Greenport, NY: 10 Things To Do All Year Round

Take a closer look at Greenport NY, you’ll find that there is much more than meets the eye. You won’t want to miss these 10 notable experiences in this former Whaling village.

It’s a partly cloudy, hot summer day. Pat and I wanted to skip the usual crowds you find on the weekend on the South Fork and do something a little bit different. We decided to drive out to Greenport, NY, a former shipbuilding center on the North Fork of Long Island. I had been exposed to the wineries in North Fork, but nothing beyond that. I didn’t know what to expect when visiting Greenport Village Historic District. It’s a completely different experience out here. The historic district is made up of over 250+ unchanged structures from the 1750s to the 1930s that each tell a different story of Greenport’s history. It is listed on the National Register of Historic Places. After spending some time exploring the village, my takeaway is that Greenport has maintained its authenticity while surging some new energy into its streets and New England style buildings.

Quick Note: Where to Stay in Greenport, NY?

After visiting Greenport a few times, there are 3 types of accommodations I would recommend in Greenport, NY. I want to preface this by saying I would recommend you try and stay clear of areas next to restaurants, bars, and shops as it can get a bit loud during summer nights! That’s why most of the one’s I recommended are just right on the edge of town:

First things first, we needed food before our 1 hour 30 min drive from Smithtown to Greenport, NY. We were craving the typical Long Island breakfast staple, an egg sandwich, and were recommended to go to Bagel Chalet in Commack. We had heard the lines were long, but moved fast, and the egg sandwiches were as good as they got on Long Island. We waited in line for about 15 minutes ordered our cold brew and waited for our egg sandwiches for a few minutes. When our sandwiches were brought out, we instantly knew they were perfection upon opening. Gooey, just like we liked them. We sat together, egg yolk and ketchup dribbling down our chins. We’ve officially found our new egg sandwich spot. We hit the road shortly after and made our way to North Fork.

1. Peconic Cellar Door

Our first stop wasn’t actually in Greenport, but in Peconic. We stopped by Peconic Cellar Door tasting room to pick up a case of wine for Pat’s family. We stepped inside and ended up chatting with Robin Epperson-McCarthy, one of the owners for over an hour. She’s a biochemist turned Sommelier with a lot of worldly experience. At the end of the day though, her experiences brought her back home with the mission to bring high-quality North Fork wines that are affordable for everyone, with a bit of a creative twist. Our pick-up came with a complimentary tasting. We joined in on the tasting with a few other couples who were in the farm house turned chic store. Keys hung from the ceiling, recalling their logo Cellar Door. We ended up tasting a bit of everything from their Salty Bird rosés, to the Haywater merlots and chardonnays, to the BOE merlots. My favorite though had to be their wine spritzer! Robin and her partner Allie are set on bringing back this delightful summer beverage. We had a blueberry flavored spritzer when there. I can tell you that going out there just for a spritzer is worth the trip.

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2. East End Seaport Museum

We spent our morning learning about the importance of Greenport at the East End Seaport Museum. The owner was hanging around and took the time to walk us through the story of the Regina Maris, a sail boat that set sail for over 100 years. It no longer exists, but the owner acquired the figurehead and has it on display at the museum. We then asked him about the lab flasks lined up on the windowsill and he went onto explain how oyster harvesting came to be an important source of economy for the North Fork. These were just 2 of the stories the owner took us through when there, but these and plenty more are in store at the East End Seaport Museum. 

3. PORT Waterfront Bar & Grill, Little Creek Oysters, Claudio’s

After visiting the East End Seaport Museum and Marine Foundation, we began to make our ways toward the boardwalk. We walked by PORT Waterfront Bar & Grill, a large laidback waterfront dining experience, with plenty of outdoor seating under yellow vibrant umbrellas and a cute bar cabana. If your not in the mood for PORT Waterfront Bar & Grill, Little Creek Oysters (the big sign that reads Bait & Tackle) is just a few feet away. Tucked into the corner of the boardwalk, string lights, high top tables made of barrels and a small laidback atmosphere will beckon you here. If your in the mood to party, head to the energetic, more vibrant and popular Claudio’s. Known for it’s bar scene and music, you’ll see plenty of boats docked around this boardwalk restaurant looking for a good time.

When I visited with my friend Nicole back in May, we had lunch at Little Creek Oyster. Formerly a bait and tackle shop, Little Creek Oyster has actually been around for over 140 years. Ian Wile, the owner, harvests his own oysters and originally sold them to restaurants and markets. However he wanted to make them available directly to the public, so opened up Little Creek Oyster. Today he offers a variety of oysters and clams from small, local producers. The most iconic experience you can have is “go shuck yourself,” where you shuck your own oysters. They give you a bucket, gloves, and a knife and have at it! Don’t worry, the staff gives you a tutorial. But on this cold rainy day on the North Fork, we chose to get ourselves 2 soups (clam chowder and chili) and do an oyster tasting of a dozen different types. Our favorite, hands down, was Mermaid Makeout. 

