Sheridan County, Wyoming

The Mountains Are Right There.
Here's What to Do With Them.

A local guide to Sheridan, Wyoming — the Big Horns, the polo fields, the rodeo grounds, and everything worth doing in between.

Sheridan County, Wyoming

Sheridan sits at the foot of the Big Horn Mountains in a way that's hard to explain until you arrive. The range just fills the western sky — massive and close, the kind of close that makes you reach for your camera before you've even parked the car. Below it: a cattle and polo town with a historic Main Street, a genuine rodeo, and a ranching culture that hasn't been manufactured for visitors. This guide is for people who want to do it right.

Whether you're here for the mountains, the events, the fishing, or just to slow down somewhere genuinely beautiful, Sheridan tends to surprise. Here's what to know — and where to stay when you get here.

Hiking, Driving & Getting Up There

The Big Horn Mountains rise from the high plains west of Sheridan and top out near 13,000 feet in the Cloud Peak Wilderness. The approach from Hwy 14 or 14A is one of the most dramatic mountain drives in the American West — and you're on it within twenty minutes of downtown.

Tongue River Canyon
20 min from downtown2–4 hrs round tripModerate

One of the most accessible and rewarding hikes in the area. The trail follows the Tongue River through a narrow limestone canyon with walls rising several hundred feet. Best in late spring through fall. Dogs welcome on leash. Trail starts just off Hwy 14 — pull over where everyone else is parked.

After →

Black Tooth Brewing on N. Broadway St — earn a pint of Saddle Bronc Brown. 30 minutes from the trailhead.

Cloud Peak Wilderness
45–60 min from downtownFull day to multi-dayStrenuous

The wilderness area covers nearly 190,000 acres and includes Cloud Peak itself at 13,167 feet. Day hikers typically access it via the West Tensleep or Hunter Corrals trailheads. Backpackers find some of Wyoming's least-crowded alpine terrain up here — granite lakes, wildflowers in July, and the kind of silence that recalibrates something.

After →

Frackelton's on Main St — white tablecloth dinner feels well-deserved after 20 miles in the backcountry.

Red Grade Road — Sheridan's Backyard Trail System
14.5 miles from downtownGravel · SeasonalBiking · Hiking · Equestrian

The road most visitors never find. Gravel, steep, and quiet in the way that mountain roads get quiet when they filter out everyone who isn't paying attention. Twenty to twenty-five miles of connected trails at the top — the Brink, Bear Knuckle, Fire Up — managed by the Sheridan Community Land Trust. The kind of place locals keep to themselves.

⚠ 2026 Closure Alert

Red Grade Road closes Monday–Friday, 8am–6pm, May through October 2026 and 2027. Weekends, holidays, and early mornings remain open. Full details and trail access →

After →

Black Tooth Brewing — the patio after a long Red Grade ride is exactly what it sounds like.

Hwy 14A — The Bighorn Scenic Byway
Starts 20 min from downtown2–3 hrs drivingAll skill levels

If the weather doesn't cooperate for a hike, this byway is the next best thing. The road climbs through Medicine Wheel Passage and passes the Medicine Wheel National Historic Landmark — a 75-foot prehistoric stone circle at 9,642 feet that's been used ceremonially for over 10,000 years. The views over the Bighorn Basin on the west side are extraordinary.

After →

The Mint Bar — cold beer, live music some nights, and a back bar that's been there since 1907.

The Magpie Cabin on a working horse ranch east of Sheridan with Big Horn Mountain views

Stay nearby · Working Ranch

The Magpie Cabin

A working equine ranch with the Big Horns filling the skyline. Horses in the pasture, Starlink internet, and a porch built for watching the light change. 2 bedrooms, pets welcome.

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The Bay Mare on a working cattle ranch near the Big Horn Mountains, Banner Wyoming

Stay nearby · Working Cattle Ranch

The Bay Mare

On a working cattle ranch at the foot of the Big Horns. Sit on the back patio and enjoy beef straight from the ranch herd — quite literally farm to table.

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The Sport That Never Left

Polo came to Sheridan County in the 1890s, brought by Malcolm Moncreiffe and Oliver Wallop — British and Scottish ranchers who ran cattle on this land, procured war horses for the British Army during the Boer Wars, and saw no reason to give up their sport in the process. Some of the Wallop family still ranches here. The ranch they built eventually passed to Bradford Brinton, whose estate is now a museum of Western art — one of the more remarkable chains of custody in Wyoming history.

The Big Horn Polo Club has been playing on that same ground since 1898, making it one of the oldest continuously operating clubs in the United States. Adjacent to it, the Flying H Polo Club draws international professionals and high-goal competition — top players often bring young horses to Big Horn to develop them, then compete at the Flying H at the highest level. Together they've made this small Wyoming valley one of the most significant polo destinations in the country. That sentence surprises most people when they hear it.

