Summertime in The Hamptons is wonderful! BUT believe it or not, the Fall is one of the best times to visit because the weather is still beautiful but the seasonal crowds are gone! The beauty of The Hamptons is everything you read about. The beaches and landscape are stunning. Many of the homes and gardens are simply breathtaking and what dreams are made of. And while many of the rich and famous do, in fact, summer there, it is possible to enjoy The Hamptons as a "normal" person. The Hamptons stretch from Westhampton out to Montauk at the end of Long Island and also north to Shelter Island. If you remember only one thing from this post it's that you should never make an attempt to hit all of the hot spots along that stretch during one summer visit. Hamptons traffic from Memorial Day to Labor Day is absolutely horrible. After Southampton, Route 27, aka Montauk Highway, becomes one lane each way. And although it's only about 13 miles from Main Street in Southampton to Main Street in East Hampton, if you travel at the wrong time, that trip could easily cost you an hour. But in the Fall, that nightmare of feeling like you could walk faster than you can drive, is over. My original Hamptons Favorite Spots post was published over a year ago, and a lot has changed. New businesses have opened, some have closed, and others that were new to me have secured a more special place in my heart (and belly!) I’m publishing it now, after my third summer there, while everything is fresh in my mind. So bookmark it! Or better yet, drive out now. At the bottom of the post, there is a special destination that is only open in September and October, so don’t leave me early. One thing’s for sure, you’ll be much more efficient at hitting more of the spots without all of the traffic if you go now!
Due to my lack of patience, many of the places featured in this post aren't too far from our home in Southampton Village. I simply prefer to spend as much time as possible relaxing versus sitting in traffic, so we usually stay closer to home. Fortunately for us, the main reason we chose to purchase a home in Southampton is because we love the town and beaches, so we don't really feel like we're missing out by not traveling much farther east. Southampton is a great place to stay because it’s a major town and you turn off just as Montauk Highway is reduced to one lane in each direction. But fear not, I’m providing a few of my favorite spots farther east for you adventure seekers.
The one really annoying thing about The Hamptons if you're a day-tripper or even a weekender is that most of the beaches require a resident permit. These have to be permanently affixed to the window of your vehicle. You obtain one only by owning a home or presenting a lease to Town Hall or Village Hall, showing you're officially "living there" for an extended period of time. But in Southampton, you can visit Cooper's Beach for the day by paying a $50 fee upon entering the lot. This gives you in and out privileges for the day. Cooper's Beach is beautiful, and it has clean bathrooms, showers, a beach "shack" (a nice one) with provisions, and the ability to rent chairs and umbrellas. Lifeguards are also present. This is probably the most compelling reason to choose Southampton if you're visiting only for a day or weekend.
If you have a parking pass, the Cut at Flying Point beach, which connects to Scott Cameron Beach, is a wonderful place for children. The Cut is a part of the bay where the water is about knee-high. It’s warmer and calm, so it’s less stressful than the ocean. Plus there are crabs in the water, making for hours of entertainment for your kids (and you) if you bring along a crab net.
There is no way I could capture all of the wonderful places to eat in The Hamptons in one blog post. You'd be reading for days. So I'm going to share a few of my tried and true that I am certain you’ll enjoy.
Elaia Estiatorio is my favorite restaurant in the Hamptons. That’s a strong statement, right? Serving authentic Greek cuisine just south of Montauk Highway, this Bridgehampton spot is a must. The beautiful, U-shaped bar is the hub of the restaurant, and this joint takes its ambiance and decor as seriously as its food. Every evening feels like an occasion to celebrate with owner Sofia Crokos, who is also a special events planner, decorating the space with fresh flowers, fresh bread, desserts, and accessories that will transport you directly to the Greek Isles. If it’s your birthday, prepare to celebrate in a big way with Greek music and lots of hoopla from the entire restaurant! On the menu, you must try the Fried Zucchini Chips (you’ll never want to eat potato chips or French fries again!) And they typically offer Saganaki, which is kefalograviera cheese that is coated with sesame seeds and pan-fried. My favorite preparation is with tomato marmalade, but their offering changes and it’s all delicious! Read more about Elaia here.
