There’s no better time to visit the North Fork than FALL! The vineyards glow with golden leaves, local farms are bursting with seasonal produce, and country roads wind past some of the most scenic landscapes on Long Island. If you’re planning a day trip or weekend getaway, this itinerary combines wine tasting, farm stand stops, and the best fall foliage drives the North Fork has to offer.
Start your adventure with one of the most picturesque drives on the East End: Oregon Road. This quiet country road stretches through the heart of wine country, lined with rolling vineyards, historic barns, and wide-open farm fields. In autumn, the views are especially breathtaking, with vibrant foliage and golden vineyard rows creating a postcard-worthy backdrop.
Pro tip: Oregon Road is a favorite spot for photographers and anyone looking to soak in authentic North Fork charm without the crowds.
At the eastern end of Oregon Road lies Suhru & Lieb Vineyards, a must-visit winery boasting 54 acres of certified sustainable vineyards. In fall, the tasting room offers not just award-winning wines, but also panoramic views of farmland and vines as the leaves turn.
Pull up a seat with a glass of Pinot Blanc, Cabernet Franc, or a seasonal special release, and enjoy the peaceful atmosphere that makes this spot so unique. With its combination of high-quality wines and pastoral views, Suhru & Lieb embodies the very best of North Fork wine country in autumn.
No fall trip to the North Fork is complete without a stop at Wickham’s Fruit Farm, one of the oldest and most beloved farm destinations on the East End. In the fall, Wickham’s is all about apple picking, pumpkin patches, fresh pies, and hot cider doughnuts.
Make time for a cider doughnut or two before continuing your wine-tasting journey.
For a midday break, stop at the North Fork Table & Inn Food Truck in Southold. This local favorite offers elevated, seasonal dishes like lobster rolls, crispy Brussels sprouts, and farm-to-table sandwiches. It’s casual enough for a quick stop, yet delicious enough to be a highlight of your trip.
After lunch, head to Macari Vineyards, known for its sweeping vineyard views that shine brightest in autumn. The tasting room overlooks rows of vines framed by fall foliage, making it one of the most picturesque wine spots on the North Fork.
Enjoy a flight that might include their popular Sauvignon Blanc or Bordeaux-style reds—perfect wines for a crisp fall afternoon.
End your day with dinner at Love Lane Kitchen in Mattituck. This cozy, locally-loved spot serves seasonal, farm-to-table dishes—think roasted vegetables, fresh seafood, and wood-fired pizzas. Pair your meal with a North Fork Merlot or Cabernet Franc and toast to a perfect fall day without having to backtrack across the island
The North Fork offers a rare blend of coastal beauty, farmland charm, and award-winning wines. Whether you’re here for a day or a weekend, this itinerary blends the best of the season: scenic drives, farm-to-table flavors, and world-class wines. Looking for more wineries to add to your day? Explore all that Long Island Wine County has to offer!
