Home » Mountain Bike Tours » Central Cascadia & Crater Lake Road Bike Tour

The best road riding of Central Cascadia and Crater Lake is now being showcased by your local guiding experts, Cog Wild. We live here and we love it, and can’t wait to show you around all of our favorite spots to ride. Bend is all about the lifestyle, so come live like a local with us for a week of legendary rides, comfortable lodging, great food, and craft beer.

Bend will be your home base for this fun and fabulous tour. Get to know our backyard with our favorite rides and get a taste for what Central Oregon is made of – snow capped mountains, bucolic pastures, ranch land, rocky crags, winding rivers, great beer, and the smells of Juniper, Ponderosa, and Sage mingling together.

You will ride over the crest of the Cascades via Mckenzie Pass and get a taste for the unique geology of the region as you explore volcanic landscapes, traversing into iconic Northwest territory of forested slopes with carpets of ferns and moss. You’ll spend time along wild and scenic rivers and even wilder riding. You will test your strength on long climbs and feel like a kid again, descending long curving switchbacks through wild woods.  You will experience one of the best road rides in the world around Crater Lake, mesmerized by its unique sapphire blue, jagged cliffs and high alpine forests.

On this tour you will experience a variety of landscapes, climate zones, and emotions from exhaustion to elation. In just 6 days, you will explore a vast region of our fabulous state of Oregon, and two of it’s seven wonders. You’ll dine on local food, sip local craft beer, and be guided by locals. You’ll go home, hesitatingly, knowing you just experienced the best of Oregon, with it’s best outfitter.

This tour includes:

  • 5 nights of high quality lodging
  • Breakfast, lunch and snacks throughout the tour
  • 4 delicious dinners
  • Deschutes Brewery beer, Crater Lake Spirits, and Humm Kombucha
  • Local, expert, caring guides
  • Transportation throughout the tour including van support during rides
  • Cog Wild t-shirt, cycling socks, patch, and water bottle
  • Carbon bike rental (Bring your own bike and save $200

Check out the itinerary below for details!

Trip Overview

3 - 8
5 - 8
Tour Style
Tour, Hotel
Tour Size
Central Cascadia Road Bike Tour
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2018 Tour Dates

  • September 1-6

These dates don’t work? Contact Cog Wild to book your private tour group for 4-12 riders.


  • $2775 per person – double occupancy
  • $500 – single room supplement, price depending on date of tour
  • $200-250 – per additional hotel nights, per room, price depends on date of tour

*Prices do not include the following:

  • Airport shuttles from the Redmond (RDM) Airport. You will need to arrange for your transportation to Bend (15 miles). We recommend Enviro Shuttle or Redmond Airport Shuttle. We will provide one return trip to the airport on the morning of departure.
  • Trip Insurance. We highly recommend purchasing trip insurance for the unforeseeable. See our cancellation policy below.
  • Guide gratuity. If you like the ride, tip your guide!

Cancellation Policy:

 Cog Wild follows the below policy for every multi-day tour guest:

    • All multi day tours will be charged a 50% deposit per person  at the time of booking, $100 of which will be non-refundable.
    • Cancellations 30-14 days prior to the tour: The participant will be required to pay 50% of trip price.
    • Cancellations within 14 days: No refund.

Note:  Personal emergencies do not void cancellation policy and tours go rain or shine. Travel insurance that covers trip cancellation as well as trip interruption is highly recommended.

Riding Distance

Up to 235 miles total riding over 6 days. Average of 40 miles per day. We offer shuttles for anyone who does not want to do the full ride. There are also opportunities to hike in addition to your rides.


Total elevation gained is up to 15,000 feet over 6 days.

This tour takes place primarily in the high desert, so expect to be riding in high elevation zones. In Bend we are located at 3,600 feet. The summit of Mckenzie pass is 5,325 feet. At Crater Lake you will be riding at approximately 7,000 feet of elevation.

Rider Level

This trip would be best suited for intermediate to expert riders who enjoy climbing and long rides. We are able to accommodate those less fit by offering van support but those who ride frequently will find the trip most enjoyable. We highly recommend training before your tour, riding at least twice a week if possible.

