Some rides stay with you. For Bailey, our social media manager and a longtime Hightail rider, Montana in 2022 is that trip. The plan was simple: leave Edmonton, head south, and chase the sun. The wish list included mountain passes, hot springs, and the legendary Going-to-the-Sun Road.
CROSSING THE BORDER AND CHASING THE SUN
Bailey and her riding buddy, crossed the border at Carway, south of Cardston, Alberta. Carway does not run 24 hours, so check their hours before you go. Their first planned destination was St. Mary, the eastern gateway to Glacier National Park.
A bit of confusion turned into a win. While the route starting from St. Mary's heading west is typically open with just a park pass, they didn't find that out until later.
They booked a reservation to ride Going-to-the-Sun Road starting at West Glacier (the most popular and busiest way to ride through the park) and needed to wait a few days to for a spot to open up.
A HAPPY ACCIDENT ON HIGHWAY 49
Their delay allowed them to find Highway 49, which leads to Looking Glass Hill, and links Highway 89 to Highway 2 near East Glacier. It is short, quiet, and full of curves with big views. They stopped in East Glacier Park Village for a stretch and huckleberry pie, then continued toward Flathead Lake. The air was clear and crisp, and the views opened wide to the horizon; perfect conditions for long hours in the saddle.
FLATHEAD LAKE TO HOT SPRINGS MODE
Flathead Lake was calm and blue, and the road offered easy pull-offs for photos. From there the ride shifted to hot spring hopping.
Stayed: Sage Oasis Garden Retreat in Hot Springs, Montana. Yurts tucked in the trees and a cozy setup.
Soak: Wild Horse Hot Springs. Outdoor pools under a huge sky at sunset.
Pro tip: the east side of Flathead Lake is the prettier ride. Think gentle parkway curves along the water.
Further south they reached Jackson and stayed near Jackson Hot Springs Lodge. The naturally fed pool glows at night and hits perfectly after a long day. Bailey also recommends ordering the ribeye. A meal that stood out after a long day of riding.
There is no fuel in Jackson, so top up before you arrive. If you have time, add Elkhorn Hot Springs to the list.
THE RIDE BACK TO GLACIER
They finally rode the Going-to-the-Sun Road on the return. Waterfalls, cliffside views, and slow second or third gear sections make it one of the most spectacular rides in the United States. Summer brings traffic, but the scenery is worth the patience.
Make sure to stop at Lake McDonald near West Glacier. The clear water and colorful stones look unreal. Near St. Mary you will pass the stretch featured in the opening of The Shining. From there they angled southeast to Great Falls and wrapped the trip at the retro Sip ’n Dip Tiki Lounge — famous for its mermaids behind glass and tiki cocktails. Then it was north to Canada to close the loop.
RIDE NOTES:
Crossing from Canada
- Carway is direct to St. Mary but does not operate 24 hours.
- If you are still on the Canadian side, Waterton Lakes National Park is a beauty and worth a detour.
Glacier access
- West Glacier often requires a reservation & park pass in peak season.
- Starting from St. Mary to West Glacier often does not. Always check current rules.
- Always buy a park pass (you need it to enter going either east or west). Your fees keep the parks in good shape.
Hidden gem highway
- Highway 49, also called Looking Glass Hill. Short, twisty, and overlooked.
Fuel strategy
-
Top up early. There is no gas in Jackson.
Hot springs hit list
- Wild Horse Hot Springs
- Jackson Hot Springs Lodge
- Elkhorn Hot Springs
Foodie stops
- Huckleberry pie in East Glacier
- Ribeye at Jackson Hot Springs Lodge
- Tiki cocktails at the Sip ’n Dip in Great Falls
Bonus ride
- If you have an extra day, ride Lolo Pass on Highway 12. It follows the river for miles and feels like a ribbon of perfect pavement.
RIDING WITH HIGHTAIL
Bailey wore her Hightail for every mile of this trip, steady and reliable through every long stretch of wind and sun. For riders who love open roads and big mileage days, Hightail keeps hair tangle free and ready for wherever the ride ends, whether that’s a mountain lodge, a diner, or a soak in a hot spring.
SEE BAILEY'S RIDE IN ACTION
See Bailey’s full reel from her Montana adventure. You'll see a mix of mountain passes, sunsets, and the kind of roads that remind you why we ride.
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Written with the help of AI to bring our riders’ stories to life with every detail reviewed and shaped by Jen.
