Exploring the East End: 3 Days in the Hamptons, Montauk, and North Fork
25 min read | Travel, Travel Diary
Ponquogue Beach at sunrise
How to Get There:
Since we’re from New Jersey and didn’t have to worry about rental car costs, we drove through NYC and across Long Island. It took us about 2.5 hours from North Jersey, which is pretty quick. We were warned about Hamptons traffic, but erred on the side of us leaving on a Wednesday morning and during the shoulder season. However, if you’re travelling from any of the NYC metro airports, especially during the summer, expect a long trip - 4 hours.
Where We Stayed:
We stayed a Tiny House in Riverhead, which is right between the North and South Fork. We wanted to explore both forks and thought finding an Airbnb was a cheaper option than finding an accommodation closer to the beach. I do want to note that it would take about an hour and a half from our Airbnb to the very end of Montauk in the South Fork and about 35 minutes to Greenport in the North Fork. If you’re looking for other accommodations, there are plenty of other (but more expensive) options.
When We Went:
We went at the very end of September. Hoping to avoid some of the summer crowds, we opted for a late September trip. The costs are cheaper at some of places, but don’t expect a huge dip. Be sure to double check what restaurants and stops you want to visit because some begin to close up right after Labor Day weekend, while others stick around for the fall season before shutting down for the frigid months. The weather was beautifully sunny, but on the cooler side (averaging low 70s during the day, 50s at night).
Day 1 (Travel Across Long Island):
Like I mentioned earlier, we were only leaving from New Jersey, but we wanted to enjoy our time making our way across Long Island and stopped at a few places along the way. Despite being a New Jersey native and working in the city, I had never actually gone west of the outer boroughs, so this was my first time in Long Island.
Our first stop on our trek was Old Westbury Gardens, a large estate that includes an extravagant historic mansion and beautiful gardens to explore. The grounds have a beautiful array of gardens, a reflection pool, and picturesque ornamental iron gates. Upon further investigation, it was a popular place for wedding and engagement shoots. We did not take a tour of the Westbury House itself, but apparently the interior was designed to reflect the Georgian Period—England’s golden age of furniture and interior design. We stopped by Levittown, which was only 15 minutes away, just so I could take a photo with the Levittown water tower (I was a planning student and this was interesting!). Levittown is the is the name of several housing developments created in the United States, post WWII, with Levittown, NY being the first. This postwar housing project essentially is known for their model homes, quick and mass production, similar to an assembly line, and being the prototype of the American suburb. Because of its ease, price, and idea of community, suburbia proliferated.
Anyways, we picked up food in Babylon and then headed over to the west end of Fire Island to Robert Moses State Park. There were a few tables available and we ate our lunch beachside before settling down on the sand to take in the Atlantic breeze. While it was late September and a weekday, there were still a few people catching some rays. We then walked along the boardwalk to the Fire Island Lighthouse. We didn’t have time to go up, but stopped inside the Lighthouse Museum where a guide told us about some lighthouse history. We also found out that on a clear day (like that day!) you could see the New York City skyline, which was about 40 miles away.
We eventually arrived at our Airbnb before heading out again for dinner at Cowfish in Hampton Bays. We got there right before sunset and enjoyed some seafood along the Shinnecock Canal.
Old Westbury Gardens // $14 pp
Babylon Burger Bar // $$ Burgers, Poutine, and More in Babylon
Robert Moses State Park (Field xxx) // FREE (off season)
Fire Island Lighthouse // $10 pp to go up the Tower
Cowfish // $$ Seafood and American Cuisine in Hampton Bays
While we didn’t go inside, the exterior of the Westbury House was very beautiful and we enjoyed walking around the terraces.
Make your way to the back and discover a verdant walled garden with seafoam-colored trellises.
Follow the boardwalk path from the east end of the Robert Moses State Park Field 5 parking lot and you’ll see the lighthouse.
