Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Hikes
United States
Connecticut
Western Connecticut Planning Region

Weston

The best walks and hikes around Weston

By Fede from komoot

·

Updated June 1, 2026

If you've ever tried planning a hike and found yourself drowning in endless lists of trails, you know the pain of trying to figure out what's actually worth your time. When it comes to hiking around Weston, the options can feel overwhelming, making it tough to separate the true gems from the filler. That's where we come in. Our komoot community has mapped, walked, and reviewed countless routes here, and we've distilled all that local knowledge into a curated shortlist, saving you the guesswork.

Hiking in Weston is all about immersing yourself in dense woodlands and exploring varied forest ecosystems. You'll find paths winding through conservation lands, state parks, and nature preserves, often alongside tranquil reservoir paths. The terrain is generally moderate, making it accessible for many, though some trails do offer steeper sections for a bit more challenge. It’s a place where you can truly connect with nature, whether you're looking for an easy stroll or a longer, more demanding day out.

If you only do one hike in Weston, make it the Saugatuck, Donahue, Den, and Pent Trail Loop. At 3.6 miles (5.9 km), it’s our most popular route for a reason, offering a fantastic cross-section of the area's varied forest ecosystems. For a slightly different feel, the Godfrey and Sap Brook Trail Loop, at 3.4 miles (5.5 km), is another top favourite, guiding you through woodlands and along a peaceful brook. With more than 100 hikers already exploring Weston with komoot, you're in good company. Dive in and discover your next favourite trail!

If you only do 3 of these routes

  1. 1

    Godfrey and Sap Brook Trail Loop
  2. 2

    Norwalk River Valley Trail
  3. 3

    Brett Woods Yellow Loop

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Godfrey and Sap Brook Trail Loop

5.45 km

90 m

Easy

Norwalk River Valley Trail

3.56 km

40 m

Easy

Brett Woods Yellow Loop

2.96 km

30 m

Easy

Godfrey Trail

1.89 km

10 m

Easy

Saugatuck, Donahue, Den, and Pent Trail Loop

5.88 km

90 m

Easy

The Driftway

2.46 km

30 m

Easy

Newman-Poses Preserve Loop

1.75 km

10 m

Easy

Godfrey, Bedford, and Pent Trails Loop

8.60 km

100 m

Moderate

Cranbury Park loop from Cranbury Park

4.39 km

50 m

Easy

Pent Trail – Godfrey Trail and Godfrey Pond loop from Weston-Wilton Forest Reserve

11.5 km

170 m

Moderate

Sign up to see all 10 routes

Sign up for free

1.

Godfrey and Sap Brook Trail Loop

5.45km

01:30

90m

90m

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.

View route

Save

Navigate with device

Send to Phone

2.

Norwalk River Valley Trail

3.56km

00:56

40m

10m

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.

View route

3.

Brett Woods Yellow Loop

2.96km

00:47

30m

30m

If you're seeking a tranquil forest walk in Fairfield, the Brett Woods Yellow Loop delivers a pleasant experience. This easy 1.8-mile (3.0 km) hiking trail guides you through a rich deciduous forest, where you'll encounter maturing beech stands and dense mountain laurel. Keep an eye out for Brett Woods Pond, a notable feature along the route, and listen for the calls of songbirds in the shrub swamps. The varied terrain includes sections of bare earth and some gentle slopes, making it a refreshing journey for all skill levels.

Planning your visit to the Brett Woods Yellow Loop is straightforward; parking is available at the trailhead for this popular route. The entire 1.8-mile (3.0 km) loop, with its minimal 88 feet (27 metres) of elevation gain, typically takes around 46 minutes to complete. It's an excellent choice for a quick escape into nature, whether you're a beginner hiker or just looking for a relaxed outing.

The Brett Woods Yellow Loop is nestled within the expansive 186.1-acre Brett Woods Conservation Area, recognized as Fairfield's largest open space. This area is vital for wildlife, providing unbroken forest cover that supports interior forest bird species and other animals like deer and turkeys. The conservation area's unique ridge and valley topography, shaped by glacial activity, adds to its natural charm, offering more than just a simple walk in the woods.

View route

guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

4.

Godfrey Trail

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.

View route

5.

Saugatuck, Donahue, Den, and Pent Trail Loop

5.88km

01:36

90m

90m

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.

