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United States
Connecticut
Western Connecticut Planning Region

Cannondale

The best walks and hikes around Cannondale

5.0

(2)

101

hikers

33

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 most popular hiking route is Loop Trail โ€“ Devils Den Nature Preserve, a 5.4 miles (8.6 km) trail that takes 2 hours 18 minutes to complete. This route winds through woodlands, wetlands, and dramatic rocky outcroppings within the preserve.
  • Another top favourite among local hikers is Saugatuck Reservoir Loop โ€“ Trout Brook Valley State Park Preserve, a difficult 16.8 miles (27.0 km) path. This trail traverses valleys and rugged hills under a mixed forest canopy, featuring wetlands and watercourses.
  • Local hikers also love the Godfrey and Sap Brook Trail Loop, a 3.4 miles (5.5 km) trail leading through forested areas, often completed in about 1 hour 30 minutes.
  • Hiking around Cannondale is defined by mature hardwood forests, wetlands, and rugged hills, often featuring rocky crests and reservoirs. The network offers options for various ability levels, from easy loops to more challenging, longer routes.
  • The routes in Cannondale are highly rated by the komoot community with an average score of 4.5 stars from over 2 reviews. More than 90 hikers have used komoot to explore Cannondale's varied terrain.

Last updated: June 28, 2026

6

hikers

#1.

Wilton Town Forest Blue Trail

5.55km

01:32

80m

110m

The Wilton Town Forest Blue Trail offers a dynamic hiking experience through a varied landscape. You'll traverse packed earth, dirt paths, and surprisingly rocky sections, winding through a mix of deciduous hardwood forest and small, serene hemlock groves. Keep an eye out for the picturesque Sheep Falls in the park's northeast corner, a lovely natural feature that adds to the trail's charm. This 3.4-mile (5.5 km) route, despite its easy rating, presents 270 feet (82 metres) of elevation gain and takes about 1 hour and 31 minutes, making it a great option for those who enjoy a bit of ruggedness.

Planning your visit to the Wilton Town Forest Blue Trail is straightforward, as there are no permits or fees required. The trail is part of a larger network, and while this specific loop is considered easy, be prepared for sections with rooty singletrack and rock gardens, particularly on the Blue East portion. Parking is typically available at the trailhead, but arriving earlier in the day can help ensure a spot, especially on busy weekends. This trail is ideal for hikers looking for a diverse and engaging walk without committing to a full-day excursion.

Beyond its natural beauty, the Wilton Town Forest holds historical significance, with features like the

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5

hikers

The Godfrey and Sap Brook Trail Loop offers a delightful escape into nature, winding through the varied landscapes of Devil's Den Preserve. You will trek through dense wooded forests, past tranquil wetlands, and alongside a stream that occasionally boasts a seasonal waterfall. The highlight is undoubtedly Godfrey Pond, a serene 18th-century mill pond that adds a touch of historical charm to the natural beauty, making this easy 3.4-mile (5.5 km) hike a rewarding experience for all. With only 287 feet (87 metres) of elevation gain, it is a gentle journey that takes about 1 hour and 29 minutes.

Planning your visit to this popular loop means considering the best time to go; early mornings are ideal for securing parking at the trailhead, especially on busy days. While the trail is generally easy, some sections have rocky footing, so sturdy hiking shoes are a good idea to keep you comfortable. There are no permits required, and the trail is accessible year-round, offering different scenic views with each changing season.

This trail is nestled within the Lucius Pond Ordway Devil's Den Preserve, which is the largest continuous preserve in Connecticut's densely developed Fairfield County. It is a haven for biodiversity, home to over 500 types of trees and wildflowers, and a variety of wildlife including red fox and bobcat. The preserve's historical significance, with the old mill pond and sawmill remains, combined with its ecological importance as part of the Saugatuck River watershed, makes this loop more than just a walk in the woods; it is a journey through a vital natural and historical landmark.

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3

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The Norwalk River Valley Trail offers a delightful blend of natural and urban landscapes, making it one of the more popular trails for an easy outing. You'll wander along the Norwalk River, through wooded sections, and past open meadows, with some parts featuring paved surfaces and others crushed gravel. This 2.2-mile (3.6 km) route, with a gentle 147 feet (45 metres) of elevation gain, is a pleasant way to spend about 56 minutes immersing yourself in the local environment.

Planning your visit to the Norwalk River Valley Trail is straightforward, as it's designed for multi-use and accessibility, welcoming everyone from families with strollers to casual walkers. While the full 38-mile (61 km) vision is still developing, several completed sections offer easy hikes for beginners. You can find various access points and parking along its course, making it convenient to hop on and explore.

What makes the Norwalk River Valley Trail truly stand out is its commitment to connecting communities and blending natural beauty with cultural points of interest. Beyond the serene riverside paths, you might encounter historical buildings or public art, like those near Oyster Shell Park. It's a fantastic example of a greenway that provides a valuable recreational resource and a family-friendly section for everyone to enjoy.

Easy

2

hikers

1.89km

00:30

10m

20m

The Godfrey Trail is a delightful, easy hike that offers a quick escape into nature, perfect for a relaxed stroll. This 1.2-mile (1.9 km) route features a minimal 43 feet (13 metres) of elevation gain, leading you to the tranquil Godfrey Pond. It's a gentle path, likely through natural ground, providing a peaceful setting for a short outdoor adventure.

Planning your visit to the Godfrey Trail is straightforward; its easy difficulty and short 29-minute duration mean you can enjoy it almost any time of day or year. While specific parking details aren't available, it's generally an accessible trail for a spontaneous outing. It's an excellent choice for those seeking a quick, family-friendly walk without the need for extensive planning.

This trail stands out as a great option for beginners or anyone looking for a low-impact activity. Its short length and easy terrain make it ideal for a quick dose of fresh air, perhaps as a warm-up for longer hikes or simply to enjoy the quiet surroundings of Godfrey Pond. It's a testament to how even a brief walk can offer a refreshing connection with the outdoors.

Easy

The Saugatuck, Donahue, Den, and Pent Trail Loop offers a delightful and varied hiking experience within Connecticut's Devil's Den Nature Preserve. You'll traverse a path that winds through dense woodlands, showcasing the region's distinctive granite topography. Expect a mix of gentle downhill sections and some more challenging climbs, with opportunities to spot beautiful Mountain Laurel and enjoy views of a tranquil reservoir from an overlook with a convenient bench. This easy 3.7-mile (5.9 km) loop, with 307 feet (93 metres) of elevation gain, takes about 1 hour and 36 minutes, making it a perfect escape for a few hours.

When planning your visit, remember that this trail is within a nature preserve, so check for any specific regulations regarding access or pets. While parking information isn't detailed, arriving earlier in the day, especially on weekends, is always a good strategy to ensure a spot at the trailhead. Be sure to wear sturdy shoes suitable for varied terrain and carry water, particularly during warmer weather. The trail is enjoyable in spring for its blooms and in autumn for its colorful foliage.

This loop is a fantastic way to experience the natural beauty of Western Connecticut. The Devil's Den Nature Preserve is known for its diverse ecosystems and conservation efforts, protecting a significant area of woodland and wetlands. The presence of the Pent Trail as a highlight suggests a well-established route within this natural setting. It's a great option for those seeking a family-friendly hike or a peaceful outing with dogs, offering a genuine connection with nature without being overly strenuous.

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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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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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