Discover Sheridan, Wyoming - Where Western Heritage Meets Bighorn Beauty

Day 1: Historic Main Street & Cowboy Charm

• Morning (9:00 AM - 1:00 PM) Arrive in Sheridan and kick off your Western adventure! Begin with a delicious coffee and pastry at POPS Coffee (130 N Main St, Sheridan, WY) to fuel your exploration. Spend the morning strolling down historic Main Street, admiring the beautifully preserved 19th-century architecture. Visit King’s Ropes and Saddlery (1010 N Main St), an iconic Western store, where you can browse authentic cowboy gear (free to look!). Next, immerse yourselves in local rodeo history at the Sheridan WYO Rodeo Hall of Fame (1889 Coffeen Ave), just a short walk off Main Street. Allow about an hour here.
  • Practical Tip: Parking is generally easy to find on or around Main Street.
  • Cost: Coffee/Pastries ~$10-15; Rodeo Hall of Fame $10/person ($20 total).
  • Distance: All activities within easy walking distance in downtown Sheridan.
• Afternoon (1:00 PM - 5:00 PM) Enjoy a casual lunch at Powder River Pizza (17 N Scott St), known for its relaxed atmosphere and tasty pies. After lunch, delve deeper into local history at the Sheridan County Museum (850 Sids Mountain Rd). This museum offers a comprehensive look at the area’s pioneer days, ranching, and Native American heritage (free, donations welcome). Finish your afternoon with a visit to Black Tooth Brewing Company (312 Broadway St) for a flight of local craft beers and a peek into their brewing process.
  • Practical Tip: The County Museum is a short 5-minute drive from downtown.
  • Cost: Lunch ~$30-40; Brewery flight ~$15-20.
  • Distance: Museum is 1.5 miles from downtown; Brewery is on Broadway, walkable from Main Street.
• Evening (6:00 PM onwards) Experience true Western dining at Wyoming’s Rib & Chop House (840 N Main St), renowned for its steaks and ribs in a lively atmosphere. After dinner, no trip to Sheridan is complete without a drink at the legendary Mint Bar (151 N Main St). This historic cowboy saloon, adorned with taxidermy and local memorabilia, offers an authentic taste of the Old West.
  • Cost: Dinner ~$80-100; Drinks at Mint Bar ~$20-30.

Day 2: Bighorn Mountain Majesty & Lakeside Trails

• Morning (8:00 AM - 1:00 PM) Start your day with a hearty breakfast at Andi’s Coffee & Market (1889 Coffeen Ave, grab-and-go options perfect for the road). Today is dedicated to exploring the majestic Bighorn Mountains. Drive west on US-14, the Bighorn Scenic Byway, a breathtaking route offering stunning vistas. Your first major stop is the Shell Falls Interpretive Site (approx. 50 miles from Sheridan, about 1-hour drive without stops). Enjoy an easy 0.5-mile paved loop trail to view the spectacular waterfalls and learn about the area’s geology. Continue along US-14, making photo stops at various pull-offs.
  • Practical Tip: Pack snacks and water. The mountain weather can change quickly, so dress in layers.
  • Cost: Breakfast ~$20-25; Gas for mountain drive ~$30-40; Shell Falls is free.
  • Distance: Approximately 100-120 miles round trip for the scenic drive.
• Afternoon (1:00 PM - 5:00 PM) Enjoy a picnic lunch (which you can pack from a deli in Sheridan or pick up in Dayton) amidst the beautiful mountain scenery. Head to Sibley Lake (located directly off US-14, about 25 miles west of Dayton). This picturesque alpine lake offers an easy, relatively flat 1.5-mile loop trail perfect for a leisurely stroll, taking in the serene mountain air and reflective waters. Alternatively, for a more secluded experience, explore a segment of the Tongue River Canyon Trail (trailhead near Dayton, off US-14 ALT), offering stunning canyon views.
  • Practical Tip: Bear spray is recommended for hiking in the Bighorns, though encounters are rare on popular trails. Cell service can be spotty.
  • Cost: Picnic lunch ~$20-30; Hiking is free.
  • Distance: Sibley Lake loop is short. Tongue River Canyon Trail is an out-and-back, you choose the distance.
• Evening (6:30 PM onwards) Return to Sheridan and treat yourselves to a refined dinner at Frackelton’s (55 N Main St), one of Sheridan’s top-rated restaurants, known for its creative American cuisine and sophisticated ambiance. It’s a perfect way to celebrate your mountain adventure. After dinner, enjoy a leisurely evening stroll along Main Street or relax back at your accommodation.
  • Cost: Dinner ~$90-120.

