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Deschutes County

Monkey Face Rock – Crooked River Caldera loop from Terrebonne

Routes

Running trails & routes

United States

Oregon

Deschutes County

Monkey Face Rock – Crooked River Caldera loop from Terrebonne

Hard

runners

Monkey Face Rock – Crooked River Caldera loop from Terrebonne

06:32

47.1km

1,510m

Running

Hard run. Very good fitness required. Sure-footedness, sturdy shoes and alpine experience required. The starting point of the route is right next to a parking lot.

Last updated: November 29, 2025

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Tips

Your route passes through a protected area

Please check local regulations for:

Crooked River National Grassland

Waypoints

Start point

Parking

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1.64 km

Misery Ridge Summit

Highlight • Summit

Gazing over the Crooked River and its remarkable volcanic rock formations, Smith Rock's flagship trail is nothing short of extraordinary. The view is simply splendid, making it the ideal locale for a memorable keepsake photograph.

Tip by

1.97 km

Monkey Face Rock

Highlight • Natural Monument

Indulge in the awe-inspiring vista of one of the most renowned climbing destinations, where brave souls ascend Monkey Face's towering 350-foot spire. This iconic rock formation defines Smith Rock State …

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4.54 km

Crooked River Caldera

Highlight • Volcano

The Crooked River caldera, born from explosive super-volcanic eruptions over 29 million years ago, carved a 26-mile-long, 17-mile wide depression. Its geological legacy, showcased in Smith Rock State Park, provides …

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6.92 km

Gray Butte Trail

Highlight (Segment) • Trail

This renowned trail offers breathtaking vistas of Crooked River National Grassland and the grand Cascades, accessible from Gray Butte Trailhead or Cole Loop Trail. A haven for runners, riders, and …

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24.9 km

Julius & Sarah McCoin Orchard

Highlight • Structure

This orchard dates back 130 years to the McCoin family who planted the apple trees on their homestead. The trees still bear fruit because of the efforts of volunteers who prune them each spring.

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43.7 km

Wolf Tree Trail

Highlight (Segment) • Trail

Gazing left, climbers scale the famed Picnic Lunch Wall. The path reveals Ship Rock and Red Wall, where nature's denizens thrive. Seek respite under a colossal ponderosa tree. In the …

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46.5 km

Northern Point

Highlight • Climb

The Northern Point, a modest cliff band, offers accessible trad and sport climbing routes. Perfect for beginners, with shorter routes and top-rope options.

Tip by

47.1 km

End point

Parking

Way Types & Surfaces

Way Types

40.2 km

5.69 km

830 m

337 m

< 100 m

Surfaces

34.7 km

11.9 km

337 m

120 m

Elevation

Highest point (1,290 m)

Lowest point (810 m)

Weather

Today

Sunday 14 December

15°C

4°C

1 %

If you start your activity now...

Max wind speed: 12.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Monkey Face Rock – Crooked River Caldera loop from Terrebonne

Misery Ridge Summit

Monkey Face Rock

Crooked River Caldera

Gray Butte Trail

Julius & Sarah McCoin Orchard

Wolf Tree Trail

Northern Point

Nearby routes

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