Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Places to see
North America
United States
Connecticut
Western Connecticut Planning Region

Lakeside Woods

Attractions and Places To See around Lakeside Woods - Top 5

Best attractions and places to see around Lakeside Woods include a variety of natural features and trails. This region offers diverse landscapes, from serene lakes and ponds to forested areas and river views. Visitors can explore a mix of natural parks, historical sites, and well-maintained routes suitable for various outdoor activities. The area provides opportunities to experience both tranquil natural settings and accessible trails.

Best attractions and places to see around Lakeside Woods

  • The most popular attractions is River Trail

Last updated: July 8, 2026

Squantz Pond State Park

Highlight • Lake

Squantz Pond State Park offers a picturesque view of the steep, forested slopes beautifully reflected in the clear blue waters of the pond. The park spans 172 acres along the …

Tip by

See rides here

Send to Phone

Save

River Trail

Highlight • Viewpoint

This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.

Tip by

Save

Sign up now to discover places like this

Get recommendations on the best single tracks, peaks, & plenty of other exciting outdoor places.

Sign up for free

Tracy Road Gravel Route

Highlight (Segment) • Trail

Well kept and secluded gravel road

Tip by

Save

Harrybrooke Park

Highlight • Forest

Harrybrooke Park is a hidden gem in an ideal setting near the river. In addition to the lovely surroundings the the Historic Harden House Museum is open to visitors.

Tip by

Save

Squantz Pond

Highlight • Lake

Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.

Tip by

Save

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Lakeside Woods

Hiking around Lakeside Woods

Gravel biking around Lakeside Woods

Running Trails around Lakeside Woods

Road Cycling Routes around Lakeside Woods

Cycling around Lakeside Woods

Tips from the Community

Zachary
September 26, 2024, View of the Housatonic River

This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.

0

0

Andrus
February 25, 2024, Harrybrooke Park

Harrybrooke Park is a hidden gem in an ideal setting near the river. In addition to the lovely surroundings the the Historic Harden House Museum is open to visitors.

1

0

Jamie S.
February 20, 2024, Squantz Pond

Squantz Pond is a 288-acre lake in Fairfield County, Connecticut on the town line of Sherman and New Fairfield. As you ride on CT-39, you get fantastic views over this large body of water.

0

0

Sue
February 8, 2024, Squantz Pond State Park

Squantz Pond State Park offers a picturesque view of the steep, forested slopes beautifully reflected in the clear blue waters of the pond. The park spans 172 acres along the shore of Squantz Pond, a natural lake connected to Candlewood Lake. It is one of the few public spaces in the 75-mile shoreline, which is mostly privately owned. The park provides ample opportunities for recreational activities such as boating, swimming, fishing, hiking, and enjoying the fall foliage.

1

0

Douglas Nadig
September 26, 2021, Harrybrooke Park

on exit path from park.

0

0

quiet and very rideable forrest road. MTB or Gravel bike recommended. You could do it on a road bike (28mm tires) too but probably less great of an experience.

0

0

Well kept and secluded gravel road

0

0

Frequently Asked Questions

What natural features can I explore around Lakeside Woods?

The region is rich in natural beauty, featuring serene lakes, rivers, and extensive forested areas. You can visit Squantz Pond State Park, which offers picturesque views of forested slopes reflected in clear waters, or enjoy the expansive Squantz Pond itself. The River Trail provides excellent views of the Housatonic River.

Are there family-friendly attractions in the Lakeside Woods area?

Yes, several attractions are suitable for families. Squantz Pond State Park and Squantz Pond are both family-friendly, offering opportunities for swimming, boating, and enjoying the outdoors. Harrybrooke Park is another great option, featuring lovely surroundings and the Historic Harden House Museum.

What historical sites can I visit around Lakeside Woods?

For a touch of history, explore Harrybrooke Park, which is a historical site near the river. Within the park, you'll find the Historic Harden House Museum, which is open to visitors and offers cultural insight into the area.

What kind of trails are available for biking in Lakeside Woods?

Lakeside Woods offers diverse biking trails. The River Trail is a well-maintained dirt road perfect for biking, especially during autumn for fall foliage views. For those seeking a more challenging ride, the Tracy Road Gravel Route is an intermediate, secluded gravel road highly recommended for mountain or gravel bikes. You can find more options for gravel biking at Gravel biking around Lakeside Woods.

Where can I go hiking near Lakeside Woods attractions?

There are numerous hiking opportunities. Squantz Pond State Park offers trails for hiking amidst beautiful scenery. For a wider selection of routes, you can explore guides like Easy hikes around Lakeside Woods, which includes trails like Cranberry Mountain Trail and Lillinonah Loop, or the general Hiking around Lakeside Woods guide for routes such as Pootatuck State Forest Loop.

What are the best viewpoints in Lakeside Woods?

For stunning vistas, visit the River Trail, which provides excellent views of the Housatonic River. Squantz Pond State Park and Squantz Pond also offer picturesque views of the water and surrounding forested slopes.

What is the best time to visit Lakeside Woods for outdoor activities?

Autumn is particularly recommended for visiting Lakeside Woods, especially for activities like biking on the River Trail, when the fall foliage transforms the landscape. The clear waters and forested slopes of Squantz Pond State Park are also beautiful during this season.

Are there opportunities for water activities around Lakeside Woods?

Yes, Squantz Pond State Park and Squantz Pond are excellent for water-based recreation. You can enjoy boating, swimming, and fishing in the clear waters of Squantz Pond, which is a natural lake connected to Candlewood Lake.

What do visitors enjoy most about the attractions in Lakeside Woods?

Visitors appreciate the diverse natural landscapes, from serene lakes and ponds to forested areas and river views. The well-maintained trails, such as the River Trail, are popular for biking and enjoying the scenery, especially the fall foliage. The peaceful and secluded nature of routes like the Tracy Road Gravel Route is also highly valued.

Are there any hidden gems to discover in the Lakeside Woods area?

Yes, Harrybrooke Park is considered a hidden gem, offering a beautiful setting near the river and the Historic Harden House Museum. Its tranquil surroundings make it a delightful spot to explore.

What kind of terrain can I expect on trails in Lakeside Woods?

The trails around Lakeside Woods offer varied terrain. You'll find well-maintained dirt roads like the River Trail, suitable for comfortable biking. For gravel enthusiasts, the Tracy Road Gravel Route features a quiet and rideable gravel surface. Hiking trails can range from easy paths to more moderate routes, often winding through forested areas and offering scenic views.

Most popular routes around Lakeside Woods

Hiking around Lakeside Woods

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

Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:

RidgefieldDanburyRidgeburyLakes EastStamfordMamanasco LakeNorwalkWest MountainLakes WestRoute 7 GatewayTopstoneTokenekeSouth WiltonBethelDarien DowntownWestonRock RidgeGlenvilleStaplesNorotonColeytownOld HillWestport VillageNoroton HeightsNew CanaanSaugatuckBranchvilleRiversideCos CobOld GreenwichRedding CenterWilton CenterPemberwickByramGreenwichGeorgetownPoplar PlainsIndian FieldCompoSheltonGreens FarmsCannondaleBridgeportOronoqueSouthportTrumbull CenterMurrayStratford DowntownFairfield UniversityLordshipPlattsvilleMill PlainDodgingtownTashuaStepneyDaniels FarmLong HillEast VillageHawleyvilleSandy HookBotsfordNewtownShermanBrookfield CenterCandlewood IsleSail HarborInglenookTaylor CornersBogus Hill

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