Last Updated:   May 15, 2024

Length:             Seymour Section; 0.2 miles

                            Derby Greenway; 1 miles    

                            Ansonia Riverwalk; West Side; 0.6 miles  

                            Ansonia Riverwalk; East Side; 0.4 miles

                            O'Sullivan Island Spur; 0.2 miles

                            Shelton Canal Locks & Dam and Shelton Riverwalk; West detour; 0.6 miles 

                            Shelton Riverwalk; East Detour; 0.7 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.

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 Northern & Central Sections .

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; West Side runs atop the dike from the end of the Derby Greenway North along the Western Side of the Naugatuck River. The Ansonia Riverwalk; East Side runs atop the dike from Main St North along the Eastern Side of the Naugatuck River. You can also access the Shelton Riverwalk from the Southern End of the Derby Greenway. 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 .


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.

From the Paul Pawlak Sr. Bypass Channel & Park parking lot [Southern End]; The paved Naugatuck River Greenway starts from the Southern End of the parking lot. Lots of informational signs. The paved trail then travels North alongside the river up to Route 87. Only 0.2 miles long


From the Northern Division Street parking lot [Southern End]; From the parking lot travel past the pavilion to the top of the dyke. 

Note; The Derby Greenway Heads right, South.

The paved Ansonia Riverwalk heads left, 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


From the Target store parking lot [Northern End]; From the Southern End of the parking lot a spur trail travels from Main St up to the trail. 

Note; Heading right, North, the paved Ansonia Riverwalk; East Side quickly ends. If you look across the Naugatuck River you'll spot the Ansonia Riverwalk; West Side along with a RR trestle that crosses the river. The next phase will continue the trail North to Bridge St. The Charger Point Lighthouse with its observation deck will be built on the Naugatuck River levy. No work begun as of April 2023.

Heading left, South, the Ansonia Riverwalk; East Side travels atop the dyke above the Naugatuck River. Pass by a couple of shaded benches before the trail ends at Main St after 0.4 miles

Note; In order to reach the Ansonia Riverwalk; West Side you'll need to travel on-road right along Main St (shoulder) to the Division Street Bridge and head right across the river. This brings you to the intersection of the Derby Greenway & Ansonia Riverwalk; West Side after 0.4 miles.


From the Southern Division Street parking lot [Northeastern End]; From the parking lot travel past a fountain to the top of the dyke. 

Note; The paved Ansonia Riverwalk; West Side heads left, North.

The paved  Derby Greenway heads right, 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, West, 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 West 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 the Shelton's Riverwalk across the river. Cross the bridge and follow the trail to the Derby/Shelton Bridge where the trail ends after 1 miles. Look right to spot the old brownstone Birmingham National Bank, built in 1892. The Bridge Street parking lot is located here, as well as, another informational board.

Note; The Bridge Street parking lot is unavailable while they redesign the Derby/Shelton Bridge with a promenade and cycle track. Construction still ongoing as of February 2024. A double-wide sidewalk has been built along Main St.

Note; From here, you can access the Shelton Canal Locks and the Shelton Riverwalk. Head left over the Derby/Shelton Bridge. After crossing the bridge take an immediate left down an access ramp which will bring you to Canal Street after 0.2 miles.


To check out the Shelton Canal Locks & Shelton Riverwalk; West; From Canal Street; Head right, North, on-road along lightly traveled Canal St. Turn right past the large brick building along a brick lined path. This leads to the short 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 0.3 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 after 0.6 miles.

To check out the Shelton Riverwalk; East; From Canal Street; Head left, South, 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 0.1 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 0.4 miles. Turn right, North and follow the double-wide sidewalk alongside Riverdale Ave which become Canal St. Complete your Loop back to Canal Street after 0.7 miles