Adventures Await with Oregon Territory Outfitters

Bike Packing

Mountain Biking

Mountain Biking

We remove obstacles and handle the logistics of long distance Bikepacking so that you can focus purely on the experience. From the introductory overnight missions to our longer multi-day route around Mt Hood - we can get you out there and back again. We also offer logistical support for riders on the Oregon Timber Trail.

Mountain Biking

Mountain Biking

Mountain Biking

Mountain Biking has a rich history here on Mt Hood. From the classic singletrack of Road 44 Trails, to a pleasure cruise on the Timberline to Town Trail, there is truly something for everyone. With our curated selection of bike and gear rental, custom guided rides, and integrated shuttle service - we've got you covered. 


Gravel Riding

Mountain Biking

Gravel Riding

Curious about Gravel? We’ve got routes! From the simple out and back to semi-shuttled, custom tailored and supported excursions - we’ve got miles and miles of forest roads and mountain views to whet your appetite for this growing segment of the adventure riding family.

World Class Trails and Stunning Vistas

MOUNTAINBIKE DAYTRIPS & SHUTTLES

Shuttle Service // Guided Rides // Custom Day Trips

"THE MT HOOD EXPERIENCE" 

This is a FULL DAY Guided and Shuttled Mountain Bike Tour.

Approximately 40 miles and 10-12k' descending with 1500' climbing sprinkled in throughout the day.

 Experience some of the Best Descents on 44 Road Trails with Minimal Climbing.

Includes: Guide/Shuttle/Refreshments // $120 per person // 4-8 people 

Starting the day at 44 Rd Trails - Finishing with Timberline to Zig Zag.

Pickup at the Zig Zag Ranger Station at 9am and be back by 5pm.

Sat &/or Sun All Season Long! OR by Reservation M-F.


"RIDE THE EASTSIDE"

This is a FULL DAY of MTB SHUTTLES on 44 Road Trails.

Ride The Best Descents on 44 Road Trails - Cooks/Lookout/15mi/8mi/Knebal/Hidden/Crane.

This is a Big Day! Approximately 30-40 miles and 8-10k' descending with 1500' climbing.

Optional Drop-off at Timberline Lodge at the end of the day.

That adds 18 miles and +/-4500' descending from Timberline to Zigzag.  

Shuttle Only // $60 per person // 4-10 people 

Pickup at the Zigzag Ranger Station at 9am.

Pickup at Summit Snow Park at 9:20am.

Eastide Pickup by RSVP only.

Sat &/or Sun All Season Long! OR by Reservation M-F.


"TIMBERLINE DOWN"

This is a FULL (OR HALF) DAY of MTB SHUTTLES on Timberline To Town Trail . 

We Provide Custom Shuttle Options on T2T/Crosstown/Pioneer.

Shuttle Only // Full Day 10am-4pm  // Half Day 1-4pm.

$30 per person // $20 half day // 4-10 people //M-F by Reservation.

 (NOW OFFERING EARLY SEASON WEEKEND TRIPS)


DEMO BIKES AVAILABLE for and additional $80 per day.

Esker Cycles - Full Suspension "Woodsey"

  

All Trails maintained in Partnership with @44Trails  @hoodlandtrails & MHNF.


Book A Trip

(971) 279-9450 - REACH OUT with Group Size and Dates
Message Us Here

BIKEPACKING

DEMO BIKES // BAGS // GEAR // GUIDED TRIPS

PLUS SHUTTLES & LOGISTICS FOR THE OREGON TIMBER TRAIL - Message  for Details

COMPLETE BIKEPACKING BIKES AND GEAR FOR DEMO/RENTAL/SALES

Take a ride on one of these fully loaded Bikepacking Bikes. 

We work with some great companies that are building high quality gear and equipment.

Each bike is set up for multi-day adventures with sleep system, cook system & storage systems.

Guided Bikepacking Trips

Ride Packages Include : Bikepacking Bike/Gear/Guide/Meals*/Coffee. 

Send us a message to get you and your group out on an unforgettable adventure.


Intro to Bikepacking - "Sandy River Shakedown" // $150 per person // 2-8 people

(lower miles, less elevation gain, less total ride time, same amount of FUN!)

