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Eastern Long Island - Montauk

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Old Apr 3rd, 2022, 12:27 PM
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Eastern Long Island - Montauk

I'm planning a trip to eastern Long Island. Want to visit Montauk (light house and village), Sag Harbor, Greenport, Fire Island Lighthouse, Sands Point Preserve, Cold Spring Harbor and Eaton Neck Lighthouse. We'll be coming into (and departing from) Orient Point on the ferry from Connecticut. We'll be in our own car.

Probably mid May but before Memorial Day. Would it be noticeably more crowded if we were to do the trip in early June?

Is two nights enough time for this? We will get into Orient Point mid day on day 1, and need to leave by 3 or 4 pm on day 3. We won't be climbing the lighthouses or touring the mansion at Sand Point, just exteriors. Besides those we just want to visit "cute" villages, walk along harbors, etc. Don't need any beach time other than looking at them/possible short walks.

Any other suggestions? Thanks
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Old Apr 3rd, 2022, 01:42 PM
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Your list may be hard to do. If a weekend is involved, probably impossible due to traffic and narrow roads. I don't think you could go to Fire Island in your time frame. We do the North Fork as a day trip without a ferry ride. You will want to visit a winery or two (I could give you recommendations) and find a few nice meals. Sands Point is a good fifty miles west. Montauk Point is at the far end of the South Fork, with no short drive from the North Fork, with a lot of narrow local roads. The South Fork has the Hamptons (upscale, etc,). You seem to want to see a lot of specific places on Long Island that are not adjacent to each other. Check a map. I would limit yourselves to the two forks. Also, where do you plan to sleep? The Riverhead area is between the two forks so could be a base. No matter where you stay, reservations would be essential in normal times, but these days, who knows?
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Old Apr 3rd, 2022, 02:35 PM
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Have lunch in Greenport, then take the small car ferry to Shelter Island. Cross the island and take another small ferry to Sag Harbor. The crossings just take a few minutes. Spend the night there, and visit the whaling museum if it is open. Then drive out to Montauk. This saves you making the very long drive to Riverhead and back out to Montauk. Have no advice about Fire Island. I went to middle school at Cold Spring Harbor High. There's a very good whaling museum there as well. I learned to sail in the area but never visited Eaton's Neck Lighthouse. Note it is possible to cross Long Island Sound either by the Throgs Neck or the Whitestone Bridge, or the ferry from Port Jefferson to Bridgeport, rather than drive all the way to Greenport again. If you do decide on that drive, Stony Brook is a nice stop.
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Old Apr 4th, 2022, 05:08 AM
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Thanks for the replies. Yes we will definitely be doing the trip mid week, probably Monday-Thursday. I was originally thinking 3 nights but was hoping 2 would be enough. But I do want to see the things I listed and realize it will probably take 3 days.

Unfortunately we will not be doing any winery or sit down restaurants or anything "inside". I am high risk and with mask mandates gone I don't feel comfortable inside. Fortunately what we enjoy anyway is scenic drives, walking around villages, window shopping (I do go inside shops briefly), looking at boats, photographing lighthouses, etc. It looks like there will be plenty of good take out food (and if not crowded we do outside table service restaurants).

Interesting that you advise the Shelter Island Ferry. Google thinks it takes exactly the same amount of time to do that between Sag Harbor and Greenport as to drive around through Riverhead. But it would be more relaxing to do that even if it wouldn't save any time. I just wonder if they are figuring in waiting for a ferry or just the actual driving and ferry time. For the Cross Sound Ferry google does not factor in the waiting time.

So that's my main concern - how accurate is google drive times. It varies greatly by locale. Where I live (western Massachusetts) it's actually usually very accurate but on road trips we've taken we've found some places it's very off. That's what I don't know about eastern Long Island traffic. I grew up in Garden City but that was decades ago so hard to judge how things are now, and how they are in the eastern end. When I lived there, other than the Hamptons, the rest of eastern LI was pretty empty.

So my questions are:
How bad is the traffic, mid week in mid May (and does it get significantly worse the first few weeks in June, which is obviously after Memorial Day)?
Has anyone done Sands Point Preserve (or Oheka) and what can you say about them? I'm really missing being in Europe and would love to just get a "taste" and they look like a way to do that.

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Old Apr 4th, 2022, 02:21 PM
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If you are not eating inside, you will be looking for takeout, I assume. On the North Fork I would recommend Pizza Rita and the Love Lane Market plus Junda's in Jamesport for bakery desserts. For an ice cream fix, check out the Magic Fountain. Also, near Love Lane is North Shore Donuts, sweet and creative and large.

As for missing wineries, Osprey's Dominion has many outdoor picnic tables and will set you up with a tray of tastes with a significant amount of wine in each cup. I think they may have a Groupon active now with the tasting, cheese and crackers, and souvenir wine glasses. We have done it several times, eating takeout since the cheese plate is small. I hope the weather cooperates. They have live music on some weekends if you have to move your days to a Saturday return home.
https://www.groupon.com/deals/osprey...6-06ae865bc0fd

For some great prize-winning goat cheese and also some nice goat milk soaps and products drop in at Catapano Dairy Farm. Get the soft cheese. You should visit the goats (outdoors). The goats are quite playful, and pose for pictures.

Before you head home, you may want to pick up some fantastic fruit pies at Briermere Farms. If you are very lucky, you might snag a few half price frozen pies to bake up at home. My favorites are cherry/plum and raspberry/anything. Also you could visit Sang Lee Farms for organic produce, although May is probably too early.

On the South Fork, see if the Longhouse Reserve will be open when you go. It is a great outdoor art museum sculpture garden. .
https://longhouse.org/products/open-days

If you do change to going on days that include a weekend day, reserve your lodging now. And Google Map times are lies.

Last edited by AJPeabody; Apr 4th, 2022 at 02:32 PM.
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Old Apr 6th, 2022, 04:08 AM
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Thanks for the suggestions. I've made note of them and plan to check them out. Especially excited about cute goats, love photographing animals.
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Old Apr 6th, 2022, 06:25 AM
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If you are up for eating at outdoor tables, they exist. I have not been to any of them for the duration of the covid, so you would have to check current conditions. Also, outdoor dining may not be feasible before Memorial Day. I always liked Alure at Port of Egypt on the North Fork. It has a water view.
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Old Apr 6th, 2022, 07:30 PM
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Bookmarking...thank you for all the info.
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