Itinerary

Day 1: Meet in Bend. Cycle from the Painted Hills – one of the seven wonders of Oregon – to the John Day River

What better way to start than with a ride to one of the Seven Wonders of Oregon! View millions of years of geological history – one gloriously colored layer atop another – in the Painted Hills.
From there head up and over a pass (or is it three passes?) to meet the John Day River, the longest undammed river in Oregon and host to one of the few remaining wild fish runs in the entire Pacific Northwest.
Continue upriver to the Monument Motel in the tiny town of Monument (pop: 128), one of the only accommodations in this remote region.
Meals: Lunch and Dinner. Lodging: Monument hotel
Distance: 83 miles, Elevation: +5040 ft / – 5773 ft.

Day 2: Savor idyllic ranches, orchards, ghost towns and a mountain pass between monument and prairie city.

Warm up riding through bright green orchards and idyllic ranches bordering the John Day River. At valley’s end, begin climbing on twisty roads. The scenery is quickly transformed into colorful rocks and soils filled with carefully stored fossils.
Pass through ghost towns and beautiful open forests of juniper and Ponderosa pine until you cross Long Creek Mountain Summit and hit the long descent into the town of John Day. Savor beautiful views of the Strawberry Mountain Wilderness on the horizon as you cruise into Prairie City (pop. 878). Stay at the historic Hotel Prairie.
Meals: Breakfast, Lunch and dinner Lodging: Hotel Prairie
Distance: 72 miles , Elevation: +5790 ft / – 4294 ft.

Day 3: Tackle two summits on a century ride on the “Old West Scenic Bikeway.”

No need to pack your bags. Just grab your trusty steed and head out the door. There is a lot to see and a lot to ride hereabouts. Today, we cycle a century loop from Prairie City on the eastern portion of what Travel Oregon has dubbed the “Old West Scenic Bikeway”. Enjoy some of the quiets, lowest traffic, paved roads anywhere on this mountainous loop with a pair of mile-high-summits and great views both local and up-close. Rivers, forests, wildlife, and big skies abound! Stay a second night in Prairie City.
Meals: Breakfast, Lunch and dinner. Lodging: Hotel prairie
Distance: 105 miles, Elevation: +7270 ft / – 7267 ft.

Day 4: A trifecta of mountain passes pave the way to Baker City

Pack your bags – we are on the move again. Pedal over three passes in the southern part of the Blue Mountains region. Pass through quiet places and (mostly) deserted towns.
Peaceful is the word of the day. The scenery is as spectacular as the cycling is challenging. On the other side of the mountains, enjoy a long leisurely descent into the beautiful town of Baker City. You earned it! Rest up at the Geiser Grand Hotel.
Meals: Breakfast, Lunch and dinner Lodging: Geiser Grand Hotel
Distance: 67 miles, Elevation: +4603 ft / – 4712 ft.

Day 5: Massive peaks beckon us toward magnificent Wallowa Lake.

Begin today with a shuttle through some of the more populated areas hereabouts. Ride beside the Wallowa River as it twists along beside the northern Wallowa Mountains of northeastern Oregon’s Columbia Plateau.
Closer to today’s destination, the roads open out into farmland with tiny glimpses of Eagle Cap Peak. Come around a corner, and – boom! – you are suddenly face to face with Wallowa Lake and the Eagle Cap Wilderness.
Thirty peaks topping out at over 8000 feet tower over a majestic lake. Stop for a photo, or maybe a dozen. Ride the lake shore to tonight’s lodging at Wallowa Lake Lodge. Watch for deer and eagles. Spend the next two nights enjoying spectacular views of the mountains and the tall pines.
Meals: Breakfast, Lunch and dinner Lodging: Wallowa Lake Lodge
Distance: 60 miles, Elevation: +3792 ft / – 2004 ft.

Day 6: You’ve earned a rest day at wonderfull Wallowa Lake

Take today off. (This place is too good to miss.) Ride the Wallowa Lake Tramway – a terrific way to ascend 3,700 feet!(not included) Swim, hike, or rent a canoe or paddle-board. Head over to the art-rich town of Joseph to shop, visit museums or the chocolate factory.
Check out one of the several breweries. Or spend the day in peace by the lodge watching the deer on the lawn. Not enough biking yet? There are two very good options for rides: a mountain bike ride from the tramway down or a road ride to Imnaha with a 30-mile descent… followed by a 30-mile climb. Lunch and dinner are on your own today.
Meals: Breakfast, Lodging: Wallowa Lake Lodge
Distance option: 71 miles , Elevation: +3671ft / – 3671 ft.

Day 7: Peer down into Hells Canyon on your way to Halfway

Ride from Joseph into the Hells Canyon Wilderness today. Non-stop views accompany us as we climb the high Wallowa Mountain Loop / Hells Canyon Scenic Byway to the Hells Canyon Overlook. Peer down the deepest river gorge in North America. Try not to get dizzy as you snap a few incredible photos. Tomorrow we head into the canyon itself. For now, pedal on to Halfway, Oregon and spend the next two nights at Pine Valley Lodge.
Meals: Breakfast, Lunch and dinner. Lodging: Pine Valley Lodge
Distance: 83 miles, Elevation: +5819 ft / – 7626 ft.