4. Boardwalk, Yachts, and Barba Bianca

A casual stroll down the boardwalk reveals a number of beautiful yachts, boats, and sailboats for those looking to escape the hustle and bustle of the Hamptons. A few boardwalks down, you’ll find a new 2017 Italian restaurant tucked away from the energetic music of Claudio’s—Barba Bianca. It’s hard to miss the isolated red farm house like building alone on the boardwalk. The restaurant features beautiful outdoor seating with views of the marina, the Peconic River, and Shelter Island.

5. Main Street: Lucharitos

As soon as we walked onto Main Street, we saw a line forming out of Lucharitos. One of Greenport, NY’s most famous and loved Mexican restaurants. Even if you don’t want to wait in line for a bite to eat, step inside for a drink or just to take in the fun atmosphere. Millennial pink and blues decor the walls with fun images, patterned walls and tables, and string lights.

6. Main Street: Hampton Chocolate Factory

Save some room for dessert. Right next to Lucharito’s is Hampton Chocolate Factory’s second location, the first is located in Westhampton. A small window display showcases s’mores, chocolate covered in sprinkles, and more. When you open the door a waft of chocolate fills the air. The chocolate is prepared through a former Daniel Boulud pastry chef in Brooklyn. The place features a create your own s’mores bar which includes a blow torch and everything, frozen hot chocolates, frozen s’mores, frozen chocolate covered oreos, and more.

7. Main Street: Greenport Fire

To the right of Lucharito’s is Greenport Fire. I couldn’t tell what the store sold from the outside but the walls and ceilings covered in records lured me in. They sell cigars, they sell antiques, and hot sauce. Yes, you heard me right, hot sauce. The owners needed something more to give it that extra something and hot sauce seemed to do it for them. Greenport Fire is a hot sauce store that offers tastings and sells hot sauces for all levels. Try one of their cheeky hot sauces and get a kick out of the experience. Hot sauce names include Reaper Evil, Oh My Garlic, DA’BOMB Beyond Insanity, and I Believe I Can Fly.

8. Main Street: Crazy Beans

Callie Martino and her husband Tim took over the old Greenport Coronet Luncheonette that had been open from 1949 to 2016. It was a North Fork landmark spot since the 1950s. Callie has strong ties to Greenport, she used to visit as a kid. Maintaining the diners original retro, 50s feel was very important to the Martino’s. Today, it’s home to Crazy Beans, their third location based out on Long Island. The diner has something for everyone and offers brunch and lunch options. They preserved a lot of the original fixtures including the retro sign outside, old photos, and memorabilia hung on the walls.

9. Main Street: Antique Furnishings

Sveva, why are you telling us to visit Goldin Furniture? I’ll tell you why. It’s more than just a furniture store. The huge Queen Anne-style building was built in 1894 as a theater, art, and entertainment building known as the Greenport Auditorium. The Great Hurricane of 1938 brought it down, but it was than bought and turned into Goldin Furniture store. It was recently listed on the endangered historic places list on Long Island. There are current efforts being made to restore it to it’s original purpose as an entertainment complex as more and more real estate agents try to chip away at the Greenport Village Historic District .

There is no shortage of vintage shops in Greenport, NY, aside from Goldin Furniture. From The Times Vintage to Lydia’s Antiques Stained Glass, The Furniture Store, and Gallery 429. Nicole and mine’s favorite was The Times Vintage, a store that felt like something straight out of That 70s Show. We even witnessed someone walk out with a Jean Pual Gaultier for just $100. The place has so many fun prints, accessories, and clothes for me and women, as well as home furnishings and records. Vintage shops are a great way to get a quick glimpse of historical items as they are displayed to their best in these small, one would almost call them, “artifact museums.”

10. Main Street: Special Effects Salon & Spa

If all of this walking around is making you tired, then Special Effects Salon & Spa should be your next stop. You won’t miss the charming pergola covered in ivy that leads to a floral backyard with lounge chairs, hand painted tables, flowers and plants, and a hammock. The business began as a spa service, and still runs as such, but recently extended its services to include a Special Tea House. The Special Tea House seats 49 people inside and outside and serves speciality teas served in beautiful painted english tea cups paired with light bites such as classic cucumber tea sandwiches, North Fork lavender shortbreads, Martine’s apricot ginger scones, chocolate dipped biscotti and more. Special Tea House includes gluten free options too.

Continue walking down Main Street and you’ll admire various architectural styles throughout Greenport, NY. Whether it’s barn style or horse stable entrances. Every building in the Greenport Village Historic District has a story.

11. Stirling Square

Stirling Square is home to a new hotel, a 1943 Pizza Bar, and the Brix & Rye cocktail bar. The name Stirling Square is based off of one of the early names for the Greenport, NY area—Stirling. Stirling Square used to be a 19th-century horse stable now turned into a bustling renovated square with chic food, outdoor dining and bars, live music, and even a speakeasy. Interestingly enough, Greenport was a huge bootlegger during the Prohibition era, so having a speakeasy in the historic village only seems fitting. It’s all you could want for a relaxing afternoon within the confines of a small square.

