The Perfect Date Itinerary to Enjoy Fall on the North Fork

The couple that explores the North Fork together, stays together. • Photo courtesy of Unsplash

Mother Nature very well may be a deity on the North Fork. She bends the will of others through the seasons on both land and sea. The most notable shift post-Labor Day on the North Fork comes with the crisp weather, leading us to swap tank tops for flannel, beaches for farm fields, and iced coffees for hot apple cider and of course, pumpkin spice lattes. North Fork in autumn is also the ideal backdrop for a date. Whether you go for the full itinerary or pick and choose, these local tips and tricks will leave hearts and bellies full.

Coffee on Love Lane

Short but bustling, Mattituck’s Love Lane is the perfect place to start your fall date, aside from the obvious reason. The tree-lined street shifts easily into fall and is perfect for a quick walk and coffee outside. Pick up a roast from Love Lane Kitchen—or stay for pumpkin pancakes—before moving on for little bites and sips from Lombardi’s Love Lane Market, the cheese, chocolate, and wine shops, or rounding the corner for an extra-sweet treat from the North Fork Doughnut Company.

Sip cider with the apple of your eye.

Apple picking at Woodside Orchards

Hold out just a little longer before diving full-on into pumpkin season. A crisp stroll through the orchard allows you to pick your own apples from the trees beginning late-September at Woodside Orchards in Aquebogue. Find a seat at the picnic tables on the front lawn to sip hard cider in tastings or pints, and enjoy fresh cider doughnuts. Take your haul home to make your own apple cobbler.

Cozy or happening, wineries are a must…

With dozens of tasting rooms to choose from on the North Fork, there’s an experience to suit every need. If you’re looking for a more intimate, cozy kind of afternoon, Sherwood House Vineyards in Jamesport has couches and a fireplace in their tasting room. Under new ownership and recently re-opened, Crouteaux Vineyards’ outdoor space evokes feelings of Provence and feels worlds away from its Cutchogue location. Keep it cool and casual at Bridge Lane Wines or indulge in fresh pizza with your wine at Jamesport Vineyards.

Cheers to a crisp day well spent—and savored.

Lunch at Orient Country Store

In true leaf-peeping fashion, take a drive. Orient is the furthest point east on the North Fork, and while not at the very end, the Orient Country Store is actually a pretty great date place. The bucolic Village Lane is stunning in the fall and being near the water, leaves are often rustling in the trees. It’s calm and quiet, and away from the hustle and bustle of some other downtown areas. Plus, nothing beats a hot sandwich on a cool fall day.

Heartwarming cocktails

Autumn and winter call for hot cocktails, like toddies and Irish coffees. Brix and Rye in Greenport will top off your coffee with hand-shaken fresh cream. Warm up with the Rusty Cage Old Fashioned made with Bulliet Bourbon, Amaro, Luxardo cherry liqueur, and bitters at Jedediah Hawkins Inn in Jamesport. When in doubt, a cinnamon rimmed pumpkin beer from a local brewery is a top fall drink.

Located inside Riverhead’s Hotel Indigo, Bistro 72 offers farm-to-table fare in a warm, romantic setting.

For a romantic dinner date…

Vine Street Café on Shelter Island steals the show. Warm, cozy, and quite intimate, the food and service meet expectations. Pull out all the stops with the chateaubriand for two. Into a trendy scene? Greenport’s American Beech has the mood lighting down and date-worthy cocktails, like Eskimo Kisses with mezcal, Campari, sweet vermouth, and sherry, to kick off the evening. Perhaps you can even snag a seat near the fireplace, inside or out. Bistro 72 in Riverhead also has indoor and outdoor fireplaces to enjoy a glass of wine or cocktails before and during dinner. On local menus, opt for dishes with seasonal produce like corn, squash, cauliflower, and of course, pumpkin.

Every date deserves a sweet ending.

Just desserts

After a day of wine and cheese, cider doughnuts, hearty lunches and autumn snacks found along the way, a shareable dessert may be all you need to end your perfect fall date outing. Try the pumpkin tart pumpkin custard with cinnamon and whipped cream at aMano in Mattituck. Split a spiced carrot cake or the famous key lime pie at The Frisky Oyster in Greenport while sipping on glass of red wine. Briemere Farms in Riverhead is worth the long lines in fall. The apple variations from classics to crumbles, traditional pumpkin, and any fruit cream pies are a sweet treat to enjoy at home.