Questions worth
asking.

Check-in is contactless via smart lock. You'll receive your access code before arrival — no waiting around, no coordinating schedules. Tyler is reachable by phone or text throughout your stay if anything comes up.

Check-in is after 4pm. Check-out is by 11am. We turn every property ourselves between guests — that window is what makes it possible to do it right.

Sometimes. It depends on what's around your stay. Ask us directly and we'll tell you honestly. We won't hold you to a hard no if the calendar allows it.

It means Tyler responds to your messages — not a call center, not a rotating staff member, not a bot. We manage every property in the collection ourselves. Superhost five years running, 4.98 rating across 1,300+ reviews. If something needs attention during your stay, you reach a person who knows the property.

No. Each property has its own character, name, and story. The Troubadour is not the Stardust. The Magpie is not the Alderman. We name them because they're different — and the differences matter. Browse the full collection to find the right fit.

Start with the collection page and read the property descriptions — they're written to help you make that call. Still not sure? Reach out. We know every one of these places and can point you in the right direction based on who you are and what you're after.

Our properties sleep between 2 and 6 guests. For larger groups or families that want to stay close together, some of our properties sit near each other and can be booked in combination. Ask us and we'll figure it out.

Yes. Booking direct means you're dealing with us from the start — no platform fees, and a direct line to Tyler before, during, and after your stay. More on how that works here.

Almost all of them. NYS, Pressroom, Stardust, Wayfarer, Cedar & Sage, Magpie, Piñon, Bondline, Troubadour, Emerald, Fenced Yard, and the Alderman all welcome dogs. The New York Store is the one exception. Check individual property pages for details — some have fenced yards, some back up to open land, and that distinction matters depending on your dog.

Sheridan is genuinely dog-friendly. Multiple patios downtown welcome dogs. There are three dog parks, two local pet stores, and trail access throughout the Bighorns — Red Grade, Paradise Falls, Steamboat Rock — all open to dogs with no restrictions. It's a good place to bring a dog.

Start at King's Saddlery Museum on Main Street. It tells the story of this region better than anything else — the ranching culture, the history, the craftsmanship that Sheridan was built around. Once you've been, you'll see it everywhere you go in the area.

From there: get up to Park Reservoir in the Bighorns, where Hemingway drafted A Farewell to Arms at Spear-O-Wigwam on the banks. Good paddleboarding, fishing, and picnicking. You'll drive Red Grade Road on the way up — take your time on it.

For more, we write about all of it in The Register →

Breakfast at PO News — 108 years in business, and the family connection to Sheridan Brewing goes back to the 1800s. Lunch at Frackelton's, a Sheridan institution. Dinner, Le Reve is the move. Honorable mention: order the brick oven pizza at Big Horn Mercantile and have a few beers while you wait for it.

After dinner, the Mint Bar is non-negotiable. Blacktooth Brewing is worth it too — especially on a summer evening when the garage doors open and the inside flows right out to the patio.

Honestly, no. It's a long day and Yellowstone deserves its own trip. The good news: you don't need it. Wildlife viewing in the Bighorns is more intimate, the hiking is excellent without the grizzly bear calculus, and the crowds are nowhere. Save Yellowstone for when you can do it properly.

Three answers, depending on your energy. A sunrise hike to Steamboat Rock is exceptional — you'll be up early, but it earns it. The Red Grade trail complex is closer to town and genuinely great. And in summer, Paradise Falls in the Bighorns is the one not to miss — huge granite tubs carved by centuries of erosion, views that stop you mid-sentence. Search "Paradise Falls Big Horn Mountains" and you'll understand immediately.

Yes, and it's legitimate. The Red Grade trail complex is the main event — Sheridan County Land Trust built it and it shows. Hidden Hoot is closer to town and exactly what the name implies. Park and ride from the trailhead; if you only want downhill, arrange a shuttle. For conditions and trail info: sheridanclt.org. For gear and local knowledge, Sheridan Bicycle Company is the only shop in town and the right call.

Fall. Temperatures have mellowed, the farmers markets are at their peak, the color change in the Bighorns is happening, and events like Born in a Barn and Third Thursday are still running. It's the season that feels most like Sheridan actually is.

Summer is excellent for the mountains — Paradise Falls in August is something else. January and February can be brutal: heavy snow, cold, limited to do. The WYO Rodeo in July is beloved by locals and visitors alike — a real thing — but it's a full scene. Book well in advance if that's the draw, and go in knowing what you're walking into.

About 45 minutes to the high country. You'll feel the elevation change start almost immediately once you leave town. Most trailheads are accessible without high-clearance, though some roads — Red Grade included — are better with some height under you.

Yes, with one exception: if you're staying downtown and have no plans to leave town, you can manage on foot. For everything else — the Bighorns, the trails, the reservoir — you need a vehicle. Uber and Lyft exist here but are limited. There's a local taxi service that works well enough. Rental cars need to be sorted before you arrive; don't assume you'll figure it out when you land.

In summer: Paradise Falls. The granite tubs carved by centuries of erosion are remarkable on a hot August day. In winter: Meadowlark and Antelope Butte. Two small, quiet ski hills — no lift lines, affordable, the kind of skiing that doesn't exist much anymore. Both fully open and worth the drive.

Cancellation terms vary by property and booking platform. The policy will be clearly stated before you confirm your reservation. Questions about a specific booking? Reach out directly and we'll walk you through it.

Of course. The tagline is "Stay longer. Leave slower." — that's not decoration. We're set up for extended stays and welcome them. Reach out directly if you're thinking about a week or more and we'll make it work.

Depends on the property and the gathering. We're not a venue operation, but we're not rigid about it either. Tell us specifically what you have in mind and we'll give you a straight answer.

Call or text Tyler directly. We respond to everything personally. This is not a call center.