The Hamptons, Montauk & Eastern LI

Everyone who I’ve ever taken to Long Island in the history of ever has wanted me to take them to the Hamptons for a day, and every single time my response has been “eh…there’s not much to do out there…” (especially in the colder months).

Until now.

I get the novelty of it – I always have. You can walk through extremely expensive stores (stock up on vineyard vines) which are surrounded by extraordinarily expensive homes which line miles of Long Island beaches. It can all seem lackluster under the wrong guidance, but with a smile and a love for adventure, your day in the Hamptons can be so much more than a celebrity hunt (Pro Tip: Don’t expect to see any celebrities out there in the colder months. They all have summer homes out there).

The Hamptons are close enough to my hometown of West Babylon that I have the ability to take it for granted, but far enough that I know how to be a tourist there. Here are my tips, separated by town/area and organized by farthest west to east.

Painful Disclaimer – Almost everything listed here would be worth the likes of three dollar signs on an app like Urban Spoon. In other words, be prepared to spend. Especially on parking.



While I’ve already discussed Riverhead’s aquarium and major outlet center in my Babylon blog, I left out some of the more Eastern LI-adult things to do. Mainly, wineries.

  • Martha Clara Vineyards – Tastings, tours, and gourmet gift shops – what else could you possibly need in an afternoon? Special features include picnic tables and a small petting zoo to keep the kids occupied (though there’s plenty else to do in the Hamptons to keep them involved). It’s also a beautiful place for a wedding ;).
  • Riverhead Raceway – It’s a little weird that this is here given that it’s not really a New York thing to do, but I guess they play baseball in the south.



This is where those unnecessarily large and beautiful houses with 12-foot hedges come in. It’s probably what you’re expecting if you’re a Gossip Girl fan. Also, I don’t think I’ve ever seen someone outside in sweatpants in Westhampton. It might be punishable by law there.

  • Cupsogue Beach County Park – There are a lot of private beaches out on Eastern Long Island, so places like these are like rare gems. Cupsogue also has great amenities – restrooms, first aid, food concession, and sometimes live music and special events. There are lifeguards, fishing is allowed and apparently bass fishing is a big thing here (I wouldn’t know, fishing is not my game). Other activities like scuba diving and camping are also permitted. Basically, it’s a fun time.


Westhampton Dunes/Westhampton Beach

This is more of a private area. The actual beach is intended for residents of Westhampton beach and there won’t be as many tourists. I would say that the owners might hate me for including this here, but most of the owners don’t live there year-round anyway. In fact, a lot of the houses in this area are rented out. See if you can snag one for a week and enjoy a virtually private beach! At the very least, it’s worth a very slow drive down Dune Ln, Westhampton Beach, to check out the phenomenal homes. If you find a place to park, take a walk down the beach. Warning: Even if you don’t want to drive slow enough to admire the neighborhood, you have to. You WILL be pulled over if you don’t drive the speed limit, which is reasonable because it’s meant to be a quiet, family-friendly neighborhood.



Southhampton is probably the beach/shopping atmosphere you picture when you picture the Hamptons. It’s also the most tourist-y section of the Hamptons, and it’s where you’ll find the best deals on hotels.

  • Cooper’s Beach – The most well known public beach in the area. You’re likely to see tons of families and kids. If you can’t find street parking or someone in your party can’t bear the walk, parking is going to kill you on this one. $$$
  • Southhampton Historical Museum – As of 1990, this museum consists of 12 structures including an old schoolhouse, barn, paint store, etc. If you’re a history nerd and have a few hours to spend, this is a good way to do it.
  • Parrish Art Museum  – If history bores you and art is more your thing, this museum has a wide variety of works that you might like. Notably, there are a lot of modern pieces and New York landscapes.



Birdgehampton belongs to the town of Southampton, but has its own small charm.

  • Southfork Natural History Museum and Nature Center – This is both a place for history nerds and families. Admission is free on Tuesdays and Thursdays, so it’s a way to keep your Hamptons trip slightly cheaper. They advertise both “real and recreated natural habitats” and a Marine Touch Tank.


Sag Harbor

This is probably the most forgotten town within the Hamptons because it doesn’t have the hamptons name attached to it. When I think of Sag Harbor, I don’t think of mansions and designer clothes, but it’s still right up there with the others. It’s a beautiful town.

  • Sag Harbor Whaling & Historical Museum – So there are a ton of museums on Eastern Long Island. If you’re out there eating sea food and fishing, this is a good museum to stop in to complete your trip. This museum closes in the winter but it’s very cheap to visit. The regular adult admission is only $6. Think, the same museum in Manhattan would have had a recommended admission of $30.


East Hampton

Would East Hampton belong to the Hamptons if it didn’t have any museums? Truth time: I haven’t actually been to any of these. I’ve always seen East Hampton as the least tourist-y part of the Hamptons and the most residential. Apparently, though, these places exist. I’ll check them out soon and get back to you. I’m most looking forward to checking out the Mulford Farm.

There’s also Cedar Point Country Park for all your picnic, camping, fishing, hiking and boating needs.



Have you been to New York City yet? If you go to Montauk Point, you will have been to both the Westernmost and Easternmost points of Long Island. But that’s not the important part. Montauk is a relaxing kind of awesome. It’s a beach town with a historic lighthouse, mini golf, and sea food.

  • Montauk Light House – The Montauk Lighthouse is a symbol of Long Island. There is a long history behind it, which you can learn all about at the museum ($10 adults $4 children). It was authorized by President George Washington in 1972. Climb to the top and you can see Connecticut and Rhode Island!
  • Deep Hollow Ranch – Have you dreamt of going horseback riding on the beach? Well, this is your chance. Or you can go for a regular forest trail.
  • Boat Rentals – This is definitely a thing all over Long Island and especially all over the Hamptons, but Montauk is probably the best place to do it because it’s the most tourist-friendly section of Eastern Long Island.
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