'Long Island's Hidden Treasure' Is A Walkable Waterfront Village Combining Beauty And History

Long Island is lined with picturesque towns, from cute harborside burgs to Atlantic beach towns, some of which are surf meccas with consistent waves. There's a lot of history to explore all over this island, which stretches 118 miles eastward from New York City to Montauk on the far tip. The island shelters the shores of Connecticut, forming the protected Long Island Sound. The Sound is a hub of boating and shipping, and the little towns along its shores have vibrant maritime histories.

From Port Washington, just east of the City, to beautiful, uncrowded hidden gems like Northport, the towns along Long Island Sound keep surprising. About halfway down its length, you'll find "Long Island's hidden treasure." At least, that's how Port Jefferson describes itself.

Port Jeff, as the locals say, is located about 60 miles east of Manhattan on a protected harbor that's always been popular for boaters. The waterfront village is dominated by a ferry terminal connecting you to Connecticut, plus a marina for small boats and yachts. Several streets nearby are lined with shops, restaurants, bars, and cafes. And, perhaps most surprisingly, parks offer some peaceful sandy beaches with beautiful views of the Sound.

The area was home to the Setalcott people long before European settlers arrived in the 1600s. It was initially called Drowned Meadow due to the area's tendency to flood daily from high tides. Its off-the-beaten-path location means it has always been small, even during its heyday when shipbuilding brought more activity. During the mid-1800s, the village was renamed, and the marshes were slowly filled for development. It became known for producing more ships than any of the neighboring towns and was home to many sailors, captains, and tradespeople.

Today, Port Jeff relies on tourism. Its beautiful coastal location makes it a port of call for sailors, and the ferry brings a steady stream of tourists. Harborfront Park is a great place to sit for a while and take in views of the boats coming and going. The main town is only a few blocks wide, with historic clapboard buildings full of eating, drinking, and shopping establishments. It's a seaside town made for casually strolling around — a must-do activity for every visitor.

Walking around the little village reveals other hidden treasures, from pocket parks and community gardens to Theater Three, the local performing arts center. The Long Island Explorium is a must-see if you're traveling with little ones — it's a hands-on science museum with a locally-appropriate nautical theme. The village hosts a Charles Dickens Festival every December and many other festivals throughout the year. For some beach time, consider a hike through McAllister County Park. There's a 3.1-mile loop that allows you to walk around towering dunes near the inlet and on one of the prettiest beaches on Long Island Sound. 

Several airlines, including JetBlue and Southwest, fly to Long Island MacArthur Airport, about 30 minutes south of town. For more flight options, LaGuardia is one hour west. The Long Island Rail Road connects the island from NYC's Penn Station out to the dreamy, sandy street-filled beach town of Montauk on the island's east end. The Port Jefferson station is only 1.2 miles south of the waterfront, making for a pleasant 30-minute walk. You can also come by sea, using the car and passenger ferry service that connects the village to Bridgeport, Connecticut.

Port Jeff is the perfect place to stay in a quaint bed and breakfast, and there are plenty of choices. Top picks include The Fox and Owl Inn and Holly Berry Bed and Breakfast. Alternatively, Danfords Hotel & Marina has waterfront views and is located in the heart of the village next to the ferry dock. It has 86 guest rooms and 100 slips for transient boaters.

The north coast of Long Island is blessed with year-round activities, but summer is the clear favorite with the tourist crowds. That's when you'll find the most going on, including streets lined with visitors and bustling outdoor cafes. But it's also an under-the-radar spot for spending the holidays. If you feel up to dealing with some chilly temperatures and snow, you can enjoy beautiful winter scenes and better deals on hotels and travel. Daytime temperatures average from a low of about 80 degrees Fahrenheit in the summer to around 40 degrees Fahrenheit in the winter.