A Summer Cycling Day-Trip: From East Hampton to Montauk (With Map)

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Susi Wunsch, the cycling savvy founder of Velojoy.com, created this scenic 40-mile route from East Hampton out to Montauk Point and back.

Well+Good is keeping Velojoy's cycling-savvy founder Susi Wunsch (pictured right) in high gear these days. Last week, we shared her dreamy Shelter Island bike ride featuring a scenic 20-mile route through nature preserves, past bobbing boats, with stops at cultural landmarks.

Susi of VelojoyThis week, she's steering us east with a ride out to Montauk Point, one of the most iconic spots in the Hamptons, with its historic lighthouse perched at the edge of the Atlantic Ocean.

Here's Wunsch's plan for a super-pleasant day-trip from East Hampton out to the fishing, surfing, and summer socializing village.

The 40-mile out-and-back route even comes with a handy map for your smart phone.

Get your bike, basket, and bell, and follow this summer cycling route.


Main Beach in East Hampton is a relaxed and familiar meeting point to begin the ride. We’ve mapped a back-roads plan that avoids Route 27, the main artery through the Hamptons, when possible.

This means, the ride takes you along Further Lane, proceeding past the golf course of the Maidstone Club, then on to a hedgerow-shielded estate district.


Bluff Road, where the scene becomes “beachier,” takes you south of the Village of Amagansett. Direct public access to the waterfront is available at Indian Wells and Atlantic beaches. (There’s a public restroom at the former.)

If you want to stop for a break, ride north into Amagansett for stir-brew coffee at Jack’s (146 Montauk Highway) or pick up fresh take-out food and baked goods for a picnic from Mary’s Marvelous (207 Main Street).

At the far end of Amagansett, cross Route 27 to Cranberry Hole Road for a northerly ride through shaded forest and past scenic wetlands along Napeague Meadow Road.


Along the Napeague stretch, Route 27 has a wide shoulder, and the Clam Bar (2025 Montauk Highway) is a popular stop for a lobster roll under a beach umbrella on the west side of the road.

At the far reach of Napeague, bear right at the fork to ride the southerly Old Montauk Highway. It’s shoulder-less here, so riding single-file is the way to go while savoring the ocean views.

You’ll rejoin the main Route 27 at the west end of Montauk. As you ride along Main Street be alert to opening doors among the rows of parked cars.

And if you're in need, Montauk Bike Shop (725 Main Street) offers rentals, as well as service.


Grab a smoothie and a wrap and park yourself on a picnic bench at the always jumping Joni’s (9 S. Edison Ext.). Off the main road, and well worth a browse: Surf Bazaar at the Surf Lodge (183 S. Edgemere St.) for irresistible beach essentials and Melet Mercantile (102 Industrial Rd.), the stylists’ secret for the best in vintage.

(Photo: Swimsuits from Melet Mercantile)

From Montauk Village, follow Route 27 directly to Montauk Point. Be prepared to encounter some hills in this stretch. Climb the 137 steps to the top of the Lighthouse, or just snap an Instagram in front, then ride on to the simple snack bar where a wide, sunny terrace overlooks the water.

For variety on the return trip, consider following the northerly Montauk Highway route through Hither Woods.


More Reading

A sweet Shelter Island bike ride

Montauk's Surf Lodge gets a healthy makeover

An upstate farm hosts yoga supperclubs


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