- The Best Hamptons Activities An All-Ages Family Weekend Getaway
- Get to Know Eastern Long Long Island
- Try These 4 Kid-Friendly Museums
- Take A Summer Ferry Trip
- 4 Spots for Chocolate & Desserts
- Family Friendly Long Island Wineries
- Sample Long Island Beer & Cider
- Get Outside With Kids
- Hamptons Restaurants Kids Will Like
- Hamptons Hotels
- Pin it for later!
We only visit the Hamptons in the off season. We can’t imagine dealing with the crowds, traffic and party scene that typifies this string of beach towns during the summer.
But in the spring or fall, when the tasting rooms are quiet. the beaches are empty and the permit-parking regulations are suspended, it’s an easy and fun family weekend getaway from new York City.
We enjoyed a spring break getaway to the East End when Tween Traveler was 6 and again this spring. We did some of the same things on both visits and discovered new fun activities, too.
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The Best Hamptons Activities An All-Ages Family Weekend Getaway
Get to Know Eastern Long Long Island
Which fork to choose?
The East End of Long Island splints into two forks just beyond Riverhead, which is about 80 miles from Manhattan.
From there you can explore the North Fork, which is densely populated with farms, wineries, local restaurants and small pocket beaches.
Or you can choose the South Fork, which includes the Hamptons towns and Montauk. It has long stretches of beach, scattered wineries and stylish towns with boutique hotels and upscale restaurants. Keep in mind that Montauk Point, the furthest tip of Long Island, is 50 miles from Riverhead on roads, not highways. Save it for its own weekend; trying to fit it into a broader visit will be exhausting.
Shelter Island sits between the forks; you get there by ferry from Greenport on the north fork and North Haven on the south fork.
Your Riverhead homebase
Twice I’ve used Riverhead as my base because from there I can easily explore both forks. It’s also has family-friendly chain hotels with indoor pools and reasonable rates. And it has a handful of casual restaurants that are good, not insanely expensive and kid friendly.
If you mostly want to hang out around Riverhead, maybe visit a North Fork winery or Two, you can take the Long Island Rail Road to Riverhead and rely on taxis when you want to get away from town. To really explore the forks though, especially the south fork, and to get to the beaches, you’ll want a car.
Quite a few microbreweries and hard cideries have opened up in and around Riverhead in the past few years. Off season they’re open on weekends and some are open weekdays after 3:00 pm. They are doing interesting things with beer and cider and several have good food. Many don’t have extensive menus. But their .flatbred pizzas, gourmet subs and wings are fine for lunch or a light, early dinner.
There is an enormous Tanger outlet center just west of Riverhead, where the LIE ends. It’s two adjaceent collections of outlets with every store you can imagine. I try to leave time for some shopping on the way home, and have found some really great deals on winter coats in particular.
It’s always 5 to 10 degrees cooler at the beach, and beaches out this way can be windy. Bundle up for winter weekends, layer in the spring and fall when days are sunny and nights can be cold. From mid-May to late September pack plenty of sunscreen, a beach hat and a windbreaker or light hoodie.
Try These 4 Kid-Friendly Museums
At 6YO Tiny Traveler loved the Children’s Museum of the East End in Bridgehampton. Three hours after arriving I could only lure her out with the promise of ice cream.
A sizable indoor playground is great for rainy days.
But the real draw is the pretend play the museum encourages with costumes and a collection of sets including a ship, lighthouse and atown’s main street with a farm stand, soda shop, workshop and library.
A compact mock-up of a potato chip factory had her enthralled
2. We didn’t get to the small Natural History Museum across the road the first time we visited and I worried Tween traveler would be too old on our latest ggetaway. But local parents have recommended it to us. They also tipped us off that there’s a nice walking trail behind it.
3. I was lukewarm on the Long Island Aquarium in Riverhead. Tiny Traveler enjoyed seeing the butterflies and penguins, exploring touch tanks and feeding tiny minnow to the rays.
But it’s expensive relative to other regional aquariums and not nearly as well executed.
The bird room had just a handful of squawking parrots, though the kids did like petting the one perched on an interpreters hand.
I couldn’t decide whether the Dr. Zaius statue in the monkey habitat was mildly amusing or unbelievably cheesy.
Tip: The Hyatt Place, right next door to the aquarium, often has “land and sea” packages that include a one-night stay and tickets to the aquarium. It’s an extremely easy overnight getaway from NYC with kids 8YO and younger. Even If you don’t have a car you can take the LIRR to Riverhead.
But Older kids and tweens are not likely to be impressed, especially if they’ve been to any of the much better aquuariums in the ares (like Mystic’s).