Zig Zag Ranger Station at 5pm // Return at 9am // Safe Overnight Vehicle Parking

https://www.instagram.com/reel/C_2jlybJgvz/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==


Intermediate Overnighter - "Trillium Lake Tour" // $200 per person // 2-8 people

(Aprox 33 mi, 3300' elevation gain/loss, 50% gravel/dirt and 50% Singletrack)

 Zig Zag Ranger Station at 3pm // Return at 10am // Safe Overnight Vehicle Parking


Advanced 3 Day Ride - "The Hood Loop" // $550 per person // 4-8 people // RSVP

(Aprox 130 mi, 15000' elevation gain/loss, 1/3 gravel/dirt, 1/3 paved, 1/3 trail)   

Meet at Zig Zag Ranger Station at 11am on Friday // Return by 6pm Sunday Evening // Safe Long Term Vehicle Parking // Backup Bailout Option Available if Necessary


*All Trips Include 1 Dinner and 1 Breakfast Meal per night (more options available for purchase). Resupply/Restaurant options in Parkdale and Government Camp for "The Hood Loop".

Introduction to Bikepacking

The Gateway to Adventure - these trips are designed to prepare you for a future full of bikepacking adventures. 


The FUNdamentals

-Bike Check and Mechanical Overview

-Gear and Supplies Preparation

-Bag/Bike Packing Strategy

-Shakedown Ride

-Navigation

-Hydration

-Nutrition



Book A Trip

(971) 279-9450 - REACH OUT with Group Size and Dates.
Message Us Here

THE HOOD LOOP

Experience "The Hood Loop"

This 3 Day Bikepacking Route takes you on an up close and personal tour of Mt Hood (Wy'East) as you travel around the forested flanks and adjacent ridge lines of this majestic mountain.  

With approximately 130 mi and 15000' elevation gain/loss, this route is nearly equal parts paved forest roads, dirt/gravel forest roads and world-class singletrack trail. 

This tour is for the intermediate/advanced rider due to mileage, elevation and technicality.

https://www.instagram.com/reel/C-ABqgkRr0H/

Views Around Every Corner

As you wind your way around the mountain you are greeted with stunning views  and changing landscapes. 

https://www.instagram.com/reel/C-ABqgkRr0H/

Spectacular Camp Sites

The Hood Loop offers some amazing places to pitch the tent, make dinner, and fall asleep under the stars. Of course, morning coffee is equally spectacular!

https://www.instagram.com/reel/C-ABqgkRr0H/

"THE HOOD LOOP" GALLERY

    Book A Trip

    (971) 279-9450 - REACH OUT with Group Size and Dates.
    Message Us Here

    Demo Bikes and Bikepacking Gear

    Learn About the Brands

    Esker Cycles Hayduke

    Esker Cycles Hayduke

    Esker Cycles Hayduke

    Hayduke has become one of the most recognized and trusted bikepacking bikes - evolving to always be at the forefront.

    Visit Esker Cycles

    Bikepacking Bags

    Esker Cycles Hayduke

    Esker Cycles Hayduke

    We're dedicated to providing high-quality bikepacking bags which is why we partner with some of the finest brands in the industry like Loam Equipment.

    Visit Loam Equipment

    Gear and Equipment

    Esker Cycles Hayduke

    Gear and Equipment

    We also partner with the best gear and equipment brands like Big Agnes.

    Visit Big Agnes

    BOOK YOUR DREAM TRIP

    (971) 279-9450 - REACH OUT! Let us know your group size and preferred dates.

    Send us a message and lets get you and your group out on an unforgettable adventure. 

    We can also build a custom trip for you and your group. 


    email : BIKELIFESTYLE@GMAIL.COM phone: (971) 279-9450

    GRAVEL RIDING

    Curious about Gravel? We’ve got routes! From the simple out-and-back to custom shuttled and supported excursions - we’ve got miles and miles of forest roads and mountain views to whet your appetite for this growing segment of the adventure riding family.


    Drop us a line to get you and your group out into the wild on a custom adventure to remember.

    (Ride Packages and Demo Bikes coming soon...)

    BOOK A TRIP // Ask A Question

    Drop an email here - OR CALL (971) 279-9450

    This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

    OREGON TERRITORY OUTFITTERS

    This institution is an equal opportunity provider, which operates under a special uses permit with the Mt. Hood National Forest, USDA, Forest Service.

    Copyright © 2025 OTO - All Rights Reserved.


    Powered by