Top 10 Things to do in Shelter Island, United States

December 26, 2017 Joeann Galban

Shelter Island is a town and island at the eastern end of Long Island in the U.S. state of New York. It is part of Suffolk County, although it is separated from the rest of the county by water. The population was 2,392 at the 2010 census.
Restaurants in Shelter Island

1. Mashomack Preserve

79 S. Ferry Rd., Shelter Island, NY +1 516-749-1001
Excellent
69%
Good
25%
Satisfactory
4%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 115 reviews

Mashomack Preserve

This Nature Conservancy property spans 2,100 acres, and accounts for one-third of the land on Shelter Island.

Reviewed By Fatemeh L - Washington DC, District of Columbia

A beautiful & pristine preserve that has miles of trails by the water and in the fields. I went in winter and it is just stunning.

2. Cross Sound Ferry

41270 Main Rd, Orient Point Ferry Dock, Orient, NY 11957-1131 +1 631-323-2525
Excellent
54%
Good
34%
Satisfactory
7%
Poor
1%
Terrible
4%
Overall Ratings

4.5 based on 370 reviews

Cross Sound Ferry

Reviewed By Russell M - North Kingstown, Rhode Island

I've been using the New London to Orient Point ferry service for decades and I will continue using it when I go to Long Island.

This is always much better than fighting traffic on the CT Turnpike, Cross Westchester Expy, and the LIE.

The snack counter/luncheonette is also decent.

The only drawback is that there was no WIFI on any of the boats which I used for the round trip.

3. Sannino Bella Vita Vineyard

1375 Peconic Ln, Peconic, NY 11958-1413 +1 631-734-8282
Excellent
86%
Good
10%
Satisfactory
1%
Poor
2%
Terrible
1%
Overall Ratings

5 based on 236 reviews

Sannino Bella Vita Vineyard

Sannino Bella Vita Vineyard's winery & tasting room is situated on a 17 acre vineyard in the North Fork of Long Island NY. Our address is 1375 Peconic Lane, Peconic. Our tasting room & winery is located in an historic barn circa 1900's. This casual and rustic setting is a great place to start your wine appreciation. Through education and our hands on approach, is what makes our winery a perfect spot to enjoy on the wine trail. We have many Estate wines to choose from cabernet Franc, Merlot, Cabernet Sauvignon, White Merlot, and Chardonnay. Our tasting room is open Thursday-Monday see website for hours. Groups larger than 6 MUST make a reservation due to our limited space. Tours and Classes are also available. Please visit our web site for dates & times.

Reviewed By Joseph M

Great Vineyard off the beaten path away from commercialized Vineyards that lose intimacy and coziness. This place has great service and even better wine making tasting simple. All of the food options compliment the wine fantastically. Cheese platters, nut platters, and chocolate platters are perfect. The wine is the main ingredient to their charm and family style atmosphere. Vino from the heart is what you will get here..

4. Sparkling Pointe

39750 County Road 48, Southold, NY 11971-5012 +1 631-765-0200
Excellent
67%
Good
24%
Satisfactory
6%
Poor
1%
Terrible
2%
Overall Ratings

4.5 based on 180 reviews

Sparkling Pointe

Reviewed By gracao2017 - Dover, New Hampshire

Visiting Long Island we decided to stop at this vineyard as we love sparkling wines
For our surprise all the decoration is related to Rio de Janeiro, Brasil, what delighted us as we are from that city and country.
Appart of the pleasure of seeing pictures and memorabilia from our country we were very impressed with the selection and quality of the wines, the knowledge of the people who served us and the beautiful vineyard they have
Would go back any time

5. Lavender By The Bay

7540 Main Rd, East Marion, NY 11939-1664 +1 631-477-1019
Excellent
47%
Good
43%
Satisfactory
5%
Poor
4%
Terrible
1%
Overall Ratings

4.5 based on 122 reviews

Lavender By The Bay

Located in East Marion New York, Lavender by the Bay has been growing the highest quality lavender on Long Island for more than 15 years. We offer seasonal fresh cut bunches, dried lavender, lavender plants, lavender sachets and crafts, and honey from our own beehives. In 2002, we expanded our company by purchasing 17 acres of farmland in East Marion, New York. We have planted twenty varieties of lavender across ten acres of farmland, yielding over 80,000 plants for cultivation. In order to preserve the beauty, form, and peaceful nature of the farm, we must now impose a per person (12 years and older) fee to enter the fields while the flowers are in bloom. This fee goes towards the upkeep and maintenance of the plants, trails, and pavilion. The fee is $8 per person to enter the fields on weekends and national holidays, of which $1 will be donated to a local charity. During the week, the fee is reduced to $5 per person to encourage customers to enjoy the fields during less busy times. The lavender is typically in bloom mid/late June through mid-July, but is ultimately up to Mother Nature.

