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Routes
Mountain biking trails
United States
Oregon
Deschutes County
Bend

Ben's and Phil's Trail Loop

Moderate

4.7

(5728)

9,927

riders

Ben's and Phil's Trail Loop

04:07

48.0km

690m

Mountain biking

Get ready for a classic mountain biking adventure on Ben's and Phil's Trail Loop, a moderate route spanning 29.8 miles (48.0 km). You will climb 2278 feet (694 metres) over an estimated 4 hours and 7 minutes, immersing yourself in the open pine forest of Deschutes National Forest. The trail offers a quintessential cross-country experience, winding through Ponderosa pines and Manzanita bushes. Expect a mix of smooth, flowy singletrack, with Ben's Trail providing a fun, twisting uphill section. Make sure to pause at the Shooting Star Shelter View for expansive scenery and a moment of fresh mountain air.

Planning your ride on Ben's and Phil's Trail Loop is straightforward, as the trailhead is conveniently located just minutes from downtown Bend. You will find restrooms and ample parking available, making for an easy start to your mountain biking day. The best time to tackle this route is typically from early spring through late fall, but always check local conditions, especially regarding snowpack, which can affect trail access. Despite numerous intersections, the trails are well-maintained with clear signage, making navigation simple.

This loop is a prime example of the Bend mountain biking scene, offering a deep dive into the region's natural beauty. The open pine forest environment provides a refreshing atmosphere, perfect for a sustained ride. It is a popular choice for those seeking a solid cross-country experience without venturing too far from urban amenities. The trail system's accessibility and well-kept paths make it a standout option for mountain bikers in the area.

Last updated: April 23, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Deschutes National Forest

Waypoints

A

Start point

Parking

Get Directions

1

2.02 km

Drake Park

Highlight • Rest Area

Drake Park is a popular community spot and an excellent central gathering place where cyclists often meet before a long ride. There are several trail connections, nearly a half mile of riverfront, lots of open lawn space, restrooms and picnic tables.

Tip by

2

23.8 km

Shooting Star Shelter View

Highlight • Viewpoint

If you start in downtown Bend and ride up Ben's, Pinedrops, and the Upper Whoops trails you turn around here for a long and fantastic descent into the Lower Whoops, Phil's and Kent's trail back to the trailhead and into town.

Tip by

3

46.8 km

Bend Brewing Company

Highlight • Pub

Bend Brewing Co. is the second oldest brewery in town and is a great place to stop. The staff is very welcoming, and the pond-side brewery serves up some of the best bar food in the city along with their award-winning beers by way of an expansive lawn, complete with food carts and an outdoor bar.

Tip by

B

48.0 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

25.5 km

11.3 km

10.3 km

689 m

226 m

Surfaces

29.0 km

8.22 km

6.74 km

3.78 km

138 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (1,700 m)

Lowest point (1,100 m)

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Weather

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Today

Wednesday 6 May

26°C

10°C

0 %

Additional weather tips

Max wind speed: 23.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Is Ben's and Phil's Trail Loop suitable for beginners and families?

Yes, this loop is generally considered a moderately popular intermediate route, but it's also known for its easy climbing and fun, twisty descents, making it an ideal introduction to mountain biking in Central Oregon and suitable for families. While largely beginner-friendly, some challenging sections and occasional rock gardens exist, but these often have ride-arounds or bypasses. Advanced areas are well-marked for those seeking more technical riding.

What is the terrain like on this mountain biking loop?

You'll experience a mix of singletrack that is generally smooth and flowy. Ben's Trail, which is uphill-only, features a fun, twisting ramble with a moderate, gentle grade through pine trees. It includes some rocky sections and challenging rocky switchbacks, though optional features are available for advanced riders. Phil's Trail offers a seven-mile descent with microberms for a flowing experience, with lower sections being very mellow.

What are the parking options and trailhead access for the loop?

The loop is conveniently located just minutes from downtown Bend, with a trailhead that offers restrooms and ample parking. Its accessibility is one of the reasons for its popularity.

What can I see along the route?

You'll be immersed in an open pine forest dense with Ponderosa pines and Manzanita bushes. Notable points of interest include the unique "Flaming Chicken" roundabout, an example of trail art. You might also pass by Shooting Star Shelter View, offering scenic vistas.

What is the best time of year to mountain bike this loop?

The best riding conditions typically span from early spring through late fall. However, this can vary with the year's snowpack, so it's always a good idea to check local conditions before you go.

Does the trail intersect other well-known paths?

Yes, the route is part of the vast Bend mountain biking trail system and intersects with numerous other trails. You'll ride sections of Ben's Trail, Phil's Trail, Pinedrops, Upper Whoops, and Kent's Trail, among many others within the network.

Are dogs allowed on the Ben's and Phil's Trail Loop?

Yes, dogs are generally allowed on these trails within the Deschutes National Forest. However, they must be kept on a leash to protect wildlife and ensure a pleasant experience for all trail users. Always practice Leave No Trace principles and pack out any waste.

Do I need a permit or pay an entrance fee to ride this trail in Deschutes National Forest?

Generally, there are no specific permits or entrance fees required to access the Ben's and Phil's Trail Loop for day use. However, some areas within the Deschutes National Forest may require a Northwest Forest Pass or other recreation passes for parking at certain developed trailheads. It's always best to check the latest regulations with the U.S. Forest Service for the Deschutes National Forest before your visit.

What makes this loop a classic mountain biking experience in Bend?

This loop is considered a quintessential cross-country experience and a classic introduction to Bend's mountain biking scene due to its diverse terrain, convenient location just minutes from downtown, and well-maintained, clearly signed trails. The system's one-way sections, like Ben's being uphill-only and much of Phil's being downhill-only, contribute to a smooth and enjoyable flow.

Are there any places to eat or drink near the trailhead?

Yes, given its proximity to downtown Bend, you'll find various options. The Bend Brewing Company is one popular spot nearby where you can refuel after your ride.

Nearby routes

Moderate

4.0

119

Ben's, Pinedrops and Phil's Trail Loop

02:18h

24.7km

370m

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