Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Hikes
United States
Connecticut
Western Connecticut Planning Region

Sherman

The best walks and hikes around Sherman

5.0

(1)

39

hikers

16

hikes

Hikes around Sherman are characterized by dense woodlands, rolling hills, and routes that often incorporate sections of the Appalachian Trail. The landscape offers a mix of lakeside paths and more challenging forest treks with significant elevation changes. This network of Sherman hiking trails provides options for various ability levels, from easy loops to demanding long-distance hikes.

Best hiking trails around Sherman

  • The most popular hiking route is Nuclear Lake – West Mountain loop from Appalachian Trail, a 12.2 mile…

Last updated: June 23, 2026

6

hikers

#1.

Pootatuck State Forest Loop

6.55km

02:01

200m

240m

The Pootatuck State Forest Loop offers a tranquil escape into a landscape of rugged, wooded slopes and fascinating rock formations. As you hike, you'll traverse shaded paths, old charcoal-wagon roads,…

Navigate with device

Send to Phone

Save

Moderate

1

hikers

5.87km

01:37

100m

90m

The Cranberry Mountain Trail offers a delightful and varied hiking experience, winding through lush forests and crossing serene streams before opening up to panoramic views of the Hudson Valley. This…

Easy
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

2

hikers

The Pine Hill to Squantz Pond Loop offers a fantastic escape into a

Moderate

1

hikers

The Deer Pond Farm: Bobcat Loop offers an easy and engaging hike through a tapestry of meadows, wetlands, and woodlands, dotted with historic stone walls. You'll experience the diverse habitats…

Easy

Hike the moderate Quaker Lake via Appalachian Trail and Red Trail, covering 4.5 miles with 882 feet of elevation gain in Pawling Nature Rese

Moderate
Sign up for free to see 12 more hikes around Sherman.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Sherman

Road Cycling Routes around Sherman

Running Trails around Sherman

Gravel biking around Sherman

Cycling around Sherman

Frequently Asked Questions

Are there any easy, family-friendly hikes near Sherman?

Yes, there are several options for easier outings. For a shorter walk, consider the Squantz Pond State Park loop. It's a relatively flat 2.3-mile (3.8 km) trail that's great for a quick nature escape with the family.

I'm looking for a challenging, full-day hike. What do you recommend?

For a strenuous and rewarding day on the trail, the Gardner Hill – Tenmile Hill loop from Wingdale is an excellent choice. This 16.5-mile (26.6 km) route involves significant elevation gain and will take most of a day, offering a true test of endurance through the region's woodlands.

What is the hiking terrain like around Sherman?

The hiking is characterized by dense woodlands, rolling hills, and sections of the Appalachian Trail. You can expect a mix of lakeside paths and more rugged forest treks with notable changes in elevation. Trails are typically on natural surfaces with roots and rocks.

Are there any good loop trails available?

Absolutely. Many of the best routes are loops, so you can end your hike where you started without backtracking. A great moderate option is the Cats Rock loop from Appalachian Trail, which offers a varied experience over 6.4 miles (10.3 km).

Can I bring my dog on the trails?

In general, dogs are welcome on many trails in the area, but they must be kept on a leash. State parks and specific trail networks may have their own regulations, so it's always a good practice to check the rules for the specific park or preserve you plan to visit before you go.

What should I pack for a hike in this region?

For any hike, bring plenty of water and snacks. Sturdy hiking shoes with good grip are essential for the area's hilly and sometimes rocky terrain. We also recommend packing layers of clothing, as weather can change, along with a map or a fully charged phone with the route downloaded for navigation.

When is the best time of year to hike around Sherman?

Spring and autumn are fantastic times to hike here. Spring offers budding trees and pleasant temperatures, while autumn provides spectacular fall foliage and cooler weather. Summer can be hot and humid, so plan for early morning starts. Winter hiking is possible but requires proper gear for snow and ice.

How many hiking trails are there in the Sherman area?

There are a handful of curated, top-rated routes in this guide, but the broader area contains a much larger network of trails. Komoot users have explored and shared dozens of routes, showcasing the variety of hiking available.

What do other hikers enjoy most about the trails here?

The area is highly rated by the komoot community. Hikers often praise the serene woodland settings, the sense of immersion in nature, and the challenge provided by the rolling hills. Access to well-maintained sections of the famous Appalachian Trail is also a major highlight for many.

Are there any hikes that are particularly good for a workout?

Yes, if you're looking for a trail with significant climbing, the Tenmile Hill – Gardner Hill loop from Tenmile Hill is a great moderate choice. At 7.7 miles (12.5 km) with over 1,400 feet of elevation gain, it provides a solid workout through the woods.

Is parking generally available at the trailheads?

Most trailheads in this region are accessed by car and have designated parking areas. However, lots for popular trails, especially those on the Appalachian Trail, can fill up quickly on weekends. It's always a good idea to arrive early to secure a spot.

Most popular routes around Sherman

Easy hikes around Sherman

Most popular attractions around Sherman

Places to see

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 HarborEast 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 FarmRidgefieldWestonNoroton 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

Nearby adventure guides

Things to Do around Lakeside Woods

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