Day 3: Western Art & Countryside Charm

• Morning (9:00 AM - 12:30 PM) Grab a quick breakfast at your hotel or a local coffee shop. Today, explore the renowned Brinton Museum (239 Brinton Rd, Big Horn, WY), located about 15 miles south of Sheridan. This stunning museum is set on a historic 620-acre ranch, housing an exceptional collection of Western art, Native American artifacts, and historic ranch buildings. Allow 2-3 hours to explore the galleries, the historic Brinton Ranch House, and the beautiful grounds.
  • Practical Tip: The drive to the Brinton Museum is scenic, passing through the charming village of Big Horn.
  • Cost: Breakfast ~$10-15; Brinton Museum admission $15/person ($30 total).
  • Distance: ~15 miles (20-25 minute drive) south of Sheridan.
• Afternoon (12:30 PM - 3:00 PM) Head back to Sheridan for a final lunch. Consider the Silver Spur Cafe (331 N Main St) for a classic diner experience with delicious home-style cooking, or a quick grab-and-go from a local deli if time is tight. After lunch, squeeze in any last-minute souvenir shopping on Main Street, perhaps picking up a unique piece of Western art or local craft. Then, head to the airport or continue on your journey from Sheridan, full of Western heritage and mountain memories.
  • Practical Tip: Sheridan County Airport (SHR) is just 2 miles northeast of downtown, a very quick drive.
  • Cost: Lunch ~$30-40; Souvenirs (optional) ~$20-50.
  • Distance: All within Sheridan.
• Evening (N/A - Departure) Departure from Sheridan.

Day 1: Western Welcome & Sheridan’s Soul

• Morning (10:00 AM - 1:00 PM) Arrive in Sheridan, Wyoming, known as “The Best of the West.” Check into your chosen accommodation. For a touch of history, consider the iconic Historic Sheridan Inn; for comfort and value, options like the Best Western Sheridan Center or Holiday Inn Express are excellent choices. Settle in and prepare for your adventure.
  • Practical Tip: Most hotels offer check-in after 3 PM, but often allow bag drop-off earlier. From I-90, Sheridan is easily accessible via Exits 20 or 23.
  • Estimated Cost: Accommodation ~$180-250/night.
• Afternoon (1:00 PM - 5:30 PM) Enjoy an authentic Wyoming lunch at the Mint Bar (151 N Main St), a legendary Western saloon famous for its taxidermy and local history; their burgers are a local favorite. Afterward, dive into Sheridan’s rich heritage with a visit to King’s Saddlery and Museum (184 N Main St). This world-renowned saddle shop boasts a free museum showcasing an impressive collection of Western artifacts, wagons, and cowboy gear. Allow 1-1.5 hours. Spend the rest of the afternoon strolling along Main Street, exploring unique shops and art galleries.
  • Practical Tip: King’s Saddlery is just a short walk from the Mint Bar. Downtown Sheridan is very walkable, covering about 4-5 blocks of shops and attractions.
  • Estimated Cost: Lunch ~$40-60 for 2. Museum is free (donations welcome).
• Evening Freshen up before indulging in a superb dinner at Wyoming Rib & Chop House (19 N Main St). Known for its expertly prepared steaks, prime rib, and fresh seafood, it offers a vibrant Western atmosphere. Reservations are highly recommended. After dinner, unwind with craft beers at Blacktooth Brewing Company (350 Broadway St) or sample spirits at Backwards Distilling Company’s tasting room (2181 Coffeen Ave).
  • Estimated Cost: Dinner ~$80-120 for 2. Drinks ~$30-50.

Day 2: Into the Bighorns – Scenery & Sibley Lake

• Morning (8:00 AM - 12:00 PM) Fuel up with breakfast at a local cafe like Midtown Cafe (212 N Main St) or your hotel. Then, embark on your first journey into the Bighorn Mountains via US-14 West, the scenic “Bighorn Scenic Byway.” Drive approximately 1 hour (45 miles) to the Sibley Lake Recreation Area. Here, you’ll find the trailhead for the Sibley Lake Trail, a beautiful 3.5-mile loop (moderate difficulty, ~2-3 hours hiking time) offering stunning views of the lake, surrounding pine forests, and opportunities for birdwatching and wildlife spotting.
  • Practical Tip: Pack plenty of water, snacks, layers of clothing (mountain weather can change quickly), and bear spray is recommended for backcountry hiking.
  • Estimated Cost: Breakfast ~$30-40. Gas ~$20-30.
• Afternoon (12:00 PM - 5:00 PM) Enjoy a packed picnic lunch amidst the beauty of Sibley Lake. After your hike, drive a little further west on US-14 to Burgess Junction. Stop at the Forest Service Ranger Station for maps and local insights. For those interested in fishing, Sibley Lake and nearby streams accessible from US-14 offer excellent trout fishing. A Wyoming fishing license is required (available online or at local sporting goods stores in Sheridan like Rocky Mountain Discount Sports, 1284 Coffeen Ave). Spend an hour or two trying your luck.
  • Practical Tip: Non-resident 1-day fishing licenses are around $14/person; a 5-day license is about $56/person.
  • Estimated Cost: Picnic lunch ~$20. Fishing license (if purchased) ~$14-56 per person.
• Evening Head back to Sheridan. For a memorable dining experience, reserve a table at Frackelton’s Fine Food & Spirits (55 N Main St). This upscale restaurant offers contemporary American cuisine with a focus on fresh, seasonal ingredients. It’s a perfect spot for a celebratory meal.
  • Estimated Cost: Dinner ~$100-150 for 2.