Day 2
Our goal for our actual first day out on the East End was to drive out east to Montauk Lighthouse and make our way inward. I didn’t know how far out Montauk was until I was doing my research for this trip, so we tried to leave early so we could get to the tip by 10am. We were finally greeted by the sight of the Montauk Light House. Based on Pinterest and Google maps, there were supposed to be a few wooden bench swings that face the lighthouse. I was looking forward to taking a few photos there, but unfortunately they were removed. The lighthouse was also apparently closed, so we couldn’t even get up close to it. We did stop by the gift shop though. Off to the left side of the lighthouse, there is a short trail to the water. They were doing some construction nearby to help erosion by the lighthouse. FYI, if the lighthouse and snack shack are closed, there is a bathroom by the lower parking lot.
In the area, is Camp Hero State Park, where there are other overlook views, picnic areas, and the site of the old Camp Hero Radar Tower. Camp Hero is known to supposedly be the inspiration behind the facilities on Stranger Things. The former military base and coastal defense station is rumored to be the location where secret experiments occurred. There are a few abandoned buildings and barracks that you can walk around, but you cannot go inside any of them.
Next up was Navy Beach Pier where we just took some photos. This seemed to be a very popular spot for locals to bring their dogs. For lunch, we went to the famous Lobster Roll aka LUNCH in Amagansett. I love a good lobster roll opportunity and am a BIG fan of them, so I was super psyched to get some during our trip (the last time I had them was on a family trip to Acadia National Park in Maine). The place was super busy, but moving. I'm not surprised how busy it got because the food was great! Their placemats also noted some of their better known patrons, including Lady Gaga, ScarJo, Billy Joel, Bill Murray, Barbra Streisand, and more!
For appetizers, we ordered clam chowder and the fried calamari. I ordered the hot lobster roll and Gabe ordered the fried shrimp.
The red, white, and blue awnings and LUNCH sign are an iconic sight along the Montauk Highway.
We walked off some of the lunch by treading through the Walking Dunes - a trail of dunes that shift or “walk” across the landscape due to the coastal winds. We then had a 4pm tour of the Pollack-Krasner House, where we learned about the history of famous painters Jackson Pollack and his wife Lee Krasner. We were able to explore their studio barn and see the remnants of their splattered paint, as well as their home. By the time we got out, many stores were already closed, but we decided to window shop around East Hampton before deciding to order takeout from a restaurant in Sag Harbor. We weren’t super hungry and also had a lot of leftovers, so we opted for carbonara and antipasto to share from Il Capucino.
Montauk Light House // Parking Fee $8.00
Camp Hero State Park // Parking Fee $8.00
Navy Pier // FREE
Lobster Roll aka LUNCH // $$ Seafood
Pollack-Krasner House // $17 pp
Walking Dunes Trail // FREE
il Capuccino // $$ Italian
The closed off Radar Tower at Camp Hero State Park
Jackson Pollack’s studio, where you can see his drip work across the floor
Sag Harbor was starting to decorate for the autumn season
We made our way to the top of one of the dunes at Walking Dunes. You don’t realize how tall and vast it is until you’re up there.
Day 3
We kicked off our third day by waking up for sunrise. We drove about 25 minutes to Ponquogue Beach. It was the perfect morning for it. When we strolled onto the beach, we weren’t the only ones with the same idea as we saw another couple sitting together and waiting to greet the sun. As the sun began to peak over the horizon, surfers, kayakers and paddle boarders began to make their way to the water. We originally planned to try to figure out some of the rideshare bikes that they had at Ponquogue Beach and ride them down the road to Tiana Beach, but we decided not to.
Gabe and I aren’t exactly breakfast people, but since we woke up at 5:30am, we were hungry. We went to Goldberg’s, which seems to be a popular East End chain. We love a good lox bagel and breakfast sandwich. We ate at Agawam Park in Southampton. The park is adjacent to their downtown area, as well as Agawam Lake. We overheard a Stonybrook PHD student at the lake explain his research to a guy that was curious about what he was doing. He was apparently changing a filter that has been examining the algae bloom in the lake that has been posing a problem in recent years.
