We visited the Hamptons nearly every summer growing up, but one stands apart—when I spent two months in Montauk in the mid-90s, living at my uncle’s house, known (reverently, even then) as The Stone House.

The Stone House sits perched on a cliff off Old Montauk Highway and remains, to this day, one of the most distinctive houses I’ve ever known. Originally built in the early 1800s as a storage building for the Montauk Point Lighthouse, it became a private residence in 1912. Fast forward to 1987, my uncle Tony restored it, and after a devastating fire in 1991, rebuilt it entirely. The reimagined home was featured in the May 1995 issue of Architectural Digest, but to me, it was simply the place I spent one magical summer.

Montauk was different then. So were the other Hamptons towns. There was no scene. No reservations. On weekends, my cousins and I spent the days between Ditch Plains and Kirk Park Beach (which we fondly still refer to as “IGA Beach,” thanks to our parking trick). We’d eat fried fare at Gosman’s Dock, strut around with Ben & Jerry’s cones like we owned the place, and beg our parents for press-on nails at White’s Pharmacy. Sandwiches came from Herb’s Market, and somehow they always tasted better with sand between our toes. At night, we’d drag our mattresses out onto the deck and fall asleep under the stars, listening to the hush of waves and the hum of crickets.

A few summers ago (thanks to a more flexible work-from-home policy at my husband’s firm), I returned to the Hamptons with my own kids, then one and three, for the month of August. The area had changed, of course—glossier, more crowded, better dressed—but the landscape was still unmistakably itself: wide beaches, quiet pine forests, and that salty air you can feel in your hair hours after leaving the ocean.

That month, our days took on a rhythm: morning walks to get coffee, early beach visits before the crowds, picnic lunches under umbrellas, and late-afternoon trips to the playground or farm stand. We kept swimsuits hanging on doorknobs and a pile of sand toys in the trunk. Some of the places we visited were new to me; others were ones I remembered from my own childhood, now seen through the lens of sippy cups and nap schedules. But each outing felt like its own little memory—simple and unscripted, in the best way.

If you’re planning time out east with kids, here are ten of our favorite things to do. These are the places that stand out in my memory because we all genuinely enjoyed them.

Amber Waves Farm (Amagansett)

This is a must for families with young kids. There’s the market and café, yes, but we especially loved grabbing breakfast or lunch and sitting at one of the shaded picnic tables while the kids explored. They have chickens, gardens, a sandbox, and plenty of room to roam. Julia and Miles attended Farm Camp, where they picked their own tomatoes, made tortillas by hand, watered the plants, mixed up “magical potions” with herbs, dug in the dirt, and spun around in a yoga swing under the trees. It’s the kind of place where you feel like everyone’s childhood is a little better. And if you’re lucky, you might spot a familiar face—we once saw Blythe Danner browsing the market, as serene and unbothered as if she were just any other local picking up lunch.

Amagansett Square

You can spend an entire afternoon here. Jack’s Stir Brew is essential for coffee (I was partial to their Happy Jack—a honey cinnamon latte), and there’s a central lawn where the kids can run barefoot while you catch your breath. We always stopped into Pink Chicken—not exactly rugged, but their whimsical, happy prints have become a staple in my kids’ closets. Yes, they’re a splurge, but the quality is excellent and they last for seasons. On longer afternoons, we’d also stop into Cavaniola’s Gourmet—a specialty food shop offering elegant cheese and charcuterie platters, imported jams, cured meats, and gourmet finds for picnic upgrades or dinner at home. It’s the kind of place where you might wander in for cheese samples and walk out with something delicious for an impromptu treat back at the cottage.

Children’s Museum of the East End (Bridgehampton)

If the beach was off the table—because of weather, overtired kids, or just needing a break from the sun—CMEE quickly became our go-to. It’s thoughtfully designed for younger kids, with spaces that encourage open-ended, tactile play. Julia and Miles could spend ages outside in the mud kitchen and the garden classes were a great way to sneak in a little education under the guise of messy fun. They planted herbs, watered tomatoes, and got absolutely filthy in the best possible way. There’s usually a rotating schedule of workshops, performances, and special events (puppet shows, music classes, storytime, etc.), so it’s worth checking their calendar before you go. And if you have a baby or toddler, there's even a quiet corner indoors with board books and soft toys—a lifesaver during overstimulated moments.

