Winter Weekend Ideas for Shelter Island, NY
 

I'm hoping some of you might have some ideas for me. My bf gave me, as a holiday present for us, a weekend at an inn on Shelter Island. I was wondering what activities there are in the winter there (is it more of a summer place?). Also, are most businesses open?

I think it will be very quiet this time of year and many if not most places will be closed. Shelter Island is mostly a beach, fishing, boating, biking place.

Ofcourse, Sag Harbor and the Hamptons are just a short ferry ride away to the south and Greenport and the other towns along the North Fork are a short ferry ride in the other direction. Enough to do at the vineyards on the North Fork and the shops and restaurants on the south fork. Sounds like maybe the boyfriend just wanted a romantic weekend at an inn. ;)

Yes, probably :o). Also, he's very into the wineries. So, no wineries on the island itself, I guess. A short ferry ride won't be too bad. I was considering putting it off to the spring, but a quiet weekend could be nice, too!

Personally, I would wait til Spring.
Even the ferries run a limited schedule, there will be very few things open.
I love it there and really wanted to live there, the winters were one reason we decided not to.
In the late Spring, you can enjoy the wineries, and just being out of doors.
* I also have a thing about taking a ferry, that is not that big, with my car , back and forth every day in rough weather :)

Good point, I guess I'll look into the ferry schedule as a reality check. Maybe I'll suggest we find a place on the North Fork instead of on the island. Thanks!

I dont think you will have a problem with the ferry schedule- even in the off season they run until around midnight. The ferry ride itself is very short- maybe 10 minutes from greenport to S.I and even shorter from S.I to sag harbor.

Shelter Island is really peaceful and laid back in winter (a nice change from nyc)but there is not much to do if you want to be very busy. There are restaurants that will be open as many local live on the island all year long. As for businesses, even in the summer season there is very little shopping on the island anyway.

If you want more activity you can go in the spring and kayak, walk in the nature preserve, sit on the beach...

The ferries run regularly all year long. If he hasn't actually purchased something on the island and you want to go sooner, I suggest staying in the Hamptons or Sag Harbor. There will be more open and more to do. The wineries in the Hamptons (there are 3) stay open all year.

The ferries do run all year but on a limited schedule..there is much more time between ferries and they can delay/stop if the weather gets terrible.
We were househunting out there a couple of years ago, and I was talking with the man that runs the ferry.. It is beautiful there but a lot of the businesses do close for the season and a lot of the people close their homes too..
I still would like to test living there though :)

http://www.liwines.com/default.ihtml...winterfestival

http://www.liwines.com/pdf/winterfestival.pdf

Greenport is very nice in the winter. There is an ice skating rink in the town park on the bay (see Sunday January 1 New York Times real estate section for article on the rink) and lots of shops and restaurants remain open all year. You can visit the nearby North fork wineries, too. It is really a very cool and cozy place and more convenient to activities than Shelter Island. If you decide to go that route, I can post info on where to stay and where to eat.

Thanks so much! I've printed out the offers from the website you shared, mclaurie (it was very helpful!)- maybe it would be best for us to look at staying on the North Fork. He has not yet purchased a weekend at the inn as we haven't yet settled on a weekend, so that will work, I think. I don't think we need a weekend full of activity and constant sightseeing, but I do think it will be good to have at least one outing each day to explore the area - even if it is just strolling around. On the other hand, the plans may change entirely to be a trip to Niagara Falls and the wineries up there. I guess the possibilities are limitless!

Just thought I'd give an update as the big weekend just passed. We stayed on Shelter Island at the Chequit, which was lovely. The room was small, but just fine. The ferries were very regular; I never waited more than 5 to 10 minutes (we lucked out with great weather). They told me that the ferry runs until midnight, which was fine. The wineries on the North Fork were all open and not crowded, which was nice. As mentioned, the island was quiet being that it is the off-season, but that was just fine. Best meal of the weekend? The Vine Cafe on Shelter Island (also the most crowded room we saw that weekend!). Thanks everyone for your advice!

Glad you had a nice time and thanks for posting back. I like the Vine Cafe too. ;) Did you get over to the Ram's Head Inn? Did you get to Sag Harbor at all?

We did take a drive around the island and saw the Ram's Head; our plan is to stay there sometime in June (We'll book early! I understand things get filled quickly w/ lots of weddings). We never did make it over to the South Fork; we'll look to do that on our next visit - Sag Harbor & South Fork wineries. It really was such a great weekend - it was such a getwaway that it didn't even feel like I was still in NY!