Sunday Matches — Big Horn Polo Club & Flying H
15 min south of SheridanJuly through Labor DayFree admission

Matches run Sunday afternoons through the summer season at both clubs. Bring a blanket, a tailgate setup, something cold to drink. At half time everyone walks onto the field for the divot stomp — stomping back the grass torn up by the horses' hooves. Standing in the middle of that field with the Big Horns filling the sky behind the far goalpost, watching polo ponies and their riders go back and forth while looking down toward Sheridan, it's hard not to feel like you stumbled onto something extraordinary. The crowd is a mix: ranching families who've been coming for decades, international professionals, and visitors who read about it online and couldn't quite believe it was real. Both clubs are on Bird Farm Road in Big Horn. Check individual schedules each season for exact match days.

After →

The Brinton Museum bistro — farm-fresh food, rotating Western art exhibits, and a cottonwood-lined drive with the southern Big Horns coming through the trees. Brunch at the Brinton, polo in the afternoon. You're moving between chapters of the same story.

Don King Days — Labor Day Weekend
Big Horn Equestrian CenterLabor Day WeekendAnnual

Named for the same Don King of King's Saddlery on Main Street. Polo alongside bronc riding, roping, and a world-championship blacksmith competition — all on the polo fields, no barriers between the crowd and the action. Friends who've been describe it as a party. The uninitiated are welcome.

It made me think how fortunate and genuinely strange it is to live somewhere that offers this, for free, on a Sunday afternoon in summer.

— Tyler, Late Checkout WY
The Wayfarer Bungalow interior in Sheridan Wyoming

Sheridan Weekend Base · 2 Bedrooms

The Wayfarer Bungalow

A comfortable Sheridan base for a weekend that ends with Sunday polo, starts with the Brinton, and has dinner on Main Street somewhere in between.

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A Sunday in Big Horn — the full story → coming to The Register

A Real Rodeo. Not a Show.

The Sheridan WYO Rodeo has been running since 1931. It takes place every July and consistently ranks among the top professional rodeos in the country — drawing PRCA competitors, a week of associated events, and a crowd that includes people who've been coming for forty years. The Indian Relay Races, held alongside the rodeo, are among the most viscerally exciting events in all of Western sport: bareback riders switching between horses at full gallop, with no saddle and no stirrups.

Sheridan WYO Rodeo Week
Sheridan County FairgroundsSecond week of JulyTickets required for main events

The week includes a parade down Main Street, a carnival, concerts, dances, and the nightly rodeo performances. Book accommodations well in advance — the town fills up. If you can only do one night, make it the Indian Relay Races. Buy tickets through the WYO Rodeo website before you arrive.

After →

The Mint Bar — the unofficial headquarters of WYO Rodeo week. Expect a crowd, live music, and no room at the bar unless you arrive early.

The New York Store Suite penthouse on Main Street Sheridan Wyoming

Directly Above the Parade Route

The New York Store Suite

A 9,000 sq ft penthouse in the 1907 New York Store Building — on Main Street, directly above the parade route. During WYO Rodeo week, the parade passes beneath your windows. There is no better address in Sheridan for it. Four bedrooms, soaring ceilings, sleeps 8.

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The Pressroom Atelier loft interior in downtown Sheridan Wyoming

Downtown · Sleeps 8 · Loft

The Pressroom Atelier

A 110-year-old brick loft half a block from the Mint Bar. Two king suites, a bunk room, rooftop terrace with Big Horn views, and a BlueStar kitchen. The kind of place people extend their stay.

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A Main Street That Actually Delivers

Sheridan's Main Street has resisted the hollowing out that took most small Western towns. King's Saddlery has been making custom saddles and ropes since 1946 and ships to working ranches around the world. The WYO Theater — a 1923 vaudeville house — still hosts concerts and films. The Mint Bar still has the original back bar. The whole street is walkable and genuinely worth an afternoon.

The Mint Bar
The Short ListMain Street downtownWorth its own evening

Opened in 1907. Ran a speakeasy during Prohibition. The original back bar unchanged since the 1940s. Thousands of cattle brands burned into the wall panels — bring a flashlight if you want to find your county. The Mint is where WYO Rodeo week ends up, where polo players drink on Sunday evenings, and where Sheridan explains itself to anyone willing to sit still long enough to listen. Our advice: drink Hamm's where Ernest Hemingway gambled. Don't look for it on a best-bars list. Just go.

King's Saddlery & Museum
The Short ListMain Street downtown1–2 hrs · Free

Don King started making saddles here in 1946. The museum in the back is free and substantial — an honest collection of Western gear, ropes, Native American artifacts, and a saddle collection that would take an hour to walk through properly. The shop still sells working gear to working cowboys. Oozes history. Incredible craftsmanship. Buy the hat, take the ride. The ropes on the wall aren't decoration. They're inventory.

Trail End State Historic Site
Clarendon Ave, 5 min from Main St1–2 hrsSmall admission fee

The Flemish Revival mansion of John B. Kendrick — cattle rancher, governor, U.S. Senator — sitting on a hill above town exactly as it was in 1913. The house is meticulously preserved and the tour is genuinely interesting, especially if you want to understand how cattle wealth shaped this county.

After →

Le Reve or Frackelton's — both on Main Street, both excellent for a proper dinner.