Closer to our home in Southampton Village is Tutto il Giorgno. It’s Italian food and a welcoming ambiance all wrapped into one. There is a beautiful and charming garden, which is my preference for seating. But don’t dismay if outdoor isn’t available because the inside is warm and cozy and has a wonderful energy to it. Favorite items on the menu are Grilled Octopus, Branzino, and I love the simplicity of the Spagehtti and Linguini with Clams (I always ask for extra garlic in both!) The restaurant takes limited advanced reservations on OpenTable, and each day at 11 am they open up their phone lines for same day reservations. Call as close to 11 am as you can, and keep pressing redial when you get a busy signal. They’re actually pretty good at trying to meet requests. Frank is our favorite waiter there in case you wanted to make a request for him, too!
If you’re in the mood for a burger, head to Union Burger Bar for the best in town. They have veggie and turkey burgers, too, if you’re not in a beefy mood. I LOVE their onion rings. And kids love the decadent milkshakes for dessert. Okay, maybe adults do, too!
Silver's in Southampton is open only for lunch. Situated amongst the many shops on Main Street, you'll want to stop by for one of their $60 lobster rolls. Yes, they're amazing, as you would expect for that price. As you might have guessed, it's a place better-suited for an adult-only meal. Closed Tuesday.
People outside of the Hamptons know Tate’s Bake Shop, primarily for their cookies. Well, if you’re a Tate’s lover, you’ll be in heaven if you visit Southampton. But truth be told, it’s not the cookies I love. I’m more of a soft and moist cookie kind of gal. But I LOVE their Three Berry Crumble pies. And I suggest you pick up one because they aren’t sold outside of the Hamptons.
For a more casual but seriously delicious Italian dinner, head to Pellegrino’s Pizza Bar & Restaurant, where they serve delicious pizza and so much more. This inviting spot is about 10 minutes from Southampton Village but worth the drive for affordable fare that will exceed your taste expectations. The pizzas are divine, and my favorite pastas are Scampi Wild Shrimp and Amatriciana. Also try the Eggplant Parmigiana Rustica—I’m a meat eater and LOVE this dish!
Another Greek restaurant that also doubles as quite a hot night spot is Calissa in Watermill. You can’t go wrong with seating because the outdoor space is beautiful and summertime festive, while the indoor space is sexy and hip. There is often a DJ at night, and that really amps up the energy. This also makes it tough to secure a reservation, but if you do, you’ll be happy to dine and spend some time having more cocktails after dinner. Check their calendar because the Gipsy Kings have been known to perform there, which makes for an extra special treat!
If you’re looking for the Hamptons with a little touch of New England, head to Sag Harbor for a meal, shopping, and even the beach. Sag Pizza serves up some of the best pizza around in a festive atmosphere that is kid-friendly while still being a place I’d be happy to go on a fun date. While they do offer the expected toppings on pizza, they have options with truffle paste (you’ll die and go to heaven!), kale, and even a pizza with clams and guanciale—yes, all on one pizza! Outdoor seating is available.
Wolffer Kitchen in Sag Harbor (there is another location in Amagansett) wants you to know they are just as serious about food as they are their wine. Situated downtown on Sag Harbor's quaint Main Street, Modern American cuisine with a Mediterranean influence is on the menu, as are most of the delicious and famously Hamptons Wolffer wines. Reservations are accepted only for parties of six or more, but there's plenty to do and see on Main Street if you have to wait a bit for your table. The restaurant is open for lunch/weekend brunch and dinner every day during summer months.
For dessert in Sag Harbor, head to Buddhaberry for the best frozen yogurt with a million and one topping options. But frozen yogurt isn’t all they do—they have crepes, açaí bowls, waffles, and shakes and smoothies. It’s a very popular spot, but it seems to be the place to be, and it lives up to the hype with so much variety in froyo flavors and other options to satisfy your sweet tooth.
Topping Rose House in Bridgehampton is a Jean-Georges restaurant and has wonderful food and a happening bar and restaurant scene. During our first meal, we dined next to Christie Brinkley, and it's also a favorite of Ina and Jeffrey. Last New Year’s Eve we dined with our children before heading to a friend’s house to ring in the New Year, and it was a surprisingly good deal for our kids, as they ate for “free” with our prix fixe meals. Open daily for breakfast, lunch, and dinner.
Canal Cafe in Hampton Bays is a meal with a view. The food is actually very good, but you really come for the view and to literally sit on the water--many of the tables are on a deck that is an extension of the boat docks. They don't take reservations, but you can have a drink at the bar or one of a few outdoor picnic tables while you wait. I love their lobster roll, and we’ve also been very happy with many of their daily specials. Closed Tuesday.
