Luxury cars and designer handbags, out running errands. Sprawling estates with ocean views. Lashings of hydrangeas. Very, very wealthy people. These were the things I expected from a weekend in the Hamptons, on Long Island’s East End.  What I didn’t expect was for somewhere so famously out of touch with the real world to bring me back down to earth. It was a breath of literal and metaphorical fresh air, a moment of calm in a year of chaos.

The Hamptons are a collection of villages and beaches on the east end of Long Island, around a 2 hour drive from New York City. It’s where Manhattan’s wealthiest routinely flee every summer, to escape the sticky New York heat, but this year, most of them have made their Hamptons estates their primary residence. As a result, visiting in October wasn’t a problem – the Hamptons are still very much open for business this year, well into the fall and winter.

I was so busy with work over the summer that I didn’t get a chance to get out to the Hamptons. As soon as things started to slow down just a little, we took the chance to get away for the weekend. I’m so glad we did!

The three main towns are Southampton, East Hampton and Bridgehampton. Montauk is another 45 minute drive past Bridgehampton, on the very tip of Long Island.

Southampton

We stayed at the Southampton Inn in Southampton, which is the prettiest and liveliest of the three towns. Even in shoulder season, accommodation wasn’t cheap – $350 USD for one night in a large, low-set hotel complex. Our room was clean, comfortable and spacious, but it’s still a lot to pay for a generic hotel experience. Welcome to the Hamptons!

We took the Hampton Jitney from Midtown to Southampton, which took two hours. After we checked in, we went to the main street for coffee & some lunch and to put our name down for a dinner reservation, at St Ambroeus. This restaurant has been in the Hamptons since 1992, and also has outposts in SoHo which I’ve been to, with the original location in Milan. The Hamptons restaurant scene is much more “big name” than “local farm to table” vibes, so I didn’t mind eating at a restaurant that’s from elsewhere. If you want a spectacular farm-to-table experience, make the trip across to the North Fork and have dinner at North Fork Table & Inn.

Southampton Village

We had coffees at St Ambroeus, which were $8 each (plus tax & tip), which was unfortunate, as David’s was nice but mine was not. Australian-style coffee has not yet caught on in the Hamptons (bizarrely, you can get a solid flat white in the tiny town of Southold on the North Fork though!).

We had a casualhealthy lunch at Golden Pear Cafe, which is super popular and has locations in all of the major villages in the Hamptons.

Coopers Beach

I’m an Australian beach snob, and having seen photos of Hamptons beaches I wasn’t sure what all the fuss was about. I was so pleasantly surprised when we got to Coopers Beach and Cryder Beach, the two main beaches in Southampton, and found them blissfully empty and totally beautiful. Photos don’t do them justice. I think part of the appeal is also that most people visiting are comparing the wide open spaces, soft sand and fresh sea air to the crowded, dirty and noisy streets of New York City.

We spent a couple of hours walking along the beach and enjoying the mild autumn weather. The water was pretty to look at, but close up was a little funky – I’m not sold on swimming in this part of the Atlantic. It was too cold anyway!

Walking along the beach, I began to feel more like myself again – which is a weird sensation, when you realize you haven’t felt like yourself in nearly a year.

The walk to & from the beach, along the wide, leafy backstreets of Southampton, was just as lovely as the beach itself. Each Hamptons home is more grand than the last!

Drinks & Dinner at St Ambroeus

We had drinks at a little bistro in town called Le Chef, which has been in Southampton since the 1980s. The owner (I assumed) was so welcoming, and I loved the local, down to earth vibe. Pre-dinner drinks are tricky at the moment, because NY State law requires food to be purchased with alcoholic beverages for some bizarre reason, so we had oysters and some dip with our wine. I would 100% have come back here, for more drinks or dinner, if we had more time.

I loved the entire experience at St Ambroeus for dinner. Due to covid regulations, the dining room was half empty, which I didn’t really mind. I quite like the “90s white table cloth” interiors, especially as they’ve been recently updated for the 21st century, while still honoring the restaurant’s history. It’s totally 90s New York, and you’d never find this particular restaurant vibe in Australia. Because we’d had pre-dinner snacks, we went straight to entrees, and we both had pasta. I loved my ricotta ravioli, David liked his carbonara but wasn’t a fan of the enormous serving size. We shared a slice of cake for dessert. I feel so bad for both restaurants and bars, who are struggling as diners try to navigate these new dining rules. If you go to a bar for a pre-dinner drink, you have to eat, which means you skip the first course at the restaurant. Most of the time, we’ve started skipping pre-dinner drinks, which is tough on bars that don’t do dinner trade.