Reviewed By Christina A

Great place to take photos and a leisurely stroll. $8 to enter the lavender field. The shop has lavender bunches, soaps, lotions, eye pillows and you can also purchase lavender bushes starting at $6. A rather hearty bush was $30. Plan to visit other places in the area. Approximately 1 hour or so visit. The people in the shop were friendly and knowledgeable.

Front Street, Mitchell Park, Greenport, NY 11944 +1 631-477-2200
Excellent
73%
Good
23%
Satisfactory
3%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 97 reviews

Antique Carousel

Reviewed By Jundullah

Great little place... Took our 1 year old. We enjoyed a lot. The ride was really nice. Small little town with lots of friendly people. Parking gets a bit tough depending on the time of the day. The ocean view next to the carousel is nice. Some kids were skate boarding in the deck, which was cool. Lots of farms on the way there.
The carousel rides were $2/pp cash. Under 3 was free. Don't miss it. Go. Saturday was open till 9pm.

7. Venture Out Shelter Island Paddle Board Rentals

35 Shore Rd, Shelter Island Heights, Shelter Island, NY 11965-2002
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 5 reviews

Venture Out Shelter Island Paddle Board Rentals

We are located right on Crescent Beach, also known as Sunset Beach. No phone call, no waiting. Find us under the blue tent in the middle of the beach and we will get you out on the water immediately. Venture Out will also drop off and pick up for free at any beach, house or location of your choice anywhere on Shelter Island. The best summer experience is waiting for you!

Reviewed By Lara878 - New York City, New York

this is a terrific operation. my fiancé and I spent three days on shelter island and we enjoyed paddle boarding so much we did it all three days. our first day we just rented boards on Sunset Beach. The second day, Matty met us near West Neck Creek and we spent the afternoon paddling there. The third day, we paddled all around Coecles Inlet. Matty was fantastic - he arrived promptly with boards at the arranged spot, and we just left them when we were done for him to pick up. He was incredibly cheerful and helpful and enthusiastic. And the island is beautiful! Paddling around was by far the best part of our trip, and this outfitter provided perfect service. Highly recommend.

8. Bay Street Theatre

Bay Street and Main Street, Sag Harbor, NY 11963 +1 631-725-0818
Excellent
71%
Good
23%
Satisfactory
2%
Poor
2%
Terrible
2%
Overall Ratings

4.5 based on 69 reviews

Bay Street Theatre

Reviewed By PAM_from_LINY - NY NY

The Bay Street Theatre offers a little bit of everything: dramatic plays, musicals, bands. It is laid out in a way that all seats - with the exception of the obstructed seating which they disclose - have good views, We have seen countless shows here, and look forward to returning. There is a bar-refreshment area in the lobby and the staff is friendly. The only down side is seeing films here--a few years ago, there was a film series and the screen and sound system were worse than a home theatre.

9. The Old Field Vineyards

59600 New York 25, Southold, NY 11971 +1 631-765-0004
Excellent
60%
Good
34%
Satisfactory
6%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 49 reviews

The Old Field Vineyards

Reviewed By Steve T - Sayville, New York

We've been here several times. The wine is good, the owner is one of a kind and the experience exceptional. The place is off the beaten path of many of the wineries. It is actually for those who really appreciate what the real wine growers do as a passion... not as a 'drunken stop on a wine tour' . Not a winery to be passed by or overlooked.

10. Shelter Island Kayak

Route 114 & Duvall, Shelter Island, NY 11964
Excellent
91%
Good
9%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 22 reviews

Shelter Island Kayak

Reviewed By 400alexan - Long Island, New York

This kayaking trip provides a lot of fun and relaxation. The company offers kayak rentals, friendly instructions and advises. The trip allows to explore wildlife at adjacent Mashomack preserve as well as the historic cabin at small Taylor's Island. This adventure is highly recommended for young children because it takes place in a quiet shallow bay without streams (an adult can accompany a child in a double kayak). Kayaking is really easy and safe here (no prior experience is needed).

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