My first recommendation for non-metropolitan New York, exploring the Adirondacks, was a strong one, but the Adirondacks are pretty far away. This week’s recommendation, the East End of Long Island, is fairly local but still outside of the metropolitan area. There are quite a few sub-sections of the East End, so let’s get right into it.
I will begrudgingly talk about the Hamptons. The main thing separating the Hamptons from most other Eastern Long Island beaches is that its demographic is, on average, snootier and richer. If you can make it here, congrats on hitting the lotto, and expect to see a lot of expensive cars in complete standstill on Montauk Highway. It might sound like I hate the Hamptons, but I actually just think that this part of the East End gets more attention than the nicer parts. I guess at least it’s mildly entertaining to see 70% of the expressway get off at exit 70 for the Hamptons.
Beyond the Hamptons lies Napeague and Montauk. Of course there is some overflow from the Hamptons, but these two villages still distinguish themselves from their neighbor to the west. Napeague is home to Hither Hills State Park, which has a fairly large woods preserve and possibly the only affordable Atlantic Ocean beach east of Smith Point. I’d also recommend grabbing some Lunch in Napeague. Lunch is Napeague’s beloved 50+ year old lobster roll shack on Montauk Highway. Once you’re done in Napeague, continue east to Montauk. Montauk is often described as an old drinking town with a fishing problem, so 21+ year olds, be sure to bring a designated driver. Montauk’s main downtown is very walkable and has some cool souvenir/t-shirt shops. If you don’t have a car, the train station is also pretty close to downtown. The main tourist attraction in Montauk, the Montauk Lighthouse, is about a 10-15 minute drive east of downtown. There’s a scenic overlook stop on Montauk Highway, so be sure to stop there on your way. Montauk Point, where the lighthouse is located, is quite nice, so I’d recommend taking advantage of the free parking and just enjoying yourself at the no-swimming beach there. Bring some lobster rolls from Lunch and have a picnic.
Let’s go across the Peconic Bay to the North Fork. To get there, most people stay on the expressway to the end and follow CR58 until they reach the 25, the Main Road. However, I’d recommend taking William Floyd Parkway to 25A and Sound Ave. This route takes you through more North Fork-esque communities and generally feels less like you’re simply driving just to get somewhere. My first recommendation on the North Fork is the Mattituck Strawberry Festival. It occurs during the summer, so it’s just something to keep in mind for next year that’s worth the mention. A little further down 25 lies Southold, home of the Custer Institute. The Custer Institute is the only observatory I know of in downstate, which makes sense because of all the light pollution as you approach the city. There are a few restaurants scattered around Southold, and I can personally recommend the Country Corner Cafe. I can’t really talk about the villages on the North Fork since the area is mostly vineyards and a few remaining potato farms, but that makes for a very nice and pretty area.
This next stop on the North Fork is a very strong recommendation: Greenport. Greenport has a charm that I simply can’t describe, but I’ll talk about the town anyway. It’s the downtown of the North Fork. Imagine a small town by the sea version of Washington Street that’s a bit more old-school. There are some Long Island classics there, like Ralph’s Italian Ice, local bakeries, and ice cream shops, and then there are the uniquely Greenport places like The Frisky Oyster and Claudio’s, which sued a restaurant of the same name in my hometown. Ask Google if you want more details on that. Honestly, there are so many nice places in downtown Greenport, and I haven’t tried even half of them, so I’m not in a place to judge which one is the best.
Finally, there’s Shelter Island. Shelter Island is in between the North and South Forks with ferries running from both places. Shelter Island is a bit of a grey area between the North and South forks. I’ve seen a few people there who are definitely too drunk to drive, so it has one of the main downsides of the Hamptons (albeit the problem is worse in the Hamptons). Shelter Island gets a lot less attention than the Hamptons, and it even gets less attention than the North Fork. That makes it quite nice; it can be a bit of a retreat, even on summer weekends. I also have to give a brief mention to the famous Shelter Island 10K race that happens every June.
At any rate, I’m running out of space, but be sure to check out the East End next summer. While you’re out there, listen to “The Downeaster Alexa” by Billy Joel to learn about what the East End used to be.
Be First to Comment