Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Hikes
United States
Connecticut
Western Connecticut Planning Region

Lakeside Woods

The best walks and hikes around Lakeside Woods

5.0

(1)

49

hikers

17

hikes

Hiking around Lakeside Woods offers diverse terrain within a 140-acre wilderness area characterized by wooded and rugged hill country. Trails provide scenic views of Lake Taneycomo and wind along bluffs. The region features a mix of natural elements, including wetlands near the lake and varied elevations.

Best hiking trails around Lakeside Woods

  • The most popular hiking route is Pootatuck State Forest Loop, a 4.1 miles (6.6 km) trail that takes 2 hours 1 minute to complete. This moderate route navigates through varied forest landscapes.
  • Another top favourite among local hikers is Cranberry Mountain Trail, an easy 3.6 miles (5.9 km) path. This trail offers accessible paths through natural surroundings.
  • Local hikers also love the Pine Hill to Squantz Pond Loop, a 4.3 miles (6.9 km) trail leading through wooded areas, often completed in about 2 hours 5 minutes.
  • Hiking around Lakeside Woods is defined by wooded hill country, bluffs, and views of Lake Taneycomo. The network offers options for various ability levels, from easy paths to more challenging routes.
  • The routes in Lakeside Woods are highly rated by the komoot community with an average score of 5.0 stars from 1 review. More than 50 hikers have used komoot to explore Lakeside Woods's varied terrain.

Last updated: June 28, 2026

6

hikers

#1.

Pootatuck State Forest Loop

6.55km

02:01

200m

240m

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

Navigate with device

Send to Phone

Save

Moderate

2

hikers

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

Moderate
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

1

hikers

5.87km

01:37

100m

90m

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

Easy

1

hikers

2.79km

00:46

50m

50m

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

Easy

1

hikers

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

Easy
Sign up for free to see 13 more hikes around Lakeside Woods.

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 Lakeside Woods

Gravel biking around Lakeside Woods

Running Trails around Lakeside Woods

Road Cycling Routes around Lakeside Woods

Cycling around Lakeside Woods

Frequently Asked Questions

What kind of terrain and natural features can I expect while hiking in Lakeside Woods?

Lakeside Woods offers a diverse landscape of 140 acres, featuring wooded and rugged hill country. You'll find trails winding along bluffs, providing scenic views of Lake Taneycomo. The area also boasts unique natural elements like wetlands near the lake, and some trails may lead you past a waterfall, caves, and grottoes, though the waterfall's flow can depend on recent rainfall.

Are there hiking trails suitable for all skill levels in Lakeside Woods?

Yes, Lakeside Woods provides a variety of trails catering to different fitness levels. The area has 15 hiking routes in total, with 8 classified as easy, 5 as moderate, and 2 as difficult. For an accessible path through natural surroundings, consider the easy Cranberry Mountain Trail.

What historical sites or unique structures can I discover along the trails?

Hikers can explore several interesting historical and man-made features. Along the Bluff Trail, you'll find the site of the historic Owen Homestead, dating back to 1911. A significant attraction is a set of 315 man-made stone steps, laid between 1937 and 1938, that lead down towards Lake Taneycomo. The property also features almost 2,000 feet of hand-built stone walls, showcasing historical craftsmanship.

Where can I find the best scenic views of Lake Taneycomo?

Many trails offer glimpses of Lake Taneycomo, but for particularly stunning vistas, look for points along the bluffs. There are also covered pavilions with stone columns that serve as picnic areas with beautiful lake views. Specifically, an overlook at the farthest point south of the Ridge Trail is known for providing excellent lake views.

Are there any circular hiking routes in Lakeside Woods?

Yes, Lakeside Woods features several circular routes. A popular option is the Pootatuck State Forest Loop, a moderate 4.1-mile trail that navigates through varied forest landscapes. Another well-liked circular path is the Pine Hill to Squantz Pond Loop, which is 4.3 miles long and leads through wooded areas.

What do other hikers say about their experience in Lakeside Woods?

The hiking routes in Lakeside Woods are highly regarded by the komoot community, holding an average score of 5.0 stars from 1 review. Over 50 hikers have used komoot to explore the varied terrain, often praising the diverse landscapes and well-maintained paths that offer a refreshing escape.

Are there family-friendly hiking options and facilities?

Yes, Lakeside Woods is considered family-friendly. Near the entrance, you'll find a nature playground and a pavilion, perfect for younger visitors. Many of the 8 easy trails are suitable for families, such as the Lillinonah Loop, which is a shorter, easy hike.

Is there parking available at Lakeside Woods?

While specific parking details for each trailhead are best checked on individual route pages, Lakeside Forest Wilderness Area generally provides parking facilities for visitors accessing its extensive trail system. It's advisable to check local signage upon arrival for designated parking areas.

What other attractions are near the hiking trails in Lakeside Woods?

Beyond the trails themselves, there are several points of interest in the vicinity. You can visit Squantz Pond State Park or enjoy the serene waters of Squantz Pond. For more natural beauty, Harrybrooke Park offers additional forest exploration.

Are dogs allowed on the hiking trails in Lakeside Woods?

Lakeside Forest Wilderness Area is generally dog-friendly, allowing leashed dogs on its trails. It's always a good idea to check for any specific signage at the trailhead regarding pet regulations, but in general, your canine companion can join you on your hike.

What is the total length of hiking trails available in Lakeside Woods?

Lakeside Forest Wilderness Area boasts an extensive trail system, offering a total of 5.3 miles (approximately 8.5 kilometers) of hiking trails for visitors to explore. These trails are spread across the 140-acre wilderness area, providing ample opportunities for outdoor activity.

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

Yes, for those seeking a more strenuous experience, Lakeside Woods offers a couple of difficult routes. While specific names for these difficult trails are not detailed here, the overall network includes options with significant elevation changes and rugged terrain to challenge experienced hikers. For a moderate challenge, consider the Pootatuck State Forest Loop with its varied forest landscapes and elevation changes.

Most popular routes around Lakeside Woods

Easy hikes around Lakeside Woods

Most popular attractions around Lakeside Woods

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 HarborShermanEast VillageBirchbank Mountain Open SpaceGlenvilleSouth WiltonPootatuck State ForestBogus HillBigelow CornersInglenookNewtownSandy 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 Sherman

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