Another small town within Southold, like Greenport or Mattituck, Orient sits on the northeastern-most point of Long Island, also known as the North Fork, and takes the cake for small-town charm with a population of just 835 in 2019.

But its small population isn’t suppressing its growth. Even The New York Times reported on Orient’s potential, seeing a surge in permanent residents when Covid-19 hit Manhattan. This coastal town is home to plenty of parks, beaches, and historical spots, so we understand its popularity!

Cover Photo by Northforker

Where to Eat

We suggest stopping at Duryea’s! Centering their ambiance around good wine and of course, good food, Duryea’s luxurious restaurant blends relaxation with a seaside breeze. This oyster bar offers both indoor and outdoor seating, and is located right on the water on Main Road.

What to do Outside

If you love to fish or are just craving some outdoors time, check out Orient Point County Park. On the far most tip of Orient, this park is home to a quaint beach, ideal for your daily dose of nature. It’s the perfect place to soak up the amazing views Long Island has to offer.

What to do Inside

Learn about Orient’s history with a stop at Oysterponds Historical Society, which is home to the Village House and Webb House, which reflect life in Orient between the 1700s and 1800s. With educational programs that run all year long, this historical society also maintains a 1873 schoolhouse, the 1862 Amanda Brown Schoolhouse, the Hallock Building, and the Red Barn.

Plus, the historic district of Orient, aside from the historical society’s campus, was recognized for both its historic and architectural significance in 1976 and was placed on the National Register of Historic Places, so there’s plenty to learn about here!

Where to Stay

Set to reopen in February of 2022, The Inn at Orient has undergone major renovations, making it the perfect stay out on the North Fork tip. The only inn in Orient proper, this stay is a delight and conveniently located right on Main Road.