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Eastern Long Island - Montauk, etc.

I'm planning a trip to eastern Long Island. Want to visit Montauk, 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. Plan to stay in Riverhead.

Probably mid-May – definitely mid-week.

We will get into Orient Point mid-day on day 1, and need to leave by 3 or 4 pm on the day we leave. I know 3 nights would be best but wondering if this would be possible in two (one full day plus to partial days)?

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. 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, 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).

My questions are:
How bad is traffic at that time of year (mid-week)? I know what google says for drive times but I don’t know how accurate that is. Google is actually very accurate for where I live (western Mass) but on road trips we’ve encountered lots of times when google was overly optimistic.

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.

Posted by
889 posts

Mid-week traffic before Memorial Day won't really be an issue. Maybe some density around Riverhead at the PM rush hour, but barely (I used to go out there for work fairly regularly).

Can't speak to Sands Point, sorry.

Posted by
847 posts

Thanks. That's what I was hoping - that traffic would not be horrible mid week in May, but it's nice to have someone who knows the area confirm.

Posted by
33 posts

Consider a stay I'm Southhold as a base to explore the North Fork. Go to Shelter Island from Greenport... Sag Harbor to Montauk and Hither Hills state park is nice. Take a look at the Hamptons, Mattituck... Orient Point is very small and a look around the small village and causeway to East Marion is scenic.

Posted by
538 posts

You will not be able to do all those things in the time you allowed. Fire Island Lighthouse, Sands Point preserve Cold Spring Harbor and Eaton Neck are in Western Suffolk and nassau and are not close even to each other. I lived near Eatons neck and had to goggle that there was a light house.
Take the previous posters advice and stay in a town on either the North Fork ( Orient) or South Fork Montauk) and enjoy the villages, Montauk Lighthouse on the East End.