Jessie Loeffler Randall’s Guide To The Hamptons
My husband and I have been visiting the Hamptons since 1999 – the first summer we started dating. We also bought a small house in Bridgehampton 13 years ago. It’s my happy place. I love my garden and work on all my interiors projects here. My dogs love the outdoor space and it’s such a peaceful place to escape to.
The Hamptons can feel very fancy, but I don’t get involved in that side too much. I mostly play tennis at the local public courts, walk along the beach and hang out with my family. If you want to, you can avoid all the glitz and fancy stuff. It’s incredibly beautiful out here. The beaches are some of the prettiest in the world and there are lots of farmers markets selling unbelievable fresh produce. Each town has its own personality, too.
My town, Bridgehampton, feels very 1950s, which I love. One of my favourite spots there is Candy Kitchen, a diner that sells burgers, milkshakes and ice cream (which you can order from the window hatch). It’s been around since 1925 and has even been mentioned in an episode of Succession.
Sag Harbor is another place I love. It’s an old whaling town with beautiful historic homes nestled quite closely together by the water. In my opinion, it’s one of the most charming areas in the entire US. There's a lovely beach, some nice boutiques and a few galleries.
The place I eat at most often is Sag Pizza. It serves the most delicious pizzas in the middle of Sag Harbor, with all the usual flavours, as well as options like the ‘Soppressata Picante’ with tomato, pecorino, caciocavallo and oregano.
Another great takeaway spot is Round Swamp Farm. I prefer to bring home food to enjoy with my family rather than sitting in a restaurant. It’s the best food market in the Hamptons, so it’s always full. I love the homemade ice-cream sandwiches, guacamole, blueberry peach muffins and spicy noodles.
For great French food, head to Pierre’s, where you’ll feel like you’ve been transported to St Barths. The owner is French, so it has a fun, European vibe. All the French-inspired dishes are delicious, and they make a real effort for birthdays and special occasions, with lots of singing and giant sparklers in your dessert. I love the beautiful flower boxes and the holiday décor here.
For a fun, boozy summer lunch or dinner with friends, go to Sunset Beach Hotel. It's a cool motel designed by André Balazs on the beach in Shelter Island (a quick ferry ride away from the mainland). The indoor/outdoor layout of the bar and restaurant overlooking the beach is bliss.
On Friday and Saturday nights, we love to bring our friends and family to Wolffer Winery. They have a gorgeous piece of land overlooking the vineyards and sometimes have live music. This is one of the prettiest places to get a drink in the Hamptons.
Carissa’s is the most elegant bakery and takeaway food spot. It has outposts in East Hampton and Sag Harbor. Go and see its beautiful flower-topped cakes or visit for delicious breakfast tacos and excellent bread.
There’s a real lack of good hotels in the Hamptons. It’s just not a place that has very many of them. Most people rent Airbnbs or stay with friends, but there are a handful worth knowing about. My first pick is Topping Rose House. It has uber-comfy beds, a huge lawn for outdoor drinks and a Jean-Georges restaurant, where the breakfast is particularly good. I also like Baron’s Cove hotel, which is a nice spot for outdoor drinks overlooking Sag Harbor.
Sage Street Antiques is my favourite place to look for vintage treasures and unique homeware. Everything is super affordable and you never know what you’ll find – I’ve picked up some of my favourite pieces here.
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Amagansett Square in Amagansett has lots of elegant shops. It’s a great place to walk around and discover local makers. My favourite stores here are The Warm for fashion and lifestyle pieces, Lazypoint for clothing and jewellery and Love Adorned for fine jewellery and accessories.
If you’re after gorgeous home décor and bedding, visit Clic in East Hampton. You’ll find a lovely selection of pillows, tablecloths, napkins and more. It also has a clothing shop across the street, which is definitely worth a browse.
Other favourite stores include Gubbins for sneakers and beach games, and White’s Apothecary for sunscreen and toiletries. But my ultimate favourite store in the whole of the Hamptons is the ‘five and dime’ in Sag Harbor, Sag Harbor Variety. I get sewing supplies, art supplies, fabric and games there.
One of my favourite things to do in the summer is visit Ocean Road. This is my favourite beach where you can spend lazy days and make s’mores as the sun sets.
I also love to play tennis. There are lots of tennis sites dotted around the Hamptons, my favourites being Mashashimuet Park, Buckskill or EHIT. Afterwards, I’ll typically visit Amber Waves Farm to pick up flowers and fresh veg.
For a culture fix, head to the Parish Art Museum or the Dan Flavin Art Institute. Both house great art collections. I also like to drive down Ocean Road where you can see a giant Richard Serra work on someone’s lawn.
Follow Jessie on Instagram at @JESSIE_LOEFFLER_RANDALL & visit LOEFFLERRANDALL.COM
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