Hold off on canceling your trip. The North Fork is full of activities–rain or shine. You just need to know where to go and what to do. Here’s my ultimate guide on what to do on a rainy day on the North Fork.
I’ll admit I was the first to reach out to my friend Nicole when I saw 3 straight days of torrential down pour over Memorial Day Weekend. What would be the point of going to the North Fork (also known as NoFo) of Long Island? The North Fork is all about the outdoors and nature! I texted her asking if we should cancel and save the money. She persuaded me not to. I, of course, being the traveler that I am, took that as a challenge. I set out to put together a 3-day fun and jampacked itinerary for a rainy day on the North Fork. Admittedly, I’m glad we didn’t cancel. We managed to fill everyday with tons of activities and exhausted every indoor rainy day opportunity possible. Here’s your ultimate guide on what to do on a rainy day on the North Fork–so hold off on cancelling your trip.
Quick Note: Where to Stay in the North Fork?
There a few areas I would recommend staying in on the North Fork. You really can’t go wrong since the wine trail goes on for miles and miles, each town has it’s own unique and distinct charm, and is surrounded by water both North and South! However, here are a few of my favorites…
- If you want to stay in a bustling area, then stay in Greenport. There are tons of restaurants, plenty of action and stores, and a ferry that drops you right off at Shelter Island. You can stay in a traditional bed and breakfast situated right on the water like Stirling House Bed & Breakfast, a more modern condo on the water like this, or a traditional Long Island cottage (my personal favorite).
- Mattituck is perfect for those who are looking to be close to farms, vineyards, famous love lane (all talked about below) and away from a bit more of the hustle and bustle. Staying in a guest house like this one nestled in nature and just a few steps from the beach will make it feel like a private retreat. If you’re looking for something a little bit less rustic and more chic with a pool, then this modern home will do the trick.
- Not in Greenport, but just outside of it is the town of Southold. This is where you should stay if you’re looking for vineyards and farms, but want to still be an arms length away form the bustle of Greenport. This classic brown shingle style home has a private dock on the water and kayaks, without the price tag of Greenport.
Day 1
Breakfast at Jamesport’s Main Road Biscuit Co.
If there is one place you’ll here mentioned over and over again, no matter where you are on the North Fork, it’s Jamesport’s Main Road Biscuit Co. It is such a staple, we even found some photographs and artwork dedicated to the place in an art gallery! So on our drive out from Connecticut to New York, a stop at Jamesport’s Main Road Biscuit Co. for breakfast was a must. We pulled in around 10AM and snagged the last table right as the place was completely booked up. The go-to order here is there famous buttermilk biscuits with eggs, bacon, and any other sides or toppings your heart desires. Everything here is made from scratch.
Stroll down Love Lane in Mattituck
Just a 6 minute drive from Jamesport’s Main Road Biscuit Co. is the town of Mattituck. On a sunny day, you may stroll the stores before heading over to the beach. But on a rainy day, you’ll find yourself seeking shelter in the quaint mom and pop stores lining Love Lane. Before you run for shelter inside the stores, find the Barkers Pharmacy mural right before the Needleart store.
Our next stop was Bauer’s store filled with trinkets and jewelry, followed by the well-known Village Cheese Shop. The idea was to stop here, grab some cheeses, charcuterie, and bread in a picnic basket and bring it to a beach nearby for lunch. But on a rainy day, we changed our plans from cheese to interesting local and unique products. Nicole and I spent a good 10 minutes browsing every single product. Some unique finds included:
- Ibizan salt: This may sound so silly, but I had it when in St. Barth last November and have been obsessed ever since
- Raw Honeycomb: An actual piece of local raw, unfiltered honeycomb from Sag Harbor Honey. Nicole was the one who actually introduced me to this. She said her family eats raw honeycombs all the time. I didn’t even know that was a thing!
- Banana Jam: I had never heard of Banana Jam before, but it was something that peaked my interest. I ended up only purchasing the Ibizan salt and raw honeycomb, but my next purchase will definitely be banana jam the next time I come across it.
Our excursion in Mattituck ended with a stop at Mint Clothing Boutique, a cute store filled with boho-chic yet Hamptons-like summer outfits.
Go Store Hopping Down Main Road in Southold
Our rainy day activities and store hopping continued. Except we moved from Mattituck to the neighboring town of Southold. During my research, I came across Main Street in Southold. Not much was said about the town, but I read that there were plenty of cute shops to visit. What I found was a street filled with unique, mom and pop shops selling everything you can and can’t imagine. It was a wonderful and whimsical way to spend the afternoon that truly brought to life the soul and community of Southold. A few of the mom and pop stores we visited sold interesting items like odes to pollock, items made by special needs adults, homemade pesto, mustard, and jam, minimalistic home furnishings, and paint by number coloring books inspired by the North Fork. It’s no wonder we spent a few hours wandering around Southold.
