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Western Connecticut Planning Region

Sherman

Attractions and Places To See around Sherman - Top 6

Attractions and places to see around Sherman offer a range of experiences, from natural landscapes to historical sites. The region features several parks, lakes, and trails, providing opportunities for outdoor activities. Sherman's cultural and historical significance is reflected in its museums and preserved landmarks. Visitors can explore both natural features and points of interest within the city and its surroundings.

Best attractions and places to see around Sherman

  • The most popular attractions is River Trail, a viewpoint that is…

Last updated: July 6, 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 …

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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.

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Tracy Road Gravel Route

Highlight (Segment) • Trail

Well kept and secluded gravel road

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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.

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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.

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Popular around Sherman

Hiking around Sherman

Road Cycling Routes around Sherman

Running Trails around Sherman

Gravel biking around Sherman

Cycling around Sherman

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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.

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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.

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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.

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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.

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Douglas Nadig
September 26, 2021, Harrybrooke Park

on exit path from park.

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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.

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Well kept and secluded gravel road

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Frequently Asked Questions

What natural features can I explore around Sherman?

Sherman offers several natural attractions. You can visit Squantz Pond State Park, which spans 172 acres along Squantz Pond, offering opportunities for boating, swimming, fishing, and hiking. Another option is Harrybrooke Park, a hidden gem near the river with lovely surroundings.

Are there family-friendly attractions in the Sherman area?

Yes, several attractions are suitable for families. Squantz Pond State Park is family-friendly, offering swimming, boating, and hiking. River Trail is also noted as family-friendly, perfect for a leisurely bike ride. Additionally, Harrybrooke Park provides a pleasant environment for all ages.

Where can I go for outdoor activities like biking or running near Sherman?

For biking, the River Trail is a well-maintained dirt road suitable for cycling, especially in autumn. If you prefer gravel, the Tracy Road Gravel Route offers a secluded forest ride, best for mountain or gravel bikes. For more options, you can explore various routes for gravel biking, road cycling, and running around Sherman.

What kind of views can I expect from the attractions around Sherman?

You can enjoy picturesque views of steep, forested slopes reflected in the clear blue waters of Squantz Pond State Park. The River Trail offers excellent views of the Housatonic River, particularly vibrant during autumn. Additionally, Squantz Pond itself provides fantastic views over its large body of water from CT-39.

Are there any historical sites to visit in the Sherman area?

While the primary attractions focus on natural beauty and outdoor activities, Harrybrooke Park is home to the Historic Harden House Museum, which is open to visitors, offering a glimpse into local history.

What activities are available at Squantz Pond State Park?

Squantz Pond State Park provides ample opportunities for recreational activities such as boating, swimming, fishing, hiking, and enjoying the fall foliage. It's a beautiful spot to spend time outdoors.

What is the best way to experience the River Trail?

The River Trail is a well-maintained dirt road that is great for biking. It offers excellent views of the Housatonic River, especially in the autumn when the fall leaves transform the trail into a scenic route.

What kind of terrain does the Tracy Road Gravel Route offer?

The Tracy Road Gravel Route is a secluded gravel trail through the forest. It's recommended for mountain or gravel bikes due to its terrain, providing a quiet and very rideable experience.

What do visitors enjoy most about the attractions around Sherman?

Visitors appreciate the picturesque views, especially the steep, forested slopes reflected in the clear waters of Squantz Pond State Park. The well-maintained trails like the River Trail are popular for their scenic beauty, particularly during autumn. The quiet and rideable forest roads, such as the Tracy Road Gravel Route, are also highly enjoyed by cyclists.

Are there opportunities for water-based activities near Sherman?

Yes, Squantz Pond State Park, located on the shore of Squantz Pond, offers boating, swimming, and fishing. The pond itself is a large body of water ideal for various water activities.

Can I find trails for different difficulty levels around Sherman?

Yes, for example, the Tracy Road Gravel Route is categorized as intermediate, suitable for mountain or gravel bikes. You can find a range of trails for running, gravel biking, and road cycling, with varying distances and difficulty grades to suit different preferences.

What is unique about Harrybrooke Park?

Harrybrooke Park is considered a hidden gem, set in an ideal location near the river. Beyond its natural beauty, it also features the Historic Harden House Museum, adding a cultural and historical dimension to your visit.

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