The Troubadour Suite near Main Street Sheridan Wyoming

Near Main St · 1 Bedroom · Couples

The Troubadour Suite

A bright, well-appointed one-bedroom just steps from downtown — hardwood floors, mid-century character, and easy walking access to everything on Main Street.

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The Iris on Main game room vacation rental on Main Street Sheridan Wyoming

On Main Street · Game Room · Pets

The Iris on Main

A Main Street address with an arcade machine, a record player, adjustable beds, and a fenced yard. Walk out the door and the whole street is yours.

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The Interactive Version

Everything in this guide, plotted on a map.

Sixty-plus places — restaurants, trails, shops, waterfalls — with distances and drive times from every Late Checkout property. Pick where you're staying and the whole territory arranges itself around you.

Explore Sheridan →

Sheridan's Creative Market

Born in a Barn is an annual outdoor market held in Sheridan in mid-September — featuring local makers, artisans, food vendors, and small businesses from across the region. It's the kind of event that reflects something real about this community: a place that values craft, keeps things local, and draws a crowd without trying too hard. If your dates line up, it's worth building your trip around.

Born in a Barn Market
Sheridan, WYMid-SeptemberDon't miss the afterparty at The Mint

Vendors typically include jewelry, leather goods, ceramics, clothing, Wyoming-made food products, and local art. The fall edition usually aligns with peak foliage season in the Big Horns — worth stacking with a mountain drive. Check their social media for exact dates each season.

After →

Smith Alley Brewing on N. Main — local craft beers in a space as thoughtfully done as the market itself.

Cedar and Sage House cozy interior Sheridan Wyoming

Near Downtown · 2 Bedrooms · Fire Pit

Cedar & Sage House

A cozy cottage a mile from downtown with a wood fire pit, private fenced yard, and garage parking. The kind of place you come back to after a full day feeling genuinely at home.

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The Bighorn River & High Country Streams

The Bighorn River, about ninety minutes south of Sheridan, is one of Wyoming's premier tailwater fisheries — cold, clear, and loaded with large brown and rainbow trout year-round. Closer to town, the Tongue River and its tributaries offer small-stream fishing in beautiful mountain terrain. Before you go anywhere, stop at the Fly Shop of the Bighorns on Main Street — they know what's hatching.

Bighorn River Tailwater
~90 min from SheridanFull dayGuide recommended for first visit

The section below Yellowtail Dam near Fort Smith, Montana is arguably the best dry-fly water in the region. Wade fishing and drift boats both work. Local outfitters in Sheridan can set you up with guides, gear rental, and licenses. Go in September if you can — the crowds thin and the fish are aggressive.

After →

Wyoming's Rib & Chop House — a cold drink and a proper steak after a long day on the water.

Tongue River — Mountain Access
20–40 min from SheridanHalf dayModerate walk-in

The upper Tongue and its tributaries hold wild brook and brown trout in classic high-country habitat. Access is straightforward off Hwy 14 — pull-offs and short trails down to the water. A Wyoming fishing license is required; pick one up at a local hardware store or online through Wyoming Game & Fish.

After →

Black Tooth Brewing — the patio is a fine place to watch the afternoon light go flat on a fishing day well spent.

The Stardust Bungalow fenced yard Sheridan Wyoming

Quiet Neighborhood · Fenced Yard · Pets

The Stardust Bungalow

A renovated two-bedroom with a fully fenced yard, fast fiber internet, and two private outdoor spaces. Good base for families and anyone traveling with dogs.

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The 56 vintage Spartan trailer in a wetland setting Sheridan Wyoming

Unique Stay · 1956 Spartan · Wetland Setting

The 56

A restored 1956 Spartan Royal Manor — built by J. Paul Getty's Spartan Aircraft Company — parked in a wetland setting where deer come through at dusk. Fire pit, cedar deck, dog-friendly. The kind of stay you photograph.

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The Big Horns in Snow

Sheridan in winter is genuinely underrated. The Big Horns receive substantial snow — Antelope Butte Mountain Resort, about an hour west, offers uncrowded skiing and snowboarding with no lift lines and reasonable prices. The valley floor stays relatively mild compared to much of Wyoming, and downtown remains active through the cold months. If you want a quiet Wyoming winter weekend with excellent mountain access, this is it.

Antelope Butte Mountain Resort
~60 min from SheridanFull dayKids under 18 ski free

A community-owned ski area that reopened after years of closure — locals fought hard to bring it back and it shows. An indie ski hill the way ski hills used to be: terrain for beginners through advanced, a warming lodge, very affordable, and kids under 18 ski free. Check their snow report before heading up.

After →

The Mint Bar — the fireplace and a whiskey after a day on the mountain is exactly as good as it sounds.

The Wayfarer Bungalow cozy interior winter Sheridan Wyoming

Winter-Ready · Fire Pit · 2 Bedrooms

The Wayfarer Bungalow

Heated tile floors, an electric fireplace, a gas fire pit in the yard, and blackout shades on both bedrooms. Exactly what a winter weekend calls for.

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