Montana

Yellowstone to Glacier

Our most epic and difficult journey across Montana
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  • From $4450
  • Location Montana
  • Duration 7 Days / 6 Nights
  • Rider Level 3 / 4 / 5

Experience Montana’s bucket-list rides on this point-to-point tour.

Our Montana-based crew loves to show off our backyard, and you’ll understand why on this challenging point-to-point trip. This trip involves two three-hour shuttles, and we move four times.  

Pack on big miles and take in breathtaking views of glaciers, craggy cliffs, and rivers as we pedal over Going-to-the-Sun Road in Glacier National Park and climb to almost 11,000 feet on Beartooth Pass. Outside of the fully supported rides, you’ll enjoy a combination of Cycling House chef-prepared food – sourced locally as much as possible – and meals at local restaurants.

Are you looking for less moving and more time to unwind? Check out our Glacier trips.

Highlights

  • Six days of guided, supported rides through Western Montana
  • Comfortable motel or lodge accommodations. We will stay in East Glacier & Red Lodge for two nights.
  • Chef-prepared or local restaurant meals each day featuring Montana produce and baked goods.
  • Enjoy two bucket-list routes: Going-to-the-Sun Road in Glacier National Park and Beartooth Pass.
  • Explore quaint Montana towns, including West Glacier, East Glacier, White Sulphur Springs, and Red Lodge.
  • Arrival Day Airport & Hotel pickups in Billings (BIL)
  • Departure Day Airport & Hotel dropoffs in Flathead Valley (FCA)

Food

You’ll eat a combination of Cycling House chef-prepared meals and food at our favorite local restaurants. We source as much local food as possible, stopping at farmer’s markets and working with local producers. The Cycling House will cover all meals, snacks, and ride nutrition.

Accommodations

On our journey through rural Montana, we’ll stay in a mix of lodges and hotels. We start our trip in Red Lodge and stay at The Pollard Hotel for two nights. After Red Lodge, it’s one night at The Spa Hot Springs Motel in White Sulphur Springs. Next, we have two nights at Jacobson Cottages in East Glacier on the edge of Glacier National Park. We finish up with one night in West Glacier at Glacier Guides Lodge.

Single room: +$900  *limited availability*

ITINERARIES

Day 1

Welcome to Montana - Arrival Day

Guests will arrive in Montana, and our staff will do Billings (BIL) and hotel pickups. After you register, we will email a list of suggested hotels for guests planning to arrive early. Please email us your arrival/departure plans, including flight numbers.

Everyone will have time to settle into the accomodations and enjoy our first chef-prepared meal.

After lunch, our mechanics will work on building guest bikes or fitting people to their rentals. We will depart for an afternoon shakeout spin once all the bikes are ready, and all the guests have arrived.

Our ride is an out-and-back that will give us a taste of what lies ahead on Beartooth Pass. Once we arrive back at The Pollard Hotel, we will have time to relax before our camp briefing and introductions before dinner.

Today’s ride: Arrival Spin

18-23 miles & 1,500-2,300′

Accommodations: The Pollard Hotel

Day 2

Beartooth Pass

We decided riding one bucket-list ride wasn’t enough for this trip, so we added Beartooth Pass. The ride starts in Montana and crosses into Wyoming, climbing many hairpin turns to the summit at 10,947 feet before circling back into Montana. You’ll get spectacular views of the Absaroka-Beartooth Wilderness, home to 25 peaks soaring over 12,000 feet. The climb is worth the effort; you get views in both directions since it’s out-and-back. The ride is reminiscent of the Galibier, a famous route in the Tour de France, with most of the climb above the tree line.

Today’s Ride: Beartooth Pass

53-70 miles & 5,300- 8,000′

Accommodations: The Pollard Hotel

Day 3

Crazy Mountains

After a big day on Beartooth Pass, we downshift with fewer miles and less climbing. Gravel curious? Today is your day!

