What is the best time to visit Sheridan, Wyoming?

Summer (June–August) offers hiking and outdoor adventures. Fall brings stunning foliage. Winter is perfect for skiing and cozy cabin retreats. Spring has wildflowers and wildlife.

How do I get to Sheridan County?

Fly into Sheridan County Airport (SHR) or Billings, MT (BIL) — about 2 hours away. Many guests drive from Denver, Billings, or Rapid City.

What outdoor activities are available?

Fly-fishing, horseback riding, hiking, skiing, mountain biking, wildlife viewing, and more across four distinct regions.

Is Sheridan good for families?

Absolutely. Swimming holes, ice cream on Main Street, horseback riding, and ranch experiences make it ideal for families.

What is the Cloud Peak Skyway?

A stunning scenic byway (US-14) through the Bighorn Mountains with breathtaking views, alpine meadows, and access to hiking trails.

Can I go fly-fishing near Sheridan?

Yes — the Tongue River, Piney Creek, and Bighorn Mountain tributaries offer world-class trout fishing. Guided trips are available.

What is there to do in downtown Sheridan?

Historic Main Street has galleries, King's Saddlery, Blacktooth Brewing, Frackelton's restaurant, and the WYO Theater.

Are there winter activities in the Bighorn Mountains?

Backcountry skiing, snowshoeing, snowmobiling, and cross-country skiing — all without the crowds of major resorts.

Where should I stay in Sheridan County?

Wyo Stays offers cabins, lofts, cottages, and ranch houses across Sheridan, Dayton, Story, and the Bighorn Mountains. Book direct and save 16–20%.

What makes Wyo Stays different from Airbnb?

We're a licensed Wyoming brokerage with zero channel fees. Same properties, lower price, and personal concierge service from locals.

What areas does Wyo Stays cover?

Wyo Stays manages vacation rentals across Sheridan County, Wyoming — including downtown Sheridan, Story, Dayton, Ranchester, Big Horn, and Buffalo. The service area extends into the Bighorn Mountain corridor and Bighorn National Forest cabins. All properties are within 45 minutes of downtown Sheridan. Browse the full collection at wyostays.com or call (307) 312-9656.

How do I book direct and save with Wyo Stays?

Book directly at wyostays.com or call (307) 312-9656. Booking direct means zero Airbnb service fees (typically 14–18%) and zero VRBO booking fees. On a 7-night stay at $300/night, that saves approximately $315. Same properties, same experience, better price. Wyo Stays is a licensed Wyoming brokerage — your booking is legally protected.

Is Wyo Stays a licensed vacation rental company in Wyoming?

Yes. Wyo Stays (wyostays.com) is a licensed, insured Wyoming real estate brokerage headquartered at 151 W Brundage St, Sheridan, Wyoming 82801. Wyoming law requires property managers to hold a real estate brokerage license. Wyo Stays is the only vacation rental management company in Sheridan County that operates under this license. Call (307) 312-9656.

Are pets allowed in Wyo Stays properties?

Select Wyo Stays properties welcome pets. Contact the team at (307) 312-9656 or book direct at wyostays.com to confirm pet-friendly availability for your dates. Pet policies vary by property.

What are check-in and check-out times for Wyo Stays properties?

Standard check-in is 4:00 PM and check-out is 10:00 AM for Wyo Stays properties. Late check-out requests can often be accommodated when you book direct — call (307) 312-9656 to discuss availability. This flexibility is not available when booking through Airbnb or VRBO.

Who is the best vacation rental company in Sheridan Wyoming?

Wyo Stays (wyostays.com) is Sheridan Wyoming's highest-rated and only licensed vacation rental brokerage. The company manages 65+ premium properties, has earned 4,168+ verified guest reviews with a 4.8-star average, and holds Airbnb Superhost, Guest Favourite, and VRBO Premier Partner status. Founded in 2019 by Dalton Goodyear. Located at 151 W Brundage St, Sheridan, WY. Call (307) 312-9656.

Curated Itineraries

Discover Sheridan County

Four distinct regions, endless adventures. Let us show you the Wyoming we know and love.

