Letterbox Planted:    September 4, 2002

Last Updated:             February 04, 2024

Length:                       Berkshire Spur Trail (Bridgeport); 2.1 miles

                                     Pequonnock River Trail; 11.8 miles

                                     Trumbull Memorial Walkway; 0.9 miles

Difficulty:                   Berkshire Spur Trail; Easy. Paved trail and wide sidewalk.

                                     Pequonnock River Trail; Easy. Flat rail trail w/stone-dust, paved and hard packed gravel sections. Three short on-road sections.

                                     Trumbull Memorial Walkway; Moderate. Narrow paved trail with a slight hill.


To start from Glenwood Park in Bridgeport [Southern End]; From Routes 8/25 take exit 5 to Chopsey Hill Rd and travel south over the river to Glenwood Ave. Head left on Glenwood Ave and quickly turn left into the Park. [You may also park in Beardsley Park, just up Glenwood Ave,  however there is a Fee

To start Twin Brooks Park in Trumbull [Southern Section]; From Route 15 westbound (Merritt Pkwy) take exit 50 to Route 127 and head right. Travel 0.4 miles and turn right into Twin Brooks Park. Follow to the first parking lot. Trail begins to your left. For Route 15 eastbound take exit 51, then get back on Route 15 westbound and follow directions above. Parking for residents only. 

To start from the Tait Road parking lot in Trumbull [Center Section]; Take exit 49 off of Route 15 (Merritt Parkway) to Route 25 north. Take exit 9 and go left on Daniels Farm Rd to Route 127. Take a right onto Route 127 and turn right again at the second entrance onto Tait Rd. There is a long parking area along the right side. The trail starts on the left.

To start from the Whitney Avenue parking lot in Trumbull [Center Section]; Take exit 49 off of Route 15 (Merritt Parkway) to Route 25 north. Take this divided expressway to a traffic light at the intersection of Route 111. Go left onto Route 111 south for 0.7 miles and turn left onto Whitney Ave. The parking lot will be on your right less then a mile down. The entrance is directly across from a white sign that reads "Parlor Rock", on the left side of the road.

To start from Old Mine Park in Trumbull [Center Section]; Take exit 49 off of Route 15 (Merritt Parkway) to Route 25 north. When the expressway ends, turn right on Route 111, then right on Old Mine Rd into the park. Parking for residents only. 

To start from Wolfe Park in Monroe [Northern Section]; Take exit 49 off of Route 15 (Merritt Parkway) to Route 25 north. Route 25 starts out as a divided highway until it crosses Route 111. Keep an eye out for the Monroe town line. Past this point watch for a right turn onto Mill St. Take this curving road to Maple Drive and then a right onto Hill Rd. You'll see a sign for the park and the road on your left. There is a Park Gate House at the entrance. NOTE: From Memorial Day to Labor Day there is an entrance fee. You may park just down the entrance road on your right at the Great Hollow Lake parking lot or if full, continue on down to the parking lots near the beach. This is a pretty impressive park with a beach, pool, playgrounds, athletic fields, tennis courts and hiking trails. Note; no bikes allowed on the park trails

To start from Cutlers Farm Road parking lot in Monroe [Northern End];  Take exit 49 off of Route 15 (Merritt Parkway) to Route 25 north. Where the divided highway ends, continue on Route 25 for 3 miles to the Village of Upper Stepney. Turn right onto Green St, which then turns into Pepper St and go 1 mile to a right hand turn onto Cutlers Farm Rd. The parking lot is on your left down a gravel road.

The Pequonnock River Trail (formally known as the  Housatonic Rail Trail) generally follows the path of the abandoned Housatonic Railway corridor and runs parallel to the Pequonnock River. It starts in Downtown Bridgeport, although the plan is to extend the trail South to Seaside Park along Long Island Sound. It travels North through Beardsley Park into Trumbull, across Route 15 (Merritt Parkway), into Twin Brooks Park, through the Pequonnock River Valley and into Monroe, where it follows the old rail bed through Wolfe Park to the Newtown town line. The trail starts out along the Berkshire Spur Trail in Bridgeport before connecting to the Pequonnock River Trail at Beardsley Park. A gap currently exists in Trumbull from Twin Brooks Park to Tait Rd. The trail then continues from Tait Rd North through Wolfe Park in Monroe, to the Newton town line. For more information visit; PEQUONNOCK RIVER VALLEY

The Housatonic Rail Bed originated in 1840 as the Berkshire Railroad linking Bridgeport and New Milford. It was later purchased by the Housatonic Railroad and later became part of the New York, New Haven and Hartford Railroad. It was abandoned in 1962. 


