The North Fork of Long Island is not the Hamptons; in fact, it is the anti-Hamptons. There is scarcely a Poupette St Barth dress in sight and even a faint wedge, much less a stiletto, would feel wildly out of place. It is rural, yet shabby chic, dotted with wineries, farm stands, goat petting zoos and countless local establishments to eat and drink. The vibe is rustic, yet refined, and on a late summer day when Hamptonites are stuck in bumper-to-bumper traffic one can easily navigate amongst the basil farms, bakeries, and pumpkin patches that supply the Barefoot Contessa themed tablescapes all the way back to Manhattan.

About two hours from NYC, the North Fork is—quite literally—the northernmost arm of the tip of Long Island which on a map looks almost as if it is trying to run away from the Hamptons and therefore makes it the perfect place for a fall weekend excursion. Briermere Farm is a must stop, just on the northern edge of Riverhead and where the North Fork truly begins. You WILL NOT find a better pie then theirs. Anywhere. I have sampled a lot of pies, from the northeast to all over the south and can honestly say that the Briermere pies cannot be surpassed in texture, freshness, crust, or flavor. In fact, I had a peach-cherry one as my birthday cake this year. They also offer other wonderful baked goods, specifically their peach and blueberry muffins, and on a hot day their fruit slushees are the perfect thing to take the edge off your sweet tooth while you place your order.

Besides the dozens of farm stands along the way, many with lots of family activities (corn mazes, pumpkin picking), there are great local places to eat, and a particularly large number of throwback, vintage style eateries like Modern Snack Bar in Aquebogue.

The restaurant’s iconic 64-year-old vintage neon sign was my favorite and has been used innumerable commercials and TV shows over the years. The Northforker has a full list of vintage eateries here.

Once you navigate your way through the vintage dining spots, fresh corn stands, gourd markets, and basil and lavender farms all the way out to the tip of the fork (if you hit Orient Point you’ve gone too far but check out the wonderfully eclectic Opties and Dinghies), you’ll be rewarded with the delightfully urban but quaint town of Greenport, which feels a little like someone surgically removed a piece of gentrified Brooklyn and plopped it out on Long Island.

Greenport has innumerable restaurants and coffee shops to choose from, a favorite being Bruce & Son, a sleek yet rustic farm to table spot. After your BLT there (the clear favorite on the menu), grab a coffee at Aldo’s and walk over the waterfront and vintage merry-go-round and peruse any of the small shops along the way.

Common Ground Jewelry is very special for its seamless merchandising and colorful selection of rocks and crystals. In the center of town is a chic, pink hotel called The American Beech with a perfectly curated lobby shop that looks like something you’d find in Miami (of course I was drawn in by the white poodle and striped awning). Down the adjacent alley is a garden bar and a sprinkling of little restaurant options from tacos to pizza. It all has a very tropical, Tulum like feel and you forget for a moment you are in rural Long Island.

There are also some great vintage and antiques stores in Greenport. At the edge of town is Beall & Bell. The owner has an eclectic eye and had just come back from a buying trip at Brimfield; his prices were reasonable and I loved his offbeat choices (hello ear bookends and upholstered chinoiserie console tables!).

Directly across the street is a The Times Vintage, a GREAT vintage clothing & accessories boutique, complete with a record collection and spinning disco ball to welcome you when you walk in. (I felt at home there, too). A perfect place to shop for a subversive Daisy Buchanan ensemble, a nod to the Hamptons but with North Fork edge.

After vintage shopping, sit down in the bohemian garden at The Special Tea House for an afternoon tea while you contemplate the route home (where you are most likely to stop at Lombardi’s Love Lane Market in Mattituck to pick up some antipasto to go with your pie). The North Fork Shack, located 10 minutes outside of Greenport, serves up terrific takes on lunch classics while The Halyard restaurant at the Sound View hotel is another (if slightly more upscale) choice for lunch.

Deserving of its own post, the well-documented North Fork wine trail also provides plenty of opportunity for exploration in and of itself. Many of the wineries have informal restaurants, walking paths, and (occasionally) live music. Kontokosta, Bedell, RGNY are among the many to choose from. Explore more about the wine trail here. Cheers to fall getaways!

Deirdre Colligan