Embrace the Clarity of Winter with our curated itineraries of a day in the life of a North Forker - the blueprint for your two-day North Fork escape from it all. From charming towns to nature walks to vineyards, find inspiration to start planning your trip or let us take care of the details for you. Browse our itineraries below and start planning your stay today - kindly confirm each experience's schedule before heading out or let our front desk team confirm for you.*
Day 1- Itinerary
8 am - Wake to the sound of the sea rhythmically lapping against the shore and dress for a cool day with hiking shoes afoot. Hop in the car and drive over to North Fork Roasting Co. and ask for an almond milk-based Bee Sting or their changing seasonal specialties.
12 pm - It's time for a well-deserved lunch at Orient Country Store on Orient's charming Village Lane and maybe one of their famous pies to take home. Make sure to check the hours in the winter.
1 pm - Work your way back west to the tasting room at Matchbook Distilling Co. Take a tour of the distillery, make your own gin, or just enjoy a tasting of some spirits.
2 pm - Time to head back to the hotel to relax and read a couple chapters in your book before stepping out on your deck for sunset at 5. Winter sunsets are a special kind of magic.
7 pm - Walk over to The Halyard Restaurant (or better yet order room service) and try something from the new cocktail menu and dinner. Back to the room by 9pm to watch a film and go to bed by the sea.
Day 2 - Itinerary
8 am - Rise and shine and it's off to Aldo's Coffee Company for old-world-style coffee and biscotti in Greenport Village.
9 am - Take a short walk over to Bruce & Son for breakfast or if you're looking for something quick and easy like an egg sandwich to eat by the marina try, Goldberg's.
10 am - Hop on the ferry to Shelter Island and spend an hour walking the coastline of Mashomack Preserve, one of the richest habitats in the Northeast.
11 am - Grab the South Ferry (and don't forget to buy your round trip ticket!) for an early lunch at Sag Pizza before a visit to the Parrish Museum.
2 pm - After a couple hours at the Parrish, make your way to the tasting room at Wölffer Estate Vineyard to sip on a taste of the Noblesse Oblige.
4 pm - Make a point to be back on the South Ferry by 4 so you can catch the sunset from the North Ferry at 5.
5 pm - Back in Greenport, it's time to head back to the hotel to relax and get cleaned up for dinner. For fine dining try North Fork Table and Inn or if you're feeling more low-key Lucharitos has wonderful Mexican, there's more great pizza at 1943 Pizza Bar or you can connect with the locals at Sophie's.
More North Fork Favorites
Lunch – Cozy local's favorite featuring new American style dishes at First & South.
Spring Awakening! Less than two hours from Manhattan, enjoy the tranquility of the North Fork during its quieter months. There is so much to see out here but with far fewer people and certainly no crowds. Be here by clicking below to book!
Save 25% on two-night stays for Sunday-Thursday arrivals.