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Curbed Cup 1st round: (1) Sag Harbor vs. (16) Montauk

Which neighborhood should advance? Vote!

Doug Kerr, James Kirkikis / Shutterstock

Curbed Cup, the annual virtual award for the best neighborhood of the year, is officially kicking off! This week, we’ll be calling for readers to cast their votes. Each poll will only be open for 24 hours, so make sure to get your vote in!

Sag Harbor (1)

Sag Harbor was the winner of our virtual trophy last year, beating out Hampton Bays by a small margin. Last year, 52.45 percent of our readers voted for Sag Harbor in the final round, with 47.55 percent choosing Hampton Bays, our 2015 Curbed Cup winner.

Sag Harbor is still a hot neighborhood on the East End, and probably the hottest bayside Hamptons town with no ocean beaches. In terms of the housing market, we’ve seen lots of century-old homes being restored and brought back to life while maintaining period details. Sag Harbor famously loves to hold on to its history, as demonstrated in the old buildings—and most notably, the restoration of the historic Sag Harbor Cinema.

Montauk (16)

Montauk won the Curbed Cup back in 2014, beating out Sag Harbor in the final round—and now they’re competing again, three years later, in our first round. As the eastern-most point on Long Island, Montauk uniquely has ocean, bay, and Sound beaches.

Notably, Montauk is on the come-up with young adults living in New York City. While it’s always been a favorite summer destination for its laid-back vibe, surf beaches, and quiet though fun atmosphere, lately it’s been the favorite weekend spot in the summer for young adults coming from the city. And after Uber returned to all East Hampton Town villages and hamlets—including Montauk—this past June after two years of being unusable, transportation only got easier for visitors.

So, readers, what do you think? Will Sag Harbor beat Montauk and get closer to its second consecutive year for the virtual trophy? Or will Montauk advance against the 2016 victorious? Each poll will only be open for 24 hours, so cast your vote!

Sag Harbor

, , NY 11963


, , NY 11954