Wyoming Road Trip Itinerary — Sheridan as Your Home Base

Why Sheridan Is the Perfect Road Trip Base

Most Wyoming road trips make the mistake of constant hotel-hopping — packing and unpacking every night, losing half the morning to checkout logistics, and paying resort prices in three different towns. There's a better way: pick one base, and drive circles around it.

Sheridan sits at the crossroads of I-90 and US-14, placing you within a day's drive of every major northern Wyoming destination. Devil's Tower is two hours east. Cody and Yellowstone's east entrance are 3.5 hours west. The Bighorn Mountains are 30 minutes south. And downtown Sheridan itself — with its historic Main Street, world-class dining, and genuine Western culture — is worth two days on its own.

The math works: instead of booking four different hotels at four different price points, you book one Wyo Stays vacation rental for five nights. You unpack once. You leave your hiking boots by the door. You come home to the same kitchen every night. And you save 30–40% on lodging costs compared to the hotel-hop approach.

Day 1 — Arrive in Sheridan

Check into your Wyo Stays property and resist the urge to drive anywhere. Sheridan's downtown is the point today. Walk Main Street from the WYO Theater to King's Saddlery — the most fascinating Western store in America, where Don King has been making saddles since 1946. Allow 90 minutes minimum. The museum in the back is free and extraordinary.

Dinner at Frackelton's — Sheridan's best restaurant, housed in a beautifully restored historic building. If the seasonal menu includes anything with local beef or elk, order it. After dinner, walk to The Mint Bar for a Wyoming Whiskey and soak in a bar that's been operating since 1907.

Day 2 — Bighorn Mountains

This is the day that makes people extend their trip. Drive US-14 west through Dayton and up the Bighorn Scenic Byway. The road climbs from 4,000 to 9,000 feet in under an hour, passing through three climate zones and some of the most dramatic mountain scenery in the American West.

Stop at Tongue River Canyon for a morning hike — the 7-mile out-and-back trail follows the river through limestone walls several hundred feet high. It's 20 minutes from downtown and feels like another planet. Pack lunch and eat at Sibley Lake, a glacial lake at 8,200 feet with views that make you forget you're in Wyoming, not Switzerland.

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The Bighorn Scenic Byway is the most underrated mountain drive in America. Three climate zones in one hour. No traffic. No entrance fee. Just the road and the mountains.

— Dalton Goodyear, Wyo Stays founder

Day 3 — Cody & Yellowstone

Leave early — 7am if possible. The drive to Cody takes about 2.5 hours via US-14 through the Bighorn Basin, and the landscape shifts from mountains to high desert to red-rock canyons. Cody itself is worth a stop: the Buffalo Bill Center of the West is five museums in one, and it's genuinely one of the best museum complexes in the West.

From Cody, the east entrance to Yellowstone is another hour through the Wapiti Valley — a river canyon that Theodore Roosevelt called "the most scenic 50 miles in America." You'll enter Yellowstone at Fishing Bridge and have the afternoon for Yellowstone Lake, Hayden Valley, and the Grand Canyon of the Yellowstone.

Day 4 — Devil's Tower

Head east on I-90 — the opposite direction from the mountains, into the rolling grasslands of the Powder River Basin. Devil's Tower National Monument appears on the horizon 30 minutes before you reach it, rising 867 feet above the Belle Fourche River. The 1.3-mile Tower Trail circles the base and takes about an hour at a comfortable pace.

The monument is sacred to multiple Indigenous nations — the Lakota call it Bear Lodge. Visit with respect. The ranger programs are excellent and explain both the geological and cultural significance. Lunch in Sundance (the town that gave the Sundance Kid his name), then drive back to Sheridan for your last evening.

Day 5 — Powder River Basin & Home

If you're leaving Sheridan today, take the scenic route south on I-90 to Buffalo — a small town at the base of the Bighorns with a beautiful Clear Creek walking trail through downtown. The Occidental Hotel, where Butch Cassidy once stayed, is worth a peek. From Buffalo, you can connect to I-25 south toward Casper, or loop back to Sheridan via US-16 through the southern Bighorns.

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The best Wyoming road trip isn't about covering the most ground. It's about having a home base good enough that coming back to it every night feels like a reward, not a compromise.

Where to Stay in Sheridan

Wyo Stays manages 40+ vacation rentals across Sheridan County — from downtown lofts walkable to every restaurant to mountain cabins near the Bighorn trailheads. For a road trip base, we recommend a downtown property: you'll want to walk to dinner after a long day of driving.

The Pearl and The Onyx are both on Main Street with full kitchens, dedicated parking, and the kind of design that makes you want to come home at the end of the day. Book direct at book.wyostays.com and save 16–20% versus Airbnb.