Oyster Bay Loop Professional Guide
Detailed Trail Description from our Guidebook
"Oyster Bay is the easternmost Nassau County town, comprising some thirtysix villages and hamlets. The 169-square-mile town spans the entire height of the island, bordering Long Island Sound to the north, Suffolk County to the east, and the Atlantic Ocean to the south. Although separated by county and town borders, the locations in this section have much in common, starting with a shared history dating back to their foundings, and courtroom battles initiated over territorial overlaps.
This section starts in northwestern Suffolk, with three rides beginning in parts of Huntington. The first heads east, through Smithtown, visiting the extensive park system along the Nissequogue River in the hamlet of Kings Park. The second starts in the Huntington Hamlet of Cold Spring Harbor and visits the northern border on Lloyd Neck, detouring through a grand estate turned State park and nature preserve. The third starts in Huntington and visits the North Shore Hamlet of Oyster Bay. The next ride circles the eponymous bay of Oyster Bay, starting in the hamlet and staying within the township; the last ride visits the small city of Glen Cove, which is entirely surrounded by the Town of Oyster Bay."