Loading...

Lake Windwing-Bennetts Pond-Pine Mountain Loop

6.8 Miles
Hard
2

Lookout/Views

Summits

Dogs (leashed)

The Lake Windwing-Bennetts Pond-Pine Mountain Loop hike at Bennett's Pond State Park near Ridgefield, Connecticut is a difficult 6.8-mile loop trail that features beautiful views.

This hike follows several trails through Bennett's Pond State Park and the surrounding public lands just west of the state park, where the hike begins.

This track begins alongside Lake Windwing and heads north while the trail straddles the base of a large hill. The trail will quickly bend to the east as it begins ascending this hill before the trail heads back downhill slightly. Just after the downhill section, around mile 1.3, the trail will head up a very steep mountain side along Pine Mountain.

Pine Mountain Overlook
Around mile 1.7, hikers will reach the top of Pine Mountain, which features a beautiful overlook of the neighboring hills and mountains. The vista can be found just after finishing the ascent up Pine Mountain from the west.

Continuing onward from the Pine Mountain Overlook hikers will reach an old stone chimney, around mile 1.9, that once belonged to a house.

After passing the old stone chimney, the trail will head downhill for approximately 1.5-miles before the trail enters the state park. Here, hikers will head back to parking while following some of the Bennett's Pond State Park trails -- mostly the green and white-blazed trails before the hike leaves the state park once again. Hikers will find a nice view of the Bennett Ponds / Bennett Lake around mile 4.1.

Bouldering Rock
The last noteworthy section of this trail is a massive boulder that lies just outside of the state park boundaries, closer to the parking area on the hike out. This large boulder can be found around mile 5.45 and is a great spot for bouldering.

Difficulty
This loop, for the majority of the hike, should be considered moderate. There are several steep climbs throughout the hike that make this hike difficult, especially for those who do not hike often.

Parking
Hikers will find a small parking turnout at the coordinates provided, located along N Shore Drive next to Lake Windwing.

Pets
Dogs are allowed if leashed and their waste must be carried out by the hiker.


View more trails near Ridgefield, CT

Hazards

Ticks - Lyme Disease More Info (CDC)
Poison Ivy/Oak

Surface Type

Dirt

Seasons

All

Get Directions


41.344266, -73.511326

Leave No Trace Partner

Loading...
Logo xs
MyHikes.org
Loading...
486 '

Total Change
1343 '

Ascent
1340 '

Descent
Download GPX with Waypoints
Note: Waypoints always include the parking location and trailhead. Campsites, waterfalls, and other points of interest are included in the GPX only if shown on the map.
Lake Windwing-Bennetts Pond-Pine Mountain Loop default picture

Photo Albums

Hiked it? Upload pictures from the trail

Find Hiking Trails Near Me:

Map of MyHikes trails in North America

1 Trip Report

Hiked it? Add a Trip Report
6.8 miles
Trail added
July 09, 2020
Updated on
October 02, 2020
Shop

Weather Forecast

In Ridgefield, CT

Explore Hiking Trails



Sign up with MyHikes today!

We're an independent hiking platform helping you find new trails to explore

Join for free

We use cookies to learn about our site usage. If your browser is set to do not track mode, we will not use statistics cookies. Learn more