Last Updated:   September 14, 2018

Length:             Seymour Section; 0.2 miles

                            Derby Greenway; 1 miles    

                            Ansonia Riverwalk; 0.6 miles

                            O'Sullivan Island Spur; 0.2 miles

                            Shelton Canal Locks & Dam and Shelton Riverwalk West detour; 0.8 miles 

                            Shelton Riverwalk East Detour; 0.9 miles                    

Difficulty:         Derby Greenway & Ansonia Riverwalk; Easy. Paved, mostly flat trail.

                            O'Sullivan Island Spur; Easy, flat paved trail.  

                            Shelton Riverwalk; Easy. Flat paved & brick path.


For the Ansonia/Derby/Shelton Sections; From Route 8 northbound, take exit 16 to Pershing Drive. At the second set of lights, take a right onto Division Street. Cross over the railroad tracks and take a right or left at the next set of lights just before the bridge. There are parking areas on both sides just below the dike.

For the Ansonia/Derby/Shelton Sections; From Route 8 southbound, take exit 17. Turn left at end of ramp onto Seymour Ave and then a quick right down Atwater Ave. Turn right when you reach Division Street and follow over the railroad tracks. Then take a right or left at the next set of lights just before the bridge. There are parking areas on both sides just below the dike.

For the Seymour Section; From Route 8 take exit 22. Northbound; Turn right on Wakely St. The Paul Pawlak Sr. Bypass Channel & Park parking lot is on your right. Southbound; Stay straight to Route 67 W. Turn left on Wakely St just before the river crossing. The Paul Pawlak Sr. Bypass Channel & Park parking lot is on your right.

The Naugatuck River Greenway is a planned 44 mile trail running north from Derby to Torrington along the Naugatuck River, with a short section along the Housatonic River between Derby and Shelton. This trail is a work in progress and currently contains many gaps. See; Naugatuck River Greenway for more information. Check out; Naugatuck River Greenway Northern Section & Naugatuck River Greenway Central Section .

The Southern Section includes the Derby Greenway, which runs along both the Housatonic and Naugatuck Rivers. The trail mostly runs on top of the dikes that keep the rivers at bay (the great flood of 1955 devastated the area), however, one section does take you down along the riverbanks and a stone-dust spur trail takes you through O'Sullivan Island where the two rivers meet. The Ansonia Riverwalk runs atop the dike from the end of the Derby Greenway.  You can also access the Shelton Riverwalk, the southern end of the Naugatuck River Greenway, via bike from the southern end of the Derby Greenway. See below for directions. Another bike trail is located close by in Shelton. See; Shelton Lakes Recreation Path . A very short section has been completed in Seymour. For more information visit; DERBY GREENWAY & NAUGATUCK RIVER .


From the Paul Pawlak Sr. Bypass Channel & Park parking lot; The paved trail starts from the southern end of the parking lot. Lots of informational signs. The Paul Pawlak Sr. Bypass Channel & Park consists of a hillside park adjacent to the Naugatuck River and a CT Department of Energy and Environmental Protection-operated fish bypass channel. Visitors can see fish migrating to their spawning points upstream between approximately April and June. The paved trail then travels north alongside the river up to Route 87. Only 0.2 miles long.

Starting from Division Street; A cross-light over Division St connects the two trails.


From the Northern Division Street parking lot; From the parking lot travel past the pavilion to the top of the dyke. The paved Ansonia Riverwalk heads north on top of the dike alongside the Naugatuck River. Hold your nose as you pass by the sewage treatment plant before coming to the Della Volpe-Cassetti Copper City Pathway Bridge over the active RR tracks that lead to Pershing Drive after 0.6 miles. 

The next segment of the Ansonia Riverwalk to be built will follow along the east bank of the Naugatuck River from Main St up to Bridge St. The Charger Point Lighthouse with its observation deck will be built on the Naugatuck River levy. Public hearings are underway in 2020. 


From the Southern Division Street parking lot; From the parking lot travel past a fountain to the top of the dyke. The paved  Derby Greenway heads south on top of the dike alongside the Naugatuck River. Split rail fencing runs the entire length of the dike and steel gangplanks jut out towards the river. A switchback takes you underneath the Route 34 Bridge where you emerge next to some active railroad tracks to your right at 0.9 miles. You now travel alongside the riverbank (picnic tables) and then pass underneath a railroad bridge at 1.1 miles. This brings you to a T in the trail where you'll find an informational board. 

Note; Left takes you along the O'Sullivan Island Spur. After passing by the RR trestle over the river you cross a pedestrian bridge over an inlet. The paved trail then takes you across the island where it rejoins the main trail after 0.2 miles.

Heading right the trail runs through a floodplain. To your left is O'Sullivan's Island and an inlet. Just before a junction at 1.3 miles you'll pass by where the O'Sullivan Island Spur rejoins the main trail. Straight ahead is a boat launch area with picnic tables. Turning right at the junction the trail heads up a slight incline beneath the Commodore Hull Bridge (Route 8) and up to the dike overlooking the Housatonic River. Follow the dike east until you come to the pedestrian bridge over the railroad tracks at 1 miles. Here a railroad trestle crosses over the river into Shelton. You can also spot Shelton's Riverwalk. Cross the bridge and follow the trail to the Derby/Shelton Bridge at 1 miles. Look right to spot the old brownstone Birmingham National Bank, built in 1892. This is the end of the trail. The Bridge Street parking lot is located here, as well as, another informational board.

Note;  Future plans call for redesigning Bridge St with a promenade and cycle track. Construction expected to be completed by Fall 2021.

Note; From here, you can access the Shelton Canal Locks and the Shelton Riverwalk. Head left over the Derby/Shelton Bridge (Bridge St) utilizing the sidewalk. After crossing the bridge take an immediate left down an access ramp which will bring you to Canal St.


To check out the Shelton Canal Locks & Shelton Riverwalk West; Head right on-road along lightly traveled Canal St. Turn right past the large brick building along a brick lined path. This leads to Shelton Riverwalk West. I have not checked out the Riverwalk yet. Turn left and follow the brick lined trail alongside the river. Then turn left back out to Canal St and continue right on-road. You'll see portions of the old canal along your left, as some sections have been covered. Railroad tracks are along your left and old brick mill buildings to your right. After 0.5 miles you'll come to a gate. Look right for the opening. You cross over an old canal lock which brings you to a hard packed dirt road. A signboard is located here with some history of the 1867 canal. For more information visit; SHELTON CANAL . The canal and railroad tracks run along your left, while the Housatonic River is down along your right. Duck Island is out in the river. Follow the road to another gate with views of the Derby-Shelton Dam. This is only 0.8 miles from the end of the Derby Greenway.

To check out Shelton Riverwalk East; Head left on-road along lightly traveled Canal St. Cross a set of RR tracks and you'll find a double-wide sidewalk you can use. You'll pass by the Farmers Market on your right before coming to Veterans Memorial Park on your left and the start of the Shelton Riverwalk at 0.3 miles. Turn left and follow the brick lined trail to the Veterans Memorial. Follow the path down to a promenade alongside the Housatonic River. Use the ramp to your left if biking. Continue alongside the river, underneath the Route 8 bridge and out to Riverdale Ave at 0.6 miles. Turn right and follow the double-wide sidewalk alongside Riverdale Ave which become Canal St. Complete your loop back to the start of the Riverwalk at 0.9 miles.