Day 8: Ride to Hell…. and back!

Today is utter hell … Hells Canyon, that is! Leave Halfway and pedal (or coast) all the way down to the Snake River. Savor a ride along the banks of the river into a rugged and remote location of Hells Canyon.
Continue beyond the dam to the Visitors Center to see what the natural flow of the river looked like before the dam. Wild! This stretch of road is so quiet and free of traffic you will have plenty of time to reflect on the past week.
Who knew eastern Oregon was so magnificent! Return to the Pine Valley Lodge in Halfway for a dinner celebration. Now you can truly say you have been to Hell and back!
Meals: Breakfast, Lunch and dinner Lodging: Pine Valley Lodge
Distance: 63 miles , Elevation: +3494 ft / – 4427 ft.

Day 9: Pedal across the Snake River and enter Idaho on your way to Boise

Enjoy another cruise back downhill to the Snake River this morning. Cross over into Idaho and cycle south along the river (now a lake) above the Oxbow Dam. Climb out of the gorge through aromatic sage and grasslands all the way up to the pines before coasting the final 15 miles downhill to the quaint little town of Cambridge. Following a celebratory lunch, we will load up and shuttle to Boise.
Meals: Breakfast and Lunch
Distance: 57 miles, Elevation: +3744 ft / – 3711 ft.

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.

Lodging

Bend to Boise epic bike tour

Monument Hotel
Hotel Prairie
Geiser Grand Hotel
Wallowa Lake Lodge
Pine Valley Lodge

The hotels, Inns, and B&B’s we use are always among the finest the area has to offer. Our smaller group sizes(max. 13) allow us to stay at some award-winning places that can’t handle groups of 25 or more. We work closely with the innkeepers to make sure they understand your needs and ours, whether that is having a place to store your bike, an early morning breakfast or a convenient place to park the van, they are as committed to your vacation experience as we are.
Lodging is based upon two people to a room with a private bath. If you’re traveling solo on any of our trips, we’ll assign you a roommate of the same gender and often of the same age bracket. There is no extra charge if we can’t find you a roommate, even if you sign up the day before the trip starts.
You can guarantee yourself a private room and bath if you pay the Single Room Fee. Occasionally a room with two beds consists of one bed plus a rollaway bed or sofa bed.

Included:

• Lodging and dining.
• All breakfasts, except 1 lunch and 1 dinner. Snacks and beverages between meals
• Road /hybrid bike, (E-bike rent possible)
• Helmet and Wahoo GPS device
• Park and other entry fees
• Luggage transfer.

Not included:

• Night before and after the tour.
• Flights to and from the tour
• Alcoholic beverages at meals
• Gratuities guides

Pricing / Tour dates

Tour price 2026: $ 5445.- pp single fee $ 1,470.- This is not required. It is an optional fee to allow a solo traveler to guarantee a private room for the duration of the tour. You can avoid a single supplement by sharing a room with another rider
Tour Dates 2026

• 04 Jun 2026
• 27 Aug 2026

Conditions

Deposit 600.00
The deposit payment for a tour must be paid within two weeks after the booking is confirmed.
The remaining payment is due 90 days before the start of the tour.
For tours that are booked within 90 days before the start of the tour you will pay 100% of the tour price

Information

Meals and dining:
We know how important breakfast is to make sure your day starts off right. Most breakfasts are served at the inn where we spend the night and are either a set menu or a continental breakfast buffet. But if there is a local restaurant with a reputation for a great breakfast, we can guarantee we will find it and you will be treated to a nutritious meal to start the day.
Lunch is provided at a state park or similar scenic setting midway during the day’s ride. Guests are always surprised at the variety and quality of lunches we prepare. Besides sandwich fixings and cold drinks, we offer fresh fruits and vegetables and hot lunches such as tortellini with pesto or veggie burritos. If you prefer a certain item of food or drink, just let your tour guide know and we will be sure to prepare just the right lunch to keep your energy up for the rest of the day.
During the day water, fruit juices, soft drinks, energy bars, fruit, and snacks are available from the van. A cold beer from our cooler waits at the end of the day, and you can relive the day’s highlights at our wine and cheese party before dinner.
Dinner is eaten together at the best restaurant in the area. At most restaurants, you order what you want from the menu. Except for alcohol, everything is included, even appetizers, salad, soup, and dessert. If we have to shuttle everyone a short distance to get to that special place, we do it. We like to eat well.

If you have any special dietary requests, please let us know in advance. We regularly accommodate vegetarians and other restricted diets. All of our meals are carefully selected to provide you with the unusually high nutritional and caloric needs of your body on an outdoor adventure.