View route

6.

The Driftway

2.46km

00:39

30m

30m

The Driftway offers a delightful escape into Scituate's coastal beauty, winding through a mosaic of sandy paths, salt marshes, and woodlands. You'll encounter diverse flora, from towering pines to unique marsh grasses, and can spot the Scituate wind turbine in the distance. The route provides a refreshing experience, immersing you in the natural landscape of the Herring River area.

Planning your visit to The Driftway is straightforward, as the park is generally accessible and features some paved sections suitable for strollers. While the trails are mostly easy, keep in mind that some unmaintained paths can get muddy, particularly at high tide. There are no permits or fees required, making it a convenient option for a spontaneous outing. This easy 1.5-mile (2.5 km) hike with only 90 feet (27 metres) of elevation gain can be completed in about 39 minutes, making it perfect for a quick nature break.

Historically, this area was a sand and gravel mining operation, with remnants of an old wharf still visible, adding a layer of interest to your walk. The park's diverse habitats make it a significant stop for migratory birds, offering excellent birdwatching opportunities. It's a fantastic choice for family friendly hikes or anyone looking for beginner hiking routes near The Driftway, combining natural beauty with a touch of local history.

View route

7.

Newman-Poses Preserve Loop

1.75km

00:27

10m

10m

The Newman-Poses Preserve Loop is a delightful short hike that packs a lot of natural beauty into its compact form. As you follow the trail, you'll experience a mix of shaded woodlands, open meadows, and wetlands, with the Aspetuck River often in view. Look for the impressive old white pine trees and the unique opportunity to walk on rocks directly in the river, making for a memorable experience. It's an easy 1.1-mile (1.7 km) route, perfect for a quick nature escape.

Accessing the preserve is simple, with a dedicated parking lot and an information kiosk right at the trailhead. While the Newman-Poses Preserve Loop hiking difficulty is easy, be prepared for potentially wet or muddy conditions, especially after rain or in late summer. Spring and fall are particularly rewarding seasons to visit, offering vibrant foliage and increased wildlife activity, though the trail is enjoyable year-round.

This preserve holds a special place, honoring Paul Newman and Lillian Poses, who contributed to its creation. Beyond the natural beauty, you might discover an "incredible stone bench" tucked away within the property, adding a touch of charm to your walk. It's a fantastic option for a family-friendly hike or a peaceful stroll when you're in the Westport, CT area.

View route

8.

Godfrey, Bedford, and Pent Trails Loop

8.60km

02:18

100m

100m

The Godfrey, Bedford, and Pent Trails Loop offers a delightful immersion into the dense woodlands and rolling terrain of the Devil's Den Nature Preserve. You'll wander along peaceful forest paths, often tracing the West Branch of the Saugatuck River, and pass the tranquil waters of Godfrey Pond, an 18th-century mill pond. This moderate 5.3-mile (8.6 km) hiking route, with its gentle 336 feet (102 metres) of elevation gain, is a perfect way to spend about 2 hours and 18 minutes enjoying Connecticut's natural beauty.

Planning your visit to this loop is straightforward, as it's situated within the Devil's Den Nature Preserve. The trails are well-marked with blazes and numbered posts at junctions, making navigation simple for hikers. While specific parking information isn't detailed, the preserve is a popular spot, so arriving earlier in the day is often a good strategy to secure a convenient spot.

This trail is a fantastic example of the diverse natural beauty found within the Devil's Den Nature Preserve, a significant natural area in Western Connecticut. The presence of Godfrey Pond not only adds a scenic element but also provides a glimpse into the region's historical past as an 18th-century mill pond. It's an accessible and engaging option for those looking for a well-maintained trail with both natural and historical points of interest.

View route

9.

Cranbury Park loop from Cranbury Park

4.39km

01:11

50m

50m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

View route

10.

Pent Trail – Godfrey Trail and Godfrey Pond loop from Weston-Wilton Forest Reserve

11.5km

03:07

170m

160m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

View route

Sign up for free to see 5 more hikes around Weston.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

See every route on the map

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.

0

0

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.

0

0

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.

0

0

Frequently Asked Questions

How many hiking trails are available around Weston?

There are 17 hiking routes around Weston, offering a diverse range of experiences from easy walks to challenging long-distance hikes through forested areas and around reservoirs.