In 2023 we introduced a hard-packed gravel segment and it was a hit! The route starts in Melville at a white-steepled church with a dramatic backdrop of the Crazy Mountains. The first 5 miles are paved and then we hit the champagne gravel. The views are fantastic and you get the true essence of Big Sky Country on a Montana backroad. Honestly, we prefer this route to the pavement, and you can easily ride this with a 28c tire; our rentals have 32c slicks. The final 7 miles are pavement, and we finish up in Two Dot, population 26. Post-ride, we have lunch and shuttle 45 minutes to White Sulphur Springs.

Not into gravel; no worries! We have. a fully paved route that starts near Two Dot and finishes in White Sulphur Springs. The route traverses the Valley between the Crazy and Little Belt mountains.

Ultimately everyone will end up at the Spa Hot Springs Motel, where we can soothe our aching muscles with a natural hot spring soak.

Today’s Ride: Crazy Mountains

33 miles & 2,000′ *Includes 25 miles of hard-packed gravel,*

30-45 miles & 1,600′ *Full pavement*

Accommodations: Spa Hot Springs Motel

Day 4

Kings Hill Scenic Byway

Today, we start from White Sulphur Springs, heading North on the Kings Hill Scenic Byway. We have two routes; one includes 6 miles of hard-packed gravel and gets you onto the path less traveled. At mile 30, we hit our high point for the day, Showdown Ski Resort. The climb up to the ski resort is gradual, and the long, gradual descent of the other side makes it worth the effort.  The final miles have a net loss, and we finish in the small town of Neihart, where we will have lunch.  After lunch, we have a 3-hour shuttle to East Glacier.  We will stay at Jacobson Cottages in East Glacier, Montana, for the next two nights.

Today’s Ride: Kings Hill Scenic Byway

40-45 Miles & 3,000′ 

Accommodations: Jacobson Cottages

Day 5

Two Medicine and Looking Glass

After a few big days in the saddle, nobody will complain about having another day to explore the wonders of Glacier National Park. There is no need to re-pack your bag this morning; we enjoy two nights  in East Glacier at Jacobson Cottages.

After a relaxing morning and breakfast, we will head North towards Two Medicine, a beautiful part of Glacier National Park with less traffic. We will have an option to hike, or guests can head back towards Looking Glass Pass. Looking Glass is a staff favorite and one of the best rides in Montana! Even if you did it the day before, it’s worth doing it again.

Today’s ride: Two Medicine and Looking Glass

30-37 miles & 2,500-3,300′

Accommodations: Jacobson Cottages

Day 6

Going to the Sun

Going to the Sun Road is a bucket-list ride with some of the best views you will ever see from the bicycle seat. We will have an optional shuttle to St Mary’s to cut off some mileage. The ride from East Glacier North over Looking Glass Pass is a staff favorite with fantastic views of Two Medicine.  The ride takes us North over several smaller passes before topping out on St Mary’s Pass, offering us breathtaking views of St Mary Lake and Glacier National Park.  In St Mary, we enter Glacier National Park and begin our journey on Going-to-the-Sun Road.  Before descending to Lake McDonald, the road crosses the Continental Divide –topping out at Logan Pass. The climb is just under 8 miles long and gains 2,000 feet with an average grade of 5%. The view from Logan Pass is spectacular.  Going to the Sun Road is an excellent opportunity to see wildlife, including mountain goats, marmots, black bears, grizzlies, and many other critters.  The ride will finish in West Glacier.

Today’s Ride: Going to the Sun 

50-80 Miles & 3,000-6,000′ 

Accommodations: Glacier Guides Lodge

Day 7

Adiós - Departure Day

Shuttles will run to the Glacier International Airport (FCA) and local hotels all morning, with the last shuttle leaving at 10 a.m. Please email us your departure times.

Today’s plan: Departure Day

We’ll be running shuttles to the Glacier International airport (FCA) for those that are flying out and local hotels.

