9. Greenport & North Fork


Suffolk County’s North Fork is rather touristy during the summer due to its numerous wineries, but each village and hamlet along the 30-mile peninsula has a unique charm and culture. The North Fork consists of a number of small communities like Greenport, Mattituck, Jamesport, and Southold, and each has its own personality that should be explored while on a trip all the way east.

As one of the largest areas in the North Fork, Greenport village is one of the North Fork’s cultural centers, with numerous ethnic eateries, upscale shops, and recently constructed parks by the water. Originally called Winter Harbor, Greenport was a prominent whaling and ship building village. Greenport actually was a center for speakeasies and rum running during Prohibition, and restaurants like Claudio’s, which is still open today after 150 years, served illegal alcohol to customers. Structures like the Greenport Railroad Station, the Congregation Tifereth Israel Synagogue, and the entire Greenport Village Historic District are listed on the NRHP. Greenport’s Mitchell Park houses the Greenport Carousel, originally built in 1920, and the Inlet Pond County Park offers beautiful scenery and wildlife viewing. Greenport is home to dozens of creative and eclectic eateries including Lucharito’s, Mediterranean restaurant Olive Branch Restaurant & Cafe, The Frisky Oyster, and Front Street Station. Tikal offers Guatemalan dishes like fish soup and enchiladas with green sauce, while the tiny Rinconcito Hispano serves Salvadoran food like pupusas and fried fish.

Bedell Vineyards

Bedell Vineyard on the North Fork

A bit west of Greenport is Mattituck, a hamlet with a very small downtown and a number of historic sites. Known as “Great Creek” by the Algonquian, Mattituck was sold to Theophilus Eaton, the governor of New Haven and was eventually settled by English settlers in 1662. Colonial Mattituck “had a minister and school teacher, a blacksmith, carpenter, cooper, weaver, fuller, tanner and miller,” according to the Town of Southold. After the LIRR added a stop at Mattituck, Love Lane became a bustling center of commerce and culture, and the increased business for farmers allowed Mattituck’s agriculture industry to thrive. The area today is known for its annual Strawberry Festival as well as its numerous wineries. Three structures, the Richard Cox House, the Andrew Gildersleeve Octagonal Building, and the Jesse and Ira Tuthill House are listed on the NRHP. Along Love Lane and Main Road in Mattituck are a number of popular restaurants like Love Lane Kitchen, The Village Cheese Shop, Salvadoran place Lucia Restaurant, and aMano Restaurant.

Southold waterfront

On the waterfront in Southold

Another quaint hamlet is Southold, first settled by English Puritans from New Haven in around 1640. Southold remained part of Connecticut until 1674, but when the colony of New York was supposed to be handed over to the Netherlands, Long Island’s eastern towns, including Southold, refused to join. New York Governor Sir Edmund Andros eliminated residents’ rights to land if they continue to resist by staying a part of Connecticut. Like Mattituck, the area grew once the LIRR reached the North Fork, as Southold developed a small downtown as well as museums like the Southold Indian Museum and the Horton Point Lighthouse Nautical Museum. Places of note in Southold include New England Colonial–style residence Samuel Landon House, the Henry W. Prince Building, and the Southold Historic District. Popular restaurants in Southold include Wednesday’s Table, Latin Fuzion Restaurant, and North Fork Roasting, and the Southold Fish Market which has seating.

Other notable downtowns to check out on the North Fork are Jamesport, known for its antique shops and rather upscale dining options, Aqueboque, part of the North Fork’s wine region, and Cutchogue. Architecture fans should make a stop at the Big Duck in Flanders, an quintessential example of roadside architecture.