3 Day Weekend in Greenport, NY

The charming North Fork town of Greenport, New York has so much to offer including boutique hotels, waterfront dining and vineyards. Just a two hour drive from NYC, it is the perfect weekend escape. Here is a three day itinerary with our favorite spots!

Day 1

While most people are not traveling and getting on planes right now, we’ve found joy in weekend road trips to ease our wanderlust. We found a lovely hotel in Greenport, NY: The Harborfront Inn. As most are still uneasy about traveling (and for good reason), we felt completely safe staying at this hotel where safety and cleanliness are the utmost priority for its guests.

If you’re staying at the Harborfront Inn you also have access to the Soundview Hotel’s beach & pool (although we preferred the pool at the Harborfront due to its comfy lounge chairs and more secluded vibe).

Head to the Soundview and spend the majority of your morning and early afternoon relaxing on the beach. The staff will set you up with lounge chairs and towels, and you can also order drinks as if you were lounging at a Caribbean resort.

For lunch, there’s a lobster roll shack right on premise - grab a lobster roll and continue lounging by the pool.

After you’re done soaking up the sun, head to Anker and enjoy a great atmosphere to sip on a cocktail and enjoy some apps. We decided to snack on shrimp cocktail and calamari before it was time for dinner.

For dinner, we recommend Port Waterfront Bar & Grill. The outdoor seating area is very spacious and the steak frites were our favorite meal of our entire trip. If you’re going with a group, definitely order a pitcher of their punch to save some $$.

As you’re walking back to your hotel, grab some ice cream at Flavors Dessert Cafe and walk around the town!

Day 2

Crazy Beans is our absolute favorite grab and go spot for coffee and breakfast. This eclectic, 50’s themed diner has a very wide-ranging and delicious menu offering creative twists on many classics. A hearty breakfast sandwich and refreshing iced latte is the perfect start to a summer morning in Greenport. 

Spend the afternoon relaxing and soaking up the sun at the Harborfront Inn’s charming outdoor in ground pool and deck. It is well-maintained, quiet and offers a lovely view of the marina. We do advise that you reserve your seat early, as the pool area is smaller in size and does fill up quickly. 

Head to Crabby Jerry’s for lunch with a great view and even better lobster rolls. The restaurant is right on the water and offers a very casual atmosphere where you order and pick up your own food, as well as choose your own seating. Order a refreshing margarita at the bar to sip on while you watch the boats go by. 

Enjoy delicious appetizers and cocktails at Green Hill Kitchen before heading to dinner. This BBQ & Bar joint is a must! We couldn’t get enough of the cauliflower nuggets dipped in buttermilk ranch or the finger lickin’ good “hot & sweet” wings. Be sure to also try their signature blood orange Matty’s Margarita. 

American Beech is a trendy boutique hotel that has one of the best restaurants in town. The space and decor is stunning, both inside & out and is definitely one of the more upscale-vibe venues in town. Friendly staff, great service & excellent menu options. It is the perfect place for a fun, intimate dinner.

Day 3

Start your Sunday with an early morning bike ride around the town! Call Dan’s Bike Rental the day before and he will personally drop your bikes off to your hotel at the requested time. He only accepts cash, so be sure to hit the ATM before! Ask him for the “cute” bikes and he will do his best to provide you with one that is perfect for your next photo op.

Stop for a cup of coffee at one of the local coffee shops before beginning your journey through the quiet streets of Greenport. End your bike route at Crazy Beans for another grab and go breakfast. This is the perfect option to take with you to the pool for your last sun bathing session at the pool.

The North Fork is New York’s version of Napa Valley and you could easily spend a whole day hopping from vineyard to vineyard. If there is one you cannot leave without visiting, it is Croteaux Vineyards. This instagram friendly spot is any rosé lover’s heaven as it is the only vineyard in the US dedicated to rosé and only rosé. Their outdoor garden is the perfect setting to try their variety of pink wines. The tasting menu includes the option of six still or three sparkling wines which can be enjoyed their tasty appetizers. Try the Provence Basket which is an assortment of olives, dips and cheeses or their lobster roll sliders.

If you’re visiting during June or July, head to Lavender by the Bay for lavender fields that will make you feel like you were transported to Provence, France. Currently they have a limited number of field entry tickets available for purchase online. Once on the farm, explore the seventeen acres of purple blossoms and head to their store where you can purchase fresh lavender and a variety of other lavender products and honey.