36 Hours in the Hamptons, NY

This is an article in the 36 Hours In… series. To find more in the series, head here.

You’ve heard of the Hamptons right? That swanky place that rich Manhattanites spend their summers in enormous mansions? Well, you’re not totally wrong! But you’ll be pleased to know that the Hamptons has a lot more to offer people like you and me than you may think.

We recently spent a chunk of time in the Hamptons and sampled all that it has to offer – from the over the top wealthy lifestyle to that of the ‘normal’ people who live there year-round.

It is certainly a fascinating place to visit and is well worth a weekend trip – just avoid the hectic summer months if you value your sanity (and if you don’t want to get into fights over parking spaces!).

Hamptons beach

Hamptons beach

Note: you’ll need a car for this itinerary – public transport in the Hamptons is quite frankly, shit. You can catch a train from NYC on the Long Island Rail Road or catch the Hampton Jitney and then rent a car in Southampton if you’d like. If coming from Connecticut or that general direction, you can catch the Cross Sound Ferry with your car from New London, CT to the North Fork of Long Island then drive to the Hamptons – the drive takes about an hour.

Friday evening

Start off in Southampton, the biggest of the Hamptons towns. The affluent towns are all on the South Fork of Long Island, and there is one main highway that goes down the spine of the fork. This means insane traffic in the summer, especially on a Friday night when half of Manhattan is heading in the same direction. There, we’ve warned you!

For dinner, grab a great locally-brewed beer and a delicious cheeseburger (seriously, those things are incredible) at the Southampton Publick House.

Saturday a.m.

Grab a good coffee and a pastry for breakfast at Sagtown Coffee in Sag Harbor, the cute old town to the north of Southampton on the South Fork. Sag Harbor (or ‘Sag’ to the locals) is full of character and old cottages, and occupies a lovely position next to the quiet waters of Sag Harbor Bay. Spot the super yachts in the marina during the warmer months!

We recommend staying in Sag Harbor – yes it’s off the main highway but it’s the loveliest of all the Hamptons towns!

After breakfast head out to Montauk, on the eastern tip of the South Fork of Long Island. This seaside escape used to be full of hippies and artists, but now it’s so goddamn expensive that guess who frequents the town – yup, wealthy Manhattanites (surprise, surprise!). If you feel like a bit of exercise, we recommend hiring a bicycle and riding out to Montauk lighthouse, America’s 4th-oldest!

Saturday p.m.

There are numerous restaurants, cafes, and bars in Montauk for you to grab lunch at. The beach is lovely and a great place to spend the afternoon if the weather is right. If you’re still there later in the day we recommend watching the sunset with a cocktail at The Surf Lodge and partying the night away at Ruschmeyer’s. Montauk Brewing Co. is also well worth a visit if you like beer!

Alternatively, pass through the pretty town of East Hampton on your way back to Sag Harbor, and window shop at the designer shops lining the main street. A girl can dream, right?

Hamptons beach

Hamptons beach

Saturday evening

There are plenty of good restaurants in Sag Harbor for dinner, although all of them are rather pricey. The American Hotel has great food (try the steak!) and an old-world atmosphere, and is a regular watering hole for celebrities in the summertime.

Sunday a.m.

Brunch is the thing to do in the Hamptons late on a Sunday morning, and a fantastic non-pretentious place to go is Estia’s Little Kitchen, located between Sag Harbor and Bridgehampton. Think omelettes, pancakes, and breakfast dishes with a Mexican slant – delicious!

Sunday p.m.

You can’t leave the Hamptons without seeing some of those ridiculous mansions, right? To see a small sample of the monstrosities, head to Meadow Lane along the beach in Southampton and gawk at a few. It’s rather ridiculous, and you can’t help thinking what will happen if those dunes wash away (like they did in Hurricane Sandy!). If you’re there between May and September you’ll need a permit to park at the beach, but a secret tip is to go to Road D (drive west along Meadow Lane until you reach it) – you don’t need a permit to park there! Wander along the beach and see those mansions from the other side.

If you have time, a worthwhile excursion is to the North Fork of Long Island. Pass through farmland, pick your own berries, and enjoy the slice of countryside away from the hedonistic Hamptons scene. The town of Greenpoint at the end of the North Fork is lovely and there’s even a brewery!

We hope you enjoyed your weekend in the Hamptons – as you can see, it’s not all mansions and Ferraris. If you visit outside the crazy summer months you’ll find a relatively quiet beach getaway with some good eateries and lovely beaches to stroll along.

P&S xx

Have you got any insider tips for things to do in the Hamptons? Share them in the comments section below!


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