What makes the perfect weekend getaway? A playlist of Talking Heads albums, a checklist of must-see spots, a comfortable pair of jeans, a surfboard, and naturally, a sweet ride. All the elements came together as photographer Emily Rosser and I hit the road, cruising from New York City through Rockaway, Queens, then east through the Hamptons out to Montauk – and back. We hit the open road in our GLK 350 as the sun rose on a brisk September morning, making stops to eat and explore along the way. Join us as we say good-bye to summer.

[Fuel consumption combined: 8,6–8,1 l/100km | CO2 emission combined: 199-189 g/km*]

Rockaway Taco
To fuel our bodies for the upcoming two-hour stretch of drive, we pulled up to Rockaway Taco and Veggie Island for a smattering of baked eggs, avocado, freshly made kale juice (one of my favorite recipes, blended just right), and iced coffee. The two establishments share a corner block, and with their vibrant colors and loud music, it almost feels we’ve been transported – momentarily – to a tropical island. (Fun fact: The Rockaways are located on a small peninsula.) The corner is mostly a hang out spot for the early morning crowd; located only steps from the local surfing beaches, bare-footed patrons filtered in for their post-dawn patrol breakfast. “The waves were small – but we saw a whale,” a local surfer tells us.

Surfing Ditch Plains
As the second weekend after summer’s official end, there’s a sharp bite of autumn in the air – yet it’s not chilly enough to skip out on one of the most popular beaches in Montauk, Ditch Plains. Fashionable beach-goers squeezed side by side, soaking in their last days of sun. And while the waves were smaller than predicted, longboarders still reveled as they took off on each crumbly wave, one by one. Ditch Plains is rich in surf history, but it’s only been in the more recent years that it’s been pegged as a ‘hot spot’ to be seen surfing – in other words, crowds during warm months are not uncommon. Emily and I got our fill of salty air and sunshine; a perfectly temperate day that straddled both summer and fall.

The Surf Lodge
A few hours in the salty surf will most definitely work up an appetite; the cure was a stop at Montauk’s The Surf Lodge. Arguably the hotel and watering hole that has defined the sweeping changes in the former sleepy fishing town the past seven years or so, Surf Lodge made significant changes in their menu last summer with the introduction of Byron (referring to the Australian-inspired meals served). Normally, a Saturday evening during the summer months would mean a tightly packed bar and loud, thumping music, but September attracts a more relaxed crowd. A watermelon salad, a roasted chicken, and a lobster roll later, we lounged on the lemon yellow cushions as the sun set over the water.

The Crow’s Nest
We had a few more minutes of sunlight left and decided to wander over to The Crow’s Nest Inn & Restaurant, an evening meeting house of sorts for the chic and well-to-do. We melt into the dreamy views overlooking Lake Montauk while sitting on a grassy knoll, sipping sweet wine. With that, I can safely say that this must be one of the most romantic spots in all of Montauk. Afterward, we peruse the hotel’s most recent addition, a shop not much bigger than a closet, filled with books, jewelry, and artifacts, curated by collector extraordinaire Bob Melet of Melet Mercantile.

Pilgrim Surf +Supply
We could’ve spent many an hour gazing at the stars, but professional surfers awaited us at Pilgrim Surf + Supply in Amagansett, the recently opened sister store to the popular Brooklyn surf shop. The shop was celebrating pro-surfer Joel Tudor with an outdoor screening of his documentary, complete with a popcorn machine and a DJ. Friends and fans sat on blankets scattered throughout the shop’s front yard, and chatted about their plans for the winter. Inside the store, patrons scoped out the selection of surfboards and outerwear, as well as the small gallery hidden in the back stocked with an exhibit of notable surfers in history photographed by Michael Halsband. Chris Gentile, the shop’s owner, explained, “There’s a lot of history that goes back to artists and creative people meandering and moving their way out here, and being inspired by how amazing the natural resources are here.” While pop-up shops and seasonal businesses are commonplace in beachy towns, Pilgrim expressed their excitement to stay open year round as a part of the town’s community.

Montauk Lighthouse and Camp Hero
After a hot cup of coffee in the crisp outdoors near Amagansett’s Louse Point the next morning, we decided it was time to explore some of the history of Montauk. A short drive east leads us to the Montauk Lighthouse and its neighbor, Camp Hero. For many locals and visitors, Camp Hero is a hotbed of urban legends, ranging from alien sightings to phenomenal military activity. The lighthouse and camp are set high up on Montauk’s bluffs, allowing vast peripheral views of the coastline. Even if the rumors are false, there’s something eerie about the plot of land. Windowless cinderblock buildings are scattered amongst the trees, and while it is a public park, rusty metal fences close off certain areas, including one with a dilapidated radar big enough that ships on the water use it as a landmark. Keep your eyes wide open when wandering these parts.

Tripoli’s Gallery
It was time to start heading west, back toward New York City, but there were still more places to be seen – one being Tripoli Gallery in Southampton, owned by professional surfer Tripoli Patterson (who will be part of another story coming soon – stay tuned). It was the day after the opening for a solo exhibition by Eric Freeman, and the walls of the gallery were filled with canvases of intense color. Natural light flooded in through a skylight-type window, adding a feeling of airiness to the space. Tripoli, a local of Long Island, spoke about the richness of the art community in the Hamptons, noting his excitement about the expansion of the Parrish Art Museum. “Being from out here, a lot of my friends are artists,” he noted. “I liked that the spotlight wasn’t on me [as a curator], as it’s been as a surfer, it’s nice to be behind the scenes and be able to put the artist in the forefront of what I’m collecting energy around.”

Playland Motel
We pull up to the Playland Motel Sunday evening, the final stop on the girls’ weekend getaway, exhausted from driving but excited to check out Rockaway’s latest nightlife addition. Inside, a small group decked out in bikinis and boardshorts huddle around the bar, watching the football game and sipping margaritas in plastic cups. The ambiance reminds me of that of a summer residence: a hanging fish on the wall, a playful sign, and a large, cold beverage in every patron’s hand. Though the outdoor area was closed for the season, the menu is packed with finger food for a laidback post-beach meal. We laughed and reminisced about our time out east while tossing backsliders and fries.

After 48 hours of traveling throughout the East End of Long Island, we returned to the hustle of the city feeling refreshed from the fresh air, the hearty meals, and all-around mellow vibes. The result of our adventure? The perfect weekend getaway.

Enjoy our photo gallery above!