The Hamptons (A Road Trip For Non-Fancy People)

Even if you don’t live in New York, you’ve likely heard of the Hamptons. And if have, you probably associate the Hamptons with the rich and famous, old money, expensive seafood, and glamorous beach parties. And certainly, a lot of that is accurate, but you can still have a fantastic, low-key experience on Long Island’s East End without breaking the bank or feeling like you won’t fit in with the scene. Use these tips below to plan your own fun and relaxing road trip out East!

When to Go

Ok, so I get that we’re mostly talking about beachfront communities here, but if you’re looking for a quiet and affordable getaway, you’re going to have much better luck in the offseason. As such, I recommend heading out to the East End in November/early December or late March/early April. You’re outside of the high and shoulder seasons, which means room rates will be lower. A LOT lower. Also, the weather is usually still pretty decent around this time of the year. It will definitely be a little chilly but not so cold that you can’t still take a walk on the beach or spend some time outdoors.

Where to Stay

There are some fabulous little towns and hamlets throughout the Hamptons, but Montauk is a great spot to stay if you want to save some money. Often referred to simply as “The End”, Montauk is at the very tip of Long Island’s South Fork and the furthest point east in New York State. (There is actually a lot of debate about whether Montauk is even part of the Hamptons, but this old fishing village is home to Julianne Moore, Robert DeNiro, and Ralph Lauren, so it’s not exactly shabby!)

The past couple of years, we’ve stayed at Daunt’s Albatross Motel, a cute little family-run motel right in town. Rooms are $100/night or less during the offseason, it’s a block from the beach, and you’ll be within walking distance to plenty of shops, bars, and restaurants. 

What to Do

This is a road trip, so if you don’t have a car, you’re going to need to borrow or rent one so that you can easily get around. And while I fully advocate just pulling off randomly when you see something that looks really interesting, here are some places we liked that you might want to check out on your own trip.

  • Milton L. Burns Park in Riverhead, NY: Riverhead’s downtown area is super cute and has plenty of places to eat and drink, including at least four different breweries. If you stop in the area, check out Milton L. Burns Park, also known as Grangebel Park, along the Peconic River. They have several very cool art installations alongside (and even IN) the river, making it a fun little stop on your way out East.
  • The Big Duck in Flanders, NY: So, there is a giant duck out on Long Island with a little museum and gift shop inside of it. And while its presence initially seemed pretty random to me, it turns out Long Island used to have about 80 duck farms that supplied the whole Northeast with eggs and Peking ducks. The Big Duck stands on the property of one of these former farms and is ready and waiting for your visit! There was also a lovely gentleman there the day we visited who gave us tips for places to visit and things to do on the East End, and they have lots of maps and brochures, too, in case you need some inspiration.
Flanders Big Duck
The Big Duck in Flanders, NY
  • The Hamptons: You’ll drive through the various villages of the Hamptons on your way to Montauk, and there are plenty of options for eating, drinking, and shopping. On our most recent trip, we stopped in at the Southampton Publick House for lunch and a flight of their beer. Last year we went to Sagg Main Beach in Bridgehampton to wander the beach, pretty much all by ourselves. Sometimes we’ll just peel off the main road to see what we find. Usually, we discover isolated stretches of beach, gorgeous houses, and pretty country roads. Enjoy getting off the main road and creating your own adventure. You never know what you might stumble upon! And even if you decide not to stop anywhere, the towns are all cute and quaint and fun to see even if you’re just driving through them.
Southampton Church
A lovely little church in Southampton, NY
  • Montauk Lighthouse and Museum: If you’re looking for great views, this lighthouse at the very tippy tip of Long Island is the place to go. Check out the museum on the ground floor and then climb the stairs to the top of the lighthouse to enjoy sweeping views of the Atlantic Ocean, the Long Island Sound, the North Fork of Long Island, and even parts of Connecticut and Rhode Island. Really, if you do one thing on your trip out East, I’d recommend doing this because it’s perfectly situated and the views are just stunning.
Montauk Lighthouse
The Montauk Lighthouse
  • Camp Hero State Park: Supposedly the inspiration for Stranger Things, this retired military installation in Montauk is definitely a little on the odd side. You can drive through and look at the old military buildings, including the former batteries and the creepy-looking radar tower. The conspiracy theory book series, The Montauk Project, alleged that the government was running secret experiments at Camp Hero. After driving through the place, it’s not difficult to see why someone might come to that conclusion. That said, there are some lovely hiking trails and paths down to the beach where you can get gorgeous views of the bluffs.
Camp Hero Bluffs
The bluffs at Camp Hero State Park
  • Watch the Sunset: No matter what you do during the day, make sure you enjoy the beautiful sunset over Montauk before moving on to your evening activities. The Montauket is a popular spot to grab a drink and watch the sun go down. Weather permitting, you can enjoy it from a table outside. If it’s super crowded like it was when we tried to go this year, just drive a bit further down the road to Duryea’s, which is closed in the offseason. We parked in their empty lot and stood outside this November (in the crazy gusting wind!) to enjoy the breathtaking sunset below. Sorry, the wind wouldn’t allow me to keep my hand steadier!
  • Enjoy the Beach: You’re not likely going to be doing any swimming in the offseason, but you will see plenty of people surfing along the East End throughout the winter and you can do it, too! Sounds awfully chilly to me, but again, the offseason means less competition for catching those waves. Also, the beaches are delightfully empty and you’ll have them mostly to yourself if you want to just take a stroll. In the evening, you may even find folks out enjoying a bonfire or fishing in the moonlight like these guys below were.
Montauk Fishermen
Just a couple guys, fishing in November under a full moon

Want more inspiration on what to do and where to go?  This article has even more great stops to consider on your way out East.

