Smithtown is considered one of the more upscale towns on Long Island. Much of the Smithtown’s area, which lies between Veterans Memorial Highway and the Nissequogue River, is comprised of wooded parks and golf courses, with residential neighborhoods west of them. In Blydenburgh County Park, be sure to stop in at the Long Island Greenbelt Trail Conference center and pick up a trail map, which will give you some ideas from the 200 miles of trails overseen by this organization!
There are two adjacent parks that have good trail running options. Blydenburgh County Park is a forested park with Stump Pond at its center. There are about 4 miles of mainly wooded trails. The best for running — flat and wide — is the 2.8 miles between the park entrance off New Mill Rd., headed east along New Mill Pond, to the Dog Park Area. Headed west of the entrance, there’s a 1.7 mile trail (hillier!) that leads to Caleb Smith State Park, which has 4-5 miles of trails.
Just west of the parks, Smithtown has some lovely residential neighborhood running. The Smithtown Inn provides a good anchor. These are leafy residential streets, generally quiet. Some have sidewalks. Create your own route in the area north of Veterans Memorial Highway and east of Indian Head Rd.