3.4
(12)
86
riders
03:47
57.6km
770m
Cycling
The Sleepy Hollow loop is a demanding touring cycling route that will test your legs and reward you with a diverse landscape. You'll navigate through rolling hills and verdant forests, experiencing a mix of paved and unpaved sections. The journey offers glimpses of natural beauty, particularly as you pass through areas like Barlow Wayside County Park, providing a refreshing forest setting.
This difficult 35.8-mile (57.6 km) loop involves a significant 2525 feet (770 metres) of elevation gain, typically taking about 3 hours and 46 minutes. It's a ride for those with good fitness and a desire for a challenge. Plan to start your ride early in the day, especially if you're aiming to complete it in daylight, and ensure you carry enough water and supplies.
This route stands out as a robust option for touring cyclists in the Sandy, Oregon area, offering a substantial workout amidst scenic surroundings. It's a great choice if you're looking for a longer, more strenuous ride that moves beyond typical flat paths, providing a true sense of accomplishment upon completion.
Last updated: June 9, 2026
Waypoints
Start point
Parking
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22.1 km
Highlight • Forest
Tip by
46.1 km
Highlight (Segment) • Trail
Tip by
57.6 km
End point
Parking
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
Highest point (500 m)
Lowest point (150 m)
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Weather
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Today
Friday 10 July
27°C
10°C
0 %
Additional weather tips
Max wind speed: 9.0 km/h
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This route was planned by komoot.
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.
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.
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.
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.
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.
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.
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.
Yes, the route passes by Barlow Wayside County Park, which features a forest, and also includes a section along Southeast Pagh Road.
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.
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.
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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