North Fork Long Island: Fall Travel & Road Trip Guide

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

In years gone by, visitors didn’t hesitate to jump in a car or catch a train to make the pilgrimage out to the Eastern End of Long Island, known for its growing wine scene and sprawling farms. But this year, things are more complicated due to COVID-19 rules and regulations. Thankfully, local businesses in the North Fork have remained flexible, adaptable, and vigilant and continue to put safety above all else.

Below is a list of places to eat, drink, play and stay, incorporating current events and things to do (at the time of publication of this article). Keep in mind that 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 closures and 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. For those interested in traveling by train, 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 Hamptons Jitney or the Hampton Ambassador luxury bus services with multiple stops throughout the North Fork. Both bus options have new safety and wellness regulations on their websites and require masks to be worn for the duration of the trip.

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 has its process down pat when it comes to cleanliness and putting their guest’s safety first. Mother and daughter duo Cristina and Ursula Illa prepare breakfast each morning for their guests in neatly packaged to-go boxes and encourage 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. Throughout the fall, if you book two weekday nights, you can get the third free (be sure to call to confirm the offer is still running).

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 outdoor dining options and expanded outdoor space to accommodate guests as well as a slew of new dedicated safety precautions.

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

The North Fork’s famed farm to table institution North Fork Table and Inn re-opened this past summer led by head Chef John Fraser, who happens to own three Michelin-starred restaurants in 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.

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. The brewery is hosting a slew of fall events including a 7-week axe throwing league on Tuesday nights, a 2-day Oktoberfest Celebration in October including food trucks, a stein holding contest, and a viewing of the film BeerFest on two large screens. Also, be sure to swing by for their Halloween movie night on October 30th where they will be screening the Rocky Horror Picture Show and hosting a costume contest for guests.

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. While the tasting room is small, they have an outdoor space where bottles to-go can be purchased. Masks are required unless seated in their outdoor space and currently they are unable to accommodate groups over six (children included).

Mattebella Vineyards is another perfect winery to visit during the Fall season. This winery is entirely outdoors with different seating configurations to accommodate socially distanced groups. The winery has produced some Provencal-style Roses this year which have been a hit with visitors, as well as a 2017 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.

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

Farm Country Kitchen is a rustic, waterfront restaurant with a plethora of outdoor space for comfortable social distance dining. The year-round restaurant has 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 throughout the month of October.

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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Kristen is a New York native who received her BA in journalism from Northeastern University in Boston. She is a lover of ballroom dancing, traveling the world and cooking at home. She has worked as a freelance travel, food, wine, entertainment, finance and nutrition writer throughout her career. Follow her latest adventures on her lifestyle blog and on Instagram @krisoliveri and @outerborobroad.

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