This section of the New England Trail in Northern Connecticut gives you a lot of "bang for your buck" with numerous stunning views as it traverses the rolling Metacomet ridge line. The terrain is relatively easy for most of the hike, with the only notable change in elevation on the ascent/descent from Peak Mountain to Route 20.
You can expect to see some crowds from the Route 20 intersection up to Peak Mountain, which many people do as an out-and-back, but the remainder of this section is much more lightly trafficked. Avoid the crowds by doing this hike on a weekday or in the winter months if the weather permits.
This section of trail also passes the Windsor Locks Scouts Primitive Tentsite, which has room for up to 5 tents. There is no privy at the site, but there is a water cache provided by local volunteers. More information on the site can be found at the New England Trail website.
To do this hike as a point-to-point, you will need to set up a car shuttle. There is room on the shoulder of Newgate Road right by its intersection with Route 20 for about 6 cars, though this area can fill up on sunny weekends in the summer months. There is also room for about 3-4 cars on Watertown Road (Route 168) near the intersection with Phelps Road. There are no fees for parking or hiking on this section.
This hike is easy enough for most children, though there are a couple spots where the trail traverses rocky ledges that present a falling hazard. Be sure to closely supervise children and pets in these areas.
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