Harborfront Winter Explorer
Adventure Like a Local
Embrace the Quiet of Nature 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 with or without a car. 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 help you.*
Day 1 - Itinerary
8:30 am – Up and off to start the day with hot coffee and great breakfast sandwiches at Fork & Anchor just up the road in scenic East Marion. Dress warm and in layers!
9:30 am – Head to the tippy-tip-tip of the North Fork & take some photos of the lighthouse from Orient Point County Park.
12 pm – Now hungry, drive back toward town but first stop in Orient on charming Village Lane for lunch at the Orient Country Store; many stand here for hours pondering which of their famous pies to take home.
1 pm – Time for your reservation for wine tasting with our friends at Lieb Cellars on their heated patio. The best White Merlot this side Sonoma pairs well with their incredible cheese platter.
3 pm – On your way back to Greenport, stop by Sang Lee Farms for some fresh veggies and a little education around their award-winning organic farm practices.
4 pm – Back to hotel for a nap or grab an espresso drink at Aldo’s Coffee Co. and sip it while walking along Mitchell Piers where many an artist find deep inspiration.
5 pm – Cocktail hour! It’s time for cocktails and dinner rituals by the sea at the waterfront Halyard Restaurant.
Day 2 - Itinerary
9 am – Start the day with a breakfast of champions at NOFODOCO. Their doughnuts are amazing.
10 am – Walk it off with a morning beach walk at Bailie Beach (also a great spot for sunset).
11 am – Take a private tour of the vineyard and winery at Borghese Vineyard with the owner himself, Giovanni.
1 pm – Now its time to find your favorite lobster roll. Some of ours can be found at The Halyard Restaurant, Southold Fish Market or Barrow Food House.
2 pm – Make an appointment for a private oyster tasting with Oysterman Peter Stein at Peeko Oysters in New Suffolk.
4 pm – Take a spin on the new ice skating rink at Shamrock Christmas Tree Farm before heading back to the hotel to read a few chapters in your book.
6 pm – Just a few steps from the hotel is Kate’s Cheese Co. where you can get an incredible Fondue De Raclette and sample some more local wines.
8 pm – End the night with a nightcap underground at the award winning Brix and Rye.
Car-Free Itinerary
8:30 am – Rise and shine and walk two blocks over to Bruce & Son for breakfast including their famous sugar bacon.
10 am – Mill about around town and spend some time at our favorite local bookstore Burton’s.
12 pm – It’s taco time at Lucharito’s at their outdoor seating area decked out for the holidays.
1 pm – Check out some of the local libations on Carpenter Street – for wine and spirits it’s Greenport Distilling and for craft beers it’s the original Greenport Harbor Brewing.
3 pm – Back to hotel for a nap or grab an espresso drink at Aldo’s Coffee Co. and walk along Mitchell Piers.
4 pm – Take a quick walk over to Little Creek Oyster Farm for sunset oysters and drinks by the fire pits.
6 pm – Dinner in town at Noah’s, 1943 Pizza Bar, or reserve one of the outdoor dining “Casitas” at American Beech.
8 pm – End the night with a nightcap underground at the award winning Brix and Rye.
More North Fork Favorites
Lunch – Wood fired pizza and wine for lunch at Jamesport Vineyard’s Little Oak.
Farms – Goodale Farms and 8 Hands Farm.
Bars – Jedediah Hawkins.
Dive Bars – Whiskey Wind & Cuddy’s.
Wineries open we love…Open daily – RGNY, Jamesport Vineyards, Lieb Cellars, Macari Vineyards, Paumanok Vineyards, Bridge Lane Wine, Suhru Wines, McCall Wines, and Borghese Vineyard.
Embrace the Quiet of Nature with 30% Off
Don’t escape winter, Embrace the Quiet of Nature: take 30% off of your two-night stay and enjoy a complimentary upgrade* for visits December through March. Escape from the city or suburbia this winter and join us in the North Fork. Sail through the crisp breeze and hike the snowy trails. Discover your favorite warm-weather activities are even more beautiful with a chill in the air.
*Offer valid for Sunday-Wednesday arrivals.
