboys along the Westward migration trails. But there is so much to do there for men of any type looking to bond during a guys trip.

So what makes a good bonding event?  No, the answer is not to end up in the famous Clearmont Jail as seen above! Rather, it is just spending time together.

Now of course this can be a bit tricky because you will also want to find activities to match the personality of your crew. So, whether you love active adventures like sports, backpacking, and fishing or you prefer a more classic gentleman-type event with art, food, and cocktails, Sheridan is the place to go on your next guy’s trip because it is packed with things to do.

Let’s dive into all the things to do for a perfect guy’s trip in Sheridan, Wyoming!

Go Fishing with the Fellas

Fly Fishing in the Big Horns National Forest near Sheridan Wyoming

The countless Flies at the Fly Shop of the Big Horns in Sheridan.

Seeing the trout at the Fish Hatchery in Story, Wyoming

 

What better place to go fishing than to one of Hemingway’s favorite locations! That is right, Big Papa loved Wyoming and would often head out on trout fishing expeditions in the Big Horns! That is probably because Sheridan has such an avid fly fishing scene.

When going on a fishing trip with the guys, start out at the Fly Shop of the Big Horns in Downtown Sheridan. These guys are great because they stock the store with the largest selection of flies and fly-tying materials around. Plus, if you and your crew want to actually hit the water, their guide services can create the perfect guys trip for any skill level of fly fishing!

Now of course you can always go on your own into Big Horn National Forest or other areas. But make sure you get your licenses in order at the Wyoming Game & Fish Department before you leave. The agency makes it really simple for you, plus they have some really fun fishing challenges to kick up your guy’s trip! For example, out of their 10 major fishing challenges, the Wyoming Game & Fish Department has their famous Cutt Slam where you attempt to catch their 4 native cutthroat trout species! If this is all confusing to you, perhaps you should start your guy’s trip in Sheridan by visiting the Fish Hatchery in nearby Story, Wyoming. Here you can explore one of the oldest fish hatcheries and feed the various trout at the base of the Bighorn Mountains!

Go Hiking with your Homies

Entering Big Horn National Forest in Sheridan Wyoming

Seeing Porcupine Falls

The River flowing from Porcupine Falls

 

There is something truly amazing about a guys trip where you go hiking and camping. So, it is a no-brainer that Sheridan, Wyoming is a major destination for male bonding while getting outdoors. That is because the Bighorn National Forest is absolutely beautiful and packed with tons of things to do. 

Now, if all you want to do is set up camp and make s’mores then the beauty of the Bighorns alone is inviting. But if you and your crew love to hike then get ready for some amazing things to find and explore. That is because the park consists of over one million acres of scenic canyons and mountains. 

Plus there are some cool things to do in the Bighorns like finding the 5 “secret” waterfalls scattered throughout the park. For the most part, finding these waterfalls make up a day trip type of adventure with your gang. But don’t let that fool you because even though it is barely a 1-mile round trip, even the amazing Porcupine Falls drops down 440 feet! Other nearby falls that are a bit longer to get to but definitely worth the trek are Paradise or Bucking Mule Falls!

Fun Fact: When visiting the Big Horns make sure you check out the Tongue River Canyon! It is perhaps the most beautiful canyon in all of Wyoming. Within the canyon is of course the Tongue River where it is said that to beat traffic, loggers would ride the 11-mile Tongue River Tie Flume down the mountain and through the Box Canyon tunnels to reach the town of Dayton. (source: Tall Tales by Sheridan Board of Tourism)

See some Art with your Amigos

The Bozeman Scout in Front of the Fly Shop of the Big Horn Mural

Street Art in Sheridan Wyoming

Fox Statue in Sheridan

Bison Union Mural in Sheridan, Wyoming

 

When you travel to foreign countries like Colombia, you almost expect to spend a day exploring street art in places like Cartagena. But if you and your friends like walking around checking out murals and pieces of western art, then Sheridan won’t disappoint. In 2001, the Grinnell Plaza project funded and then displayed over 100 permanent pieces of art throughout the downtown. So it is a treat to walk around with your crew amid what is known as the Sheridan Public Arts! Then afterwards as you are walking around downtown at night, be sure to check out the amazing display of neon lights. The glow from neon upon all of the classic buildings alone is an art lover’s dream.

Now for those guys who prefer walking amid various styles of art in a gallery, you can find some amazing displays at the Brinton Museum in Big Horn. Here you will be greeted with some of the finest art and artifacts from American Indians in the region. Plus, the original owner, Bradford Brinton collected beautiful works. Inside you will find pieces from Western American Artists like Remington, Reiss, and Kleiber as well as many others.

