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Trail List

Alice Newton Street Memorial Park

Easy Walk to Moderate Hike

The Blue Trail is a remnant of the Old Naugatuck Trail. Dirt trail and gravel areas are prominent. Most of the trails have some land bridges or boardwalk crossings. 

Total distance of all trails is approximately 4.5. miles.


7 Meetinghouse Lane

Park behind the church’s meeting house.

Bishop Estate East & Darling House Trails

Blue and Blue/Yellow Trail: 0.64miles. Hard Hike/ Difficult Climb. The blue trail starts off on a gentle slope through RWA land and ascends up over the mountain. About 0.25 miles climb up rocky terrain almost 300 ft. Red Trail: 1 mile. Easy Hike. Minor slopes. Can be both wet and dry.

Total distance of all trails is approximately 2.43 miles.


1907 Litchfield Turnpike

Park in the field adjacent to the historic Darling House.  

Bishop West 

Easy Hike The Bishop West Trail has a slow rise in elevation. The trail twists and turns through hemlocks and mountain laurel. Mostly a high and dry hike. Total Trails Length: Approx. 1.3 miles.


1907 Litchfield Turnpike

Park in the field adjescent to the historic Darling House.

Bladen’s Brook, Russell Swamp Road & Round Hill Trails

Easy or Difficult hike

The Bladen’s Brook and Russell Swamp trails are a leisurely hike. The Round Hill trail, alternatively, offers more of a challenge. Total Trails Length: Approx. 1.4 mile


Parking lot on Route 67.

The parking lot is directly on Route 67.

Elderslie Preserve Trail System

Easy to Hard Hike The trail system at Elderslie Preserve offers a varying degree of difficulty. The Red trail is an easy walk, the Yellow trail is a moderate hike, the Orange trail is a hard hike and the Blue trail begins as an easy hike in the south and becomes more difficult. Total trails distance is approx. 3.75 miles


Parking lot entrance on Peck Hill Road.

The lot entrance is difficult to spot.

Fitzgerald Tract Trails

Easy Hike

The Fitzgerald Tract Trails are an easy walk through and around the Woodbridge Community Gardens. There are two surrounding trails that one can extend their hike on if they wish. Total trails distance is approx. 2.5 miles


Parking lot on Beecher Road.

Historic Indian Trails Park Lane Area

Moderate to Hard Hikes on White, Blue, Red, and Yellow Trails

The trails lead north through historic Indian Lands. Many arrowheads, spearpoints, and artifacts have been found here. It is believed that there is an Indian burial ground somewhere in the vicinity. Total trails distance is approx. 2.5 miles


On-street parking along Park Lane.

Massaro Community Farm Nature Trail

Easy Hike The Nature Trail has two loops (pink and blue). The trail guides are generally posted at the farm information map located in the parking area, and the trailhead.


41 Ford Road

Park in the parking area provided between the house and the dairy barn. Overflow parking is available along Ford St, perpendicular to the farm house. Respect farm manager’s residential privacy.

Meadows Tract to Fitzgerald Tract

Easy walk to Moderate Hike.

The trail runs along a paved road at the northern and through some wet river areas to some waterfalls. Continues through Alice Newton Street Memorial Park (Private) owned by the Woodbridge Park Association into some town owned land where these is a pavillion as well as Kimberly and Sandra Hitchcock Memorial Playground, a small children play park. Trail length is approx. 2.0 miles


Park in the town center.

There are multiple trail heads but its easiest to park in the town center to access these trails.

Newton Road Park Trail System

Hard Hike

90% of the hiking grounds are wetlands and some of the river crossings have no bridges. Boots are recommended. Total trails distance is approx. 1.0 miles


On-street parking on Hampton Dr.

Racebrook Estates Blue Trail System

Moderate Hike

The trail winds through residential development with 28’ corridor, some open space, across race brook stream, to another paved road to powerlines. Connects with Indian Trails. Can be wet in some areas. Total trail length is approx. 0.75 miles


Park at the Fitzgerald Tract.

With multiple trail heads the best parking is at the Fitzgerald tract.

Racebrook Tract

Easy Hike

One of the largest open space sites is the Racebrook Tract with 230 acres in Orange and 181 acres in Woodbridge. Four blazed trails meander across fairly level land, passing through mixed hardwoods and impressive stands of white pines. A handicapped accessible trail leads from the northeast corner of the parking area. The paved asphalt trail slopes to a boardwalk that makes a loop over the wetlands within the brooks floodplain. Total trails distance is approx. 3.61 miles


Parking in Woodbridge at the end of Clearview Rd.

Alternatively, park in the main lot in Orange and hike to the Woodbridge sections.

Regional Water Authority Trails

Regional Water Authority “RWA” trails require the purchase of an RWA Recreation Permit. Those can be purchased here.

Amity Road to Dillon Road

Easy to Moderate Hike

The RWA land that falls Amity Road (Route 63) and Dillon Road in Woodbridge offers easy to moderate hiking difficulties along with a connection to Lake Chamberlain Trails. Total trail length is approx. 1.89 miles.


Roadside parking on Dillon Road or the nearby Blue Trail Dr.

Lake Chamberlain

Wide Range of Trail Difficulties

A Regional Water Authority (RWA) Recreation Area. The West River and its tributary, the Sargent River, flow through the valley west of West Rock Ridge. Five reservoirs were created between 1889 and 1925 on these rivers to form the West River water supply system. Originally constructed in 1890, Lake Chamberlain was enlarged in 1958 to over five times its original size. Total trail distance is approx. 7.5 miles

Trailhead Address

Gated parking lot near the intersection of Sperry Road and Morris Road.

Pine Hill Trails

Easy Hike

Hike, jog or cross country ski the Regional Water Authority’s Pine Hill Trail System. You will find varied terrain and features: Seasonally wet to rocky and steep to relatively flat. You will traverse through mixed aged forests ranging from wetland species to dry ridge species. There is evidence of past agricultural use and timber and fuel harvesting. Total trails length is approx. 3.31miles

Trailhead Address

Park at the end of Hemlock Hollow Road.