After walking around a little bit more, we went to the Parrish Art Museum. Gabe and I studied architecture in college, so we love a good photographic, architectural space. The Parrish Art Museum was designed by Herzog and de Meuron. You might recognize their work, like 56 Leonard in NYC or the de Young museum in San Francisco. We paused and gawked at a few pieces, but mainly focused on the pitched roofs of the museum and the exterior art. I also wanted to see the Dan Flavin Art Institute, which is a part of the Dia Art Foundation, also known for Dia: Beacon in Beacon, NY, but it wasn’t open during our stay. Not hungry, we then went to Sag Harbor to kill some time. We sat at the pier and watched a few boats go by.
From Sag Harbor, we Ubered to Wolffer Estate Vineyard for a wine tour. It was a bit loud inside the main building, so the indoor portions of the wine experience were a bit lost on me, but the outdoor portions were a lot better. We walked out to the vineyard, where our guide told us about the different ways grapes can grow and how certain wines can be labeled - Hamptons, North Fork, Long Island, etc. Our group then sat under a pergola and sampled some red wines. Nearing the end of the tour, we saw some of the workers haul in some handpicked grapes on pallets. They were swarming with bees, but we were able to sample a few grapes. We sampled 4 different wines. We grabbed a few bottles of their signature wines and non-alcoholic drinks from their store.
Sag Harbor was our final destination for the day (we Ubered back from Wolffer). We wanted to just leisurely walk around the town and explore the cute shops, and it was also where we eventually had dinner. There are a bunch of nice restaurants to choose from, but sushi was calling our name. We had an early dinner at Sen and grabbed a few rolls. I’ll be honest, for the price, Sen wasn’t really worth it. I think we could have gotten more bang for our buck elsewhere, but there are plenty of restaurants to choose from in Sag Harbor.
Ponquogue Beach // Free (offseason)
Goldberg’s Famous Bagels in Southampton // $ Bagels and Breakfast Sandwiches
Parrish Art Museum // $12 pp
Wolffer Estate Vineyard // $$$ Winery
Sen // $$$ Japanese
There were a handful of surfers, kayakers, and more that made their way to the water during sunrise.
You can browse the interior exhibits, as well as walk around the museum grounds where there are additional exterior sculptures.
After sampling white wines in the building and walking around, our tour group sat under a pergola to sample some reds.
It was amazing being able to sit beneath the grapevines, while learning more about the fermenting process.
Day 4
Day 4 was dedicated to exploring the North Fork. Our first stop was Horton Point Lighthouse. The lighthouse wasn’t actually open, but they have a set of stairs that descend along the bluff and onto a rocky beach. We were there pretty early, before 9am. We got to enjoy the peace and quiet to ourselves before a few locals showed up, either to walk along the beach or run up and down the stairs as their morning workout. Not even 10 minutes away, we also visited 67 Steps, which is the more popular and recognizable set of stairs along the water. In comparison, 67 Steps is basically a straight run of stairs, while Horton Point has a bend. Horton is also surrounded by more trees and shrubbery, while 67 Steps has more of a clearing. Both areas said you needed a permit to park, but since it was off season we took our chances. Both are at the ends of residential streets, so I can see why they wouldn’t want a bunch of random cars in the area. However, none of the people we ran into gave us a problem.
We had some time to kill and went to Goldberg’s again, but in Greenport - a waterfront village dotted with restaurants and local shops. This location was particularly busy. We took our breakfast to the waterfront and enjoyed the morning breeze. Plenty of people were out, walking along the water and enjoying their Saturday morning. There’s an antique carousel that sits on the green along the water and was open and running by 9am. We decided to visit a few shops before heading over to a recommendation from my sister and brother-in-law called Lavender By the Bay - a lavender farm not even a 10 minute drive away. Because we weren’t there for full bloom, walking around the fields was free. A few rows had lavender still and you could smell it faintly. I can only imagine how scenic the entire place would be during their French lavender bloom which occurs in early July. I stopped by the store and picked up a dried lavender bouquet, a sachet, honey, and culinary lavender that I could use for baking and tea.
