Radey Pond – Hesseky Meadow Pond loop from Southbury
Radey Pond – Hesseky Meadow Pond loop from Southbury
2.5
(4)
35
riders
Radey Pond – Hesseky Meadow Pond loop from Southbury
02:09
43.1km
530m
Road cycling
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.
Last updated: May 18, 2026
Waypoints
Start point
Parking
Get Directions
5.25 km
Bates Rocks
Highlight • Natural Monument
Tip by
8.73 km
Radey Pond
Highlight • Lake
Tip by
9.34 km
Hesseky Meadow Pond
Highlight • Lake
Tip by
33.3 km
Quassy
Highlight • Structure
Tip by
43.1 km
End point
Parking
Way Types & Surfaces
Way Types
21.8 km
19.9 km
1.47 km
< 100 m
Surfaces
38.1 km
4.59 km
446 m
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Elevation
Highest point (250 m)
Lowest point (60 m)
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Weather
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Wednesday 15 July
30°C
19°C
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Description
If you're looking for a road cycling route that truly earns its views, the Radey Pond – Hesseky Meadow Pond loop from Southbury is one to consider. This 26.8-mile (43.1 km) road cycling route, rated moderate by Komoot, packs in 1724 feet (525 metres) of climbing over an estimated 2 hours and 8 minutes. While the official rating is moderate, be prepared for a challenging ride with significant elevation changes, making it ideal for cyclists who enjoy a good workout and scenic rewards.
What to expect on Radey Pond – Hesseky Meadow Pond loop from Southbury
This loop takes you through the picturesque rolling terrain of Southbury, Connecticut, offering a journey rich in natural beauty. You'll pedal past the tranquil waters of Radey Pond and Hesseky Meadow Pond, integral parts of the Hesseky Brook drainage system, surrounded by wetlands and mixed deciduous woodlands. Expect a dynamic ride with numerous climbs and descents, especially along roads like Transylvania Road, which cuts through areas of moderate to very steep slopes. The effort is well worth it for the views of these serene water bodies and the surrounding forested landscape, making it a great option for experienced road cyclists seeking a scenic challenge.
Planning your visit
Given the hilly nature of the Radey Pond Hesseky Meadow Pond loop Southbury road cycling route, ensure your bike is in good condition and you're prepared for significant elevation changes. While specific parking for this exact loop isn't designated, you'll likely start from a local road or public area in Southbury; always check local regulations for parking. The area is beautiful year-round, but the best time of year to cycle Radey Pond loop is during spring or fall when the weather is cooler and the foliage adds to the scenic experience. Always carry enough water, especially on warmer days.
Trail details
- Distance: 26.8 miles (43.1 km)
- Elevation gain: 1724 feet (525 metres)
- Difficulty: moderate
- Estimated time: 2 hours and 8 minutes
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