Greenport is a historic seaport village on Long Island’s North Fork. There is some pleasant running in this area — here are some recommendations for creating your own route:
Greenport Village. Attractive residential streets for running with very little traffic. Use the train station as an anchor point, and then run the side streets off Main Rd., Front St., and N Rd. Then, head further east and enjoy some of the pretty streets around Stirling Basin and down to Youngs Point.
Orient Area. Very pretty country roads, with farms and vineyards. For a long, scenic stretch, take Narrow River Rd., which stretches for ~2 miles. Further east, there are some pretty roads and paths around Orient Point. You can actually run along Main Rd. (Rt. 25), which has a decent shoulder. To combine Narrow River Rd. and Orient Point, it’s ~5 miles one-way.