Starting from Barnum Blvd East parking lot in Bridgeport; I haven't checked out this section yet.


Starting from Fairfield Ave/Strafford Ave/Water St in Bridgeport [Southern End]; The Berkshire Spur Trail begins next to the Bridgeport Transportation Center. This urban trail travels North along the Eastern Side of Water St as a widened sidewalk before becoming paved as it travels alongside Housatonic Ave and out to North Ave at 1.3 miles.

Note; Several options are under study for connecting the trail through downtown from Housatonic Ave to Beardsley Park. I direct you along the shortest route with off road options.

A cross-light takes you over Lindley St (old Berkshire Spur continued straight) and alongside North Ave where the trail eventually changes from paved to wide sidewalk. Cross Island Brook Ave before coming to Boston Ave. You'll need to head left to access a cross-light over to Glenwood Ave. Continue North on-road along Glenwood Ave, passing by the entrance to Glenwood Park parking lot at 1.9 miles. Spot a dam on Pequonnock River creating Bunnells Pond on your left.  Here the road is residential with a slight hill. Come to the start of the paved Pequonnock River Trail after 2.1 miles

For information on completing the trail from Beardsley Park to Seaside Park See; BRIDGEPORT EXTENSION STUDY; 2018 .


Starting from Glenwood Road & Crown Street at Beardsley Park [Southern End]; The paved Pequonnock River Trail travels North and enters the Southern border of Beardsley Park. Spot a stone pedestrian bridge on your left next to the pond. The trail parallels the park road passing by BEARDSLEY ZOO at 2.3 miles. Nice promenade overlooking the pond. Head down a slight hill where you come alongside the river. Travel past a play ground and ball fields before exiting the park and traveling underneath Route 8 at 3.3 miles as you cross into Trumbull. Pass by an out of place stone castle feature before crossing a bridge over the river where you'll find a Map Board. You then come to the Quarry Road parking lot at 3.6 miles. The trail then takes you up a slight hill alongside Quarry Rd, then into the woods and underneath an on-ramp for Route 15. An old RR bridge takes you over Route 15, followed by another tunnel underneath an off-ramp and out to Rocky Hill Rd. Short on-road (residential) section out to Route 127 where the paved trail continues left to a cross-light over Route 127. This brings you to a small Vietnam Veterans Memorial Park. Go around this memorial to a narrow wooden bridge/boardwalk across the Pequonnock River to an intersection in Twin Brooks Park

Note; Right leads to a playground.

Head left along the paved trail. This leads to another intersection at 5.1 miles. 

Note; Right leads past some restrooms to Twin Brooks Park parking lot.

Head left crossing a causeway with a pond on your right and come to a third intersection.

Note; Right, Northeast, takes you along the paved Trumbull Memorial Walkway past the pond and over a stone bridge to Twin Brooks Dr. Head left along a narrow paved trail that passes by a parking lot a gazebo as it parallels the road. Pass by a second parking lot where the trail winds through the woods uphill. After 0.9 miles the trail ends at Old Dike Rd. 

Head left up a slight hill where the trail winds through the woods and alongside the Pequonnock River. Travel West underneath Route 25 where the trail ends at Manor Drive at 5.5 miles.

Note; To connect to the next section requires an 0.7 mile on-road (residential) detour. Follow Manor Drive West and take your first right on Gregory Pl. Turn left on Laurel St and follow to Daniels Farm Rd. Head left (sidewalk available along with wide shoulders) out to Route 127. Cross Daniels Farm Rd where a sidewalk quickly brings you to Tait Rd. Head right and you'll come to the Tait Road parking area after 6.2 miles.