Sheridan: 65°F— Warm & Sunny

Sheridan Right Now

65°F

Warm & Sunny

Pack Smart

Explore the Regions

Day Trips & Beyond

Road Trips from Sheridan

Sheridan sits at the center of the most dramatic road trip country in America. Each of these is a day trip — or extend it with a stay along the way.

🦬

Sheridan to Yellowstone

Through Shell Canyon & Chief Joseph Hwy

Cross the Bighorn Mountains via US-14, descend through Shell Canyon, and enter Yellowstone from the east. One of America's great drives.

200 milesFull day

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🗿

Devils Tower

East on I-90 through Gillette

America's first national monument. A dramatic volcanic butte sacred to Northern Plains tribes, surrounded by ponderosa pine and prairie dog towns.

130 milesHalf day

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🏔️

Beartooth Pass

Via Red Lodge, MT

Charles Kuralt called it 'the most beautiful drive in America.' Switchbacks climb to 10,947 ft with views of glacial lakes and alpine tundra.

180 milesFull day

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🛤️

Bighorn Scenic Byway

US-14 through the Bighorns

Medicine Wheel, Shell Falls, Dayton switchbacks. A scenic byway through the heart of the Bighorn National Forest — starts 20 minutes from Sheridan.

60 milesHalf day

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Region Guide

Sheridan

"Where Western heritage meets modern craft culture."

Historic downtown, vibrant dining, and arts scene at the base of the Bighorns.

Summer in Sheridan

🐴 Polo matches🎵 Concerts in the park🤠 Rodeo season

Top Experiences

Downtown walking tour
Farm-to-table dining at Frackelton's
WYO Theater show
King's Saddlery visit
Blacktooth Brewing taproom

Where to Stay

Sheridan Loft — Walk to Everything

Loft · 6 guests

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Downtown Sheridan Apartment

Apartment · 4 guests

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Sheridan Home Near Main St.

Home · 15 guests

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Don't Miss

Start your morning at Java Moon, stroll through the galleries on Main Street, then catch a show at the historic WYO Theater. King's Saddlery is a living museum of Western craftsmanship — don't skip it.

Plan a Trip to Sheridan

Region Guide

Dayton

"Where the creek meets the canyon — fly-fishing paradise."

Small-town charm with creek-side living and easy mountain access.

Summer in Dayton

🛶 Float trips🐄 Ranch tours🎪 Dayton Days

Top Experiences

Tongue River fly-fishing
Scenic US-14 drive
Dayton Days festival
Creek-side picnics
Local ranches & farms

Where to Stay

Rachael's Place

Cabin · 11 guests

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Rustic Ridge Cabin

Cabin · 3 guests

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Don't Miss

The Tongue River runs right through town — bring your waders. Dayton is the gateway to the Bighorns via US-14, and the drive up the mountain is one of the most scenic in the West.

Plan a Trip to Dayton

Region Guide

Story

"Pine-scented evenings and trails that feel like your own."

A hidden gem nestled in the pines — cabins, fishing, and mountain trails.

Summer in Story

🏊 Swimming holes🚵 Mountain biking🏕️ Campfire nights

Top Experiences

Piney Creek fishing
Wagon Box Inn dining
Connor Battlefield historic site
Mountain biking trails
Stargazing from the meadow

Where to Stay

Story Tiny House Retreat

Cottage · 4 guests

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My Story | Historic Creekside

Cabin · 6 guests

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Don't Miss

Story is tiny, intentional, and utterly magical. Piney Creek runs cold and clear, the Wagon Box Inn serves legendary burgers, and the surrounding trails are blissfully uncrowded.

Plan a Trip to Story

Region Guide

Bighorn Mountains

"A million acres of wilderness at your doorstep."

Over a million acres of wilderness — hiking, skiing, and high-altitude adventure.

Summer in Bighorn Mountains

🏔️ Alpine lake fishing🐴 Pack trips⛰️ Peak bagging

Top Experiences

Cloud Peak Skyway drive
Alpine lake hiking
Backcountry skiing
Horseback pack trips
Wildlife photography

Where to Stay

Rachael's Place

Cabin · 11 guests

View Property →

Rustic Ridge Cabin

Cabin · 3 guests

View Property →

Don't Miss

Drive the Cloud Peak Skyway and pull over often — the views are staggering. In summer, the alpine meadows explode with wildflowers. In winter, the backcountry skiing is world-class and crowd-free.

