Long Island Forks: Wine Country to Montauk

From New York to the eastern tips of Long Island: wine tasting on the North Fork, ferry across Shelter Island, and beaches to the lighthouse on the South Fork.

A classic weekend coastal getaway for New Yorkers. Spend the first day exploring North Fork wineries and Greenport, then take two short ferries across to Sag Harbor to avoid backtracking through Riverhead. Follow the South Fork villages and beaches to Montauk on the second day, and visit the lighthouse before returning to the city on the third day. This route focuses on a relaxed pace rather than rushing through wineries, and excludes hiking on Shelter Island. Summer weekends are extremely congested and expensive; May–June and September–October offer a more leisurely experience.

Route 27 experiences severe traffic congestion on summer weekends, and many shops close during the off-season.

Day by day

Day 1 · North Fork Wine Country to Sag Harbor

The Hamptons（North Fork Wine Country、Greenport、Shelter Island、Sag Harbor）

Drive from New York to the North Fork (approx. 2 hours); take the two ferry segments via Shelter Island from Greenport (approx. 30 minutes total).

Ferries do not require reservations; pay in line at the dock. Expect longer wait times when vehicle volume is high.

Stay: Sag Harbor

Day 2 · South Fork Villages & Beaches

The Hamptons（Southampton Village、Coopers Beach、Parrish Art Museum、East Hampton Village、Main Beach, East Hampton）

Drive from Sag Harbor to Southampton (approx. 30 minutes), head east to East Hampton (approx. 35 minutes), and continue to Montauk (approx. 35 minutes).

Many beaches restrict parking to residents during summer days; non-residents must purchase day passes or ride bicycles.

Stay: Montauk

Day 3 · Montauk Lighthouse & Return

The Hamptons（Montauk Point Lighthouse、Camp Hero State Park） → New York City

Drive about 15 minutes from Montauk town to the lighthouse; drive back to New York after lunch (approx. 3 hours, longer on Sundays).

Westbound traffic is often heavily congested on Sunday afternoons; leave early or depart after dinner.

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