Don’t make the same mistake we did by getting a filling breakfast because we ended up not getting lunch. There were plenty of restaurants I would have liked to try in Greenport, but we both weren’t hungry.
I thought the steps at the Horton Lighthouse were more picturesque since it seemed more hidden away amongst the foliage.
67 Steps is the more well-known spot in the area.
Instead, we went out to the eastern edge of the North Fork which is Orient Point. Gabe took a nap in the car, while I watched a ferry dock. Upon further research, I learned this was the Cross Sound Ferry that connects passengers from Orient Point to New London, Connecticut! It was one of those ferries where you could bring your car on board. After Gabe’s quick nap, we made our way to our reservation at Kontokosta Winery. During our drive through the North Fork, we passed a dozen of wineries, but I had selected Kontokosta because it was close to Greenport and known for being adjacent to the water. On this day, Kontokosta wasn’t offering any tastings, only glasses and bottles. Gabe and I ended up enjoying their Orient Chardonnay vineyard-side and got a bottle of red to go. The other side of the building is where there is a field full of picnic tables and if you keep walking, you’ll be out on a coastal bluff. Unfortunately, Kontokosta was closing early that afternoon for a wedding (what a beautiful location!), so everyone was swarming the bayside, so Gabe and I enjoyed the quieter vineyard side.
We then went back to Greenport to kill some time and enjoy the afternoon sun. The downtown area of Greenport is pretty small, so we went over to Town Beach to kill more time. There was a perfectly worn in swing for us to enjoy as Gabe and I checked Zillow to see how much houses were in the area haha. I was excited for our dinner plans since I picked out another waterfront restaurant. Check out the Halyard Restaurant if you want a beautiful sunset dinner. I was super bummed that we couldn’t get outdoor seating, but everyone, including myself, was able to go out on the balcony and take photos. I got a half dozen oysters, the pork belly, and their drink “Paid Time Off” which was a lemongrass infused vodka cocktail. Gabe got the clam chowder, the swordfish, and the non-alcoholic Beachcomber. We went back to Greenport again to end off the night with some ice cream!
Horton Point Lighthouse and Steps //
67 Steps Beach // FREE
Goldberg’s Famous Bagels in Greenport// $ Bagels and Breakfast Sandwiches
Lavender By the Bay // FREE to explore the grounds (off season)
Kontokosta Winery // $$ Winery
Greenport // FREE
Town Beach // FREE (off season)
Halyard Restaurant // $$$ Seafood
Greenport Creamery // $ Ice Cream
There’s an oversized lavender sign and purple Adirondack chairs we took photos with.
Kontokosta was a great place to wind down ;)
The Halyard is perched right above the water and if you’re lucky you can get seats on their balcony during sunset.
Day 5
I consider our last day of the trip as mostly a travel day. We didn’t have too much planned since we had work the next day. We saw the Big Duck! We left the East End to meet up with Gabe’s cousin who is currently studying at Stonybrook University. If you have more time before you leave the Hamptons, you could always grab brunch on your way out or stop by the beach one last time.
Big Duck // FREE, giftshop inside
Tips:
Be mindful of parking, especially during the peak season which is Memorial Day Weekend (end of May) thru Labor Day weekend (early September). Much of the beaches in the area require a parking pass, and many of them are also only residents-only. If you go during off-season, many beaches will be free.
Book your reservations as soon as you can. While some restaurants may only let you reserve 2 weeks advance, stay on top of your reservations.
The local grocery store is IGA, so if you want to pick up some groceries, head there.
Expect traffic, especially in the South Fork and especially near Southampton.
If you’re looking for more wineries, head to the North Fork. The South Fork is known for Wolffer Estates and Duck Walk, but there are plenty of options in the North.
If you’re looking for a idyllic Hamptons playlist, I’ve been listening to the Gurney’s Summer Beach Club (Gurney's Montauk Resort & Seawater Spa is a very popular spot!)
Regarding Covid-19, I would say 90% of restaurants and stores we went to had all their staff wear masks. I, along with my partner, are both vaccinated. I also got tested after my trip as a precaution.