Weekend Travel Guide: Greenport, Long Island, NY

Last weekend, I went to Greenport with my boyfriend to escape the city for a brief moment. We’ve both been super busy recently, especially on the weekends, so we took full advantage of booking a mini getaway over this particular Sat-Sun we found ourselves both available for.

FACT: This was my first trip “away” with T, let alone with a boyfriend in general. I’ve never spent one-on-one time in a new setting with a guy I’m dating before; but honestly, I had zero hesitations when we decided to plan this weekend trip. We were both on the same page with our expectations of it, as well as genuinely excited to have the opportunity to share a rare weekend alone together.

WHY IT FELT RIGHT: For starters, this trip was just for 2 days and located only 2 hours from the city. The only thing that could’ve triggered any sort of frustration would’ve been the traffic, which we somehow avoided during rush hour thanks to Waze! But ultimately, the reality of why it felt right is because we both view our relationship as pretty solid & stable; we both know each other well enough to trust we’d get along for 48 hours nonstop, on top of sharing a bathroom…

IN MY OPINION: A weekend trip like this is a great test to take if you’re progressing in a serious relationship. You get to know someone pretty well in a short amount of time, which can help strengthen your compatibility or shed light on something that’s otherwise possibly overlooked by the hustle & bustle of every day life.

Needless to say, our weekend was fantastic! We binged our hearts out with food, wine, & beer and treated ourselves to two mornings of sleeping in. I highly recommend visiting Greenport, NY if you’re looking for a quick weekend getaway with a significant other, or even with a small group of friends.
Photo courtesy of The Harborfront Inn


The Harborfront Inn

With several B&Bs in the area, our first thought was to book one of those; but ultimately, we were sold on the idea of having a king-size bed with a balcony overlooking the harbor, along with a touch more privacy.

The Harbor Front Inn is located on the main road in the heart of Greenport, right next to the historic carousel. Although the bed was a tad too hard for my personal preference, the location couldn’t be beat. The best part was having a balcony we could overlook the water from, as well as open the door to for a cool breeze at night; BTW there’s nothing more wonderful than waking up to birds chirping and the smell of salty air, especially if you’re used to living in a city.

Despite arriving pretty late on Friday evening, as in 11pm, we were still able to check-in without an issue. We were even provided with a complimentary bottle of rosé, as well as given an extended check-out time of 12pm on Sunday! A complimentary parking pass was also provided & because of our location, we were able to easily walk to breakfast & later on, dinner as well as wander about this historic, charming fisherman town.

Click to see Specials & Packages when booking your East End getaway here


Front Street Station

Upon arriving late Friday night, we were starving and desperate for food. Luckily, Front Street Station happened to be right across the street from our hotel. Not only were we greeted by the kindest local staff, the food menu was so good that we ended up taking our time to decide what to eat – despite being SO HUNGRY!

The restaurant’s unique space sold me on the dining experience, given the history nut I am. The bar was inside a converted old style, dining train car with an attached greenhouse-inspired atrium for larger dining tables.

Whiskey Wind Tavern

Provided we were visiting “off season,” a lot of bars & restaurants stopped seating & serving around 10pm – including the hours of nearby liquor stores. We found probably the one & only bar scene open until 1am – Whiskey Wind Tavern.

To be honest, it reminded me of a cozy dive bar with a touch of college nostalgia; nonetheless, we had a great time getting late night drinks after our Friday night dinner. Good music, good company, & fab prices!

Bruce & Son

Saturday morning breakfast happened at Bruce & Son, as we both found ourselves opting for a lighter, healthier menu selection. We both choose a simple plate of 2 eggs any style with toast + a side of brown sugar bacon that I swear tasted like candy!

This restaurant offers a variety of plates that meet special dietary requests, including vegetarian, vegan, & gluten-free options. I suggest getting there around 9am to avoid the crowd, because even during the off-season this place is popular!

The Frisky Oyster

We ate our hearts out, while satisfying our seafood palates to the max, by dining at The Frisky Oyster. I’m still thinking about my Seared Scallops over Risotto plate and I’m pretty sure T is currently day dreaming about his Miso Glazed Mahi-Mahi Coconut Curry dish. The food menu is updated daily but you can still see what’s being served online.

ALSO IN MAJOR TASTE BUD NEWS: I tried oysters for the 5th time, expecting disappointment, and was shocked to find myself LOVING them!! I kid you NOT, I’ve tried to like oysters for YEARS but my taste buds never agreed with my brain’s desire. But all of a sudden, I found myself borderline in tears from delight of FINALLY liking them! I couldn’t be more grateful for the restaurant’s variety, as well as T’s perfect application of Mignonette sauce per oyster I ate.

