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Pumpkins are a major draw to the North Fork this time of year. But here are some pumpkin-adjacent reasons to visit each farm. (Credit: David Benthal)

With temperatures often reaching into the 70s, plenty of blue skies and less crowds than the peak of summer, October is a perfect time to enjoy the North Fork.

With so much to do, it can be difficult to pack it all in. For help we asked some of the area’s realtors for their ideal ways to spend an afternoon or even a full weekend.

Experiencing The Harvest

“Autumn certainly is an ideal time to enjoy the beauty surrounding the North Fork,” says Alexis Meadows, licensed real estate salesperson, NoFo Real Estate. “What tends to pique my interest most is the changing landscape within the farms and nurseries that host charming options for home decor. A visit to Trimble’s Nursery and Krupski Farms are a must. Likewise, visiting the historic Wickham’s Fruit Farm in Cutchogue is an annual tradition, both for their cider donuts and picking our favorite Honeycrisp apples.  The East End’s mums, ornamental grasses and unique assortment of pumpkins make their debut on our porch early in October.”  

“October is peak pumpkin season on the North Fork,” says Marianne Collins, licensed real estate salesperson, Brown Harris Stevens. “Depending on your preference, you can plunge in and embrace it, visiting the iconic farm stands to pick pumpkins, take a hay ride, pick apples or navigate a corn maze.  Take advantage of all the amazing produce at our farms during this harvest season; pick up late tomatoes by the bushel at Wesnofske Farms and head home to make sauce, preserving the last of summer for the coming winter.”   

Staying Active

“My ideal North Fork Fall weekend would start with putting on my favorite fall suede hat from Mint, the boutique clothing store on Love Lane in Mattituck,” says Erica Guja, real estate salesperson, Daniel Gale Sotheby’s International Realty. in the fall on the North Fork is to take a walk through the Laurel Lake Preserve with my husband and our one-and-a-half year old Border Collie. During this time of year, the foliage starts to change, and the temperature cools off, creating the perfect weather to take a walk in.” 

“October is the last full month that I can enjoy all of my outdoor activities before shutting down for the winter,” says Thomas McCloskey, licensed real estate broker, Douglas Elliman. “I love to start the weekend with a fishing trip targeting striped bass, false albacore and bluefish, leaving the dock at first light.  October is one of the best fishing months on the North Fork; the Long Island Sound’s beaches provide fantastic opportunities to fish if you do not own a boat. If conditions are not good for boating and fishing, a bike ride from New Suffolk up to and along Oregon Road is a great way to enjoy the cooler weather and take in the bucolic atmosphere of the North Fork.”

“Take the path less traveled,” says Collins. “Get off the main roads, bike along the most beautiful stretches of Oregon Road or Narrow River Road, or walk the now much-quieter beaches. Try Bailie’s or Goldsmith’s on the Sound, Orient State Park, Nassau Point Causeway on the bay.”

Food and Drink

“Picking produce and navigating corn mazes can be an exhausting morning so in the afternoon, it’s time to unwind and listen to live music at one of the many local wineries or stop at Greenport Harbor Brewery in Peconic for a Leaf Pile,” says Mills. “After drinks, head to Kenny’s Beach in Southold to recoup and watch the sunset. Next up, dinner at North Fork Table where the menu is inspired by the North Fork’s surrounding waterways and farmland. Just remember to make reservations ahead of time as this is one restaurant you won’t want to miss out on.”  

“During the nice weather we love to take the opportunity to sit outside. Not only is the air crisp, but people watching on Love Lane is always a good time,” says Mariah J. Mills, real estate salesperson, Daniel Gale Sotheby’s International Realty. “During the fall my favorite brunch is their Green Eggs, with a side of sweet potato hash, paired with a fall mimosa. Since any fall day is a cheat day, we may even get crazy and share a side of their pumpkin or ricotta pancakes, which are to die for.” 

“After an active morning I like to catch lunch at an outdoor venue,” says McCloskey. “Jamesport VineyardBilly’s by the Bay and Southold Fish Market are great this time of year.”

“If we were feeling wine, our go-to spot in the fall is Lieb Cellars, where we can order their Cabernet Franc and cozy up at one of their fire pits as the sun begins to set,” says Mills. If we were feeling a beer, our go-to spot would be Jamesport Farm Brewery which has the best pumpkin beer with a cinnamon sugar rim.”