Southampton ’s Railway Trail includes some of the route’s most deeply forested stretches, tunneling through spice tree and fiddlewood groves on a high ridge above Middle Road. It cuts across the Fairmont Southampton Princess Hotel property and then meanders beneath Gibbs Hill Lighthouse  (a tribe road cuts up from the trail to the lighthouse for easy access). A couple of breaks in the trail heading west mean you have to cross Middle Road and stay on the main road for a half-mile section after Barnes’ Corner before a paved stretch of the trail picks up again, leading into the rural beauty of Sandys .
The wide, grassy verges of South Shore Road make it safe from traffic for walking and running. Fringed by spider lilies, goldenrods, and Spanish bayonets, the route sweeping high above the beaches makes for dramatically scenic territory.