Fun Fact: In nearby Clearmont, the UCROSS Foundation is a 20,000-acre working cattle ranch in northeastern Wyoming. But what is really cool is that it also operates as a retreat for visual artists, writers, composers, and artists in all creative disciplines. Plus for those of guys who love Longmire, the author, Craig Johnson, uses the hills of his Ucross home as inspiration for his crime drama novels.

Play some Games with the Gang

As you can see there is no shortage of things to do in Sheridan, Wyoming. But perhaps one of the coolest things to do with your guys is to and play some fun games. Now of course you can always go shoot pool or throw darts in the Rainbow Bar or toss corn hole at some of the beer halls.  But if you want to have a real adventure you should bring your gang over to the Big Horn Axe to throw axes! Since early 2020, they have been “throwing blades” as they put it and it is truly an event. The staff will set you up with their computerized scoring which is much like a bowling game. Then, off you go to test your skills at throwing various hatchets!

Now for those who are into more bizarre-type activities, nearby at the Koltiska Distillery, you can test your skills at Butt Darts! From what we gather, you drop as many quarters from your rear into a shot glass placed on the floor in order to “Win!” So have fun trying to win Butt Darts on your next guy’s trip. At least at the distillery, there is no shortage of Cowboy Coolaid!

Go Biking with your Brothers

There is something truly iconic about riding a motorcycle across America and there is no shortage of amazing motorcycle rides in and around Sheridan, Wyoming. So whether you are riding the winding roads towards Bighorn National Forest or you are hitting the open road down towards Clearmont, you’ll love the views. But perhaps some of the most fun rides are those heading to Dayton and Ranchester. Here you will cruise through small communities that time forgot and stop at some iconic bars and restaurants. For many, a stop-off at the Historic Dayton Mercantile for lunch is one of the best bucket list experiences ever. The old Mercantile is still operational and offers amazing plate lunches inside at their old counter. Fair warning though, make sure you and your boys are respectful. The ladies working the counter at the Mercantile take no flack from any road warrior!

Attend a Polo Match with your Pals

It may sound weird to attend a real-life polo match in Wyoming. But it is truly an awesome experience for any guy’s trip. The Big Horn Equestrian Center has been in operation for more than 100 years now and allows people to come in and watch both training and matches during the season. Set upon 60 acres, the beautiful grounds are well-groomed beneath the Big Horn Mountains. But the highlight is seeing some of the most beautiful horses in the world as their riders play to win! Then to boot, there are a plethora of events on the grounds. Depending on the time of year, you can enjoy music festivals, soccer matches, or even an epic fireworks show. 

Fun Fact: It is said that many famous people can often be seen at the Polo Grounds during the official season. For example, Joan Rivers was a long time fan of Wyoming & the sport of Polo. In fact, it is said that she loved both so much that after she died, she gave a last request: “please have my ashes scattered where the buffalo roam and where the polo mallets whirl…” (source: Tall Tales by Sheridan Board of Tourism)

Get your Chums Classed Up

The White Swan Barber Shop

Shopping Inside of Kings Ropes

Exploring the Inside the Mint Bar in Sheridan

 

Sometimes you want to roll out like the Rat Pack on a guy’s trip. So if you need to turn your guys from Neanderthals to high-class gentlemen, then head to downtown Sheridan. Here you will find a plethora of stores like King’s Ropes & Saddlery, where they can purchase some nice clothes or find great accessories. But perhaps one of the neatest things to do is to head over to the White Swan Barber Shop where you and your gang can get a haircut and a classic straight razor shave in one of the oldest continually operating barbershops in the country!

Afterward, you and your gang of gentlemen can hit the town. So, of course, that would mean a stop at the historic Mint Bar. Founded in 1907, this timeless bar is laden with historical pictures and various animals mounted on its walls. Even Hemingway himself ponied up to the bar drinking while writing A Farewell to Arms. To boot, during prohibition, the Mint Bar pretended to be a cigar company and soda shop in the front while they ran a speakeasy out of the back.

Take your Friends to the Fort

There is something about learning American History that just seems to fit a true guy’s trip. That is why a trip to Fort Phil Kearny just south of Sheridan is a perfect day adventure to go on. It is an interesting interactive site. What is really cool is that you can learn about the Indian Wars. Plus they offer insights into the struggles of the early pioneers traveling along the Bozeman Trail. On a beautiful day, you can walk the original grounds amid the reconstructed stockade and imagine the battles the army had with the local Native American tribes while living there. 

