Montana

Glacier to Yellowstone

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 every night – new for 2023 – less packing! 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 Flathead Valley (FCA)
  • Departure Day Airport & Hotel dropoffs in Billings (BIL)

Food

You’ll eat a combination of Cycling House chef-prepared food and meals at our favorite local restaurants. We source as much local food as possible, stopping at farmer’s markets along the way and working with a farm in the Flathead Valley to provide our dairy. Our bread and pastries are baked fresh at Le Petit Outre in Missoula, and we provide an abundance of beer from Missoula’s Big Sky Brewing Company

Accommodations

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

ITINERARIES

Day 1

Welcome to Montana - Arrival Day

Guests will arrive in Montana, and our staff will do Glacier International (FCA) 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 arrival day spin will be an out-and-back route into Glacier National Park for a small taste of what lies ahead. On the way back, we will make a quick stop for an optional swim in the Middle Fork of the Flathead River. Once we return, we will have time to relax before our camp briefings and dinner.

Today’s Ride: Arrival Spin

Arrival day ride: Shorter: 20-28 miles & 1,300-1,800′

Accommodations: Glacier Guides Lodge

Day 2

Going-to-the-Sun-Road

Going to the Sun Road is a bucket-list ride with some of the best views you will ever see from the saddle. The climb is just under 11 miles long and gains 3,200 feet with an average grade of 5%. The road crosses the Continental Divide, topping out at Logan Pass before descending to Saint Mary Lake. The view from Logan Pass is spectacular and well worth a stop. You may spot some wildlife, including mountain goats, marmots, black bears, and grizzlies. We’ll get an early start to avoid traffic on this memorable day on the bike.

As we exit Glacier National Park, we will have a picnic lunch and shuttle option. 

Guests looking for more miles will continue up St Marys Pass to Looking Glass Pass, the final pass of the day. If you choose to shuttle post-lunch, don’t worry; you will have a crack at Looking Glass Pass the next day. 

We’ll spend the night at Jacobson Cottages in East Glacier, originally an Amtrak stop on the outskirts of Glacier National Park. We will spend two nights at Jacobson Cottages.

Today’s ride: Going-to-the-Sun-Road

51-71 miles &  3,500-5,200′

Accommodations: Jacobson Cottages

Day 3

Two Medicine and Looking Glass

After a big day 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 another day 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 4

Kings Hill Scenic Byway

We’ll shuttle to Monarch (2.5 hours) from East Glacier and get off the beaten path on this spectacularly scenic route. The first 20 miles climb gradually towards the day’s high point – the Showdown Ski area, where we’ll stop for lunch at 7,200 feet. After lunch, there’s a net loss into White Sulphur Springs, where we will stay at The Spa Hot Springs Motel. Guests can soak in the thermal hot springs and stroll an authentic Montana town.

Today’s Ride: Kings Hill Scenic Byway

40-53 miles & 2,500 – 3,600′

Accommodations: Spa Hot Springs Motel

 

Day 5

Crazy Mountains

Today’s routes will take us South towards Red Lodge, and the base of Beartooth Pass. We will spend the next two nights at The Pollard Inn in Red Lodge, Montana.

Gravel curios? Our staff favorite for today is the 33-mile route from Two Dot to Melville. It includes 25 miles of hard-packed gravel, and the views are spectacular! The gravel can be ridden on a 28c tire. We start with a 30 minute van shuttle to Two Dot. Post ride, we will have a picnic lunch in Melville before shuttling the rest of the way to Red Lodge (1 hour 45 minutes).

No worries if you don’t want to ride gravel. For the full pavement option, we will start the day with the 3 hour van shuttle to Red Lodge. Once in Red Lodge we will have lunch and then do an afternoon ride up the West Fork. It’s a beautiful ride, and you can easily cut out the ride up the Ski hill to make this day shorter. We want everyone feeling fresh for Beartooth Pass.

Today’s Ride: Crazy Mountains 

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

25 miles & 2,500′ *Full pavement*

Accommodations: The Pollard Hotel

Day 6

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.

Our final night at The Pollard Inn in Red Lodge, Montana.

Celebrate our final evening together in Red Lodge.

Today’s Ride: Beartooth Pass

53-70 miles & 5,300- 8,000′

Accommodations: The Pollard Hotel

Day 7

Adiós - Departure Day

Shuttles will run to the Billings International Airport (BIL) 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 Billings airport (BIL) for those that are flying out (1 hr 15 min shuttle).

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 Flathead Valley (FCA)
  • Departure Day Airport & Hotel dropoffs in Billings (BIL)

What’s Not Included

  • Airfare
  • Bike rentals
  • 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

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LEAVE A REVIEW
Mike M., Edwardsville, IL
July 30, 2019
This trip was outstanding! Food was excellent, lodging was good, but the best part was the Cycling House staff. They took the time to get to know everyone, handled any details that needed to be addressed quickly and with enthusiasm. They were very knowledgeable about the regions we rode through and inspired confidence in the guests each day. Special thank you to Shaun Radley. My bike had minor damage in shipment to Montana. Shaun notified me immediately. It was rideable but required an insurance claim with BikeFlights. Shaun in the office took care of everything and the insurance check even beat me back home. To not have to worry about the insurance claim during the trip was much appreciated and allowed me to enjoy the trip to the fullest.
Allison, Portland, OR
August 16, 2019
Great crew, beautiful rides, awesome food! I've ridden with other cycling outfits over the past few years, and will definitely return to The Cycling House. They have a great price point for the type of support they offer.
Show All Reviews
Mike M., Edwardsville, IL
July 30, 2019
This trip was outstanding! Food was excellent, lodging was good, but the best part was the Cycling House staff. They took the time to get to know everyone, handled any details that needed to be addressed quickly and with enthusiasm. They were very knowledgeable about the regions we rode through and inspired confidence in the guests each day. Special thank you to Shaun Radley. My bike had minor damage in shipment to Montana. Shaun notified me immediately. It was rideable but required an insurance claim with BikeFlights. Shaun in the office took care of everything and the insurance check even beat me back home. To not have to worry about the insurance claim during the trip was much appreciated and allowed me to enjoy the trip to the fullest.
Allison, Portland, OR
August 16, 2019
Great crew, beautiful rides, awesome food! I've ridden with other cycling outfits over the past few years, and will definitely return to The Cycling House. They have a great price point for the type of support they offer.
Laura L., Raleigh, NC
December 10, 2021
Had a fabulous trip with TCH, experiencing epic Montana and Wyoming/Yellowstone! Everything was great, so supportive and helpful managing our private trip & big bunch, delicious meals, AMAZING routes, scenery, and wildlife, too! Will definitely plan on another trip! Thanks again for a trip to remember & cherish!
Jasmine A., Oak Creek, CO
August 22, 2021
The Glacier to Yellowstone trip was wonderful. I enjoyed the breathtaking views and experiences throughout the trip. The hospitality of the staff trumped the views and experiences. What a great team of people; they really made the trip. I could not have asked for a better vacation.