We woke up in Southampton to a dull grey sky — not exactly the glamorous Hamptons morning we’d hoped for. Still, with a full day of exploring ahead of us, we threw on our jackets and wandered down to the main street for breakfast.
The Golden Pear Café provided our now traditional breakfast of bagels piled high with cream cheese and a couple of decent coffees to get us moving. The plan for today was straightforward: drive The Hamptons, admire some multi-million-dollar homes and see where the day took us.
Unfortunately, at some point I either forgot to take photos or accidentally deleted half of them, so today and tomorrow’s entries are lighter on images than planned!
Driving Through Bridgehampton and East Hampton
We headed east along the main Hamptons route, passing through Bridgehampton and East Hampton. The houses and roads looked exclusive and beautifully kept, but the biggest estates — the ones belonging to America’s elite — were securely hidden behind gates, walls and long sweeping driveways.
Who Lives in The Hamptons?
The Hamptons has long been a retreat for the rich and famous. Homeowners over the years have included:
- Steven Spielberg
- Jennifer Lopez
- Robert Downey Jr.
- Anderson Cooper
- Calvin Klein
- Ralph Lauren
- Beyoncé & Jay-Z (holiday home)
The weather may have been bleak, but the rugged Atlantic coastline more than made up for it. We pulled over at several windswept beaches and watched huge waves roll in — dramatic, moody and very photogenic.
Montauk and the Lighthouse
Our first proper stop of the day was Montauk. The town itself was quiet, almost sleepy, so we continued on to Montauk Point to visit the historic lighthouse.
Walking down the coastal path we noticed a crowd gathering at the shoreline. A group of surfers were attempting to ride the enormous waves crashing onto the rocks. We watched them for fifteen minutes, amazed at their bravery (or madness), before heading back to the car.
Sag Harbor – A Nautical Gem
About Sag Harbor
Sag Harbor is one of the oldest and most charming villages in The Hamptons. Founded in the early 1700s, it became one of the busiest whaling ports in America and its maritime heritage is still visible today in its preserved clapboard houses, wooden docks and historic Main Street.
The village has a more relaxed feel compared to Southampton and East Hampton, with boutique shops, bookstores, galleries and cafés lining the streets. We wandered up and down the main drag, bought a few souvenirs and then settled on LT Burger for lunch.
The burgers here were filthy in the best possible way — stacked, juicy and delicious. Throw in a couple of over-the-top milkshakes and we were set for the afternoon.
Dune Road, Westhampton Beach
Next we drove towards Westhampton Beach and joined Dune Road, a 14-mile stretch hugging the coastline with multi-million-dollar homes on either side. It’s one of the most exclusive residential areas on Long Island.
Who Lives on Dune Road?
The road has been home to various celebrities over the years, including:
- Roger Waters
- Patti LaBelle
- Michael J. Fox
- Donna Karan
One end of the road felt surprisingly industrial, with fishing boats and locals casting lines from the shoreline. The other opened onto sweeping dunes and a vast golden beach. Even in bad weather it was stunning.
Back to Southampton – and Mixed Feelings
By late afternoon we’d had enough of driving in the gloom, so we headed back to Harpoon House. We bumped into another guest who, like us, wondered if anyone actually worked there. Still no staff, no welcome and no information — not exactly boutique-hotel service.
A Brilliant Evening at Fellingham’s
The evening, however, completely redeemed the day. We walked to Fellingham’s Restaurant & Sports Bar and the atmosphere was the polar opposite of the previous night. The local baseball team was in celebrating the end of the season, the staff were warm, friendly and chatty, and the whole place had a great buzz.
We enjoyed:
- tasty salads
- fries and frickles (fried pickles!)
- plenty of cold beer
We chatted with the waitress about the UK, Europe and the Hamptons, and left feeling far more positive about Southampton than we had 24 hours earlier.
A final stop at Walmart to stock up on sweets and chocolate for tomorrow’s drive to JFK, and we headed back to the guesthouse for an early night.
Tomorrow: the final stretch back to New York and the end of the road trip.
Day 14 – Falmouth to The Hamptons: Diners, Murder Houses and a Sunset Ferry to Long Island
Day 16 – Leaving The Hamptons and Flying Home: The Final Day of Our East Coast Road Trip