Ice Cream Outside The Southampton Fudge Company
For a cold treat on a hot summer night (or day) in Southampton, visit The Southampton Fudge Company for ice cream (and fudge and other candy) or Sant Ambroeus for gelato. The Village of Southampton has plenty of benches on which you can enjoy your sweet treats.
We seldom drive farther east than Bridgehampton, but there are a few places that are worth the drive. Take a drive to East Hampton, do a little shopping, and then head to The Lobster Roll, also known as LUNCH, in Amangansett. It’s open every day from lunch until 9:30 pm. It’s such a festive beachside “shack” decorated in red, white, and blue with umbrellas, picnic tables, and a pebbled outdoor space. And the service is warm and friendly. Do I even need to tell you what to order? Well, perhaps. You can actually get a lobster salad roll made with mayo, but my favorite is the hot lobster roll. The lobster comes served in melted butter with the roll on the side so you can stuff as much as you want into the roll or just enjoy the sweet taste of lobster. One last tip: Don’t be dismayed by the crowd of people you see waiting to be fed. It actually moves rather quickly, and they serve up tasty beverages (some with alcohol if you need help chilling during the wait)—I was quite pleased with my piña colada during our last visit!
A sweet friend of mine is a Montauk regular year-round since her family has a home there. She has impeccable taste about everything, especially food (which she doesn’t like to share…even with her husband…just FYI if you ever dine with her—LOL! But I still love her to pieces!) She recommends The Crow’s Nest for its food, stunning grounds, and a cute little bar down by the water so you can have a drink while you wait for your table. It’s also part of a small boutique hotel. She’s never stayed at the inn, but judging from the website, it’s super cute and boho chic!
If you’re planning to spend a day on the beach in Montauk, make sure to make a pitstop at Herb’s Market on Main Street to pick up provisions for a picnic lunch. They’re known for their fried chicken, even by people who typically don’t eat fried chicken. But there is so much more, including prime meats, if you’re planning to cook a meal at home that evening.
FUN EVENING ENTERTAINMENT
Sunset While Waiting for the Drum Circle Performance to Begin
Drum Circle festivities at Sagg Main Beach in Sagaponack begin every Monday during the summer around 6 pm. The drum circle musicians don't appear to be on a strict schedule, beginning somewhere around 7 pm. Bring your beach blanket and chairs, wine (AND cups to conceal it), and any food you like for an evening picnic. The kids will enjoy the company of other kids who are running in the sand, dipping their toes in the water, jumping from the lifeguard chair, flying kites, and dancing to the beat of the drum circle. To park in the lot next to the beach, you'll need a sticker on your ride. Otherwise be prepared for a parking ticket.
You might think you need to ditch the kids to go wine tasting. Not in The Hamptons. Make your Friday or Saturday evening a treat for all at Wolffer Winestand. From 5 pm to sunset, it's a "picnic" like no other. Bring your blankets and beach chairs and find a spot on the grounds right alongside the vines. The Winestand sells wines by the bottle, cheese platters, and other lite bites that you can enjoy with friends while your kids run, frolic, dance to the live music, and roll down the small hills into the vineyard.
For the first time this past summer, because my little guy is now 4 years old, we went kayaking. And it couldn’t have been easier thanks to Main Beach Surf & Sport. We arrived at the shop, told them we wanted to rent kayaks, we drove about a half mile, parked the car, and two guys showed up with kayaks and life vests, and helped us launch them into the water. Then they directed us to Georgica Beach. So we kayaked there and had lunch on the sand. This was actually a treat because it’s typically a private beach for residents of the neighborhood, but not when you arrive by kayak! Main Beach even sold us a dry bag to keep our belongings safe and dry when strapped onto the kayak.
If you’re in the mood for a hike and a quiet beach, visit the Elizabeth Morton Nature Preserve. Hike down to the beach while observing and listening to wild birds. You might even spot a wild turkey. And if you take a little bird seed, stand quietly still, hold the birdseed in the palm of your hand, and a bird may just come take it from you. Hike to the beach and use the free telescopes to see for miles. Or just act like a kid and skip rocks. Parking is $5 on the honor system.
For a splashing good time during Summer months, take the family to Splish Splash in Riverhead. The lines can be long, but for a small fortune, they offer a speed pass to minimize your wait times.
Berry (and other fruits and vegetables) picking is a favorite pastime for my kids and me in the Hamptons. There are so many places throughout the East End. We’ve been to Hank’s and Seven Ponds Orchards and have enjoyed both. Just make sure you call ahead or check their websites to confirm what they’re currently picking.
