Oyster Bay & Sagamore Hill

Oyster Bay is one of the prettiest spots on Long Island, and there’s some attractive running here. There’s also a train station in town. Our recommendations on the best places to run in Oyster Bay:

Roosevelt Park & West Shore Rd. Waterfront. Very pretty running along the water with views of Oyster Bay. Follow Main St. headed west, and then run along W Shore Rd. for as much as 3.7 miles, to Bayville Bridge and then a short section along W Harbor Dr. There’s a sidewalk with a guardrail separating the road along W Shore Rd., so it’s safe for running. You can also add ~ 1 mile of running in Theodore Roosevelt Memorial Park.  ROUTE MAP

Cove Neck Rd. & Sagamore Hill. Sagamore Hill is the former summer home of Theodore Roosevelt, known as the ‘Summer White House’. It’s run by the National Park Service. There are pretty grounds, and a ~1 mile runnable nature trail that leads to Eeel Creek (pretty boardwalk). We also recommend running a section of Cove Neck Rd. There’s a sidewalk and pretty water views from just south of Tennis Court Rd. to Sagamore Hill (~1.3 miles, 168 foot gain). It’s possible to run run from Main St. in Oyster Bay, though part of the road lacks a sidewalk/shoulder.  ROUTE MAP