Where to Eat and Drink

One of the downsides of offseason travel is that some of the bars, restaurants, and shops you would normally enjoy in the summer won’t be open. However, this does not mean there won’t be plenty of delicious options to keep you fat and happy.

  • Montauk Bake Shoppe: Great for breakfast and lunch, the Montauk Bake Shoppe is one of our favorite places to eat in Montauk. They make great wraps for breakfast, but they also have fantastic baked goods, including the best scones I’ve ever had. I don’t even particularly like scones because they’re often dry and crumbly, but the Montauk Bake Shoppe must have perfected the recipe because they are AMAZING. Stop here to get your coffee fix and grab a little somethin’-somethin’ to go.
  • Tauk at Trail’s End: Tauk at Trail’s End is a great spot to enjoy happy hour and lots of food specials during the week. There is definitely a low-key vibe, but the food is a little on the pricier side if you miss the happy hour specials. We haven’t eaten here, but everything looked and smelled scrumptious. 
  • The Point: For a better bargain at dinner, try The Point Bar & Grill, which is our favorite place to eat in Montauk. They also have happy hour and food specials during the week, but their regular menu is affordable and delicious as well. I really enjoyed their steak sandwich, and the brownie sundae for dessert is the perfect way to wrap up a meal.

    The Point Bar and Grill
    The Point Bar and Grill in Montauk, NY
  • Montauk Brewing Company: If you want to do a little beer sampling, then the Montauk Brewing Company is the spot for you. Stop in and have a flight before heading out to dinner. (They have a delicious pumpkin beer in the fall if you’re into that kind of thing!) It’s a small place, but everyone was really friendly when we visited and didn’t mind sharing tables. You may even meet the resident golden retriever who is adorable!
  • The Shagwong: Yep, funny name. My husband can never remember it, and we end up laughing hysterically at all the interesting variations he comes up with instead. We’ve tried eating at Shagwong before, but it’s always packed. It seems to be the bar where all the locals hang out, so even if you can’t make it in for dinner, you can still throw back a couple drinks and have a good time here. They also have a pool table, which was what originally brought us here. 
Shagwong Restaurant
Shagwong Restaurant in Montauk, NY. They have a pool table, too.

And For the Extra Adventurous…A Jaunt to the North Fork

If you run out of things to do on the South Fork of Long Island and you want to get extra adventurous, you can always head to the North Fork! And, by far, the coolest way to get there is via ferry. 

  • Shelter Island: When you leave Montauk, head back west to Sag Harbor and board the ferry to Shelter Island. In the offseason, there’s hardly any traffic and you should be able to drive right onto the ferry with little to no wait. The trip itself is not even 10 minutes! Once on Shelter Island, check out the Shelter Island Craft Brewery or take a little hike at the Mashomack Preserve. If you’re hungry, grab some breakfast from the counter at the Shelter Island Heights Pharmacy. When you’re ready to move on, keep heading north for the ferry to Greenport, NY on Long Island’s North Fork.
Ferry to Shelter Island
Front row seat on the ferry to Shelter Island!
  • Greenport, NY: This town is super cute, with tons of bars, restaurants, and adorable little shops. There is a carousel in town, a maritime museum, the Greenport Harbor Brewery, a railroad museum, and more. Even if you don’t plan to stay long, simply taking a stroll through town is a delightful experience, especially in the offseason when there aren’t any crowds!
  • Orient, NY: If you head a bit further east of Greenport, you’ll find yourself at the very end of the North Fork in Orient, NY. Go to the Point where the ferry departs for New London, CT, and you can take a nice walk out on the beach for views of the lighthouse, as well as two of NY’s most mysterious islands, Plum Island and Gardiner’s Island. Plum Island is known for its weird experiments related to infectious animal diseases and Gardiner’s Island is a private island, owned by the same family since the 1600s. Neither are accessible to the public, but you can get great views of both on a sunny day at Orient Point.
Orient Point
The Orient Point lighthouse and Plum Island off in the distance
  • Horton Point Lighthouse: As you work your way back west on the North Fork, check out the Horton Point Lighthouse. It’s closed in the offseason, so you can’t climb up inside of it, but you can still wander the grounds and admire the view. It’s up on a huge hill, and if you have the energy, you can also go down the 5-6 flights of stairs to the beach. This was a totally unanticipated stop for us this year, and we loved it. The views alone make it a worthwhile stop!
Beach at Horton Point Lighthouse
The stairs down to the beach at the Horton Point Lighthouse
  • Wineries: And of course, no trip to the North Fork is complete without a visit to a winery or two. There are tons to choose from, and this handy map can help you narrow down your options. Just remember to drink responsibly or be sure you have a designated driver if you’re going to be visiting several wineries on your road trip. 

So, if you prefer to avoid crowds or if you’re thinking that summers in the Hamptons may be a little too fancy for you, I hope this guide will help give you some ideas for planning your own low-key trip out East. There are so many beautiful places to see and tons of fun things to do, so don’t be intimidated. Go hit the road! We recently returned from our 2018 trip out East, and we’re already excited for all the new spots we hope to discover next fall.

If you find something fun on your own trip, leave me a note below so we can check it out, too!

Or let me know if you already have a favorite spot out at “The End”!

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