Enjoy Adult Beverages with your Brothers

Blacktooth Brewing Bucket List

The Beer at Black Tooth Brewery

Inside Black Tooth Brewery

Smith Alley Brewing Beer

Inside Smith Allen Brewery

Exploring the Brewery in Smith Alley Brewing

Cocktails at Frackletons in Sheridan Wyoming

McGregors Cocktail Bar in Sheridan at the Myland Market

Cocktails at McGregors in Sheridan Wyoming

 

Ernest Hemingway once said, “I drink to make other people more interesting.” Hopefully, this isn’t the case when wanting to celebrate with your friends on an epic guy’s trip. But just in case, there are a ton of great options for the guys to meet up for adult beverages. 

For those of you who love beer, then look no further than downtown Sheridan. With major establishments like Black Tooth Brewing you are bound to find a beer you enjoy. Plus they are right around the corner from the Big Horn Axe company. However, you may want to wait to toss back a few before tossing sharp weapons near your boys. If you are willing to try something new and a bit smaller, the local style brewery of Smith Alley Brewing and Public House offers not only excellent beer but a great menu of food to pair with your suds.

For the guys who consider themselves cocktail connoisseurs, you don’t have to fret. Of course, Wyoming is known for its beer but the cocktail scene in Sheridan is growing nicely. Of course, you can always sit at Frackleton’s bar and enjoy their Happy Specials on drinks. But perhaps the best secret in Sheridan is at McGregor’s Bar & Grille. This place has some of the best cocktails in all of Wyoming. But what is also awesome is that you can sit outside beneath the most beautiful views of the Bighorns!

Where to Stay in Sheridan, Wyoming

There are plenty of places to stay in Sheridan, Wyoming that will fit your guy’s style and budget. Whether you are looking for a simple motel, an active hotel and event center, or a quiet luxury hotel, you won’t be disappointed with your options.

• Basic: There are several bargain franchise-style hotels and motels in Sheridan. For example, there’s a Holiday Inn, Quality Inn, Econo Lodge, or a Super 8 by Wyndham to name a few. Of course, these typical bargain hotels don’t come with many amenities. But with all the things to do in Sheridan, you won’t want to spend much time in your room anyway. To find the best budget hotel in Sheridan check here.
• Quiet & Easy: If you are looking for convenience and a good price then check out the Best Western Sheridan Center. This hotel is located near many great sites of Downtown Sheridan and offers a clean, furnished, and quiet guest room. Plus what we liked most of all is the various food options! First, they offer an amazing breakfast with your booking that they brag offers PROTEIN! There is nothing worse than getting one of those crappy continental breakfasts. You know the kind that is basically an old bagel, a cup of yogurt, and some watered-down juice. Not at the Best Western Sheridan! Plus, if you and your guys are wanting an easy dinner, the Bistro 307 is attached to the hotel. There you and your crew can snag a hearty dinner, local beers on tap, or just watch your favorite sports on the many televisions inside. 
• Historic & Luxurious: For those looking for a bit of luxury mixed in with history and fun, look no further than The Historic Sheridan Inn. Once the stomping grounds of William F. “Buffalo Bill” Cody and his Wild West Show, the inn was considered the “finest hotel” between Chicago and San Francisco. Declared a National Historic Landmark in 1964, this hotel is absolutely beautiful inside with a large wrap-around porch. This way you and your guys can sit right across from the restored train depot plotting your next adventure. 

Book Your Stay in Sheridan, Wyoming Today

Now Gather up the Guys & Go!

There are many things to see and do, in Sheridan. That is why it is the perfect destination for your next guy’s trip! Whether your boys like history, sports, getting outdoors or just relaxing, you’ll find it all around Sheridan, Wyoming. What do you guys think? Is Sheridan the kind of place you would tell your mates to meet you? Would your long-time buddies enjoy all the different aspects and things to do in Sheridan? Or is there something else that we totally forgot to mention? Maybe you think there is a must-see in or around Sheridan that should be on every guy’s bucket list! Let us know in the comments below & help inspire some men to build better bonds with the guys in their life!

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Disclaimer: The Bucket List Project was a guest of the Visit Sheridan Tourism Board & the Best Western Sheridan Center. With that said, All opinions in “The Ultimate Guide to a Guys Trip in Sheridan, Wyoming” are our own. Also, this post may contain affiliate links. Using the links doesn’t cost you any extra, and it helps keep the site free, fun, and community supported! Eric & Darcee will never recommend a product that we don’t genuinely believe in, actually use ourselves, have researched, and trust. Please see the disclosure policy for more information.