Not really a day excursion, but I can’t figure out where to place this. Agawam Park in Southampton is a wonderful playground, often with some shade, and my kids (and husband and I) have the best time there. And if you’re not into running around, just enjoy the beautiful sunsets.
WHEN YOU'RE THE CHEF
We are definitely not the Hamptons people who go out every night. I'm a real housewife of NYC, but I'm a real housewife of NYC, so I'm used to cooking. But truth be told, I love entertaining and welcoming people into my home. I enjoy visiting local farm stands and markets, and cutting fresh herbs from the herb pots that my kids and I plant every summer, to create something special for our guests. And it's sort of nice to come in from the pool or beach, have a glass of rose, and hang out with family or friends without getting all gussied up every night. So if you're the chef, here are a few of my favorite spots to procure goods for cooking at home.
North Sea Farms
I love to visit North Sea Farms for fresh chickens when I'm making beer can chicken. In addition, they have all the fresh produce you could want, including organic corn that's wonderful on the cob or in my simple but delicious summer corn salad. My favorite thing about this local farm stand is that they have a sign every day detailing what is organic and what is conventional, and this is terrific if you're like me and are finicky about what you feed your family.
Eye Candy at North Sea Farms
The Green Thumb's Wooden Train
The Green Thumb in Water Mill is a short drive from Southampton and a reliable place for quality produce. They also sell fresh herbs in pots so you can plant your own for the season. Most weekends, they sell pies prepared by local bakers. They're delicious, even if they are on the expensive side. And outside of the farm stand is a wooden train that your kids can play on while you're shopping, and it's right next to a small chicken coop that also houses a beautiful peacock. And you may get lucky and run into Katie Lee or Brooke Shields (who is so lovely!)
Round Swamp Farm has two farm stand locations, one in Bridgehampton and the other in East Hampton. It has a reputation for two reasons. First, they have amazing baked goods, fish, meats, prepared foods and produce. But second, some of the items for sale (especially their prepared foods) don't have a price tag or they’re hidden on the bottom, which is sort of obnoxious and one of the reasons The Hamptons gets a bad rap. So be sure to pay attention when you're checking out. Thanks to a friend of ours who appears to be a grill-master, we visited Round Swamp to purchase burgers from Pat LaFrieda, a meat purveyor that used to pack meat in our old 'hood, The Meatpacking District. The burgers are the best I've purchased and grilled in The Hamptons.
If fish is on your menu, be sure to visit the Clamman Seafood Market in Southampton. They have every kind of fish you could imagine, caught daily, plus more live lobsters than the waters of Maine (well, not really, but you get the point). And if you're not in the mood for cooking, they have a fantastic and reasonably priced takeout menu with everything from fried clams and oysters to grilled fish.
Peconic Prime Meats is right next door to the Clamman. Any cut of meat you could want, along with housemade sausages, are available for the best cookout of the summer.
If you've never made it inside its location in New York City, you may want to try Levain Bakery in Wainscott to get a thick slice of their chocolate chip banana bread or one of their killer giant cookies. They have lots of other flatbreads, breads, and pastries, but I just named my favorites. This location is open Friday-Sunday.
Ye Olde Bake Shoppe in Southampton is the best kept secret in The Hamptons. Stop by and get one of their to-die-for cinnamon rolls. Really. Don't leave without buying one. You will thank me later.
HAMPTONS SPECIAL EVENTS
Taking in the Scenery at the The Hamptons Classic
The Hamptons Classic is a horse show that happens every August in Brideghampton. The kids will love watching the jumping competitions, as will you. And because it's in The Hamptons, it's sponsored by wonderful brands who bring lots of extra stuff for the family to enjoy. There is typically a kids tent with loads of arts and crafts activities like cookie decorating from Citarella, an area with farm animals, pony rides, and even playground equipment. For the adults, food trucks, cars on display from luxury automotive companies, and a shopping tent and mobile shopping trucks from brands like M. Gemi.
The Southampton July 4th Parade is the quintessential small town holiday parade. Residents bring their beach chairs to line Main Street and watch old cars, marching bands, and the like stroll by.
There are a few carnivals in the Hamptons that my kids love. The big one is the North Sea Fire Department’s Carnival during the week of July 4th. This is the Mac Daddy of summer carnivals because they have a great fireworks show a few nights at around 10 pm. I also like that it’s run in large part by volunteers for the fire department, so it has more of that hometown carnival feel than some of the others.
