Growing up my aunt who lived on Long Island would take me to Montauk as a kid. Her ex-husband’s family had a house and we would summer in Montauk. Fast forward to today, Montauk and the Hamptons is where the city people go to escape the hot city. It was my aunt’s birthday and we were all craving lobster rolls so we did a quick day trip to the Hamptons and Montauk.

Our first stop was for lunch in Amagansett at LUNCH Lobster Roll Amagansett. I ordered a frozen lemonade which was okay. For an appetizer we split the crab dip and fried calamari. (My dads fave app is calamari). My husband and I personally wanted to try the fried clam strips, maybe next time.

A short drive from Amagansett is Montauk. We walked around for a bit to burn off the lobster rolls. Initially we wanted to go to the light house, but it was closed for a concert. We decided to go on a nature walk at Shadmoor State Park. I definitely wasn’t prepared for all the walking as I was wearing sandals, but the ‘hike’ is doable in sandals.

Before it became a public preserve, this land hosted Camp Wikoff in 1898—a quarantine site for Theodore Roosevelt’s Rough Riders returning from the Spanish–American War, suffering from malaria and other illnesses. Decades later, during World War II, it formed part of the coastal defense system with two concrete observation bunkers (now visible) once armed to guard against enemy threats. During lunch, my dad mentioned how in Montauk, German spies from WWII were caught by a local fisherman.

A 99 acre NYS Park in Montauk created in 2000 that has 2 concrete bunkers that once housed artillery guns to protect the Atlantic coast during WWII. The Roosevelt trail leads to the bluffs overlooking the Atlantic Ocean which eventually leads to an unmarked trail to the beach where you can gaze up at the bluffs, see what has washed ashore, and see the remains of a road along the bluffs that has long ago eroded away (perhaps part of the original Montauk Highway before it was rerouted further inland). Part of this road can also be seen at Montauk’s Camp Hero just east of Shadmoor. Named for the dense shadbush (also called shadbush) that once dominated the landscape, its open rolling topography earned it the “moor” in Shadmoor.

We parked in the small parking lot and walked the walking path. A short walk to the clifftop trails, you’re greeted by panoramic Atlantic Ocean vistas framed by dramatic clay and sand bluffs. The elevated platforms allowed glimpses into both woodlands and wetlands—a haven for migrating shorebirds and woodland species among the shadbush and black cherry groves.

Along the trails we spotted clusters of the rare, federally‑endangered sandplain gerardia flower, a delicate reminder of the region’s fragile ecology. The path looped us through freshwater wetlands—perfect places to listen for frogs, spy dragonflies, and catch sight of birds skimming nearby ponds.

After a rewarding hike through Shadmoor, we drove west into East Hampton Village for a classic summer treat: a scoop of ice cream. In my opinion, East Hampton is the best out of all the surrounding areas. (Probably because of all the shopping. But remember that there’s a luxury tax when shopping in the Hamptons.)

Since it was only a day trip, it was time of us to head back to the city. Our next day adventure will be heading to the North Fork. Definitely going to try and buy one of those pies people are raving about.