4. We also didn’t get to the smallish Railroad Museum of Long Island in Riverhead.
In the warm weather kids can ride a scaled down outdoor train on the weekends. A collection of working Lionel trains are a novelty for kids and return to childhood for parents and grandparents. This is a good bet with kids under 7YO.
Take A Summer Ferry Trip
In summer you can hop on the Shelter Island Ferry for an easy and fun day trip. There are several wonderful family friendly restaurants; just choose the one that appeals to you.
After lunch, you can hit the links at Whale’s Tale Miniature Golf & Ice Cream Parlor. It’s an old-fashioned place and the ice cream is only Hershey. But kids love both the golf and a cone afterwards. They have frozen yogurt and pies, too, to keep parents happy.
4 Spots for Chocolate & Desserts
1. Lured by a sign promising chocolate tastings, we sat in the parking lot of North Fork Chocolate, 3 miles east of Riverhead, for 15 minutes waiting for it to open. We weren’t disappointed.
The store itself is big and bright. Chocolate bars, lollipops, truffles, chocolate-covered pretzels and s’mores are displayed in inviting ways. A piano was covered in chocolate bunnies and other animals for Easter.
There is a cozy couch and a welcoming porch where customers can sit and enjoy chocolate, ice cream or coffee and one of a small selection of tempting pastries.
You can buy a “tasting” of four truffles for about $8. A box of four truffles is a few dollars more. The only difference, I think, is the wrapping. Tween traveler and I couldn’t agree on four truffles to share. So we each got our own tasting. They used a lot of local ingredients in their truffles from honey and fruit to wine and beer.
She went for rasberry, strawberry and vanilla fillings. Mine incorporated local rum. honey and apple cider. They were excellent: The chocolate had a good meltiness and the flavors were interesting and well-balanced.
2. After lunch in Southampton we stopped into The Fudge Company, a small store on Main Street that makes old-fashioned and very kid-friendly candy and chocolate. We bought a box of long, skinny taffy that was standard. And a bag of non-pareil pretzels that we loved for their pleasing mixing soft chocolate, crunchy non-pareil and salty pretzels
3. I have several friends who never hit the North Fork without a stop at Hampton Chocolate Company in Greenport. They’re lured by chocolate-dipped waffles and made-to-order ice cream sandwiches with homemade cookies. This was another spot that closes for the winter, so sampling these desserts will have to wait for another visit.
4. Gingerbread University is about 10 minutes north of central Riverhead. For $20 and up you can buy a giant, seasonally appropriate gingerbread cookie, a large pastry bag of icing and a pile of candy for decorating.
Tiny Traveler could choose a heart, flower or butterfly and went with the first. She really liked decorating and more candy went onto the heart than into her mouth, which is very surprising.
It’s the kind of activity that can appeal to kids in a range of ages. Even tweens can get their creative juices flowing when there’s candy involved. Look for gingerbread turkeys in fall and bunnies in spring.
Family Friendly Long Island Wineries
The North Fork is full of wineries and vineyards that have only gotten better over time. The days of hitting a bunch of wineries in one day seem to be over (especially if you have kids). The still offer flights for sampling. But the thing to do these days seems to be to settle in with a picnic (BYO or purchased from the winery) and a couple of glasses of wine or a bottle to share.
This approach makes them more family friendly, especially in the quiet off-season. Look especially for the wineries with outdoor terraces or picnic areas, where kids can roam around a bit while you sip.
1. On our latest visit we stopped into Jason’s Vineyard, which has alpacas, sheep and a half dozen picnic tables next to its vineyards, making it one of the best wineries to visit with kids along.
It was a sunny, warm April afternoon. Kids ate, visited the animals, explored the empty covered deck and even played catch on a patch of grass near the tables while their parents sampled the reds, whites and rosés.
We did a flight that included a dry rieseling, a steel-tank fermented chardonnay, a rosé, a meritage and a very rich and port-like dessert wine. We liked both whites and the dessert wine but it was the rosé that we went back to order by the glass.
Tip: The Jason who owns the winery is Greek and the longboat on the bottles and the logo is for argonauts, not vikings.
2. On our previous visit, Tiny Traveler snuggled with me by a fireplace and had a snack while I tasted a flight of reds and whites at Roanoke Vineyards. Afterward, with permission from the staff, I showed her the rows of budding grape vines out back.
Had it been a smidge warmer I would have sat on their outdoor patio and let her run around on the grass.
In addition to the vineyard tasting room in Riverhead, Roanoke has a wine shop on Love Lane in Matituck. It has outdoor tables where small groups can sample its wines and those of Wölffer Estate Vineyard on the South Fork.
