New York's Coast Hides A Quaint Historic Town Full Of Shopping And Picturesque Views

Long Island's topography and convoluted coastline have always been havens for small towns with rich character. Each little settlement on this downstate New York island has a distinct feel depending on what part of the island it is located on, like the town on Long Island's Gold Coast that's an uncrowded version of the Hamptons. You could spend quite some time exploring all the hidden pockets on this island, but we'd highly recommend starting with the quaint fishing village of Greenport.

About 100 miles from New York City and situated on Long Island's North Fork, Greenport has a rich maritime history that gives it a rustic charm. The town was initially an oyster and whaling hub before tourism became a more lucrative way to utilize its picturesque coastline. Unlike many other places with similar trajectories, however, Greenport hasn't sold out to appease tourists, and you can still enjoy local art, culture, and shopping without the inevitable premiums and thronging crowds.

The architecture ranges from Victorian and mid-century to experimental, and a bevy of quaint places to eat and drink around the relatively compact town can make you forget about everyday troubles and let you soak in the picturesque small-town life. Greenport offers fun experiences in almost every season and makes for a nice day trip. However, stay back for a day or two in one of the former fishing village's many family-run cottages and you may never want to leave.

Greenport got its current name when the town was incorporated in 1838, before which it was called Winter Harbor. Until then, the town had been a prolific fishing village. However, once its importance as a seaport started to wane, tourism became Greenport's focus. The East End Seaport Museum, therefore, is a great place to dive into the town's seafaring history. The thriving local art scene is also replete with works inspired by the gorgeous Greenport coastline, which is fitting in more ways than one since walking around town can sometimes feel like you're in a painting. There are multiple art galleries you can tour as well, including the Nova Constellatio Gallery, which features a gorgeous collection of maritime-themed art.

If you don't find anything worth buying in the galleries, Greenport has a thriving local shopping scene. Walking down the town's main streets, you can pop into everything from leather shops to jewelry stores, along with antique shops and thrift stores. Revel North Fork and Silver by the Sea both offer great gifts from local artisans, while at Greenport Fire, you can peruse a daunting collection of hot sauces.

Visit Greenport in September to experience the popular annual Maritime Festival. The small town's streets turn into a colorful playground of food, music, and themed costumes. Experience everything from kayak races to a parade where participants dress up as pirates and mermaids. Keep an eye out for stalls selling local wares and, of course, some fantastic seafood. And in case you can't make it to the festival, head to the Greenport Farmers' Market to explore an eclectic variety of local and artistic souvenirs. The longest-running farmers market on the North Fork, it is active from May to October every year.

Greenport is a great spot for a relaxing day trip. However, the town has enough to keep you occupied for at least a weekend and possibly longer if you are content simply soaking in picturesque surroundings. While fall is arguably the best time to visit Greenport since that's when the town's event calendar and local wine tours are at their peak, every season has its charm. In spring, the cherry blossoms are in full bloom, or you can come in summer as well to enjoy some outdoor concerts. You can also go hiking or cycling in some of the area's many parks and nature preserves, such as the Elizabeth Alexandra Morton National Wildlife Refuge.

The Greenport Harbor Brewing Company is a great place to wind down in the evening with the locals and some live music. To make the most of your stay, look no further than one of Greenport's several family-run cottages that you can rent out. You can pick from a range of architectural styles or even pick one by the sea to make the most of your visit to this historic maritime town.

How could a visit to a seaside town be complete without enjoying the beach? Greenport's Sandy Beach is great for swimming, while the 67 Steps Beach offers breathtaking views and is famous for its boulder formations. A 20-minute drive to the tip of Long Beach Island brings visitors to the peaceful Orient Beach State Park, which includes cedar forest and saltwater marshes. Across the Long Island Sound, you can take a car and a ferry to Connecticut to see the laidback coastal town of Mystic or Milford's beautiful Silver Sands State Park.