Clearwater Beach (Springs)

Tucked away in Springs, this bay beach is perfect for littles: calm, shallow water, easy parking, and a mostly-local crowd. There’s a small playground just off the lot if your kids still have energy to burn after swimming, and the beach itself is ideal for low-stress water play—no crashing waves, just gentle lapping and space to dig, collect shells, or float. We often went in the late afternoon, when the sun softened and the crowds thinned. We’d bring a blanket, a small bag of snacks, and let the kids run wild while we eased into the early evening. It’s not flashy or expansive, but it’s peaceful and beautiful in that familiar, lived-in way.

Crow’s Nest (Montauk)

This is one of those unicorn dinner spots that truly works for both adults and kids—effortlessly cool but completely unpretentious. You’ll want to get there by 4pm (they open at 4:30) to be near the front of the line for a walk-in table, especially if you're hoping to sit outside. There's no reservation system for early diners, but the payoff is worth it. The food is thoughtful but unfussy, with just the right balance of indulgent and fresh, especially the whipped ricotta and lobster tagliatelle. While you wait—or even once you’re seated—the kids can run around the grassy lawn or follow the sandy beach path down to the water. It’s the rare place where you can enjoy a great meal while also letting your kids roam a little free. The setting feels almost cinematic: string lights overhead, Adirondack chairs scattered near the fire pit, and a dusky glow settling over the lake.

Mashashimuet Park (Sag Harbor)

Hands down the best playground in the Hamptons. It’s big, shaded, and designed in a way that works for a wide age range—which is not always the case out here. There are huge wooden climbing structures, shaded baby and big-kid swings, tennis courts, baseball fields, and lots of open grassy space for running, scootering, or impromptu cartwheels. There’s easy parking right next to the playground, and it’s close enough to downtown Sag Harbor that you can pair it with lunch, errands, or a stroll through town. After a good playground run, we’d often head over to Big Olaf’s for ice cream—classic, generous scoops served out of a window, with plenty of benches out front to regroup before nap time or beach round two.

Moby’s (East Hampton)

This is where we went when we wanted a real meal that still welcomed kids—two sets of grandparents, toddlers, and sometimes cousins in tow. Moby’s strikes that perfect balance: seasonally driven Italian food, picnic tables under string lights, and enough lawn space for the kids to roam safely while adults linger over wine or cocktails. The wood-fired pizzas kept the kids happy, while the rest of us shared pastas, grilled fish, and whatever was fresh on the menu. It’s upscale but unpretentious, and one of the few places where everyone left full and genuinely content. Make a reservation or go early for walk-in space.

Soak Hides Preserve Nature (East Hampton)

When we needed a break from the beach crowds or just wanted a quieter afternoon, we took Julia for a nature walk at Soak Hides Preserve. The trail is well-marked and family-friendly, with a mix of soft forest paths and stretches of boardwalk that wind past wetlands and water views. It’s shaded, peaceful, and just wild enough to feel like a little adventure. We spotted deer almost every time, and Julia loved searching for frogs, pointing out birds, and collecting leaves like treasure. It’s a low-key, low-effort way to feel immersed in nature without straying far from town—and a great option when you need some reset time.

Springs Farmers Market (East Hampton)

Held Saturdays from 9am to 1pm on the lawn at Ashawagh Hall, this market is a hyperlocal gem—unpolished in the best way. We’d start with coffee and baked goods (often still warm), then make our way through stands selling fresh-caught seafood, local produce, artisanal breads, and small-batch pantry staples. The kids roamed freely, bopping to live folk music, sampling fruit, and stopping to pet every dog in sight. There’s a real sense of community here—no branding or pretense, just people who live nearby and grow or make good things. It's also one of the few weekend activities where no one is in a rush, and no one seems to mind if your toddler has jam on their face or your stroller takes up too much space.

Wiborg Beach (East Hampton)

This easily became our favorite early morning ritual. We’d head to Wiborg by 7:30am with coffee and a bag of overpriced muffins from The Golden Pear, when the beach was still quiet and mostly filled with locals and their dogs. We brought our own pup, Frankie, who loved nothing more than ambling down the shoreline and eyeing a rotating crew of off-leash companions. The kids dug in the sand, occasionally stopping to squeal with delight as dogs raced past them into the waves. There’s nothing polished or planned about Wiborg—it’s just sand, sea, and salty air—but those mornings felt like magic.

Bringing My Kids Back to the Hamptons: A Summer Revisited