12. Front Street: The Olive Branch Café

The Olive Branch Café is not a place with a lot of history, but it is one of the first Mediterranean and Turkish places to open in Greenport, NY. The property is located in a cute courtyard on Front Street facing Mitchell Park, right next to Tea & Tchotchkes, a boho lifestyle shop with local and hand crafted artisanal goods from around the world. The Olive Branch Café is broken up into three areas, a self-serve cafe, a kitchen that puts the fresh farmers market herbs, fruits, vegetables, and ingredients used to cook on display, and a sit-down restaurant. The cocktail bar area is set to open up in the next few weeks around August 2019, we got a sneak peak of the inside…see the picture above!

13. Front Street: Antique Carousel (Northrop Grumman Carousel)

Located across from The Olive Branch Café in Mitchell Park is the antique Greenport carousel. The carousel was built in 1920 and used in the 1950s for company events at the Calverton plant. It eventually got donated to Greenport. The carousel features Disney classical music, it is one of the 150 remaining carousels from the 1880s to the 1930s. There used to be about 4000.

14. Front Street: Aldo’s Coffee

Aldo has been in Greenport running the same business for the last 32 years and he is still going strong. He even beat out a Starbucks that tried to set up shop in Greenport, NY. The Starbucks didn’t last very long. He is known not only on Long Island, but throughout the world for his high quality and unforgettable coffee, scones, and most of all biscotti. None of which I got to try unfortunately during my time there! So I cannot share my opinion with you, but I’ll definitely try it next time I’m there. What I was most curious about where the hand made croissants, I am YET to find a place that sells croissants the way they make them in Italy.

15. Front Street: The Village Blacksmith

You can feel the heat emanating from The Village Blacksmith shop just steps from Aldo’s Coffee. Peak your head inside and you’ll catch Thomas Barry hard at work as he hammers away recreating an important part of Greenport’s history. Thomas carries on the work of Greenport’s last blacksmith, German-born Paul Nossolik, who worked till the age of 90! He passed away in 1987. Paul also had done some work for bootleggers during the Prohibition era. Today Thomas does occasional demonstrations, particularly in the summer, and offers his items at a low price for people to take home and share Greenport’s stories with the world.

16. 67 Steps Beach

On the other side of Greenport village is this small gem of a beach. It’s rocky, but idyllic. It’s 67 steps lead you down to the Long Island Sound were you can lay on a towel or picnic blanket enjoying a picnic box full of sandwiches, fruit, and chips you pre-ordered from Fork and Anchor.

17. Country View Farm Stand

After a long day exploring Greenport, we were beat. But we couldn’t go home empty handed (aside from two bottles we had purchased from Peconic Cellar Door) so we stopped by one of the many farm’s in North Fork and picked up some fresh produce. We drove by Country View Farm Stand in Southold and pulled into the lot. It’s vivid colors, beautiful sunflowers, and big sign that read Fresh Baked Pies Daily drew us in. Country View Farm Stand is a family-business that has built a loyal following over the years. It’s been open for over 9 years now. The produce featured comes from a family farm in Aquebogue and Southold. We were super tempted to buy one of their hot from the oven pies, but knew we would finish it within 24 hours. We avoided temptation and bought some cherries and blueberries instead. I had almost forgotten what real fruit tasted like. The fruit was beyond flavorful when we had it later on that night! It’s times like these that I wish I lived out on North Fork and had my own farm.

18.Dinner: The Halyard at Sound View Or Hellenic Snack Bar & Restaurant

If you’re staying for dinner, here are some options for dinner in Greenport. The Halyard Restaurant at Sound View Greenport sits directly on the Long Island Sound. This was another restaurant that Nicole and I had on our bucket list, not for the food, but for the ambiance. The Halyard is located directly on the beach. On a sunny day, you can enjoy dinner out on the pier as you watch the sunset behind the Long Island Sound as you listen to the sounds of the waves crashing below your feet. It’s quite a sensorial experience. In the summer they even host bonfires out on the beach and happy hours with live music. On a rainy day, the view is just as stunning, except you enjoy it from the indoors.

Now I know Greek Food while taking a trip out East may sound strange, but that’s what Nicole and I were craving. A light meal. Something not too complicated and expensive. We stumbled upon Hellenic Snack Bar &  Restaurant. Unpretentious, simple, and great reviews on Google Maps. It was a short 5 minute drive from Greenport so went there for dinner. It did not disappoint. The place is not an actual “snack bar.” But the restaurant kept the name to remind themselves of their humble beginnings. It was a family venture started more than 35 years ago. Once a four-table snack bar, it’s now a 40-table restaurant.

Shopping, eating, and getting pampered in Greenport is just the start. Each and every one of these unique places has made Greenport a notable historic village.

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