Where to play
Napeague Stretch
Amagansett to Montauk
The flat isthmus run is 4.7 miles each way — Amagansett to the foot of the Hither Hills climb — so about 9.4 miles out and back. It is a striped bike lane on NY 27 (Montauk Highway, then Montauk Point State Parkway), two lanes of asphalt posted at 55 mph, not a separate path. The ground stays between 1 and 3 m the whole way; the climb only starts where Hither Hills does.
Shelter Island Loop
Shelter Island
Island loop with serious climbs. South Ferry from North Haven charges $5 one way / $8 round trip for a bicycle and rider; walk-on is $2/$4 and a car is $18/$25. Fares effective 12 May 2025.
Sag Harbor to Bridgehampton back roads
Sag Harbor
The direct link is the Bridgehampton–Sag Harbor Turnpike: 3.5 miles of two-lane asphalt, 35 mph at the Bridgehampton end and 45 mph across the middle, with no bike lane mapped on any segment of it. Rolling rather than flat — the road runs between about 4 m and 31 m. Millstone Road, 2.5 miles of 35 mph tertiary road joining Noyac to Scuttle Hole Road, is the quieter parallel to the west.