Two days and a night in the Hamptons/LI - Is there Anything to Do?
June 17, 2012 8:32 AM   Subscribe

The girlfriend and I have decided to take a two day driving tour of the Hamptons/Long Island. We'll leave tomorrow, Monday morning, stay somewhere, and come back Tuesday night. The thing is, neither of us knows anything about the area - we need advice on everything! Where to stay, what to see, where to eat. Some details inside.

This is very much a whim as neither of us have spent much time in the Hamptons/Long Island despite having lived in NYC for a while. We just want a relaxing, easy trip to get away from work for a bit. Budget is not a big issue. We like good food, wineries, beaches, hiking, walking around quaint towns, good tours, odd experiences, local color, etc. A couple specific requests:

(1) Where should we stay on Monday night? Any particular B&B, hotel, motel recommendations? What town should we stay in that will have a good restaurant and perhaps a bar or two on Monday night?

(2) Can't miss places to each lunch/dinner and breakfast/lunch/dinner on day one and two?

(3) Particular beaches that are accessible and better than others?

(4) Any wineries on the North Fork that people recommend?

(5) What are the best towns to stop it? What's the best driving route to take? Go up the south coast stopping in the various hamptons then come back on the north side?

I'd greatly appreciate any ideas people have - we'll have fun regardless, we're pretty laid back and really just looking to meander our way through two days, but would be great to have some idea of what to look for! Thanks!
posted by slide to Travel & Transportation around New York, NY (8 answers total) 8 users marked this as a favorite
Montauk. It's the best.
posted by These Birds of a Feather at 8:43 AM on June 17, 2012

And best news of all, the cute place I stayed in last time I went has a deal for $99 a night right now!
posted by These Birds of a Feather at 8:49 AM on June 17, 2012

Camp Hero! You can walk about the "village" part in a couple hours, then drive to the lighthouse.

I'm not sure what you mean by #5 -north & south forks are separated by a good deal of water, you would have to drive west and then head east on the other fork. There is the Martha Clara vineyard near Riverhead though. Oh, and totally go to the Riverhead aquarium when you are in the area.
posted by kellyblah at 8:58 AM on June 17, 2012

It is also possible to go from one fork to the other via the Shelter Island ferries, which connect Greenport and (ultimately) Sag Harbor.
posted by tomboko at 9:12 AM on June 17, 2012

While going through Shelter Island on your way to the North Fork (it's the only way to get from one fork to the other), go for a walk in the Mashomack Preserve. Run by the Nature Conservancy, it takes up about 1/4 of the island and is a great way to spend an hour or the day.

When driving back through the North Fork, stop at Briermere Farms for a pie, or at least a muffin or two. It'll be crowded, but it's worth the hassle. Their pies and muffins are amazing. Tip - if you're not going to eat it that night, get a frozen pie - cheaper, and they re-heat in the oven quite well.
posted by swngnmonk at 9:47 AM on June 17, 2012

slide: "What's the best driving route to take? Go up the south coast stopping in the various hamptons then come back on the north side? "

That sounds good to me. (FYI, the two sections of eastern Long Island are known as the "South Fork" and "North Fork.") Note that as tomboko says, you'll have to take ferries from one to the other (from north to south: Sag Harbor -> Shelter Island -> Greenport). A decent itinerary might be NYC -> Montauk (possible stops along the way include the villages of Southampton, Bridgehampton, East Hampton, and Amagansett), then turn around on Tuesday and check out Sag Harbor and Shelter Island, then wend your way back along the North Fork. I've put together this very simple route on Google Maps just so you can get a sense of how it would look.

Montauk definitely has a different, more laid-back feel than the rest of the Hamptons, so it might suit you well. As you'll note, though, it's also at the very far end of Long Island (one house of worship on the road out there years ago used to have a sign that read, "Last Anglican church before England"), so it would add a bunch of time to your trip.

Since your trip is quite short and you will be driving both days, I don't know that you'll want to stop and spend half a day on the beach. I also don't know if the weather will permit it, as it's going to be unseasonably cool the next couple of days. But there are great beaches all throughout eastern LI; the only issue is which you can park at. (Some require resident stickers, so you could conceivably have to park very far away, which is not worth it. Others allow you to pay by the day at the parking lot. You probably won't have too much of an issue on a Monday/Tuesday—just again, as long as you're not at a resident-sticker-required beach.)

If you hit the North Fork, seconding Briermere Farms, though I doubt they'll be crowded on a Tuesday. Even if they are, as swngnmonk says, very much worth it. As you seem to have deduced, the North Fork is also home to far more wineries than the South Fork. I don't have any particular recommendations (I'd be New York Magazine or Time Out New York or even the NYT has done some reviews), but you'll see them dotted along the side of the highway up there. Very easily accessible. It's possible that some may not be open for tours/tastings early in the week, though.

And by the same token, though it's less and less the case nowadays, some restaurants may only be open closer to the weekend; Monday and Tuesday are the quietest days out there. So if you have your heart set on someplace, just check their website or call ahead to make sure they're open.

Every town has a number of good restaurants, and quite a few are super-expensive. The nice thing about going this time of week is that reservations shouldn't be a problem. Since you have a car, everything will be very accessible to you—there are all sorts of restaurants that are kind of off on their own and not in the middle of one of the towns. I've never spent much time exploring the bar scene out there; I think it's definitely less-developed than the restaurant scene (which can be ridic). But if you want a drink, I'm sure you'll find something.

Some specific recommendations: If you like beer and German food, and you're headed to Montauk, Zum Schneider (of Lower East Side fam) just opened a location out there. My wife just went yesterday and gave it a thumb's up. On the drive out to Montauk on the local road known as 27, there's also a no-frills local seafood place called the Lobster Roll (also known just as "Lunch"—that sign is bigger) that I and many others have long loved. (Though some people don't like it, and there's definitely some grousing about the prices, which aren't cheap despite the humble surroundings—but hey, it's the Hamptons.) If you like live music, Stephen Talkhouse in Amagansett has long been popular.

There will also probably be lots of farms on both forks which allow you to "pick your own"—whether it's berries or tomatoes or what-have-you. That can be a lot of fun. One final suggestion: The Milk Pail, a farm stand on the South Fork, has awesome donuts. Take some home with you!
posted by Conrad Cornelius o'Donald o'Dell at 3:32 PM on June 17, 2012

I grew up on the North Fork (fairly recently, as I'm still a youngin'), so MeMail me if you have specific questions about what is (in my opinion) the Hamptons' fairer neighbor to the North.

Also, I actually used to pour at Martha Clara. Dunno who of the old crew is there still, else I'd tell you who to ask for specifically to get a more lengthy and extensive tasting.
posted by weaponsgradecarp at 7:47 PM on June 17, 2012

What'd you guys decide to do? Have a fun trip?
posted by Conrad Cornelius o'Donald o'Dell at 8:28 PM on July 2, 2012

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