For many of our guests, the journey to Montauk will be part of the experience and we highly encourage making a weekend of it. October is one of the most beautiful times of year on the East End, with vineyard season in full swing, crisp coastal weather, and the Hamptons a little quieter and more charming than summer.

For guests traveling from New England, the easiest and most scenic option is taking a ferry across the Sound to Long Island. We strongly recommend booking roundtrip tickets in advance, especially for weekend travel in the fall.

Cross Sound Ferry

New London, CT ↔ Orient Point, NY

Vehicle and passenger ferry service with multiple daily departures. Once you arrive in Orient Point, Montauk is about a 2 hour drive through the North and South Forks.

Book here:

Cross Sound Ferry Reservations

Viking Fleet Ferry

New London, CT ↔ Montauk, NY

A seasonal passenger ferry that brings you directly into Montauk Harbor.

Book here:

Viking Fleet Ferry Reservations

A few travel tips from frequent ferry travelers: book early, arrive 20 to 30 minutes before departure, and if the weather is nice, grab a seat outside for the ride across the Sound.

The drive out to Montauk is part of the magic. If you have a little extra time, we highly recommend turning the trip into a mini Hamptons road trip with a few classic East End stops along the way.

Food & Wine

For one perfect vineyard stop, we recommend Wölffer Estate Vineyard in Sagaponack for beautiful grounds, great wine, and the quintessential Hamptons atmosphere.

Looking for the classic New York food experience? Make a stop at Goldberg’s Famous Bagels for an authentic bagel and coffee, then grab a classic deli sandwich from Hurricane Deli on your way east.

For a true New York slice, Tonino's Pizza is a favorite local stop.

Shopping & Exploring

If you want to stretch your legs and explore a bit, spend some time walking through Southampton and East Hampton. Newtown Lane in East Hampton and Main Street in Southampton are filled with beautiful boutiques, designer shopping, cafés, and classic Hamptons charm.

Montauk offers everything from beachfront resorts to laid back surf lodges, with plenty of great options near town or along the beach for a perfect weekend stay.

Montauk Yacht Club

Waterfront luxury with marina views and wedding room block available. If you would like to extend your stay beyond the reserved dates or have special rooming requests (including multiple guests or room configurations), please contact Andie Obeid at andie.obeid@montaukyachtclub.com for assistance.

Daunt’s Albatross

Classic Montauk surf motel with relaxed, nostalgic charm.

Solé East Resort

Stylish boutique stay with laid back Hamptons energy.

Hero Beach Club

Chic beach retreat with upscale, intimate atmosphere.

Gurney’s Montauk Resort & Seawater Spa

Iconic oceanfront resort with luxury weekend vibes.

Marram Montauk

Minimalist beachfront escape with quiet luxury feel.