Terrain & Roads

You will see a variety of different landscapes on this tour from river canyons, farm land, mountain passes, volcanoes, and forests. We never get bored riding in this landscape, and we are sure you won’t either! Most of our routes are on low trafficked roads, however expect to share the road with vehicles.

Recommended Clothing & Gear

Prepare for 5 full days of riding in various elevations, so bring adequate clothing to accommodate a range of temperatures and weather. Bend is an outdoorsy mountain town, calling for casual clothing for hanging out in town.

Day 1: Saturday

Your tour starts at noon from McMenamins St Francis Hotel in Bend. We pick you up and take you to our Cog Wild headquarters where we will have a nice lunch and go over our plans for the day and a brief overview of the week. We will start out our week with a local’s favorite ride that encompasses the beauty of Central Oregon.  Expect mountain views, babbling creeks, and bucolic pastures on this moderate loop. End your ride with a local brew and get to the bottom of what makes Bend one of the best places for beer in the country. After you have time to pamper yourself, we will meet for dinner at one of our favorite restaurants downtown.

Distance: 36 miles

Elevation gain: 1815

Lodging: Mcmenanis Old St. Francis School

Day 2: Sunday

We will meet in the morning at your hotel after you have enjoyed breakfast. We will shuttle about 45 minutes east where few tourists have the opportunity to ride. Meander through the Crooked River Canyon on perfect roads along side world class angling, and after lunch we will have the option to ride to Smith Rock or shuttle to the park to hike alongside world class climbing. You will have the evening to explore Bend on your own tonight.

Distance: 20 or 40 miles

Optional Hike (if not riding to Smith): 2 or 5.8 miles (elevation 1856 feet)

Elevation gain: 624 or 1024 feet

Lodging: Mcmenanis Old St. Francis School

Day 3: Monday

Say a temporary farewell to your home away from home in Bend, as we head to the Old West town of Sisters. Cruise past the false fronts of main street as you head into Ponderosa forests to make your way to the top of Mckenzie Pass. You’ll watch the landscape change as you climb into different climate zones and pass over the top of the Cascade range into Western Oregon. You’ll love descending the switchbacks all the way down to the Mckenzie River where we will stay in idyllic cabins along its banks. Stop for a short hike to Proxy Falls to cool off and awe at the wonders of the Pacific Northwest. We will have relaxing dinner at the Inn.

Distance:  38 miles

Elevation gain: 1800 feet

Lodging: McKenzie Riverside Cottages

Day 4: Tuesday

You probably won’t want to leave our paradise by the river, but the best is yet to come! Our fourth day carves through classic Northwest scenery along the famously scenic Aufderheide Drive. You will test your legs on this marathon of a ride through towering forests, past crystal clear streams, ferns, moss, and prime pavement. We will celebrate the end of the ride with beers at the end of the ride in the mountain bike mecca of Oakridge before we hop in the car and head to the crown jewel of the week, Crater Lake.

Distance: 65 miles

Elevation gain: 3852

Lodging: Crater Lake Lodge

Day 5: Wednesday

Our penultimate ride is around the rim of Crater Lake. You will circle around the lake marveling at the sapphire blue of the water on one side of the road and the jagged mountain peaks on the other. This ride has plenty of punchy climbs and curving descents in between scenic pull outs to offer you an equally challenging and mesmerizing ride. This is arguably one of the most spectacular road rides in world, but we’ll let  you decide for yourself. After we finish the ride Cog Wild style, we’ll let you nap in the van as we drive the hour and a half back to Bend. We will drop you off at your previous hotel where you can take advantage of the mineral soaking pool for your legs before we pick you up for our farewell dinner.

Distance: 33 or 40.7 miles

Elevation gain: 4502

Lodging: Mcmenanis Old St. Francis School

Day 6: Thursday

We guarantee you’ll get a great night’s sleep after all that riding, and if you have any legs left, we can do a short ride in the morning before you depart.  If you are more inclined to a leisurely morning, you can enjoy a walk around town to one of our favorite coffee shops or hit up a yoga class.

Leave Bend like a local, and know you experienced the best, with the best!

Distance: 10-20 miles

Elevation gain: 200-1200

*Can’t get enough? Add on a day of mountain biking with us and we’ll throw in an awesome discount!