Driving the Hamptons provides something for everyone. Many consider this area as having the largest collection of collectible cars per capita anywhere in the country so you will never know what classic car or vintage car pass by along your drive.
The legendary Hamptons, a cluster of wealthy enclaves on Long Island’s South Fork, remains a celebrity summer playground, with splashy restaurants and nightclubs galore. But lovely beaches, fishing and kayaking attract off-the-A-list visitors, as well. Old money oozes throughout Southampton, while new wealth reigns in East Hampton. Montauk is a hit with fishermen and surfers. The Long Island Railroad travels the Hamptons in an hour. The Sag Harbor Whaling Museum and Montauk lighthouse are popular stops.
It may be just ninety minutes from New York City, but when you visit the Hamptons, you enter an entirely different and refreshing part of New York State. The destination has gorgeous beaches, dramatic dunes, shingled windmills, and famous light that attracted artists like Jackson Pollock and Winslow Homer to paint in its hamlets. The Hamptons are a group of towns on Long Island — perhaps the most famous area on Long Island — that have gained famed as the residence or summer home of some of America’s most elite. Thousands escape the hot city each summer to Southampton and East Hampton and their many hamlets and villages, including Sag Harbor, Water Mill, and Bridgehampton. They have miles of museums, quirky antique shops, and placid bays that are perfect for beachcombing.
Things Not to Miss in the Hamptons
- Let a Hamptons tour guide show you around Sylvester Manor, a 17th-century estate on Shelter Island
• Long Island Aquarium and Exhibition Center at Riverhead offers an in-depth look at the ecology of the Hamptons.
• The Montauk Point Lighthouse was built at the end of the 1700s and is well-worth a visit and photo-op.
When to Go to the Hamptons
For a respite from the crowds, the best time to travel to the Hamptons is before the tourists arrive at Memorial Day or after the end of the summer season at Labor Day. However, the Northeastern region gets quite cold in the winter, so do not plan your Hamptons travel around the holiday months.
Driving
The best route runs from Patchogue Village with plenty of stores, brewery, and restaurants along Montauk Highway all the way out to Montauk Point. The drive includes local roads, highway, and even some 2-lane open roads.
During the summer season the route along route 27 thru the Hamptons can become quite congested. Timing the drive is key to avoid the early morning and late day rush hours. Once in the Hamptons there are back roads to avoid the main road traffic as well as a great detour to Sag Harbor or catch the ferry over to the North Fork headed to Greenport.
There is plenty to see along the drive no matter what part of the road you are on.
You will be driving thru farmland with roadside produce stands and dinning.
To open road thru national parks.
And quite a few small towns with a lot of history.
The route takes you right up to the front door of the Montauk Lighthouse at the east point of the United Sates.
Things to Do
Beer and Wine
From Patchogue to the Hamptons there are multiple breweries and wineries along the route for a variety of refreshments and local beverages.
Golf and Miniature-Golf
There are golf courses some of which are of professional caliber along with driving ranges and miniature golf courses.
Shopping
Along the route the small villages have numerous local shops as well as national chains. You can find everything from local artwork & gifts all the way up to high priced fashion.
Parrish Art Museum
The Parrish Art museum is to the Hamptons what The Whitney is to Manhattan. It features a variety of ultramodern and, sometimes, unconventional works from notable artists. Perhaps the most impressive exhibition on show currently is “Picture,” which includes photorealism style paintings and juxtaposed figures from Michaelangelo’s Sistine Chapel ceiling.
Guild Hall
Guild Hall is an established, multidisciplinary arts center, with a mix of everything from live Cuban music performances to art exhibitions and film festival screenings. Check the website for a list of events coming up this season.
Sag Harbor Whaling & Historical Museum
Particularly popular with families, the Sag Harbor Whaling & Historical Museum presents a glimpse into the village’s rich history. There are also contemporary exhibits on display.
The Breakers
Each season, The Breakers is known to host a number of fashion, lifestyle, and wellness pop-ups, and recently started a series of HIIT classes along with bootcamp and yoga sessions.
Southampton Hunt & Polo Club
Learn how to play polo at Southampton’s Hunt & Polo club, which offers classes for all levels. It is also open to the public for watching tournaments.
Montauk Lighthouse
On the easternmost point of Long Island lies Montauk Lighthouse — a historic site that hosts a wide variety of events and festivals.
Best Beaches
Cooper’s Beach
Ask anyone what their favorite beach is in the Hamptons, and chances are they will say it is Cooper’s Beach, which has pristine white sand and never gets too packed. It is an appealing destination to park up for a day of sun and relaxation with a civilized crowd.
Atlantic Avenue Beach, Amagansett
Families, groups, and singles alike flock to Amagansett’s Atlantic Beach, which is a popular spot during the height of the season. You can rent umbrellas and beach chairs for the day, and there is a casual takeout joint called the Beach Hut where people go for milkshakes and burgers.
East Hampton Main Beach
Often featured on lists of the beach beaches in America, East Hampton’s Main Beach is a popular spot during the summer season. Like Cooper’s Beach, it has pristine white sand and a decent crowd. Parking can be a challenge, so it is recommended to arrive early in the day or catch an Uber.
Ditch Plains Beach
Located in Montauk, Ditch Plains Beach is considered one of the best spots for surfing. The currents can become quite strong, so you will see a lot of lifeguards on the shoreline.
Cupsogue Beach County Park
Slightly more removed, Cupsogue Beach County Park tends to draw older crowds that want the beach without the scene. Many have caught on, so you will still need to arrive early to secure a carpark.
Places to stay
If you want to make a weekend of it then plan way ahead as most of the hotels, motels, and bed-n-breakfasts book early. There are plenty of location for an overnight with most being in the areas surrounding the town of Montauk.
There is plenty to see and do all along the Hampton route; just plan accordingly.
