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South Shore Long Island, reasons to fall in love with these small towns

I grew up here on the South Shore of Long Island. I always loved the excitement of NYC, but as I get older I realize how much I love these small towns. In short, here are some of the places I returned to during a recent visit.

My old home in Sayville on the south shore of Long Island, NY
My childhood home

Returning Home

A few years ago, I went back not that long ago for a high school reunion. Interestingly enough, not much had changed except for the pizza toppings had become fancier and Sayville Junior High was now Sayville Middle School. Also the trees grew up on the street that I lived on and the new owners of my house had fixed it up a lot. However, Sunrise drive Elementary looked the same. One of my classmates told me that he still rides bikes with his kids and points out my house.

If you plan on traveling by plane here are some affiliate links for things to make traveling a bit more comfortable:

South Shore Long Island: Sayville

Shows the front of a Friendly's Restaurant in South Shore of Long Island
My second job!

I grew up in a small town on the south shore of Long Island where main street was filled with quaint shops with offices above. As teens we would hang out at the local movie theater which expanded to have 3 movies. In the summer we would walk to Carvel. I would always get a mint chocolate chip cone with colored sprinkles. Weekends you could find a crowd hanging out in the parking lot behind Sayville Pizza until someone called the cops and we would all disperse. Then it was off to bonfires at Lotus Lake or parties behind the bleachers.

Our town was an old fishing and resort village and was preserved by the Sayville Historical Society. No fast food restaurants were allowed and it was controversial when a Friendly’s Restaurant moved in. I worked there during my senior year of high school and then during college breaks. I started at the ice cream counter making endless Fribbles, Jim Dandy’s, and Heath Bar Sundaes. Then I got promoted to waitress when I turned18.

shows the store front for Hot Bagels
Best Cinnamon Raisin Cream Cheese

In addition, Sunday mornings we would head to Hot Bagels on Montauk Highway. They had the best cinnamon raisin cream cheese.

Loughlin Vineyard

south shore Long Island vineyards at Meadowcroft Estate
The Vineyards
shows an estate house at Meadow Croft
Meadow Croft Estate
shows a shack used as a tasting room at the winery
Tasting Room

A little known fact, is that there are some amazing vineyards on Long Island. This time around, my husband and I made a stop at the Loughlin Vineyard. The entrance is a hidden driveway that winds back to the Roosevelt Estate that can’t be seen from the road so you will have to hunt for it. With that in mind, the tasting room is open Saturdays and Sundays between 1 and 4pm. The tasting room is a shed out back and the accompanying outdoor area. Consequently, closures are based on weather. In addition, families and their dogs are welcome to come and picnic on the grounds. However you will need to bring your own food.

Sign for Loughlin Winery
Misleading sign for the winery

The Grange

Located near the Eastern part of town stood The Grange. I remember attending the bi-centennial celebration here with my dad as a kid. An old fashioned church and schoolhouse are among the old buildings standing here. Festivals always brought hayrides and apple cider. Now they host a farmer’s market on Sunday mornings.

Poppa Mia’s Ice House

shows three people eating Italian ice outside a takeout stand
The Best Italian Ice Ever!

As kids we would have to work in my dad’s garden, and if we got all the weeding done he would take us for Italian ice. My sister and I would make a bucket list of all the flavors we wanted to try during the summer and cross them out as we ate them. After getting the ice my dad would drive the car to the marina and we would walk along the dock picking out which yachts we wished we owned.

Fire Island

Every memorial day my friends and I would ride our bikes or walk to the ferries if we couldn’t get a ride and head the to the Fire Island Beaches. We usually rode over to Barret beach which was the teen hangout.

South Shore Long Island: Patchogue

shows the front of a cottage in South Shore Long Island
Our country house in Patchogue

When returning home for my reunion, I wanted to bring my teenage kids to see where I grew up. The hotel they reserved for the reunion didn’t seem feasible as the rates were still expensive and increased after the reunion weekend. So we hunted through Airbnb and found a three bedroom cottage on the south side of Montauk Highway in Patchogue. When I was growing up Patchogue was run down. However, it has drastically changed since I left. Main Street now boasts of quaint shops and trendy bistros.

