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Hiking trails & Routes
United States
Connecticut
South Central Connecticut Planning Region

Westwoods Trail

Moderate

2.9

(9)

29

hikers

Westwoods Trail

02:51

10.6km

130m

Hiking

Embark on the Westwoods Trail, a moderate hiking route spanning 6.6 miles (10.6 km) with an elevation gain of 412 feet (126 metres), typically completed in 2 hours and 50 minutes. You will hike through varied terrain, including deciduous forests and old woods roads, encountering rocky outcrops along the way.…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

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1

1.20 km

Indian Cave

Highlight • Cave

2

4.53 km

Lost Lake

Highlight • Lake

The Lost Lake is located in the southern section of the Cockaponset State Forest and if you are hiking along the lake trail, you can enjoy multiple spectacular views of the lake.

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3

5.56 km

Granite Cliffs

Highlight • Natural Monument

In this area of the Cockaponset State Forest, you will find impressive granite cliffs surrounding you as you hike through the area. Additionally, there are multiple huge boulders lying around from the receding glaciers of the last ice age.

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B

10.6 km

End point

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Way Types & Surfaces

Way Types

10.4 km

211 m

Surfaces

10.4 km

165 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.

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Weather

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Today

Sunday 5 July

27°C

20°C

75 %

Additional weather tips

Max wind speed: 16.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park for the Westwoods Trail?

The Westwoods Trail system has multiple access points and parking areas. While specific parking lot details aren't provided, it's generally recommended to check local Guilford, CT resources or komoot's tour details for the most convenient trailhead parking for your chosen route.

Are there any permits or entrance fees required for Westwoods Trail?

No, there are no permits or entrance fees required to access the Westwoods Trail system. It is a publicly accessible recreational area.

Is the Westwoods Trail dog-friendly?

Yes, the Westwoods Trail is generally dog-friendly. However, it's always best to keep your dog on a leash and practice Leave No Trace principles by cleaning up after your pet.

What is the best time of year to hike the Westwoods Trail?

The trail can be enjoyed year-round. Winter months offer more visible views of Legend Hill and the surrounding valley due to less foliage. The 1.5-mile stretch along Lost Lake is particularly scenic when leaves are off the trees. Spring and fall offer pleasant temperatures and beautiful scenery, while summer can be warm but provides lush green woodlands.

What is the terrain like on the Westwoods Trail?

The terrain is highly varied, ranging from gentle paths to challenging, rocky ascents. You'll encounter a mix of deciduous forests, old woods roads, and areas with uneven footing and occasional wet spots. Unique geological features like rocky outcrops, cave structures (including an Old Leatherman Cave), and distinct rock formations are common. Some sections also feature long plank walks across marshy areas.

What natural features or viewpoints can I expect to see along the route?

The trail boasts diverse natural features. You can explore Indian Cave, enjoy the scenic views along Lost Lake, and marvel at Granite Cliffs. Other notable formations include "Dinosaur Rock," "The Crawl," and a "Splitting Rock Tree." The landscape also features saltwater and freshwater marshes, an inland tidal lake, and historic stone walls.

Is the Westwoods Trail suitable for beginners?

The Westwoods Trail system offers a wide range of difficulties. Some trails, like the Blue Circle, Green Triangle (Nature Trail), and Green Square, are considered "easy walking" and suitable for beginners. However, more challenging sections with "strenuous cliff sections" exist, such as the Yellow Circle, which is recommended only for experienced hikers. It's best to consult a map and choose a route appropriate for your skill level.

Are there different route options or loops within the Westwoods Trail system?

Absolutely! With approximately 39 miles of networked trails across 1200 acres, Westwoods offers an almost infinite combination of routes. You can easily create loops of varying distances and difficulties by connecting different marked trails. This allows hikers to tailor their experience to their desired length and challenge.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the Yellow Triangle, cross trail white-orange, Green Diamond, Patrick Trail, and Green Circle, offering opportunities to explore different parts of the extensive Westwoods network.

Are there any particularly challenging sections on the trail?

Yes, the Yellow Circle trail is known as "the hardest trail in the WestWoods," featuring strenuous cliff sections that can be dangerous, especially when wet or slippery. This section is recommended only for experienced, surefooted hikers. Other trails like the Green Circle, Orange Circle, White Circle, Red Diamond, and Red Triangle also offer more challenging, harder walking or steep climbs.

What should I bring for a hike on this trail?

Given the varied terrain and potential for wet spots, sturdy hiking boots are highly recommended. Bring plenty of water, especially for longer routes, and snacks. A map of the extensive trail system is essential for navigation, as some areas may require careful attention to blazes. Insect repellent can also be useful during warmer months.

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