From the Tait Road parking area in Trumbull; [Continuing Mileage] A short paved path leads up to a Map Board where the hard packed stone-dust trail begins. The trail starts off traveling North through a residential corridor before heading into the woods. This section is well shaded as it follows a shelf of land along a steep slope of trap rock to your left and the Pequonnock River below to your right. The river has some very scenic rocky chasms and small rapids. You'll pass a wooden 0.5 Mile Marker on your right. There are also Mile Markers stamped on the back rest of the benches along the left side of the trail. You come to a Map Board just before the Whitney Avenue parking lot at 4.6 miles. The trail then crosses Whitney Ave where it is now paved. A sign indicates your entering Parlor Rock Park. This was the site of a late-1800's amusement park built by the railroad to attract passengers. There is a path just up the trail that will take you to a nice overlook of a rock gorge on the river. An old dam was also here, which now forms a small waterfall. Worth the quick side trip. The trail pulls away from the original rail bed that got swallowed up by Route 25 and winds up through the woods to a boardwalk alongside the river that will take you underneath Route 25. Next you'll come to the Old Mine Park parking lot at 5.5 miles. This is the site of an old tungsten mine that was operated by the American Tungsten Mining & Milling Company from 1899-1906. Remnants of the operation are still visible along the parks hiking trails. There are picnic tables, a pavilion, Map Board and a small pond the river flows through here. The trail continues straight following the entrance road out to Route 111 where a cross-light gets you over this busy road. At 6.1 miles the trail splits. 

Note; Straight is just a Spur Trail out to Main St (Route 25). 

Continue right up the small hill along the "Spring Hill Road Trail Route" where you'll wind through the woods and out to Spring Hill Rd. Continue straight across the road and past a gate where the trail continues alongside the river. The trail turns to hard packed gravel at 6.6 miles and takes you around a small pond as you cross into Monroe. When you come to Victoria Dr turn left and cross the bridge. The trail continues on your right. After crossing over a wooden bridge follow a narrow dirt path out to Maple Drive at 7.3 miles. 

Note; A short on-road detour is required. Turn right along Maple Drive (low traffic residential road). You'll pass by the old Stepney Depot, Circa 1850 on your right and head up a short hill to Purdy Hill Rd. Turn right and travel down to the entrance for Wolff Park on the left.

Just past the gatehouse is the 0 Mile Marker for this section of the trail at 7.6 miles. The trail follows the entrance road and brings you to the Great Hollow Lake parking lot at 7.9 miles. Continue into the park along the entrance road until you come to the brown gate on the left where you'll leave the entrance road. At the beginning of the trail are some benches that overlook the beach at Great Hollow Lake in the park. Mileage Markers dot the trail. This section of the trail is well maintained with a wide hard  packed surface. After you pass by the 1.1 mile post on your left (This post may be missing),  you enter the Wind Gap, a railroad cut through a 150 foot deep pass between two hills lined with steep slopes and ledges. You emerge into an open area and pass by a bench on your left. Just past this bench will be a path that crosses the trail. Follow this path right as it runs along a stone wall for 10 paces (1 pace = 2 steps). A Maple tree on your right will be reaching out over the stone wall to grab your attention. At the base of the tree, directly underneath the overhanging limb will be a square rock on top of a flat rock on top of the stone wall. Lift up these two rocks and reach up under the stone to find  the Housatonic Rail Trail North Letterbox. Continuing along the trail you pass through a marshy area and cross over Cutlers Farm Road to a parking lot at 9.4 miles. You may continue North by crossing over Pepper St at the cross walk. You'll come to a nice stone arched bridge at 9.9 miles where the trail has to detour around a housing development. 

Note; The 0.6 mile detour is on-road and not recommended for kids on bikes. Follow the trail right out to a cul-de-sac (Grant Rd) and travel on-road out to Pepper St. Note that there are arrows on the road showing the way, as well as bike route signs. Use the cross-walk and turn left along Pepper St. There is a BIKE LANE marked along the road. Another cross-walk guides you back over Pepper St where you'll return to the trail at 10.5 miles.

You ascend a small hill and turn right back on the original rail trail. The trail crosses back over Pepper St at 11.1 miles. The maintained trail ends at the Newtown town border after 11.8 miles

Note; You may continue North, but the trail is narrow and rough in parts and a mountain bike is recommended. You head down a straight, but relatively smooth path. The original RR tracks appear alongside the path, having never been pulled up. The path then winds roughly through the woods before crossing over a double set of tracks and bearing right. You emerge on old pavement among a lot of junk, but if you continue straight, you'll run into an active rail line after 0.5 miles. If you look right along the fence line you can see where the tracks used to merge into this line. You are now in the Botsford section of Newtown. If you follow this old road left you'll emerge onto Swamp Rd.





JUNE 17, 2022