The Southampton Carnival seems to come and go a few times throughout the summer. It’s a small town carnival with a huge potato sack slide, a small roller coaster, games, candy apples, and the whole shebang. It’s a great carnival for smaller children. The carnival sets up shop on County Road 39 as you're driving into Southampton.
There’s also a carnival in Bridghampton on Montauk Highway near the Carvel store. It’s probably the closest to North Sea’s in terms of size and types of rides. All carnival dates change every summer, so just check local updates when visiting.
Kite Flying on Cooper's Beach (Kite from Kites of the Harbor)
Kites of the Harbor in Sag Harbor is a must if you're in The Hamptons and have kids (or just like kite flying). The beaches usually have a nice breeze, perfect for this pastime. The best thing about the shop is that the employees know which kites are easiest to fly and those that are more difficult so that your kids won't be disappointed on even their first attempt. The shop also carries fun costumes, toys, and gadgets and is located on the town's quaint Main Street.
Topiaire Candy Shop in Southampton Village is reminiscent of the old penny candy shops that I frequented as a child to purchase Mary Janes and Squirrel Nut Zippers. It's a charming spot and will delight kids and adults alike with the candies from our younger days, as well as giant gummy sharks that my kids seem to enjoy.
One King's Lane has a wonderful store, now in a new location on the corner of Jobs Lane and Main Street in Southampton. Stop by to see some of the beautiful things that you typically only see online. Their staff is quite helpful and has assisted me in purchases to complete our home decor.
A beautiful tabletop at Goop
For at least the last two summers, there has been a Goop Pop-Up in Sag Harbor. There are so many wonderful shops in The Hamptons that I can't list them all. But many of them, like MONC XIII, are in Sag Harbor, so if you can only shop one day, make it the day you visit this beautiful town that is reminiscent more of Nantucket than the rest of The Hamptons.
The view inside MONC XIII
Serena & Lily only has a handful of brick and mortar stores throughout the country, so be sure to visit their Beach Market location in Wainscott. They have lots of fun events with cocktails and book signings throughout the summer, so be sure to check their Instagram and website if you'll be in the ara.
ON A RAINY DAY
On a rainy day, there is still lots to do in The Hamptons. Long Island is home to wonderful wineries on the North and South Fork. Near Southampton alone are Wolffer, Channing Daughters, and Duck Walk. The Parrish Art Museum is a wonderful place to visit and get some culture. Just don't go on a Tuesday because they are closed.
If you have young kids, they'll enjoy The Children's Museum of the East End in Bridgehampton. Or take a short drive to Riverhead to Safari Adventure, an indoor play area with bouncy slides, arcade games, and a multi-level human crawling maze, complete with slides, that even adults can enjoy. You can also hit the Long Island Aquarium to feed stingrays, see sharks, be entertained by a live sea lion show, or walk around with a butterfly on your head in the butterfly conservatory. This aquarium is truly worth a visit. The Montauk Lighthouse is a fun destination because it’s literally right on the end of Long Island. Kids will enjoy walking up the spiral staircase to the top. Just be patient because it’s a narrow staircase and can get a little cozy with people going both directions.
HAMPTONS OFF SEASON
I’m publishing this at the beginning of October. The Fall is one of the best times to visit the Hamptons because the crowds are gone, rental homes and hotels have lower rates, but the weather is still wonderful. Just look at the weather the past few weekends—perfect beach days. And you don’t even need a beach pass, so you can park for free, without fear of a ticket, at some of the most beautiful beaches on the East Coast. Most shops and restaurants are still open. The one destination I’ll add for the Fall is Hank’s Pumpkintown. This is a child’s dream spot for the day. And they have everything you could want to celebrate this season on one plot of land. Pumpkins, of course. Apple cider donuts, apple picking, a hayride of the best kind (without hay to make you itch and sneeze), corn mazes, slides coming out of giant farm equipment, pedal dune buggies, a giant bouncy pillow, face painting, apple blasting (a MUST!), a corn train ride around one of the pumpkin patches, mums and gourds for sale, and even more, but I’m exhausted listing it all. Trust me, you and your kids will have a fabulous time, and they’ll sleep well. Pumpkintown is only open from the weekend after Labor Day until Halloween, giving you one more reason to visit after Summer’s end.
This list is always work in progress. My hope is that it will make your trip to The Hamptons stress-free and more enjoyable.