DATES & PRICES

DETAILS

What's Included

  • Six nights/Seven days accommodations (double occupancy)
  • All meals (breakfast, lunch, dinner) for seven days
  • Mechanical support (including bike build and breakdown)
  • Professional trip guides
  • Daily sag support
  • Ride nutrition products
  • High-quality ride photos
  • Arrival Day Airport & Hotel pickups in Billings (BIL)
  • Departure Day Airport & Hotel dropoffs in Flathead Valley/Glacier International (FCA)

What’s Not Included

  • Single room: +$900 *limited availability*
  • Bike rentals +$350
  • Airfare
  • Single occupancy rate
  • Café stops
  • Gratuity for guides
  • Personal shopping

Optional Activities

  • Lake swims
  • Hiking
  • Yard games

Questions?

Have more questions? View our FAQ page or call us at 406-312-5770.
SEE ALL FAQs

BIKE OPTIONS

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Rent A Bike

Traveling through the airport with a bike—and paying for it to fly—is not everyone’s idea of a fun way to start a vacation. Fortunately, we offer high-quality, full carbon bikes on all of our trips across the United States and Europe. Want to just show up and ride? Just bring your shoes, pedals, helmet, and saddle (if you want), and rent one of ours.

Available this trip:
Cervelo Aspero 2021-Tucson Rental Bike
Cervelo Aspero Road/Gravel Bike
Manufacturer: Cervelo
Type: Gravel Bike
Cost: $350 / trip
Specialized Vado SL 4.0 E-Bike
Manufacturer: Specialized
Type: Gravel Bike
Cost: $350 / trip
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Bring Your Own

Your bike is yours—we get it. Bringing your own bike has obvious advantages in terms of individual comfort. Before your trip, we suggest getting a tune-up at your local bike shop so it’s ready to roll for your week of riding. Once you arrive, we’ll be sure to have our mechanics build it and help with any necessary tweaks. Check out some helpful resources here:

Shipping your bike

Flying with your bike.

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Skip The Bike

If you or your travel partner want to enjoy the trip and explore a new destination without a bike, drop us a line and we’ll discuss options. Some trips are better suited for non-rider participants than others.

TRIP TEAM

GUEST REVIEWS

Share your trip experience with others by leaving a review.

LEAVE A REVIEW
Anna M., Mount Tremper, NY
July 28, 2022
Can't say enough wonderful things about The Cycling House. Our trip from Yellowstone to Glacier was amazing. The guides, Brendan, Elsa, Jacob, and Landon took great care of us, from pacing us up the road, to making sure we have the fuel we needed. Liz and Pat, TCH chefs for the week, kept our bellies full of delicious food, and ours hearts filled with laughter. Can't wait to be back for another trip!
Tracy S., Dahlonega, GA
July 31, 2022
I recently participated in the “Yellowstone to Glacier” trip put on by The Cycling House, and it was outstanding! I was extremely impressed with all facets of their support. Their guides were super attentive and able to make our entire group of 10 (ranging from beginner to advanced) feel both comfortable and challenged. Simply put, they know the things that matter in creating a good cycling vacation experience and are excellent at all of them. From mechanical support to amazing scenery to informative pre-ride meetings to delicious food to timely coffee, they got you covered and will ensure treasured experiences and special memories are created. If you’re looking for a biking tour in one of the locations they serve, I would highly recommend going with The Cycling House.
Show All Reviews
Anna M., Mount Tremper, NY
July 28, 2022
Can't say enough wonderful things about The Cycling House. Our trip from Yellowstone to Glacier was amazing. The guides, Brendan, Elsa, Jacob, and Landon took great care of us, from pacing us up the road, to making sure we have the fuel we needed. Liz and Pat, TCH chefs for the week, kept our bellies full of delicious food, and ours hearts filled with laughter. Can't wait to be back for another trip!
Tracy S., Dahlonega, GA
July 31, 2022
I recently participated in the “Yellowstone to Glacier” trip put on by The Cycling House, and it was outstanding! I was extremely impressed with all facets of their support. Their guides were super attentive and able to make our entire group of 10 (ranging from beginner to advanced) feel both comfortable and challenged. Simply put, they know the things that matter in creating a good cycling vacation experience and are excellent at all of them. From mechanical support to amazing scenery to informative pre-ride meetings to delicious food to timely coffee, they got you covered and will ensure treasured experiences and special memories are created. If you’re looking for a biking tour in one of the locations they serve, I would highly recommend going with The Cycling House.