Boston to Long Island: A Wine Country Day Trip

The journey from Boston to the North Fork of New York's Long Island is an easy day trip for wine lovers.

A day trip to Long Island Wine Country from Boston sounds impossibly crazy, but it is easier than you think—and it doesn't involve a four-hour, stop-and-go drive to and through New York City. In fact, you don't even need a car.

Hop on Amtrak Northeast Regional or Acela Express from South Station or Back Bay and find yourself in New London, Connecticut, in 90 minutes. Here, the Cross Sound Ferry (moored directly across the tracks from the train station) catamarans travelers over to Orient Point, Long Island, (the North Fork, for those not in-the-know) in 45 minutes.

Cross Sound Ferry's SeaJet
Cross Sound Ferry's SeaJet

Miles saved: 200. Aggravation averted: Incalculable.

If you do travel with a car, you can ferry that across as well, but who needs their own wheels when Jo-Ann Perry of Vintage Tours can be your guide.

Perry has been showing visitors around the vineyards and wineries of the North Fork for two decades. Her comfortable van even picks up right at the ferry dock. On her itinerary: the region’s best vineyards, of course, as well as other local attractions, lunch included.

The East End of Long Island is climatically perfect for growing grapes, and the North Fork is like Napa minus the commercialization and crowds. Driving along the green, country roads with often dramatic views of Long Island Sound, you’ll see grapes growing everywhere. The area boasts over 50 producers and 3,000 acres of vines. Long Island winemakers grow as many as 30 varietals, including Merlot, Cabernet Sauvignon, Cabernet Franc, Chardonnay, Riesling, Sauvignon Blanc and Viognier.


Kontokosta Winery's modern tasting room
Kontokosta Winery's modern tasting room

Down a quarter-mile-long dirt road surrounded, Kontokosta Winery is a beautiful, modern, barn-like building situated on a bluff that overlooks the ocean. Former attorney Michael Kontokosta is almost spiritual about winemaking when he discusses the impact of the sea air on his grapes, the sustainability of his wind-powered operation, and the serendipitous results of some of his end-of-year blends. His remarkably delicious 2015 rose tastes like liquid strawberries.

At Bedell Cellars, a friendly Golden Retriever meets you at the front door, and thirsty wine lovers gather around a chic bar to sip syrah, malbec, gewürztraminer, viognier, and/or chardonnay. The framed artwork on the walls was commissioned specifically for the vineyard’s labels. Bedell Cellars is especially proud of its lush merlot, and its 2009 merlot was poured at President Obama’s 2013 Inauguration luncheon.

Of course, at both Bedell Cellars and Kontokosta Winery, visitors can purchase bottles to bring home.

Arrange with Perry to stop for a bite at Little Creek Oysters in the picturesque village of Greenport. Located in an old bait shop by the pier (legend has it that the bait shop was originally the wheelhouse of a whaling ship), this tiny—less than 20 seats—restaurant serves only shuck-your-own oysters, shuck-your-own clams, New England clam chowder, pickles, olives and a shot glass of chocolate pudding/torched marshmallow s’mores. All the shellfish is harvested locally; the wines (and many of the beers) are local as well. Yes, Little Creek will shuck the bivalves by request—but it’s not nearly as much fun.

For a multi-sensory experience, spend an hour at Lavender on the Bay, a 17-acre farm that grows French and English lavender. Visitors can walk into the fields and literally lay down next to the brilliantly colored, hypnotically aromatic blossoms. Lavender is a member of the mint family, and the farm grows 80,000 plants of multiple varieties.

Fresh English lavendar from Lavendar By The Bay
Fresh English lavendar from Lavendar By The Bay (©Mat Schaffer)

Visitors can pick their own or purchase already-picked, fresh and dried bunches, as well as the farm’s-own lavender honey and other lavender-scented souvenirs from soaps to sachets.

Heading back to the ferry, make sure to drop by Sep’s Farm farm stand and pick up some locally famous tomatoes and sweet corn or jars of homemade jam, salsa, chutney, mustard and relish. Four generations of the Sep family have been farming here since 1915. The farm stand opens when the asparagus is harvested in late April/early May and remains open until the last Brussels sprout stalks have been pulled, post-Halloween. In season, visitors enjoy strawberries, carrots, broccoli, garlic, beets, greens, herbs and a rotating selection of seasonal pies made from the farm’s fruit.

While Bostonians are frequent day-trippers to Cape Cod, Martha’s Vineyard, and Nantucket, a day trip to Long Island’s Wine Country has always seemed exhaustingly out of reach. Clearly, it’s delightfully doable.