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Routes
Bike touring routes & trails
United States
Oregon
Clackamas County
Sandy

Sleepy Hollow loop

Hard

3.4

(12)

86

riders

Sleepy Hollow loop

03:47

57.6km

770m

Cycling

Prepare for a difficult touring bicycle ride on the Sleepy Hollow loop, a challenging route that stretches 35.8 miles (57.6 km). You will climb a significant 2525 feet (770 metres) of elevation, which typically takes around 3 hours and 46 minutes to complete. As you pedal, you will experience picturesque…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

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1

22.1 km

Barlow Wayside County Park

Highlight • Forest

Tread where pioneers once walked, as the park sits alongside the historic Barlow Road, a segment of the legendary Oregon Trail. Immerse yourself in the beauty of a majestic forest …

Tip by

2

46.1 km

Southeast Pagh Road

Highlight (Segment) • Trail

A quiet farm road with beautiful scenery and a calming effect. Enjoy the various creatures and picturesque sights along this area. A great part of your journey in the countryside.

Tip by

B

57.6 km

End point

Parking

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Way Types & Surfaces

Way Types

47.4 km

6.49 km

2.50 km

1.11 km

100 m

Surfaces

33.7 km

23.5 km

372 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 (500 m)

Lowest point (150 m)

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Weather

Powered by Foreca

Saturday 6 June

13°C

7°C

72 %

Additional weather tips

Max wind speed: 6.0 km/h

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Frequently Asked Questions

How challenging is the Sleepy Hollow loop for touring cyclists?

This loop is considered a "Hard bike ride," demanding very good fitness. While primarily paved, some segments might be unpaved and difficult, potentially requiring you to push your bike if your fitness level isn't sufficient. It's a substantial ride with a significant elevation gain of 770 meters over 57.6 kilometers.

What is the terrain like on this cycling route?

The Sleepy Hollow loop primarily features paved surfaces, making it suitable for touring bicycles. However, be aware that some parts of the route might be unpaved. This loop is distinct from the nearby Sandy Ridge Trail system, which is known for mountain biking single-track.

Where can I park to access the route?

While specific parking details for the Sleepy Hollow loop are not provided, the area around Sandy, Oregon, generally offers access points. It's advisable to check local resources or maps for designated parking areas near the start of the loop, such as in Sandy itself or near the Barlow Wayside County Park.

Is the Sleepy Hollow loop dog-friendly?

The information available does not explicitly state the dog policy for the Sleepy Hollow loop. Generally, paved touring routes in public areas may allow dogs on a leash, but it's always best to check local regulations for Sandy, Oregon, or specific park rules if you plan to bring your dog.

What is the best time of year to cycle this route?

Given the potential for unpaved segments and the significant elevation, cycling this route is likely best during drier seasons to avoid muddy conditions. Spring, summer, and early fall would generally offer the most pleasant weather for a challenging ride in the Sandy, Oregon area.

Do I need any permits or pay entrance fees for this route?

There is no indication that permits or entrance fees are required for cycling the Sleepy Hollow loop. It appears to be a publicly accessible route. However, always be mindful of any signage or local regulations you encounter along the way.

What kind of scenery can I expect along the way?

While specific scenic details for this touring loop are not extensively detailed, the broader area around Sandy, Oregon, is known for picturesque views. You can expect lush forests, potential views of the valley, and diverse flora similar to what's found in the region, such as purple foxglove, Shasta daisies, and wild iris.

Are there any notable points of interest or highlights on the loop?

Yes, the route passes by Barlow Wayside County Park, which features a forest, and also includes a section along Southeast Pagh Road.

Does the route intersect other well-known paths?

Yes, the route intersects with several other paths. You'll find sections that overlap with trails such as Tickle Creek Trail, PGE Road, Neighborhood Trail, TNT, Falls Loop Trail, Hide and Seek, Homestead Loop, Bridge Connector, Little Joe Loop, TBBV Path, Meinig Avenue, Meinig Park Access, Ten Eyck Path, East Sladky Lane, Hamilton Ridge Tot Lot Path, Miller Road Path, Road Access, Tupper Road Path, Haskins Path, Laura's Loop, Little Monkey, and North Loop.

Is this route suitable for families or beginner cyclists?

Given its classification as a "Hard bike ride" with significant elevation gain and potential unpaved segments, this route is generally not recommended for families with young children or beginner cyclists. It demands very good fitness and some experience with challenging terrain.

How long does it typically take to complete the loop?

The estimated duration for completing the 57.6-kilometer loop is approximately 3 hours and 47 minutes (13,599 seconds) for touring cyclists. This is an estimate and actual time may vary based on your fitness level, breaks, and weather conditions.

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