and itching to hit the road for a day trip or a quick weekend escape, you’re in luck. Within just a couple of hours, you can find mountains, canyons, historic main streets, and some seriously cool Western history — all
.
To keep this guide true to the “road trip” spirit, everything here is in one of these nearby counties:
.
Let’s dive into 10 short out-of-county road trips from Gillette that are perfect when you’re asking, “Where can we go this weekend?”
1. Devils Tower National Monument (Crook County)
If you only do one road trip from Gillette, make it this one.
Devils Tower in Crook County is one of the most iconic sights in Wyoming — and honestly, in the entire U.S.
You’ve probably seen photos of it: a massive rock tower rising straight out of the prairie. It’s about a
1.5–2 hour drive from Gillette, depending on your route, and the drive itself is beautiful.
- What to do:
- Walk the easy paved Tower Trail (about 1.3 miles) around the base.
- Watch rock climbers scaling the columns.
- Look for prairie dogs in the nearby prairie dog town.
- Stop at the visitor center for history and Native stories about the tower.
- Why it’s great for Gillette travelers: Close enough for a day trip, but epic enough to feel like a full vacation.
Want a tip? Try to arrive early or stay near sunset. The tower glows deep orange when the light hits just right.
2. Historic Sundance & Vore Buffalo Jump (Crook County)
Pair your Devils Tower outing with a stop in
Sundance, Crook County. This small Western town offers a relaxed main street and a taste of Old West history without feeling touristy.
- Things to check out in Sundance:
- Walk downtown and pop into local shops and cafés.
- Visit local museums (seasonal hours, so check ahead).
- On the way:
- Stop at the Vore Buffalo Jump near the Wyoming–South Dakota border. It’s an archeological site where Native peoples hunted buffalo for hundreds of years.
- Learn how the jump worked and see real excavation areas.
If you enjoy history and small-town charm, this is an easy add-on to a Devils Tower trip or its own day-long loop from Gillette.
3. Buffalo & Fort Phil Kearny (Johnson & Sheridan Counties)
Head west from Gillette and you can step into the heart of
Wyoming cowboy country. The town of
Buffalo in Johnson County, along with nearby
Fort Phil Kearny over the line in Sheridan County, makes a fantastic day or weekend trip.
- In Buffalo (Johnson County):
- Stroll the historic downtown and check out Western-style storefronts.
- Grab a burger or steak at a local restaurant.
- Visit local museums if you’re into frontier history.
- Fort Phil Kearny (Sheridan County):
It’s about a
2–2.5 hour drive from Gillette, depending on stops. If you love stories of soldiers, Native warriors, and old trails, this route is full of them.
4. Sheridan: Western Main Street & Mountain Views (Sheridan County)
Looking for a road trip that mixes
shopping, dining, and mountain scenery? Head to
Sheridan in Sheridan County. It’s roughly a
2-hour drive from Gillette, and it’s one of the most inviting small cities in Wyoming.
- What to do in Sheridan:
- Walk Main Street and browse Western wear shops, galleries, and outfitters.
- Have lunch or dinner at a local steakhouse or café.
- Check out historic buildings and unique public art.
- Why it’s a good Gillette getaway: It feels like a mini-vacation: different restaurants, a lively downtown, and the Bighorn Mountains right in the background.
On a clear day, the mountains look so close you feel like you can reach out and touch them.
5. Bighorn Mountains Scenic Drive (Sheridan & Johnson Counties)
If you’ve ever wanted to go from open plains to mountain passes in just a couple of hours, the
Bighorn Mountains are your road trip dream.
From Gillette, you can head toward Sheridan or Buffalo, then drive up into the mountains via U.S. Highway 14 or U.S. Highway 16.
- Highlights of the Bighorn Mountains:
- Cooler mountain air in summer (a nice break from hot prairie days).
- Scenic pullouts with big views over valleys and cliffs.
- Picnic spots, short hikes, and chances to see wildlife.
- Good for:
- Day trips with lots of photo stops.
- Quick hikes and picnic lunches.
- Fall drives when the leaves change color.
If you grew up on flat land, the first time you wind up these mountain roads will feel almost unreal.
6. Crazy Woman Canyon (Johnson County)
With a name like
Crazy Woman Canyon, how can you not be curious? This rugged little gem sits in Johnson County and is often reached through the Buffalo area.
