The trip begins midday in Terrebonne, Oregon, a place of stunning high desert beauty. Our guides will meet you at the airport and take you to our home-away-from-home for the night, a small lodge with a collection of cozy cabins perched upon the rim of the Crooked River Canyon for a light lunch and a chance to meet the rest of the group. Later on we’ll head out for late afternoon shakeout run on a nearby trail that weaves through fragrant sagebrush and juniper, with plenty of chances to peer over the edge to the wild river far below and a high likelihood of spotting golden eagles gliding along the canyon walls. That evening we’ll kick back with dinner at the lodge, soak in the magical light of a high desert sunset and then get some rest – we’ve got an early start tomorrow!

Running: 6-8 miles, single track trails
Meals: Lunch and Dinner (L,D) included

Today begins at sunrise with coffee, light snacks and a short drive to our start line for the day. A true geological wonder (don’t worry, we’ll tell you all about it!), Smith Rock has long been established as a mecca for rock climbers but also happens to be a spectacular place for a morning run. This one isn’t easy – there is very little flat terrain around here – but the chance to run amongst these surreal rock formations, take in sweeping views of snow-capped volcanoes in the distance and potentially spot otters playing in the river make it worth every bit of effort.

After the run and a well-deserved breakfast we’ll get showered, pack and wave goodbye to the canyons – it’s time to head to the mountains! Along the way we’ll pass through the vibrant adventure town of Bend for lunch before continuing on to Westfir, a tiny town nestled deep in the Williamette National Forest that is home to a cozy family-run riverside B&B that we’ll settle into for the next two nights.

Running: up to 7 miles, 1200 ft. gain, mix of dirt road and single track trail
Meals: B, L, D included

Enjoy a relaxed morning, waking up to coffee, breakfast and the sound of the river right outside. Judging by the steep, thickly forested mountain slopes surrounding us on all sides you might be apprehensive about today’s run, but not to worry – the trail run we have planned may be steep, but it’s the type that will make you feel like you’ve discovered something that no one else knows about and will leave a big silly grin on your face the entire time. Expect flowy single track, thick old-growth forest, viewpoints of surrounding mountain peaks and a finish line right back at our B&B.

After that? Lunch, downtime and, for anyone who still has a bit left, a short hike to a couple of our favorite waterfalls!

Running: up to 14 miles, 1500 ft. gain / 2500 ft. descent, single track trail
Meals: B, L, D included

Today we will say goodbye to Westfir, but not to the forest – believe it or not, the best is still ahead! You’ll probably want to take it easy today – yesterday was big, and tomorrow can’t be missed! – so we’ll start the day with a riverside shakeout run. After showers and breakfast we will enjoy a relaxed float down the North Fork of the Williamette River with expert guides, giving you a chance to see some areas that are only accessible from the water. Afterwards, we’ll take the scenic route towards the legendary McKenzie River valley!

The winding drive will route through thick forest and narrow canyons, and we’ll take our time. We’ll get glimpses of an area devastated by recent wildfires, and the contrast will make the arrival to our lodging for the night - set amongst towering old-growth forest - that much more impactful. We’ll get settled into our final home-away-from-home, a sprawling house nestled in the forest with spacious suites and plenty of gathering space to both indoors and out. The evening will be nice and relaxed with plenty of time for conversation, contemplation and and a stellar feast prepared by a private chef.

Running: up to 8 miles, single track trail
Meals: B, L, D included

This is the final full day of the trip, and it’s an unforgettable one! We’ll start with a relaxed morning before taking a short shuttle to the start of our run. This trail is pure magic: it weaves and rolls alongside a wild, rushing river and through lush old-growth forest, passing by thundering waterfalls, big lava flows and turquoise pools. There is no rush today – this is the type of trail you’ll want to spend all day on! When you do eventually finish we’ll have lunch waiting for you, following by a final evening together back at the house. Kick back, trade stories, enjoy dinner and stretch it out as long as you possibly can!

Meals: B, L, D included
Running: up to 12 miles, 800 ft. gain, single track trail

Chances are that you’ll be ready for a day off by this point, but anyone who wants to sneak in a few quiet morning miles will be able to do so. After a big farewell brunch we’ll pack up and wave goodbye before heading back over the mountains to complete our trip.

We’ll drop you off back at the airport or somewhere in Bend for those who want to extend their adventure even longer!

Running: No organized run
Meals: B included