Can you take a day trip to the Hamptons? And should you? I tried it.
As a “beach person,” my first few years living in New York City were sometimes tough. Although the coast is right there, it can seem so hard to get to.
I started reserving Sundays for spots like Jacob Riis and Rockaway, but the thick crowds made me miss the sparsely populated Mid-Atlantic beaches of my childhood.
The Hamptons have always intrigued me, not because of the notorious parties, the gossip, the real estate, or the latest celebrity tribulations, but because of the gorgeous, desolate sand and grassy dunes.
It looked like the edge of the Earth (perfect), yet only a couple hours from the city.
But is a day trip to the Hamptons even possible? Would people think I’m crazy? Where, even, is the beach?
So when I had the chance to visit Long Island for Memorial Day, I jumped on it. I had no budget — no overnight stay, no reason for fancy dinner reservations, nor any interest in scene-y schmoozing. This was about exploring, relaxing, and the simple pleasure of my toes in the sand.
Making my plan
As I’d be arriving via bus, I wanted a destination with a town area where I’d have access to food and, crucially, bike rentals, so I wasn’t relying on Lyfts.
My bus was making stops at Southampton, Bridgehampton, and East Hampton. Of those options, I learned Southampton has the better “strollable main street,” plus a bike shop for my transport needs.
As I planned my routes on Google Maps, I figured I would walk 18 minutes from the train station to Southampton Village, where I could rent a bike for $12 an hour.
From there, it was only a 10-minute bike ride from town to Cooper’s Beach, which is open to the public and has been rated one of the best beaches in the United States.
Starting my adventure
As my bus pulled up to the Southampton train station, I observed a PedalShare bike rack stocked with pink beach cruisers in the adjacent park. A-ha! It looked like I wouldn’t be walking to town after all.
After downloading an app called Bloom and easily setting up an account, I was on wheels — albeit rusty ones — and on my way to the beach.
I took it slow. (Isn’t that the point?) My phone’s navigation guided me from the little basket on the front of the bike, and I enjoyed the mild breeze as I moseyed along the leafy streets.
After skirting the edge of Southampton’s cute town area, I turned left onto First Neck Lane, a quiet boulevard with tall old trees, flowering rhododendrons, imposing privacy hedges, and enormous estates with names like Normandy House and Swan Lawn.
Now I was really poking along as I took in all the manicured beauty. Bentleys and Mercedes SUVs gave me a wide berth as they passed — maybe to take care with my life, or perhaps because it was bizarre to see a lady on a broken down bike in an area with so many multimillion-dollar mansions.
In no time, I was pulling into a mostly empty parking lot of Cooper’s Beach. This was surprising because it was a sunny day over Memorial Day weekend. But maybe most folks were already returning to the city.
I locked my bike at another convenient PedalShare rack and walked over the dune to the sand. The view was spectacular: white sand, glittering ocean, no crowds. I sat on a bench near a pristine open-air shower station, removed my shoes and tied them to the straps of my backpack.
A few couples and families frolicked, and a group of lifeguards hung out without much to do — the water was still too cold for swimming. I let the waves lap at my ankles for a few minutes, then found a comfy spot on dry sand and took a seat. The salty air transported me just how I needed it to.
After about an hour, I wanted lunch. A cafe on the beach was offering burgers, fish sandwiches, and lobster rolls, and a few folks were chatting over beers on the deck. I wanted to explore some more and decided to hop back on my bike and find out what town had to offer.
Hitting the town
As I strolled up Main Street, there were lunch options everywhere. The pretty sidewalk cafes reminded me of Paris, right down to the cane rattan chairs.
The menu at Cheese Shoppe offered tasty-sounding grilled sandwiches for $16, which is what we’re calling reasonable these days, I guess. But the kitchen was already closed for lunch (it was about 3 p.m.).
Thus I journeyed farther north, among passers-by in shiny sandals and billowy skirts, through rich perfume clouds (so many patchouli notes, FYI), and past shop windows with $500 maxi skirts, straw hats, and housewares.
Everyone on the street used hushed voices. It was a true respite from the city — even more so than I’d hoped. This was not the all-party Hamptons I’d seen people brag and complain about online.
I wondered if holiday-weekend hangovers played a role. I was there on the Monday after Memorial Day, after all. But I also noted how everyone looked so similar: white shirts, French florals, crisp denim. Was the vibe chill… or orderly? Even compared to other high-end beach towns I’ve visited, this felt like anti-chaos.
I arrived at the Golden Pear on the corner, where several clusters of twentysomethings slouched at cafe tables with coffees and green juice.
It seemed like a good bet for a quick lunch. I later discovered the Golden Pear is a small local chain, which explains why it felt accessible.
The older gentleman taking my order shouted good-naturedly to be heard and kiddingly chided me for forgetting to grab a beverage from the cooler. It was the most energy and emotion I’d witnessed all day.
I ordered a turkey and brie panini with a side salad and “prebiotic” soda for $33, including tip. He asked where I’d be sitting and I gave an uncertain look around the crowded joint.
The man quickly waved me off. “Eh, I’ll find you,” he said in a tone that communicated zero doubt. I had to wonder if my bike-friendly jersey dress and REI backpack made me stand out even more than I realized.
What to know before you go
There is a dress code.
Even if you’re not visiting the Hamptons to rub elbows in high society, you’re subject to high society’s rules. On my bus ride back to the city, someone mentioned Southampton’s dress code, and I smacked my head. It is a real thing governing where and how you can wear a swimsuit or expose some skin.
Turns out I wasn’t in violation — imagine being imprisoned for exposing a butt cheek? — but I’m sure I broke the unwritten fashion rules, which based on my observation might be: look very fabulous and very wealthy, with bonus points for donning white and blue.
There are also regulations about where you can ride a bike. The popular Instagram account Kook Hampton documents silly tourists behaving badly (hope they thought my rent-a-bike was cool??).
You can do a day trip.
The Long Island Rail Road has off-peak round-trip service between Penn Station and Southampton for $57 — and you’re allowed to bring your bike on the train, provided it’s not too crowded.
You can park a car at Cooper’s Beach for $50 (parking a bike is free), and it offers umbrella and chair rentals for $20 and $15 respectively. There’s also free sunscreen!
If you’re not visiting the Hamptons for the scene, I recommend bringing lunch or picking up a sandwich and heading to Agawam Park for a picnic overlooking a small lake.
My on-the-ground total for the day came to about $53; I blew up my spending by taking the Blade bus – but had I taken the LIRR, my total would have been around $100 for the day.
I’d have been happy to spend a little more for that glass of wine and entry to the Southampton History Museum (it was closed).
Then again, Jacob Riis has a $20 parking fee and you can take a ferry to Rockaway Beach for $4.
Spring for a better bike.
Had I stuck to my original plan to rent a decent bike from Rotations ($45-$120 per day), I probably would have made it to Duck Walk Vineyard, located a 10-minute bike ride from town. Sadly, I had to pass, as I was afraid my PedalShare would be too slow or pop a tire and cause me to miss my bus.
Would I take a day trip to the Hamptons again?
Probably not, but I’m glad to have finally satisfied my curiosity.
link