North Fork Long Island: Fall Travel & Road Trip Guide

By | Food, Travel, Wine, Finance and Lifestyle Journalist
Last Updated: October 7, 2022
North Fork Long Island: Fall Travel & Road Trip Guide • Winetraveler

When the temperatures drop and the leaves begin to fall, the North Fork beckons.

Locals and visitors alike have long loved making the pilgrimage out to the Eastern End of Long Island, known for its growing wine scene and sprawling farms. It’s the perfect combination of beautiful surroundings, high end dining, farm fresh produce, and family fun. Below is a list of places to eat, drink, play and stay, incorporating current events and things to do. As always, it’s best to check with individual properties before visiting to ensure hours and activities have remained the same.

Winetraveler Tip: Stay social. Many of the local businesses in the North Fork update their Instagram accounts before their websites, so be sure to follow your favorites to keep an eye out for updates before your visit.

Learn about how to visit the North Fork of Long Island with our road trip travel guide. See a list of places to eat, drink, stay, current events and things to do that are perfect for a fall road trip.
A stroll through the woods of Long Island in the fall is nothing short of refreshing. Image courtesy Mike Rega / iStock.

Getting To The North Fork of Long Island

For those traveling from New Jersey and New York City, you have a variety of options to choose from. The Long Island Rail Road makes stops in the North Fork (with a quick change in Ronkonkoma) and for those who prefer bus travel, check out the Hampton Jitney or the Hampton Ambassador luxury bus services with multiple stops throughout the North Fork. 

The North Fork, however, is arguably best explored by car, providing visitors with the optionality to stop at the many open-air farm stands scattered throughout the Fork. Search for items like local produce and specialty items like oysters (Little Ram Oyster Co. ), honey (Sep’s Farm), lavender (Lavender by the Bay), and scrumptious baked goods (Countryside Markets).

You can get there by taking Interstate 495 (the Long Island Expressway is better known as the LIE) and follow the signs to Orient (you’ll see all the North Fork Wine Country stops along the route).

Winetraveler Tip: If you have some extra time, get off the LIE at Riverhead and swing by the open-air Tanger Outlets to kick off your trip.

For visitors coming from Connecticut, skip the traffic and take the Cross Sound Ferry from New London to Orient Point. Ferries can accommodate cars and passengers. Be sure to check the seasonal ferry schedule while planning.

If you’re flying into the New York area, you can check current flight deals and times with Skyscanner right here.

Hotels in the North Fork

The Harvest Inn

This charming B&B in Cutchogue is run by mother and daughter duo Cristina and Ursula Illa, who prepare breakfast each morning for their guests to enjoy it either in the comfort of their own rooms, or outside on their wrap-around porch with beautiful views. For those planning wine tasting excursions, Cristina can create curated trips for guests based upon their wine preferences alongside organizing transportation in private car services. 

The Preston House & Hotel

This boutique hotel in downtown Riverhead is conveniently located close to the outlets, great restaurants like the Farm Country Kitchen and the Barrow Food House, historic downtown Riverhead and wineries like Jamesport Vineyards. They have many dining options, all with a more urban vibe despite its location.

Bay Breeze Inn

For a cozy cottage experience, try Bay Breeze Inn in Jamesport. Just a short walk to the beach, it’s comprised of both a main house and a stand-alone cottage as well as a bar and lounge area with ample outdoor seating.

Things To Do in the North Fork

The North Fork’s famed farm-to-table institution North Fork Table and Inn re-opened this past summer lead by Michelin starred chef John Fraser of New York City. Fraser and his team have reinvented the design of the restaurant and maximized its outdoor space to accommodate those who wish to eat in the open air.

RELATED: An Alternate Route For Exploring Long Island’s North Fork

Want to stay away from crowds or not into dining out? What about controlling your environment with a three-course, wine-paired meal? That’s exactly the type of experience A North Fork Affair brings to patrons who want to taste the North Fork in their own space like their rental home, boat, deck, or patio. Curated by events guru Tracy Kessler, the two-person dining experience curates three courses from local caterer Grace & Grit alongside fresh local flowers, a bottle of North Fork wine, doughnuts from NoFoDoCo, candles, and a date-night Spotify playlist.