The canyon road is narrower and rough in spots, so it’s best for higher-clearance vehicles and drivers comfortable with dirt roads. But the reward is worth it.
- What to expect:
- Towering rock walls right beside you.
- A creek running alongside the road.
- Shady, peaceful pull-offs perfect for a snack break.
- Why it’s special: It feels wild and tucked away, even though it’s not that far from town.
If you’re looking to add a little adventure to your Wyoming road trip from Gillette, this is a great pick.
7. Story & Tongue River Canyon (Sheridan County)
Tucked between Sheridan and the Bighorn Mountains is the small town of
Story in Sheridan County. It makes a cozy base for exploring
Tongue River Canyon and some quieter trails.
- In and around Story:
- Walk or drive through this forested, cabin-filled town — it feels like a mountain retreat.
- Head to nearby trailheads for hiking, fishing, or just walking along the water.
- Tongue River Canyon:
- Trail along the river with towering cliffs on both sides.
- Great for a family-friendly hike if everyone can handle a few miles.
This area offers a quieter alternative to the busier scenic points, and it’s still just a few hours’ drive from Gillette.
8. Newcastle & Osage: Small-Town Wyoming Drive (Weston County)
Looking for a mellow drive without big crowds? Head east into
Weston County and explore
Newcastle and the nearby community of
Osage.
- In Newcastle:
- Walk downtown and check out local businesses.
- Grab coffee, lunch, or a quick snack at a local spot.
- Drive around town to get a feel for small-town Wyoming life.
- On the road:
- Enjoy open views, rolling hills, and that wide Wyoming sky.
- Watch for deer and pronghorn along the way.
This trip is less about “big attractions” and more about the simple pleasure of a relaxed drive out of Campbell County.
9. Douglas & Ayres Natural Bridge (Converse County)
Southwest of Gillette lies
Converse County, home to the town of
Douglas and a cool hidden gem: the
Ayres Natural Bridge area.
- Ayres Natural Bridge:
- A natural rock bridge spanning a creek — one of Wyoming’s lesser-known scenic spots.
- Grassy picnic areas and water nearby make it a great place to relax.
- Douglas:
- Known as the “Home of the Jackalope,” with fun jackalope-themed touches around town.
- Grab a bite to eat and stroll around after your stop at the bridge.
If you’re looking for something different from mountains and canyons, this natural bridge and riverside setting will surprise you.
10. Casper Mountain Side Trip via Converse County Route (Converse County)
If you’re up for a slightly longer day, you can route through
Converse County toward the
Casper Mountain area. While Casper itself is in Natrona County, much of the drive and surrounding land passes through Converse.
- On the drive:
- Long stretches of open highway with big-sky views.
- Classic Wyoming landscapes: ranches, rolling hills, and distant ridges.
- Near Casper Mountain:
- Trails and overlooks (if you choose to continue beyond Converse County).
- Cooler temps and pine trees, especially nice in summer.
This route makes a great “see more of Wyoming” day, especially if you enjoy road trips just for the drive itself.
Tips for Planning Your Gillette Road Trips
Before you hit the road from Gillette to explore these nearby counties, keep a few basics in mind:
- Fill up before you go: Distances can be longer than they look on the map, and gas stations can be spread out.
- Check the weather: Mountain roads in Sheridan and Johnson Counties can change quickly with storms or early snow.
- Pack layers: It might be warm in Gillette and chilly in the Bighorn Mountains on the same day.
- Bring water and snacks: Perfect for impromptu picnics at places like Ayres Natural Bridge or roadside pullouts.
I’ve found that some of the best moments on these trips aren’t planned at all — like pulling over to watch a herd of pronghorn or stopping at a tiny café you didn’t even know existed.
Share Your Favorite Road Trips From Gillette
Have you driven from
Gillette to any of these spots in Converse, Crook, Johnson, Sheridan, or Weston County? Maybe you’ve found a quiet picnic area, a great little diner, or a scenic overlook that deserves more love.
- Which road trip on this list would you try first?
- Do you have your own favorite out-of-county getaway from Gillette?
Drop your recommendations and experiences in the comments — your tips can help other travelers plan their next Wyoming adventure.
And if you found this guide helpful, please
share it with friends and family who are looking for fun things to do near Gillette, Wyoming. The more we share our favorite routes and hidden gems, the more enjoyable these Wyoming road trips become for everyone.
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