A Perfect Day: The Cyclist, East

While there’s nothing wrong with riding in flip-flops, surf board tucked under one arm and towel around your shoulders, this itinerary is geared more for the clip-in type. With that said, we fully encourage clipping-out to enjoy all the stops below and turning these 20 some-odd miles into a full day of exploring. Your tour “to the east” is right this way…



Home of “The Best Coffee in Town,” just like it says on our tees, the Bake Shoppe is ground zero for super tasty breakfast items to go (to the picnic tables outside). And it’s right across the street from the Bike Shop, where you’re headed next.

Montauk Bake Shoppe
29 The Plaza (631) 668-2439


Be there at 9 on the dot to rent one of the fast, light Giant road bikes and any other gear you need. Ask a Chris (strangely, there are 3 who work there) or Lenny any questions you may have and be on your way.

Montauk Bike Shop
725 Montauk Highway (631) 668-8975 (right across Main Street from the Bake Shoppe)

Hang a left when you leave the Bike Shop and consider all or part of this east-bound loop. You can see it mapped out here: http://bit.ly/1TEzdo9


First stop: the Point (the park, not the bar). It’s a straight shot out to the lighthouse and as with most longer adventures, it’s best to set out for this ride on the early side: cooler, often less windy and less traffic.

Montauk Point State Park
2000 Montauk Hwy. (631) 668-3781 (5.7 mile mark, several long, steep hills)


On your way back from the lighthouse, hang a right on East Lake Drive and go all the way to the end where Gin Beach, on Block Island Sound, is a perfect rest/swim stop. And, bathrooms. Before you leave, look across the inlet at your next stop – Gosman’s Dock. Return same way, back to Rt. 27.

Gin Beach
541 East Lake Drive (11.6 mile mark, hilly, windy)


While you could have saved 3 miles by swimming 100 feet across the inlet from Gin Beach, we’re taking you the long way around. Hang a right on Old West Lake Dr. (then Westlake Dr.) to Gosman’s Dock. Explore the shops and pick a leisurely lunch spot. We’d suggest Topside or the Clam Bar.

Gosman’s Dock
500 Westlake Drive (631) 668-5330 (17.7 mile mark, hilly, windy)


Frozen yogurt? Why not. It’s right behind the Bike Shop and you deserve it.

43 South Euclid (631) 668-8393 (20.9 mile mark, fresh and delicious)


And you’re back. With plenty of time to spare before the Bike Shop closes at 5. If you had a few too many beers at lunch or fell asleep on the beach and arrive back late, worry not. You can always lock your rental to the rack outside if the shop is closed. Hope you had fun and stay tuned for our Cyclist (WEST) route.

Montauk Bike Shop
725 Montauk Highway (631) 668-8975 (21 mile mark, the end)


Photography by Randy Harris