One of the best ways to slow down and take in the North Fork is with a guided tour. One of our favorites is the Mattituck Guided Farm and Wine Country Bike Tour. Mattituck is an adorable old village nestled in the heart of North Fork wine country, and this tour provides a relaxing way to take it all in. 

Apple and pumpkin picking on your to-do list? Check out the rustic Breeze Hill Farm and Preserve, who serve up some of the best apple cider and apple cider doughnuts on the East End. They also have a spacious apple orchard ripe for the picking that has fewer crowds and exceptional apple trees and pumpkin picking throughout the rest of the Fall season.

Goodale Farms, located in Riverhead, is a perfect stop for specialty items like goat cheese, farm fresh eggs, and their own homemade honey. It’s also home to an adorable petting zoo where children can stop to feed the local animals and snag an adorable Instagram-worthy photo.

Speaking of little ones, a pumpkin patch is a must-do for those with young families and Krupski Farms has one of the best Fall pumpkin experiences on the North Fork. Take a family photo, go on a hayride, and purchase a few pumpkins to decorate. Don’t forget to snag a few winter squashes or gourds—great to add to a seasonal centerpiece.

If wine isn’t your thing or you simply prefer beer, check out the Long Ireland Beer Company. The brewery was opened by friends Dan Burke and Greg Martin in 2009. It’s currently open for normal business in their outdoor garden and at reduced capacity in their tasting room, following strict social distancing guidelines.

North Fork Wineries To Visit

One Woman Wines and Vineyards is a sustainable, boutique winery in the North Fork run by winemaker Claudia Purita who grew up in her family’s farm in Calabria, Italy. Tasting is available outside on a first-come, first-served basis. Please note that reservations, busses, and groups over 6 are not allowed – all to keep the experience intimate and relaxed. 

Mattebella Vineyards is another perfect winery to visit during the Fall season. This winery has produced some Provencal-style Roses this year which have been a hit with visitors, as well as a sparkling white made from 100% Chardonnay, a perfect celebratory wine to toast to the season. Be sure to check out their seasonal snack and food menu while visiting.

Consider a wine tour to designate a pro as your driver. A Long Island Winery Tour will take you through some top tasting spots along the North Fork and you’ll be able to try as much wine or cider as you like without worrying about transportation. Win-win!

RELATED: More Top Wineries, Hotels and Restaurants in the North Fork

Another great spot for both food and drink is Jamesport Vineyards. The vineyard which has been in operation since 1986 is also home to Little Oak Wood Fire Kitchen. The menu boasts small plates, charcuteries, cheese, and a variety of pizzas to enjoy during your visit. Be sure to plan ahead and make a reservation, as they are currently required. The vineyard can only accommodate groups of eight or less at this time.

Restaurants & Culinary Delights in the North Fork

Farm Country Kitchen is a rustic, waterfront, year-round restaurant with a seasonal menu that highlights soups, sandwiches, wraps as well as main courses like local Crescent duck or an island cioppino. You can also organize a pickup of boxed lunches for groups who prefer to take food on the go while touring the wineries.

Junda’s Pastry Shop is a perfect stop for something sweet. The bakery specializes in strudel, as well as homemade bread, pie, tarts, cupcakes, cookies, and breakfast pastries like doughnuts, muffins, and coffee cake. If cake isn’t your thing, but ice cream is, swing by Patty’s Berries and Bunches to try their homemade berry ice cream. Visitors can also stroll through their farm and admire and purchase their beautiful floral arrangements.

Of course, a long day of tasting and farm hopping wouldn’t be complete without visiting some NOFO staples like: North Fork Roasting Company, NoFoDoCo, and Hampton Coffee Company in Aquebogue to complete the food and travel experience.

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