Wölferr has some interesting white wines and a good rosé. But for the past few years it’s also been making sparkling hard ciders and its dry rosé cider is fantastic. A four-pack of small bottles of cider is handy for the beach or a picnic.
Sample Long Island Beer & Cider
A cluster of microbreweries and hard cideries has sprung up on the East End, many of them in and around Riverhead. Unfortunately, most aren’t open for lunch on off-season weekdays so we didn’t get to check them out. It’s too bad I was very curious, especially about the cider makers.
1. Blue Point Brewing Company, one of the more establised breweries out there is worth checking out; its toasted lager is great with its namesake oysters.
2. Brand new Peconic Breweing Company has a deck overlooking the Peconic River right in Riverhead. And it has tempting bar snacks like flatbread pizzas to go with its brews. I’ve heard Long Ireland Brewing Company has some good beers and food trucks on summer weekends.
3. Woodside Orchards is a small working farm and cidery across the road from North Fork Chocolate. Your kids can nosh on their homemade cider doughnuts while you sample ciders that mingle flavors like cinnamon, rasberry and blackberry mango with their apples. It’ open on weekends off-season.
4. Riverhead Cider House, 15 minutes north of town, has a big, barnlike tasting room, and serves up flatbread pizzas and hot heros to go with its long list of. They also have a kids menu.
I’ve been told they took on a new cidermaker two years ago and he skilled and doing good things. Some of the former cidermaker’s ciders are still on the menu so be sure to ask for the latest flavors on tap. I hear the pineapple and blackberry habañero are good.
Get Outside With Kids
Visit a farm stand
In the summer and early fall it’s not hard to find farmstands on the main roads through the North Fork. Look for local tomatoes, corn, salad greens and berries.
On the South Fork, families with younger kids will want to seek out Seven Ponds Orchard in Water Mill (near Southampton). It’s not as well known as some of the other Hamptons farms but it’s a local favorite.
In the summer kids can pick raspberries, blueberries and blackberries. In the fall it’s apples and pumpkins. There are also other vegetables and flowers you can pick, depending on the season.
When you’re done picking produce, there’s a playground and hayrides, and a small corn maze in the fall. The farm stand is a fantastic place to stock up for your beach house, even if you don’t explore the whole farm.
Hits Long Island Beaches and Parks
One advantage of visiting the Hamptons and the rest of the East End off-season is that the parks, beaches and beach parking that are reserved for residents in summertime are open to the public.
1. On a sunny March day we had the tide pools and dunes on the long stretch of beach outside of Southampton all to ourselves. We ran around until we were cold and exhausted. This is an Atlantic Ocean beach and it can be windy. In summer it has rougher surf than the beaches on the bay and the sound.
We returned to Southamton Beach on our recent visit and took a good long walk, collected stones and shells and even put our toes in the water (very briefly). It was a sunny warm day and with many summer folk living in the Hamptons yearround right now, we didn’t have the beach to ourselves this time, but we had plenty of space to do our thing.
2. The North Fork doesn’t have the long stretches of beach that the Hamptons do. But we took a nice morning walk and collected more stones on bay-facing South Jamesport Beach (top), which has a parking lot and playground.
Iron Pier Beach and Bailie Beach Park are two beaches on the Long Island Sound that have room to stretch your legs or kick a soccer ball.
3. The Quogue Wildlife Refuge, which has seven miles of walking trails, is open yearround.
Indoors, you can visit native animals, including a bobcat, owls, falcons and eagles, that the staff has recued.
4. The Elizabeth Morton Wildlife Preserve in Sag Harbor is open all year round and is a great, free outing for most ages. Bring birdseed. During most of visits, the chickadees and other birds will come and eat out of your hands (even little kids can do it!).
Keep your eye out for turkeys, chipmunks, and other local wildlife as you walk along any of several scenic trails. One popular trail leads you to a lovely bay beach where you can take a break and have a picnic.
5. A quick and easy way to get outside is the Peconic Riverfront Park in Riverhead. It’s quaint and scooter and stroller friendly and you’re likely to see ducks, herons and other sea birds. Just head toward the river from Main Street and you’ll find it.
Winter Only: Look For Seals
One thing you can only do in the wintertime is go seal watching from the shore. The Coastal Research and Education Society of Long Island offers seal walks from December in to early spring.
Or you can try your luck on your own at Montauk Sate Park and Cupsogue Beach County Park in Westhampton. Either way, dress very warm and bring binoculars.
Summer Only: Outdoor Music
During the summer months, Sag Harbor, Southampton, Easthampton and Montauk each has weekly free outdoor concerts in its park. It’s yet another place where we bring a picnic– or pizza if we’re feeling lazy.
