Welcome back to gravel riding season in Bozeman! Did you miss these route guides? We sure missed sharing our favorite routes!
To kick off 2026, we’re jumping back into our gravel series with a route that feels like a greatest-hits album of Montana riding. This is Route #6 in our gravel guide series, and it’s a staff favorite for good reason.
The Paradise Valley Lollipop is scenic, remote-feeling without being intimidating, and delivers big views pretty much the entire time. It’s the kind of ride that reminds you why gravel bikes exist in the first place. Smooth stretches, a little spice, plenty of time to settle into a rhythm, and views that’ll have you soft-pedaling just to take it all in.
Alright, let’s get into it!
Route Overview
The Paradise Valley Lollipop starts and ends at the Chestnut Trailhead and heads south into Paradise Valley before looping back with a steady climb and a long, rewarding descent to finish things off. You’ll ride a mix of pavement and gravel, with the gravel sections being the real star of the show.
Expect rolling terrain, gradual climbs, and long downhill stretches that make this ride feel adventurous without being overly punishing. The final climb back toward the start is where you’ll want to look around and soak it all in. Those views are easily the highlight of the day!
Tip: This route is best ridden when conditions are dry. Some gravel sections can get bumpy, and like most Montana dirt roads, things get messy fast if there’s been recent rain.
For navigation, check out the full route map and waypoints on Ride with GPS below:
- Route Length: 40.7 miles
- Elevation Gain: 2,493 ft
- Ride with GPS file: https://ridewithgps.com/routes/50733035
Who picked it: Robin
Why she loves it: “Big views, quiet roads, and a layout that flows perfectly from start to finish.”
The Journey – Mile-by-Mile Breakdown
Getting There
Park at the Chestnut Trailhead, which also happens to be a great mountain bike spot once things melt out in the summer. From Bozeman, head south toward Paradise Valley and follow signs to the trailhead. Parking is straightforward, and it’s an easy roll-out to start the ride.
Miles 0–6: Settling In
The ride starts with a paved stretch and a slight, gradual climb. This is a great warm-up section—easy spinning, steady effort, and a chance to get your legs under you before hitting the gravel.
Miles 6–13: Gravel Downhill Bliss
At mile 6, the pavement gives way to gravel, and things start trending downhill. This section can be a bit bumpy in spots, but it’s fast, fun, and incredibly scenic as you drop into the valley.
Miles 13–17: Rolling Through the Valley
You’ll hit a short climb around mile 13 before rolling into more downhill terrain. These miles are all about flow, with open views and quiet roads that make it easy to settle into a comfortable pace.
Miles 17–22.8: The Valley Climb Begins
Here’s where the route turns back toward home. The climb is gradual and manageable, following the valley floor before you hang a right and start heading back into the hills.
Miles 23–27.8: Creekside Climbing
This section follows the creek as the road climbs steadily back up. It’s a consistent effort but never feels overwhelming, especially with the scenery doing its best to distract you.
Miles 27.8–34: Views for Days & the Ride Home
After turning left back onto the road you started on, you’ll tackle the last part of the climb. Take a look around—this is the best viewpoint of the entire ride. From here, it’s a rolling downhill all the way back to the trailhead, making for a very satisfying finish.
Optional Add-On (For the Extra-Motivated)
If you’re feeling good and want to stretch the day a bit, you can add mileage to this lollipop. From the southern end of the route, riders can continue farther south toward Emigrant before crossing the highway onto East River Road. From there, you’ll ride north back toward Pine Creek, cross the highway again, and rejoin the original lollipop route.
A heads-up: this add-on is primarily paved and sees more traffic than any of the gravel sections, though River Road is usually relatively quiet compared to other valley highways.
Route Highlights
This Paradise Valley gravel route checks all the boxes: quiet roads, varied terrain, long scenic descents, and just enough climbing to make it feel earned. It’s approachable for intermediate gravel riders and still exciting enough for seasoned riders who want a classic Montana loop.
Paradise Valley Lollipop Ride Practical Tips
Equipment:
Gravel-specific tires are a must for handling the mixed terrain. We have plenty of options to suit your bike and riding style!
While this one is pretty straightforward, it’s always a good idea to bring a navigation tool like a Garmin GPS.
Bring plenty of water and snacks. There are no reliable resupply spots once you’re out there.
Weather:
As is the case for any riding in Montana, check the weather forecast before you go, and always bring a shell if you’re riding in the afternoon in the summer. Weather changes quickly in the mountains, and the temperature can drop quickly too, so be prepared.
Post-Ride Fuel:
After the ride, you’ll want to refuel, and Bozeman has some great options. Our team’s current favorites?
Bozeman Gravel Rides | Owenhouse Cycling
Be sure to check out the Ride with GPS link for easy navigation and to catch all the key waypoints along the route. And, of course, Owenhouse Cycling has all the gear you need to be gravel-ready—from tires and gloves to navigation tools and everything in between. So gear up, grab a friend, and get ready to enjoy one of Bozeman’s best gravel adventures!
Have you done the lollipop? Let us know on social! We’d love to hear from you. Follow us over on Instagram and Facebook, and stay tuned for more gravel route guides from the team!