*Long story short, you NEED to book a reservation here for dinner – you won’t regret it!

Crazy Beans

Our final meal in the village of Greenport was Sunday breakfast at Crazy Beans, a fun diner-inspired eatery with a delicious menu of made-to-order plates of heaven!

I treated myself to pancakes with real VT maple syrup while T chose the healthier route of the Farmer’s Omelette. The coffee came in fun mugs I’d probably purchase myself and in diner-fashion, our food orders & refills came fast and frequent!

This is another place I suggest getting to before 9am, even during the off-season and especially during the actual season.


Walked & Shopped in Greenport Village

The Village of Greenport is full of history, which is half the reason we were so drawn to visit it. I’ve mentioned I’m a history nut & love spending time in charming residences that have stories to tell. Both me & T grew up on/in/around water so provided this is a historical fishermen’s town, it only felt right to explore our weekend surroundings.

After wandering down a few marina docks & spotting more red jellyfish than I feel comfortable admitting this time of year, we also stopped in a few shops along Front St & Main Rd and picked up a few local finds:

Aldo’s Coffee Shop

A great place to stop for that first or second cup of much-needed coffee! It’s located right next to the historic carousel on Front St on the way into town. Inside reminded me of destination where you can both reconnect with friends or set up shop to work remotely.


Clarke’s Garden & Home

Although we didn’t purchase any plants, we were SO tempted to do so. I love anything that sells living greenery, for both inside & outdoor pleasure. I kind of wish we took advantage of getting a few succulents though; they were definitely cheaper than those you’d find in the city.


Greenport Fire

If you love hot sauce, then you’ll greatly appreciate Greenport Fire’s mild to out-of-this-world spicy selection. Ranging from degree of heat clockwise & categorized by flavor, I suggest going into this store with a specific taste preference in mind. I picked up something different than my go-to smoky sauce, choosing a flavorful blend of pineapple, lemongrass & ginger with a manageable kick!


The Weathered Barn

Super cute boutique with an assortment of locally-made soy wax candles, decadent soaps, & wooden kitchen tools + utensils. I picked up Hyacinth & Malaysian Bamboo candles that both burn like absolute heaven, a bar of all natural lemongrass & oatmeal soap that smells too good to use, and a tin of locally-made Sea Salt with lemon, rosemary, & thyme that I recently used on an oven-roasted chicken dish.

Greenport Harbor Brewery

We visited the Greenport Harbor Brewery & Restaurant for lunch on Saturday after hearing such positive reviews & recommendations about it. The menu is so fab, as well as the beer selection on tap. Large, long picnic tables both inside & out offered plenty of seating along with several Adirondack chairs in the grassy space adjacent to the main building.

Customers ranged from bachelorette parties, to one-on-one dates, to families celebrating a two-year-old’s birthday! Everyone (including your dog) is welcome with open arms, holding two pints of beer.

*Tours of the brewery are by appointment only, but you can visit the bar/restaurant anytime without a reservation!

The Old Field Vineyards

If there’s any place that made this trip feel complete, then it’s The Old Field Vineyards. Located on a farm surrounded by chickens, you’ll find inside the barn a cozy tasting room with a crowd that makes you feel like family. This winery is definitely a hidden gem & highly-recommended if you enjoy the simpler things in life, with a quality that can’t be matched!

*Open to tasting for groups up to 5 without reservation. Groups of 6 or more by appointment only, due to limited space inside the barn.

Kontokosta Winery

On our way back to the city Sunday, we stopped at Kontokosta Winery for a quick glass to enjoy while overlooking the Long Island Sound. We actually realized our hotel – The Harbor Front Inn – is the sister business of this winery; therefore, we had complimentary 2-for-1 vouchers to use upon arrival!

Guests are welcome to enjoy the tasting room, sample a variety of wines, or enjoy a full glass of their choice at this waterfront winery. We arrived on the earlier side but I can definitely see how this place can get packed quickly – I mean, the view is so gorgeous!

Catapano Dairy Farm

Our last stop on our way out of Greenport was the Catapano Dairy Farm. My best friend’s boyfriend recommended we check it out because, 1) CHEESE, and 2) GOATS.

After giving out several chin scratches to some very friendly goats – see more on IG Highlight “Greenport” – we found ourselves sampling every variety of cheese available for purchase. Needless to say we left with over 5 varieties & a free cooler to transport them back home in!

That evening, we devoured one of the 2 Sheep milk cheeses as an appetizer, and used an entire carton of Chevre goat cheese in a healthy salad recipe you can catch on IG Highlight “Good Eats.”

Update: It’s only Thursday and we have 3 cheeses left…