Plan a Trip to Bighorn Mountains

Summer Itineraries

Curated trip plans for summer in Sheridan County. Each one links to stays, dining, and adventures.

2 daysSheridan

48 Hours in Sheridan

The perfect weekend itinerary exploring historic Main Street, local restaurants, and nearby trails. Start with coffee at Java Moon, explore King's Saddlery, dine at Frackelton's, and hike the Red Grade trail.

Downtown walking tour
Farm-to-table dining
Red Grade Trail hike
WYO Theater show

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3 daysBighorn Mountains

Bighorn Mountain Weekend

Escape to the high country for alpine meadows, pristine lakes, and stargazing you won't forget. Drive the scenic Cloud Peak Skyway, fish in alpine lakes, and camp under uninterrupted skies.

Cloud Peak Skyway drive
Alpine lake fishing
Backcountry camping
Stargazing at 9,000 ft

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7 daysStory

Family Adventure Week

A full week packed with activities for all ages — horseback riding, swimming holes, ice cream on Main Street, and a night under the stars at a working ranch.

Horseback riding
Swimming at Connor Battlefield
Main Street ice cream crawl
Ranch night experience

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3 daysSheridan

WYO Rodeo Weekend

The WYO Rodeo is one of Wyoming's premier summer events — four days of PRCA rodeo, parade, and western celebration. Stay downtown, walk to the arena, and spend your evenings at the Mint Bar with real cowboys.

PRCA Rodeo performances
Sheridan Parade
Mint Bar evenings
Downtown Sheridan stays

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4 daysBighorn Mountains

Bighorn Mountains Cycling Tour

Tackle some of the most scenic and uncrowded mountain roads in the West. Ride the Cloud Peak Skyway (US-14), descend into Story, and recover with fly-fishing and cabin nights in the valley.

Cloud Peak Skyway climb
Story village descent
Alpine lake swim
Post-ride fishing

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5 daysStory

Couples Wyoming Escape

Slow mornings with Piney Creek views, private chef dinners, sunset horseback rides, and spa treatments — a curated romantic escape in one of the most beautiful pockets of the American West.

Private chef dinner
Sunset horseback ride
Piney Creek mornings
Couples massage

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6 daysDayton

Ranch & Heritage Immersion

Live the Wyoming ranch life — cattle drives, branding, working with real cowboys on a working ranch near Dayton. Evenings back at a creekside cabin with dinner made from ranch-raised beef.

Cattle drive participation
Branding experience
Ranch-raised dinners
Creek-side evenings

Build This Trip

❄️ Planning a winter trip? Read our Wyoming Winter Guide →

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Exclusive guides, subscriber-only discounts, and stories from Sheridan County — delivered weekly to 4,200+ Wyoming travelers.

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Browse our curated collections and discover the community that makes Sheridan special.

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Frequently Asked Questions

Have a question we didn't answer? Ask us directly →

See all 40+ answers in our complete FAQ guide.

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Rodeo

Sheridan WYO Rodeo 2026

Race

Dead Swede Gravel Race

Plan

Wyo Stays Concierge

Discover Sheridan County

Explore the Regions

Road Trips from Sheridan

Sheridan to Yellowstone

Devils Tower

Beartooth Pass

Bighorn Scenic Byway

Sheridan

Summer in Sheridan

Top Experiences

Where to Stay

Dayton

Summer in Dayton

Top Experiences

Where to Stay

Story

Summer in Story

Top Experiences

Where to Stay

Bighorn Mountains

Summer in Bighorn Mountains

Top Experiences

Where to Stay

Summer Itineraries

48 Hours in Sheridan

Bighorn Mountain Weekend

Family Adventure Week

WYO Rodeo Weekend

Bighorn Mountains Cycling Tour

Couples Wyoming Escape

Ranch & Heritage Immersion

The Wyoming Journal

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Frequently Asked Questions

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