One of the best reasons to stay in Bellport is what sits just to the east. The village is far enough out on Long Island that the East End is an easy reach, but not so far that you are already paying Hamptons prices for a bed. Point the car east, and the island splits into two arms: the South Fork, with the Hamptons and Montauk, and the North Fork, with the wineries and farm stands. You can taste your way through wine country one day and walk a Hamptons beach the next, then come back to a quiet dinner in Bellport. Here is how to make the most of both.
Getting East from Bellport
The drive east is straightforward. Sunrise Highway and Montauk Highway both run out toward the forks, and from Bellport you are on your way in minutes. The Long Island Rail Road’s Montauk Branch also stops in Bellport and runs east through the Hamptons to Montauk, which is handy if you would rather not deal with parking. The one honest caveat: in July and August, South Fork traffic is no joke. A trip that takes 40 minutes in May can take twice that on a summer Friday, so plan early starts and easy returns.
The North Fork: Wine Country and Farm Stands
The North Fork is the quieter arm of the East End, a flat stretch of farmland, vineyards, and bayfront hamlets. Riverhead is the gateway, about half an hour northeast of Bellport, and from there the road runs through Aquebogue, Jamesport, Cutchogue, Peconic, and Southold, with tasting rooms scattered the whole way. This is the heart of Long Island wine country, and it is the main reason most people point the car this direction. For a look at where every winery sits before you go, our map of Long Island wineries lays them all out so you can plan a sensible loop instead of doubling back.
If you would rather follow a plan than wing it, our practical guide to touring the North Fork and the Hamptons walks through how to build a day around tastings, including how many stops is reasonable and which areas cluster well together. Two or three wineries in an afternoon is plenty; any more and the wine starts to blur together.
A word on logistics, since tastings and driving do not mix. Plan a designated driver, or look at hiring a car or joining a tour so everyone can relax. Our notes on how to get to the Long Island wineries cover the options, from driving yourself to booking a guided trip.
Wine is not the only draw out here. Greenport, at the far end of the fork, is a walkable harbor village with a working waterfront, an antique carousel, and a ferry across to Shelter Island. Along the way you will pass farm stands selling whatever is in season, bakeries known for their fruit pies, and oyster spots pulling from the bay. It is an easy place to spend a slow afternoon.
The Hamptons
Head down the South Fork instead, and you are in the Hamptons. Westhampton Beach is the first you reach, roughly 25 minutes from Bellport, with a tidy Main Street of shops and restaurants and a wide ocean beach just past it. It is the most low-key of the Hampton villages and the easiest for a quick visit. Southampton, about 35 to 40 minutes out, is the grand one, with big shingled houses, a strong shopping street, and some of the best beaches on the island.
Keep going, and you hit Bridgehampton and Sagaponack, where Wolffer Estate has made the South Fork a wine stop in its own right, especially for its rosé. Sag Harbor, tucked on the bay side, is an old whaling port that has kept its character, all narrow streets and a pretty harbor, and it is many visitors’ favorite village out here. East Hampton, just under an hour from Bellport, brings galleries, more beaches, and a town green lined with historic homes.
Montauk
At the very end of the island, about an hour and 15 minutes from Bellport, Montauk is a different animal from the Hamptons. It is more rugged and more casual, built around surf beaches, fishing boats, and seafood shacks rather than boutiques. The lighthouse at Montauk Point, the oldest in New York State, sits at the easternmost tip, with bluffs and ocean on three sides. It is far enough out that it works best as a full day or an overnight rather than a quick hop.
Day Trip or Overnight?
From Bellport, the North Fork wineries and the nearer Hamptons like Westhampton and Southampton make comfortable day trips. You can leave after breakfast, have lunch and a few stops, and be back for dinner. East Hampton and Montauk are doable in a day if you start early, but they reward an overnight if you have the time. The nice part about basing yourself in Bellport is that you can pick one direction per day: wineries one afternoon, an ocean beach the next, without committing to a single expensive home base.
Make Bellport Your Base
That central position is the whole argument for staying in Bellport. You get a quiet, walkable village with the bay at its feet, and you are still close enough to dip into the East End whenever you like, then retreat from the crowds at the end of the day. When you are ready to book, our guide to where to stay in Bellport covers the inns and other options in and around the village.
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Disclaimer: Travel times vary widely with season and traffic, and winery hours, tour availability, and ferry schedules change. Please confirm details directly before you go.
