How To Spend a Weekend in the Hamptons During Autumn

By | Food, Travel, Wine, Finance and Lifestyle Journalist
Last Updated: September 17, 2023
Weekend in the Hamptons Itinerary: Things To Do During Autumn

Hamptons Itinerary: Best Things to Do in the Hamptons This Fall

The beautiful fall sky and crisp air beckon visitors to the Eastern End of Long Island

The Hamptons is a quintessential fall weekend trip that has it all: fall foliage, apple picking, pumpkin hunting, outdoor drinking and dining options that can satisfy families, couples and individuals alike.

Choosing a place to stay should be the first decision to make, as the Hamptons span a vast area with small towns that each have something unique to offer. If you want to go as far as Montauk, that could be a destination unto itself. If you want to stay closer to Southampton or East Hampton, look for hotels or B&Bs that are close to your desired activities or a quick walk/drive into their respective towns.

Once the town has been chosen, crafting a weekend itinerary will fall into place (pun intended). A seasonal activity, a visit to a local winery and an evening dining experience is the perfect trifecta for a fall weekend in the Hamptons.

In this itinerary, we suggest a number of places to stay across various Hampton towns, in addition to various restaurants and activities we recommend during the autumn season.

How to Get to the Hamptons

Best Things To Do on a Weekend in the Hamptons
Classic houses line the beaches in the Hamptons.

An easy journey from New York City, the Hamptons are accessible via three modes of transportation: bus, car and train. Renting a car from the New York City area is an easy way of getting out there, and expect around a two to three-hour drive from most areas in New York. A car provides additional optionality for when you are there and want to explore different neighboring towns in the Hamptons.

There are bus services known as the Hampton Jitney that leave directly from several stops in Midtown Manhattan. For a more luxurious experience, you can hire a private driver to pick you up in New York City and customize a day or weekend trip, stopping at shops, restaurants, mansions, vineyards and more.

If you’d prefer to travel by train, the LIRR makes several stops to the Hamptons.

A cautious reminder: should you be getting there by bus or train, make sure to find a local cab company to help with transportation while there as car rideshare apps like Uber are not popular in the region. This is another reason why we do recommend hiring a local driver during your stay.

RELATED: The Best Long Island Wineries & Wine Tasting Experiences to Try

Things To Do and Places to Stay in the Hamptons

If you’d like to stay in the very place that locals call “The End”, spend time in Montauk, a fishing village turned hipster hot spot complete with incredible lodging and dining options to satisfy the most seasoned travelers. Check-in for a stay at Ruschmeyers, a landmark property that was once a campground. Today it boasts 19 cabin-style rooms, a restaurant on the property, and a location that can’t be beaten. It’s a quick walk to Fort Pond and a short drive to hotspots like Ditch Plains Beach, Downs Golf Course, Montauk Point and Lighthouse and the marina.

For a luxury hotel experience, both Gurney’s Montauk Resort and Seawater Spa and Gurney’s Star Island have excellent accommodations complete with restaurants and bars on property.

RELATED: Top Wineries, Hotels and Restaurants on Long Island’s North Fork to Explore

While in town, be sure to book a reservation at Morty’s Oyster Stand—a beautiful roadside restaurant with a colorful bar and outdoor and indoor dining options open throughout the fall. The kitchen is led by seasoned chef Richard Biondo who made the move from Brooklyn to the East End to bring his special touch to the menu, evidenced in dishes like the fresh Mediterranean-style seafood salad ceviche, the yellowfin tuna tostada as well as a Montauk favorite, the lobster roll. Be sure to pair your meal with one of their inventive cocktails, like the Sabrosa, a frozen cocktail comprised of mezcal, fresh watermelon, apricot, lime and a hint of spice (think Frose, but so much better). The cocktail menu was crafted by beverage industry veterans who bring a true passion for what they do to their creations.

If Montauk is too far East, a few other great options include the Capri Southampton, the Southampton Inn both in Southampton, and the 1770 House in East Hampton. Both the towns of Southampton and East Hampton are great for walking and boast a variety of stores, coffee shops, and restaurants.

For the ultimate weekend splurge, The Topping Rose House, a 5-star resort complete with a Jean George restaurant, is another option in Bridgehampton. That property is only a short walk from local restaurant favorites like Bobby Vans Bridgehampton.

Eat, Drink, Pick Pumpkins

There is no shortage of apples and pumpkin picking joints on the East End. While there are several options to choose from, if you take a moment to curate an afternoon activity to manage drive time and seasonal traffic, you’ll be glad you did.

A great local spot for pumpkin picking is Hank’s PumpkinTown in Water Mill. Chances are there will be long waits no matter what time you visit, so try getting there early. Spend time in the fields, snag a photo opp, pick out a pumpkin and enjoy refreshments like local pies, doughnuts, roasted corn and apple cider in a beautiful outdoor setting. When you’ve gotten your fill of pumpkins, head directly across the street to Duck Walk Vineyards to recoup, grab a glass of wine and listen to live music in their spacious vineyard.

Winetraveler Tip: Save yourself from needing to drive and have a chauffeur take you around for a guided day tour of the Hamptons, stopping by Southhampton, Sag Harbor, Shelter Island and various North Fork Long Island wineries.

Another great seasonal option is the Milk Pail also in Water Mill, closer to East Hampton. Plenty of U-Pick apple and pumpkin options are available and when you get hungry, be sure to peruse the Fresh Market filled with seasonal items like muffins, pies, cakes, brownies and more. They also operate a food truck on-site, should you get hungry during your afternoon activities.

Frequently Asked Questions about Visiting the Hamptons

Looking for more things to do and see in the New York area? Check out some of these other great travel guides:

More New York Area Travel Guides

North Fork Long Island: Fall Travel & Road Trip Guide

Finger Lakes Itinerary & Travel Guide: How To Spend a Long Weekend in Seneca Lake

Haunted Wineries, Hotels & Attractions in the Finger Lakes

Hudson Valley & Catskill Mountains Road Trip Itinerary

5 Top Wine Bars To Visit Across New York City

22 Ways To Experience “Old School” New York City

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