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United States
Connecticut
Western Connecticut Planning Region

Cannondale

The best walks and hikes around Cannondale

4.5

(2)

84

hikers

31

hikes

Hiking around Cannondale offers diverse landscapes, characterized by dense woodlands, wetlands, and rugged hills. The region features significant preserves like Devil's Den Nature Preserve and Trout Brook Valley State Park Preserve, providing varied terrain for outdoor enthusiasts. Hikers can explore mature hardwood forests, rocky crests, and picturesque ravines, with elevations ranging from gentle slopes to more challenging ascents. The area is defined by its natural features, including reservoirs and a network of trails.

Best hiking trails around Cannondale

  • The mostโ€ฆ

Last updated: May 16, 2026

5

hikers

#1.

Wilton Town Forest Blue Trail

5.55km

01:32

80m

110m

Embark on the Wilton Town Forest Blue Trail for an easy hiking experience that takes you through a beautiful natural setting. This route covers 3.4 miles (5.5 km) with aโ€ฆ

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Easy

5

hikers

Embark on an easy hike along the Godfrey and Sap Brook Trail Loop, a pleasant route that winds through the peaceful wooded areas of the Devil's Den Nature Preserve. Thisโ€ฆ

Easy
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3

hikers

The Norwalk River Valley Trail offers an easy hiking experience, perfect for a quick outdoor escape. You will follow the Norwalk River, enjoying pleasant riverside views as the path windsโ€ฆ

Easy

2

hikers

3.44km

00:55

40m

40m

Embark on an easy hike along the Weir Pond Trail, a 2.1-mile (3.4 km) loop that takes you through a diverse landscape of tranquil woodlands, wetlands, and open fields. Youโ€ฆ

Easy

2

hikers

1.89km

00:30

10m

20m

Embark on the easy Godfrey Trail for a peaceful hike through wooded areas, where you can enjoy scenic views, especially around Godfrey Pond. This short route covers 1.2 miles (1.9โ€ฆ

Easy
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Tips from the Community

Matthew
February 16, 2024, Godfrey Pond

Godfrey Pond is a small body of water within Devil's Den Nature Preserve. A few different trails pass by the pond, but it is so heavily surrounded by trees that the views of the pond are spotty.

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Wilton Town Forest is Wilton's largest and best open space park and sits just north of Popes Pond. In its northeast corner is a lovely waterfall known as Sheep Falls. It has numerous walking and biking trails and is quite a rugged but popular recreation area.

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This is a beautiful National Historic Site that contains the immaculately preserved Weir house, barn and art studios. A stunning setting among more than 60 acres of woods, fields, and waterways. Take some time to visit the home and studio of America's most beloved Impressionist, J. Alden Weir.

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Matthew
August 22, 2023, Godfrey Pond

Godfrey Pond is a small body of water within Devil's Den Nature Preserve. A few different trails pass by the pond, but it is so heavily surrounded by trees that the views of the pond are spotty.

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Anette
December 22, 2022, Pent Trail

The path is quite rocky and sometimes a little muddy. But it is a wonderful hike through forest and along streams.

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Frequently Asked Questions

How many hiking trails are available around Cannondale?

There are nearly 20 hiking routes available around Cannondale, offering a diverse range of experiences for outdoor enthusiasts. These trails traverse varied landscapes, from dense woodlands to rugged hills.

What kind of terrain and difficulty can I expect on hikes near Cannondale?

The terrain around Cannondale is diverse, featuring dense woodlands, wetlands, and rugged hills with rocky crests and outcroppings. You'll find trails ranging from easy, accessible paths suitable for families, to more challenging routes with significant ascents. For example, some trails in Trout Brook Valley State Park Preserve include an 800-foot climb, offering technically challenging sections.

Are there family-friendly hiking options around Cannondale?

Yes, several trails around Cannondale are suitable for families and children. Many paths are easily accessible, making them ideal for shorter hikes and kid-friendly excursions. The Godfrey Trail and Godfrey Pond โ€“ Pent Trail loop from Weston-Wilton Forest Reserve is an easy option that winds through forested areas.

Can I hike with my dog on trails near Cannondale?

Yes, some areas around Cannondale are dog-friendly. Trout Brook Valley State Park Preserve, for instance, offers specific trails where dogs are permitted off-leash. These routes often wind through meadows, hardwood forests, and by quiet streams, providing a great experience for you and your canine companion.

Are there any circular hiking routes in the Cannondale area?

Yes, many trails around Cannondale are designed as loops, offering varied scenery without retracing your steps. A popular example is the Loop Trail โ€“ Devils Den Nature Preserve, which takes you through woodlands, wetlands, and dramatic rocky outcroppings.

What natural features or viewpoints can I see along the hiking trails?

The trails around Cannondale offer numerous natural features and scenic viewpoints. In Devil's Den Nature Preserve, you can explore a 600-million-year-old rock formation, the picturesque Ambler Gorge with its rocky cascade, and enjoy spectacular views from the Great Ledge. Many routes also feature wetlands, watercourses, and mature hardwood forests. You can also find highlights like the View of Saugatuck Reservoir.

Where can I find parking for trailheads in Cannondale?

Parking availability varies by trailhead. For popular preserves like Devil's Den Nature Preserve and Trout Brook Valley State Park Preserve, designated parking areas are typically available. It's always recommended to check specific preserve websites or trail guides for detailed parking information before your visit.

What is the best time of year to go hiking in Cannondale?

The Cannondale area offers enjoyable hiking experiences across multiple seasons. Spring and fall are particularly popular for their mild temperatures and vibrant foliage. Fall provides stunning autumn colors, while spring brings fresh greenery and blooming wildflowers. Summer is also pleasant, especially in shaded woodland areas, though it can be warmer.

Are there any less crowded hiking routes around Cannondale?

While popular preserves like Devil's Den and Trout Brook Valley can see visitors, exploring some of the less-trafficked trails or visiting during off-peak hours (weekdays, early mornings) can offer a more solitary experience. Routes like the Godfrey Trail and Godfrey Pond โ€“ Pent Trail loop from Easton might offer a quieter alternative.

What do other hikers enjoy most about hiking in Cannondale?

The hiking routes around Cannondale are highly rated by the komoot community, with an average score of 4.7 stars. Hikers often praise the diverse landscapes, including dense woodlands, wetlands, and rugged hills, as well as the well-maintained trail systems that cater to various fitness levels. The natural beauty and opportunities for wildlife viewing are frequently highlighted.

Are there any historical sites or landmarks to explore while hiking?

Yes, Devil's Den Nature Preserve includes historic sites such as Morris Cemetery. Additionally, the region is rich in natural history, with features like the ancient rock formations in Devil's Den. For broader historical interest, Weir Farm National Historical Park is also located nearby.

What are the longest or most challenging hikes in the area?

For those seeking a challenge, the Saugatuck Reservoir Loop โ€“ Trout Brook Valley State Park Preserve is a difficult 27.0 km (16.8 miles) path. This trail traverses valleys and rugged hills under a mixed forest canopy, featuring wetlands and watercourses, and includes significant elevation changes.

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