Bennett's Pond is part of the Connecticut State Park System. Together with Ridgefield's Hemlock Hills, Pine Mountain, and Lake Windwing [Ridgefield Open Space Association (ROSA)], it forms one of the largest nature preserves in the Southwest portion of the state. Glacial activity has left numerous erratic boulders and small cliffs throughout the area. Featuring a wide variety of terrain it's a picturesque place and any ride here is bound to be memorable.

The area consists of meadows, woodlands, wetlands, and steep ridges all traversed by great trails of varying difficulty. The ride down to the pond is an easy and fast downhill but as you go north into Pine Mountain or further west into Hemlock Hills, the terrain can be challenging. Trails feature twisty tight single track along rock-strewn ridges; there's even a massive slick rock section. With some hike-a-bike in the northern reaches—Bennetts is still a diamond in the rough but an awesome park to explore.

 

About the Landscape

Connecting Wooster Mountain State Park and Ridgefield's Hemlock Hill/Pine Mountain/Lake Windwing Open Spaces, the Bennett’s Pond area provides a large undeveloped habitat for a wide variety of wildlife and has inspired visitors for countless years.

The land on the north side of Bennett’s Pond slopes sharply upward, rising to become Wooster Mountain on the Ridgefield-Danbury town line. The 70-acre Bennetts Pond area is in the headwaters of the Saugatuck River, a vital watershed that supplies the drinking water for a good portion of lower Fairfield County.

 

Historical Spots of Interest

The Bennetts Pond/Pine Mountain area shares a unique and colorful history.

• In the early days it was home to the Outpost Nurseries (one of the largest nurseries operating on the east coast);

• Visible in the south end of the State Park are the remnants of Colonel Conley's mansion, later transformed into "The Fox Hill Inn."

• Up on Pine Mountain. a chimney still stands, all that remains of Charles Ives' get-away shanty.

This picturesque area was acquired by the Town of Ridgefield in order to protect the land from inappropriate development and environmental damage. Preserved as both an "open space" and set aside as a State Park, this mosaic of meadows, woodlands, wetlands, and steep ridges is a unique and beautiful environment. Its rocky slopes, open fields, historical ruins, and abundant wildfire make any visit an adventure to remember.