Making up a large part of the Woodbridge Greenway, the Naugatuck Trail
winds its way through Woodbridge and parts of New Haven. This 11.5 mile trail was originally part of one of the oldest Native American trails in Connecticut. Easily followed in sections with parking along the way, the trail features a mixture of easy sections and quite challenging ones.
Starting on the Woodbridge/New Haven line, roadside parking can be found along Fountain St. (Hwy 243), or more out of the way parking can be had about half way into the trip along Park Lane. Follow the blue or occasional blue/yellow blazes north through Race Brook Estates, Fitzgerald Tract, Alice Newton Street Memorial Park, and Elderslie Preserve. Then continue east following the Naugatuck Blue Trail
along the Bladen’s Brook area through Russell Swamp and climb Round Hill, through the Regional Water Authority (You'll need a pass from the RWA to continue into the RWA land between Amity Rd. (Hwy 63) and Dillon Rd.
To go around, head south on 63 and then east on Dillon Road, catching back up with the trail going south just after Blue Trail
Dr.) Lastly, continue south along the east branch of the Naugatuck Trail
through Bishop Estate to the parking lot at the Thomas Darling House (1907 Litchfield Turnpike, Woodbridge).