In the early 2000s, the Old House Society of Cutchogue hired someone to take an inventory of all the barns on the North Fork.
The examination showed that while the number of barns elsewhere on Long Island had significantly dwindled, Southold Town was still loaded with them. In her research, Mary Ann Spencer, identified over 730 barns here, and published photographs of many of her favorites in a book called “The Barns of the North Fork,” which was published in 2005 and can still be found online today.
In the decade since, some of those barns have no doubt been razed or fallen into disrepair. Others, meanwhile, have been built or restored.
Barns are still very much a part of what makes a Sunday drive across the North Fork a feast for the eyes.
We recently popped on a playlist and rolled down the windows on a late summer day, scoping out some of our favorite barn buildings across the area to be photographed. Some are used as event spaces, some still serve an agricultural or working purpose and others are simply adding an aesthetic value to a residential property.
These are just some of the many great barns of the North Fork.
Located on vineyard property directly across from the Mattituck tasting room, Macari’s red barn is an aesthetically pleasing backdrop that brightens up drives along Sound Avenue. The property is available as an event space.
Half Hollow Nursery
Whether it’s the perfectly placed flag or the way the setting sunlight reflects off the chipped paint, this nursery barn is an Instagram favorite. Cars can often be seen veering off the Main Road in Laurel to capture this gem.
This Tabor Road beauty leaves passersby both awed and perplexed. Is it a barn? Is it a house? Well, it’s actually a woodworker’s shop, designed in the spirit of an old barn. So fitting for Orient.
Dart’s Tree Farm
Located off Main Bayview Road, the barn at Dart’s Tree Farm dates back to the 18th century. Today it serves as one of the more attractive event spaces in Southold on a property best known for selling Christmas trees.
If you want to see multiple breathtaking barns in one short drive, head down Oregon Road through Mattituck and Cutchogue, where commercial and residential structures coexist. The ‘sunflower’ barn is perhaps the prettiest on the North Fork and it’s located only a few properties down from the ‘gas pump’ barn (below). It doesn’t get much more bucolic than this.