Sag Harbor, which sits in both East Hampton and Southampton, is a lovely waterside village listed on the National Register of Historic Places. There are lovely streets in this old whaling town, such as the Whalers Church, Jermain Library, Whaling Museum, the Old Burying Ground, Oakland Cemetery, Mashashimuet Park, and Otter Pond, and a marina and Yacht Club off Bay St.
This is a lovely area to go running. We have two recommendations:
Sag Harbor Village Tour. Self design your own tour here, enjoying the historic Main St., and the tree-lined side streets of the village, which are quiet and feature lovely homes.
Sag Harbor-North Haven Loop. This is a lovely 6-mile run over two bridges, with great water views much of the way. Start in the center of Sag Harbor, and run along W. Water St. to Glover St. to Noyac Rd. (no sidewalk/shoulder in spots) Then, take the Noyack-Long Beach Rd., using Park Access Rd. along the water to North Haven, about 2 miles. From North Haven, it’s a quick 1 mile over a small bridge, using Ferry Rd., back to Sag Harbor.