Day 3: Cloud Peak Wilderness & Mountain Passes

• Morning (7:30 AM - 1:00 PM) Grab a quick and delicious breakfast from Java Gypsy Coffee House (various locations, e.g., 200 Coffeen Ave) for coffee and pastries. Today, you’ll venture deeper into the Bighorns towards higher elevations and the majestic Cloud Peak Wilderness. Drive west on US-14, then connect to US-14A West (the “Medicine Wheel Passage” - check seasonal opening, typically late May to October). Head towards the Tongue River Trailhead (near Ranger Creek), about 1.5 hours (60 miles) from Sheridan. Hike a section of the Cloud Peak Wilderness via the Tongue River Trail. This is an out-and-back hike, choose your distance (e.g., 4-6 miles round trip, 3-5 hours total) for significant elevation gain and breathtaking mountain scenery.
  • Practical Tip: This hike requires sturdy hiking boots, plenty of water, high-energy snacks, sun protection, and a keen awareness of mountain conditions. Always tell someone your hiking plans.
  • Estimated Cost: Breakfast ~$20-30. Gas ~$20-30.
• Afternoon (1:00 PM - 5:30 PM) Enjoy a well-deserved packed lunch on the trail or at a scenic overlook. Continue your drive along the dramatic Medicine Wheel Passage (US-14A). This byway is renowned for its steep grades, switchbacks, and panoramic views from high mountain passes. Make a essential stop at Shell Falls Interpretive Site (on US-14A, ~1.5 hours from Tongue River Trailhead) to admire the powerful waterfall cascading through a granite canyon and learn about the area’s unique geology.
  • Practical Tip: Driving on US-14A requires caution due to winding roads and elevation changes. Shell Falls is an easy, short walk from the parking area.
  • Estimated Cost: Packed lunch ~$20.
• Evening Return to Sheridan after a day of intense mountain exploration. For a relaxed and satisfying meal, head to POPS Pizza & Grill (37 N Main St). Their wide selection of pizzas, pastas, and comfort food will hit the spot. Enjoy a quiet evening reflecting on the day’s epic views.
  • Estimated Cost: Dinner ~$40-60 for 2.

Day 4: Historic Ranching & Mountain Lakes

• Morning (9:00 AM - 1:00 PM) Enjoy breakfast at your hotel or revisit a favorite local spot. This morning, explore Sheridan’s rich history beyond the Bighorns by visiting the Trail End State Historic Site (400 Clarendon Ave). This beautifully preserved historic mansion was once the home of John B. Kendrick, a wealthy cattle baron and Wyoming senator. Explore the elegant rooms, immaculate grounds, and gain insight into early 20th-century ranching life. Allow 1.5-2 hours for your visit.
  • Practical Tip: Trail End is located within Sheridan city limits. Admission is around $4-6 per person.
  • Estimated Cost: Breakfast ~$30-40. Trail End admission ~$10-12 for 2.
• Afternoon (1:00 PM - 5:30 PM) Grab lunch in Sheridan, perhaps at a different downtown eatery you’ve yet to try. Then, head south of Sheridan (about 20-30 minutes, 15-20 miles via I-90 S/US-87 S) to Lake DeSmet. This large, picturesque reservoir is popular for fishing (trout, walleye, perch) and offers stunning views of the surrounding plains and the distant Bighorns. Spend a relaxing afternoon fishing from the shore or a designated pier, or simply enjoying the tranquil lakeside environment.
  • Practical Tip: If fishing, ensure you have your Wyoming fishing license. Bait and tackle can be purchased at local sporting goods stores in Sheridan.
  • Estimated Cost: Lunch ~$40-60. Gas ~$10-15.
• Evening For your farewell dinner in Sheridan, consider a casual, local classic like Ole’s Pizza & Spaghetti House (925 N Main St) for hearty Italian-American fare, or return to a restaurant you particularly enjoyed earlier in the trip. Check the local Sheridan tourism website for any evening events, live music, or rodeos happening during your stay.
  • Estimated Cost: Dinner ~$60-100 for 2.

Day 5: Last Views & Departure

• Morning (8:00 AM - 12:00 PM) Enjoy a final breakfast in Sheridan, perhaps a last visit to Midtown Cafe for their popular cinnamon rolls. Depending on your departure schedule, you can revisit a favorite downtown shop for last-minute souvenirs or take a short, easy scenic drive into the Bighorn foothills for one last glimpse of the majestic mountains. A quick loop to Fetterman Battlefield Interpretive Trail (15 minutes from Sheridan off I-90 W) offers a short historical walk with views. Check out from your accommodation.
  • Practical Tip: Allow ample time for breakfast and any last-minute activities, considering your travel time to your next destination or airport.
  • Estimated Cost: Breakfast ~$30-40. Gas ~$10-15.
• Afternoon (12:00 PM onwards) Depart from Sheridan, Wyoming, carrying unforgettable memories of your “Bighorn Backcountry Adventure” and the charming Western hospitality of Sheridan.