Curbed Cup 1st Round: Hampton Bays (4) vs. Shelter Island (13)

Hampton Bays became Curbed’s Town of the Year after winning last year’s Cup. One reader nominated the town thus: "Best restaurants (Canal Café, Edgewater, Villa Paul, Cowfish, Rumba, The Inn Spot, 1 North, Sundays on the Bay, Oakland's, Orlando's Café, Hampton Maid to name a few), freshest seafood, most glorious and beautiful bays and beaches, best shopping/services, quaint, close knit town, geographically perfect and the nicest residents and visitors are all here, not to mention some upcoming, exciting real estate developments!" Good luck to this scrappy little town this year.

Sylvester Manor Educational Farm

Shelter Island has never won a Cup. Is this its year? The sleepy town is known for more reasonable real estate prices than the mainland, but some ultra-pricey properties have come on the market recently, including a stunner asking $32M. One Curbed commenter enthused about Shelter Island: "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.