The house we stayed at was a country oasis. The owner had inspirational sayings everywhere. There was an outdoor shower, however we didn’t get to the beach. At night my husband and I sat on the front porch drinking wine and watching the millions of fire flies. At one point we thought a big dog was running across the cul de sac. However, it turned out to be a deer. In the morning my daughter and I took a walk down by the beach. We spotted a deer through the trees and another galloped across the road ahead of us.

A deer hiding in the trees on South Shore Long Island
Hidden deer
shows a canal leading to Great South Bay on South Shore Long Island
Great South Bay
a girl stands posing on the beach in South Shore Long Island
Posing on the beach

South Shore Long Island: Bayport/ Bluepoint

This town has no main street. The town consists of a bait &tackle and a deli. It is located between Sayville and Patchogue. There is a small town beach with a playground where my dad taught me to swim as a child.

Bluepoint Brewery

people enjoying live music while drinking beer outside Bluepoint Brewing Company
Live music at Bluepoint Brewing

Ironically located in Patchogue not Bluepoint, the Bluepoint Brewing Company is open to visitors. Munch on an appetizer of Buffalo Cauliflower Bites, Crab Baked Oysters, or good old fashioned chicken wings while you sip on local beers. Then dine on sandwiches such as Blue Crab Roll, Island Shrimp Tacos, or BBQ Pork Sandwich. During the warmer months live music plays while you enjoy enjoy your fare outdoors. Seasonal beers are available such as Summer Ale, Oktoberfest, or Pumpkin. The brewery also creates small batch brews such as Spectral Haze or Beach Plum Gose. Definitely worth a visit.

The Greek Festival

As a child my family would go to this festival every year. Each year St. John’s Greek Orthodox Church, located at 77 Montauk Highway in Bluepoint, hosts this festival which has free admission. Try authentic Greek cuisine such as spanakopita, pasticcio, moussaka, and of course gyros or souvlaki. Make sure to pair your meal with a bottle of Greek beer or a glass of reek wine. The ladies from the church make homemade baklava, and other delicious pastries for dessert. My favorite are the loukoumades which are fried dough with honey.

The festival usually takes place at the end of June. There are also rides and games. Vendors sell clothing, jewelry and Greek items. In addition enjoy live Greek music and dancing. Parking is scarce so make sure to come early.

JT’s on the Bay

A family eating dinner at an outdoor restaurant on South Shore Long Island
There’s nothing like family

During our visit we met up with my cousin Kathleen and her family for dinner. JT’s on the Bay is located at 1 Curtis Road in Bluepoint. We chose a table outside at the dock and got to watch boats travel back and forth in the bay. Long Island is known for local clams so I recommend ordering from the raw bar. Dinner choices include steak with lobster mac and cheese, blue Point Beer battered shrimp and chips, and seafood pasta. However, for landlubbers there are options such as Grilled Rib Eye or Chicken Milanese.

Check out these affiliate links for some great gift ideas for travelers:

Port Jefferson (OK, so this isn’t a South Shore Long Island town)

a family holding up signs after completing an escape at Hour Escape in Port Jefferson
We did it!

We were supposed to head to a local beach in Massapequa with my cousin, but plans changed and we headed to the north shore for a day trip to Port Jefferson. Port Jefferson is located on the north shore of Long Island on the Long Island Sound. Stroll streets lined with cute shops such as Amazing Olive, art galleries , and restaurants. We ate lunch at the Harbor Grill which was reasonably priced and kid friendly. Of course, we ate on the deck watching the marina. Then we explored the shops and did some souvenir shopping. We explored the Thomas Kinkade Signature Gallery. Finally we ended up at Hour Escape for a fun family escape room experience.

For more information on where to stay and what to do on the South Shore of Long Island you can look up the individual towns on Trip Advisor. For unique and cozy places to stay search Airbnb.

author profile picture

Donna Emperador is a travel and food blogger and copywriter. Donna believes in learning about different cultures while sharing good food and cocktails. She has lived in South Florida for over 20 years and enjoys spending time exploring the road to find unique places to share with readers. She can be found on FacebookInstagram, and Pinterest.

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2 thoughts on “South Shore Long Island, reasons to fall in love with these small towns”

  1. Seeing all this made me homesick for Long Island again. I love Florida, but will always have a soft spot in my heart for Sayville and other small towns on Long island. Love the blog.

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