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Visit A Winery: Croteaux Vineyard
When you mention the North Fork, the first association people make are wineries. It is one of the most well-visited wine regions on the Northeast. If you’re from the tri-state area, you know this already. But many who are not from the tri-state area are always surprised when I tell them we have a huge winery scene here. And while the best time of year to visit is sunny days in the spring, summer, and fall, there is plenty to do on rainy days as well. There are many wine tasting rooms beautifully designed to accommodate indoor tastings. But while it may be raining...you can still enjoy your wine outside believe it or not at Croteaux Vineyard.
Yes, I will admit. What drew me to Croteaux Vineyard was not the fact that it is the only vineyard in the US dedicated exclusively to making dry, fresh, fruity, rosé wines–although that is a cool fact. But it was the décor that drew me. Even when it’s raining, the winery has plenty of indoor-outdoor areas that cover you from the rain. Nicole and I enjoyed a glass of rosé under the old barn with lavender and dry flowers hanging above our heads.
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Browse Photo-Art At Alex Ferrone Gallery
A great rainy day activity in the city is museums. Well there is no shortage of those on the North Fork either. They’re smaller and more dispersed, but they’re free and full of local art. Nicole and I visited Alex Ferrone Art Gallery, a photo-based gallery that takes a lot of inspiration from the North Fork. The Gallery is divided into 3 or 4 rooms, each with their own theme. She even sells small take home photography prints within the store. Some interesting pieces we came across include photographs of local stores that are deep-rooted establishments within the North Fork community juxtaposed against a plain background. The point was to put emphasis on the architecture of these local stores and distract from all the noise in the background. Of course, low and behold, what were 2 of the establishments that were photographed? The Village Cheese Shop and Jamesport’s Main Road Biscuit Co! Nicole and I had already immersed ourselves into the heart of North Fork culture without even realizing it and Alex Ferrone’s art gallery underscored that.
Dinner: The Halyard Restaurant at Sound View 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.
Following dinner we checked into our inn at Greenport, just to wake up to another day of rain the next day.
Day 2
Spend the morning at the 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.
Visit 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.
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Grab Lunch at Little Creek Oysters
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.
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Store hop in Greenport
There is no shortage of shops in Greenport, both modern boho, antique stores, and vintage shops. Whether you’re looking for a vintage purse, beautiful old school china, an old sled, furniture, lamps, and more, you can find it in any of these shops. 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.”
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Have Tea Service at Special Effects Salon & Spa
After lunch, we had managed to explore stores down Main Street, avoiding the rain as much as possible. Ultimately, what drew us back indoors for a quick break from store hopping and the rain were scones, cream, and a cup of tea. I mean, the ideal rainy day activity has to be afternoon tea. What better way to warm you up than sitting in an idyllic cottage sipping tea and eating scones? Special Effects Salon looks like a cottage right out of a fairy tale. It’s insides are so bright, that even on a gray rainy day everything seems so light. The basic tea service includes 2 choices of tea or herbal teas and your choice of a scone. I went for sweet, Nicole for savory. The table next to us was just finishing up their tea service and getting ready for their facials and massages. Yes, the ultimate in relaxation for a rainy day, Special Effects also offers spa services! We didn’t indulge, but were content with our nice tea break. Our favorite was French lavender herbal tea.
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Dinner: Greek Food at Hellenic Snack Bar & Restaurant
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. When we arrived, we were escorted to our table by a waiter, who seemed to have a Greek accent, we were already off to a good start in my book! The tables next to us were packed with locals and families. This was an even better sign. My power bowl was exactly what I wanted and needed. Lamb with organic quinoa and local veggies locally sourced from NoFo.
That night, we pulled an 90s move. We stayed in in our PJs and skimmed through the numerous magazines we had brought with us for this special rainy day on the North Fork. With both of us working in media, it’s routine for us to spend hours flipping through magazines. And what a great past-time for a rainy evening? That…and flipping through Hinge profiles!
Grab a Pie from Briermere Farms on the way out
On our last day in Greenport we got lucky…we had overcast and some sun! So we spent the day biking Shelter Island. On our way back we stopped by the famous Briermere Farms, known for their cream pies. We stocked up on strawberry rhubarb bars and raspberry peach pie (the non-creamy pie) and took them home with us as souvenirs of our trip out to the North Fork.
In short, as you can see, there are plenty of activities to keep you busy on a rainy day on the North Fork. The North Fork isn’t all wineries and beaches. A rainy day on the North Fork gives you the opportunity to experience the true culture and people that make up this wonderful area of Long Island on a deeper level. So take advantage of this and don’t cancel your trip.
>> Next: Wineries in North Fork: Mattebella Vineyard
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