What are the different difficulty levels of hikes in Weston?

Weston offers a variety of hiking difficulties. There are 8 easy routes, 8 moderate routes, and 1 difficult route, catering to different fitness levels and preferences.

Are there any family-friendly hiking options in Weston?

Yes, Weston has several easy routes suitable for families. A great option is the Godfrey Trail and Godfrey Pond – Pent Trail loop from Weston-Wilton Forest Reserve, which is 3.5 miles long and leads through forest reserves and past Godfrey Pond.

What kind of landscapes can I expect to see while hiking in Weston?

Hiking in Weston is characterized by dense woodlands, reservoir paths, and varied forest ecosystems. You'll find trails winding through conservation lands, state parks, and nature preserves, often featuring wetlands and diverse natural environments.

Are there any circular hiking routes in Weston?

Yes, many of the trails in Weston are circular. For example, the Loop Trail – Devils Den Nature Preserve is a moderate 5.3-mile route that explores the natural features of the preserve in a loop.

What are some notable natural features or landmarks to look out for on the trails?

Hikers can enjoy views of the Saugatuck Reservoir and explore areas like the Devils Den Nature Preserve. You might also encounter Godfrey Pond along some routes.

What do other hikers enjoy most about hiking in Weston?

The hiking routes in Weston are highly rated by the komoot community, with an average score of 4.7 stars. Reviewers often praise the quiet woodlands, varied terrain, and the opportunity to explore natural preserves.

Are there any longer, more challenging hikes for experienced hikers?

Yes, for experienced hikers seeking a challenge, the Saugatuck Reservoir Loop – Trout Brook Valley State Park Preserve is a difficult 16.8-mile path offering extensive views around the reservoir and through the state park preserve.

What kind of wildlife can I expect to see while hiking in Weston?

Given the dense woodlands, wetlands, and nature preserves, hikers in Weston may encounter various local wildlife. The region's ecosystems support diverse flora and fauna, making it a great spot for nature observation.

Are there any trails that go past reservoirs or lakes?

Yes, several trails in Weston feature reservoirs and lakes. The Saugatuck Reservoir Loop offers extensive views of the Saugatuck Reservoir, and the Godfrey Trail passes by Godfrey Pond.

What is the typical elevation gain on hikes in Weston?

Elevations in Weston are generally moderate. While some trails include steeper sections, many routes have manageable elevation gains. For instance, the Loop Trail – Devils Den Nature Preserve has an elevation gain of about 102 meters.

Are there any historical sites or attractions near the hiking areas?

While the trails focus on natural beauty, nearby attractions include the Lockwood-Mathews Mansion Museum, offering a glimpse into local history and architecture.

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Hikes in other regions.

BotsfordSquantz Pond State ParkSail HarborShermanEast VillageBirchbank Mountain Open SpaceGlenvilleSouth WiltonPootatuck State ForestBogus HillBigelow CornersInglenookLakeside WoodsNewtownSandy HookCandlewood ShoresPoplar PlainsIndian Well State ParkSheltonHawleyvilleKellogg PointCandlewood IsleRock RidgePemberwickOronoqueBridgeportIndian FieldBranchvilleLong HillStepneyPlattsvilleColeytownDodgingtownKnollcrestRidgeburyBall PondTaylor CornersBrookfield CenterRocky Glen State Park Scenic ReserveTrumbull CenterRiversideCandlewood OrchardsCandlewood Lake ClubCandlewood KnollsTashuaWilton CenterDaniels FarmRidgefieldNoroton HeightsNew CanaanBethelDanburyWooster Mountain State ParkTopstoneNorwalkCos CobGreenwichRoute 7 GatewayTokenekePaugussett State ForestOld GreenwichMurrayMamanasco LakeByramMianus River State Park Scenic ReserveNorotonLakes WestLakes EastCannondaleGeorgetownDevils DenStamfordFairfield UniversitySouthportRedding CenterSeth Low Pierrepont State Park ReserveMill PlainPutnam Memorial State ParkStratford DowntownLordshipWest MountainOld HillStaplesWestport VillageGreens FarmsCompoDarien DowntownStewart B. Mckinney National Wildlife Refuge Sheffield Island UnitSaugatuckCollis P. Huntington State ParkTrout Brook Valley State Park Reserve
background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy