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Curbed Cup 1st round: (6) Southampton vs. (11) Shelter Island

Which neighborhood should advance? Vote!

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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!

Southampton (6)

Even though Southampton got taken down in the first round of last year’s Curbed Cup, we have high hopes for it this year. Given Southampton is one of the biggest neighborhoods on the East End—and definitely one of the busiest—it usually has more going on than some of the neighboring towns and villages.

This year, the Lobster Inn went up for sale, and there was a lot of talk about the historic Mocomanto home renovation while pizza heir, Anthony Sbarro, sold his massive Southampton estate, and part of Montauk Highway got a much-needed repaving.

Shelter Island (11)

Summer, Shelter Island ferry #tbt #ahhhhh #shelterisland #summer #outeast

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Though there’s a bit of local dispute as to whether or not Shelter Island is considered to be part of the Hamptons, we’re going to say that it is. While the small island in between the North and South Forks has always been a popular seasonal destination for out-of-towners, it’s also been gaining traction as a weekend hot spot for locals to head to in recent years. In the summer, locals from both forks will catch a ferry out to Shelter Island to hang out at the popular Pridwin Hotel and on-site restaurant.

Neither of these towns advanced past the first round in last year’s Curbed Cup. Southampton was beat out by Water Mill, and Shelter Island was taken down by Hampton Bays, who would go on to be a finalist in the competition. Who will advance to the second round this year? Polls are only open for 24 hours, so be sure to cast your vote!

Pridwin Hotel

81 Shore Road, Shelter Island, NY 11944 Visit Website

Montauk Highway

Montauk Highway, , NY

The Hamptons

, , NY