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  >  Destinations  >  United States  >  Cycling from East Hampton to Montauk Point

The Hamptons, a string of villages often known as a summer escape for Manhattan’s elite, have become more of a year around destination this year with COVID having many flee the city for their more spacious summer homes.

The Hamptons are filled with an abundance of beautiful homes, restaurants showcasing local produce and seafood, and beaches. Picture Adirondack chairs on the porches, manicured lawns with deer wandering through the yards, and air that smells like the nearby ocean.

It may just be just a couple hours from New York City, but it’s an entirely different experience. 

We spent the weekend in East Hampton, with the primary goal of the weekend being a cycling trip from East Hampton to Montauk point.  Arriving Friday night, we had dinner at East Hampton Grill, one of the best restaurants in town. And it held true – everything from the heavenly rosemary biscuits to the filet mignon and roast chicken were delicious.

Saturday was the big biking day. After grabbing breakfast from Goldberg’s Bagel Shop we made our way to Montauk taking the most scenic route and avoiding Route 27 as much as possible.  We peddled along Skimhampton Road to Further Lane and then along Bluff Road, where the scene became beachier.  At the far end of the village of Amagansett, we crossed over Route 27 to Cranberry Hole Road, a windy road through with gorgeous houses and scenic wetlands.  From there, we passed Napeague State Park and made our way back to Route 27 via Napeague Meadow Road.  After a few miles on 27, we came to a fork and veered right to Old Montauk Highway which brought us to waterfront views.  We rejoined 27 once in Montauk.  It was still 6 miles out Montauk Point, and while a hilly ride along 27, we felt like it was a must do given the iconic lighthouse perched at the edge of the Atlantic Ocean.

Montauk Point Lighthouse

Montauk Point Lighthouse is the oldest lighthouse in New York State, built in 1792.  It was an overcast day but it was nice to get off our bikes and take a look to check out the lighthouse as well as all the surfers riding the large swells.

Montauk Point lighthouse

On our way back, we stopped at Montauk circle burger for lunch, and then made our way back to East Hampton.

Montauk circle burger

We ended our 40 mile day with dinner at Wolffer Kitchen in Amagansett.

While we considered an additional ride on Sunday, it turned out to be significantly colder, so instead we walked through the village of East Hampton and then made our way to Sag Harbor for a quick breakfast at Grindstone Donuts before heading back to the city.

East Hampton Windmill