Young Kids kids play and dance Tweens and teens might take the opportunity to dive into their phones or a book. Just pour a glass of chilled local rosé and enjoy whatever the music happens to be that evening.
Hamptons Restaurants Kids Will Like
We were too early for all the wonderful farm stands to be open but did find other places to eat in both Riverhead and the South Fork towns.
1. Jerry & the Mermaid, a clam shack next door to our Hyatt Place, the Aquarium and a marina could be pretty run of the mill and do okay. But it’s actually very good. They staff is friendly; when we couldn’t agree on a salad dressing the waitress just brought both without us asking her to. They carry local wines and beers, and have a kids menu.
Better still, someone in the kitchen cares and does creative things like offering spicy-sweet Long Island duck wings in lieu of the usual Buffalo chicken wings.
On our second visit steamer clams and frogs legs were on specials board. We skipped the latter but did order the steamers (thin-shelled clams unique to New England). They were the biggest steamers I’d ever seen in my life, steamed in wine and garlic and served with drawn butter. A win.
We also shared a generous house salad, the duck wings and meaty fried clam strips—all the fried-fish baskets come with waffle fries. Someone at the next table was eating a really fresh and tempting lobster salad.
A lot of families at the hotel next door get take-out from here and they’ll deliver to the hotel, too. If you’re at the aquarium, skip the crowded and overpriced café for lunch and eat here instead
2. A play at the at the Children’s Museum looked like an old-fashioned soda shop. On the wll there were photos of its real nearby counterparts, including Sip’n Soda, a 1950s luncheonette in Southamton. Feeding a 5YO it was a no-brainer to head there for lunch.
I had a burger and a vanilla ice cream soda. Tiny Traveler had a hot dog and scoops of ice cream. She loved it and it was a bargain, especially for Southamptons.
There are similar retro soda fountains on the main streets in Riverhead (Star Confectionary Store, below) and Bridgehampton (Bridgehampton Candy Kitchen). They all serve breakfast and lunch and make their own ice cream.
3. On our recent trip we just parked in Southampton and strolled up main street looking for lunch. 75 Main caught our eye. The brunch and lunch dishes people were eating at sidewalk tables looked good. And a table full of teens eating on our own made us think it would inexpensive.
Wrong. We forgot Southampton is the sort of place where teens carry their own credit cards.Three lunches, two glasses of wine and a Sprite ran close to $150 after tax and tip.
At the very least lunch was good. Tween Traveler had a side-order of steak and skinny, crispy fries. Rich had eggs Benedict that were good but could have used a small salad, the two eggs on muffins looked a little lonely on their large plate. I ordered a pepper stuffed with quinoa, mushrooms and vegetables. It was that rare and welcome combination of healthy and tasty.
4. I have long been wanting to eat at the Southampton Publick House, but again it eluded us. Sitting on the edge of town it has a bright, kid-friendly back dining room, outside deck and gastropub menu with handpacked burgers and real onion rings. Look for the well-regarded house beers on the drinks list.
Tip: We chose pretty casual places to eat, where jeans and sneakers were fine. But Bridgehampton and Southampton have their stylish cafés and bistros, especially in the summer season and at dinner.
If you plan to try any of those, pack something stylish and plan to leave your mom shoes home for the evening. Check reviews or call ahead to find out how they feel about kids.
1. On both of our Hamptons visits we stayed at the Hyatt Place East End in downtown Riverhead. Being right in town makes it easy to park and walk to dinner at the end of the day.
The rooms to be pretty spacious and I like that all the rooms have a fridge and a sitting area that’s separated from the sleeping area by a half wall.
The indoor pool is a decent size with a big window to let the sun in. It was pretty warm on our most recent visit (it was very cold the first time, so this was a welcome improvement). In the summer there’s an outdoor pool with a poolside bar and grill. Neither pool has a hot tub.
In normal times the complementary breakfast is generous and pretty good. During out covid visit an employee served potatoes, scrambled eggs and bacon, and we could help ourselves to extra like boiled eggs, yogurt, juice and coffee and tea.
There’s also a bar in the lobby and family sized booths where we saw families eating take-out dinner on both visits.
The off-season rental market has been tighter than it would usually be lately. But you can still also find affordable vacation rentals for longer stays, both further out around Greenport, Shelter Island or Montauk, or in the towns just west of the forks like Rocky Point.
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I had help on this post from Jennie Magaro, co-founder of Hamptons Family Concierge, a travel-planning service that will customize itineraries, plan events and schedule services and activities for families visiting the Hamptons.