East Hampton

The following morning, we took an uber to the train station, and caught the train to East Hampton. It took less than twenty minutes! The Long Island Rail Road is a great way to get between the villages of the Hamptons, but you need to check the timetable because the train runs infrequently.

Babette’s

We walked through town to Babette’s, which is one of the most popular brunch spots in the area. We were still full from dinner the night before, we so stuck to coffee & a green smoothie for breakfast. Truthfully, this is not my kind of coffee, but the food menu looked nice – straightforward, homestyle cooking.

While we were sitting at a table outside, a bee flew into the sleeve of my jumper and stung me! It was the first time I’d been stung by a bee, and as a result I was very jumpy around the rest of the bees we saw in the Hamptons (there are lots).

Bostwick’s Chowder House

We walked through East Hampton’s pretty main street and then across town to Bostwick’s Chowder House, a locally loved institution which specializes in East Coast seafood. It’s super casual and laidback, very family friendly and has a lot of fried food, but it was a really nice spot – especially on their patio under the trees. I tried the Seafood Chowder, which is a regional specialty from New England. I love trying regional cuisine when I travel, and the USA is such a great place for it. While I won’t be rushing to order seafood chowder again, it was fun to try!

Main Beach

We caught an uber from Bostwicks’ down to Main Beach. On the way, we drove past a long motorcade of Trump supports, who had decorated their trucks in Trump memorabilia. Their energy was really aggressive and even a little scary. Locals and holidaymakers in East Hampton lined the streets to give them the finger as they drove by – America is at it’s own throat these days. I really hope that once Biden is sworn in, the country can start to heal and become less divided.

Main Beach in East Hampton is maybe even prettier than Coopers Beach in Southampton! It’s essentially one big stretch of beach, so it’s the same beach, but the beachfront houses are even more magnificent in East Hampton.

We cancelled our late lunch reservation at Tutti i Giorno, regretfully, so we could spend the afternoon on the beach, and then in Bridgehampton. We called several hours in advance, so I hope it wasn’t too much of an inconvenience – working in the restaurant industry, I’m shocked at how many people simply don’t show up for their bookings.

The walk back to town from the beach was gorgeous, just like the leafy backstreets of Southampton.

Bridgehampton

Bridgehampton’s village is a lot smaller than Southampton and East Hampton, but there are quite a few notable restaurants, such as Bobby Van’s, Almond, Topping Rose House and Pierre’s. Bobby Van’s was the only place that was open before 5pm, so we stopped in there for oysters and wine to finish off our trip.

Bobby Van’s Steakhouse

Bobby Van’s is a historic Bridgehampton restaurant, dating back to 1969 when Bridgehampton was more of an artists colony than an enclave for the uber rich. Bobby Van’s was once a hangout for Bridgehampton’s literary set, and Truman Capote is rumoured to have finished his true crime novel, In Cold Blood, at Bobby Van’s. There’s a piano in the corner, which Bobby Van refused to give over to anything but jazz – until one night, Bob Dylan sat down and began playing his own tunes!

We had a glass of wine and oysters at the bar. It was so nice to sit at the bar in the Hamptons, which currently is banned in New York City. The vibe at Bobby Van’s is very old New York hotel bar / steakhouse, which I love.

I was so disappointed that we had to catch the jitney back to New York City that night, and was really keen to book a second weekend in the Hamptons, this time at Montauk, before we left the USA for good. Unfortunately, we ran out of time, and as New York City was so gorgeous with autumn foliage in November, I’m glad we stayed in town. If I do get back to the northeast USA, I’d like to spend a weekend out in Montauk or back in the Hamptons again. It was my last “weekend away” in the USA before we moved, and I’m so glad we made it out there – everything is over-priced, but it’s a world of it’s own.

Have you been to the Hamptons? Would you like to visit? Let me know in the comments!

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