clock menu more-arrow no yes

Filed under:

Curbed Cup 1st Round: Sag Harbor (3) vs. Shelter Island (14)

New, 7 comments

The Curbed Cup, our annual award to the Hamptons neighborhood of the year, is kicking off with 16 towns/villages/hamlets vying for the prestigious fake trophy. This week we'll have two matchups per day, and all the results and the full tourney bracket will be reviewed on Friday. Voting for each pairing ends 24 hours after it begins. Please remember—no wagering.

The Curbed Cup kicks off this week. Let's give a warm Curbed welcome to Sag Harbor (3) and Shelter Island (14)!

Red-hot Sag Harbor is the winner of several past Cups. It's looking to win again this year, and why not, with a perennially popular real estate market and a thriving downtown with great restaurants and shops? New hotel Baron's Cove opened this year with a well-regarded restaurant. The Harbor's Edge development opened for sales this year, while sales at Watchcase remain strong. Another condo development is planned for One Ferry Road, although town officials want to buy the property and turn it into a park. Speaking of which, resident Mike Gaynor has been the talk of the East End with his dueling with village government, which is documented in hilarious ads in the Sag Harbor Express.

Shelter Island is a newbie to the Cup race, but the sleepy town is getting more notice with the opening of the Chequit, a boutique-style renovation of the town stalwart, which includes the Red Maple restaurant, garnering excellent reviews. One Curbed commenter nominated Shelter Island thus: "Good restaurants, accessible via the North or South Fork, fantastic boating, proximity to Greenport and Sag Harbor, and blissfully quiet as compared to South Fork because the ferries keep traffic down." Can't argue with that. Good luck, Shelter Island!

Poll results