10 Best Hidden Gems Of Long Island

I have a habit of driving around without any type of planned destination. It happens more often than it should but I always end up finding a new, interesting place to go. Long Island has some of the best coastline, state parks and gold coast mansions just waiting to be explored. Here are some of many hidden gems (some not as much as others) on the island.

1. Cold Spring Harbor

Located right on 25A on the border of Nassau and Suffolk Counties lies the cutest, little town on the island (personal opinion, it’s OK if you disagree). It used to be a whaling town back in the 1800s, so there’s a whaling museum you can check out while you’re there. The cafe, Sweetie Pies On Main, is a place I recommend you try. The ice cubes in the iced coffees are just frozen coffee, so it never gets watered down.

2. Sagamore Hill

The home of President Theodore Roosevelt, located right in Oyster Bay, is both a national park and a museum. If you’re up to doing a little walking, I suggest you find the nature trail and take the hike down to the boardwalk. I promise you won’t regret it, and you’ll end up at a beautiful beach.

3. Cordwood Park

I can’t label myself as the founder of this park based on the fact that my friend found it first, but it’s something that not many people know about. It’s a tiny park located in Head of the Harbor, seriously off the beaten path. The park overlooks Stony Brook Harbor and is full of benches and picnic tables. If you ever need some place to think, I suggest you go here.

4. Cupsogue Beach

I wouldn’t really consider this to be so much as a “hidden gem,” but every time I bring it up to someone, they never seem to know what or where it is. Cupsogue Beach is a beach located in West Hampton at the west end of Dune Road. My dad used to take me here all the time when I was a kid, so it holds a place in my heart. It’s about an hour’s drive depending on where you live, but I promise you that it’s worth it. Nice sand, even nicer water and beautiful, huge homes. How much more Kardashian Hamptons can we get?

5. Greenport

Located on the north fork of the island lies a town that I consider to be better than the Hamptons. Greenport's town motto is “You don’t have to go far to get away,” so what does that already tell you? The town is full of local shops and the best seafood ever. If you’re in the mood for lobster, clams and mussels, I advise you hit up Claudio’s. It’s been in business ever since 1870. Before you leave, make sure you take a ride on the old carousel!

6. Callahans Beach

Also located off of 25A (it’s my favorite road) in Northport, is Callahan’s Beach. It’s a pretty small beach, and unless you live in the town, you would never even know it’s there. It’s on the north shore so the sand is a bit rocky and the waves are non-existent, but it’s a good, quiet place to relax. If you forgot to bring a lunch, 10 minutes down the road is a street side hangout called “The Shack.” It’s seriously the only place I’ll eat fried clams.

7. Connetquot River State Park

This park is one that I always drive by but never really knew what it was. Recently, I discovered that it is 3,400 acres of land that consist of hiking trails, numerous amounts of deer, a beautiful lake, a fish hatchery and a small bridge. There are five different hiking trails with the longest one being 8.4 miles that covers the entire park. It’s definitely a place to go during the summer months.

8. The David Weld Sanctuary

This place is a bird sanctuary located in the Nissequogue that most people drive by without much concern to what’s in it. A trail leads from the tiny parking lot into the woods and if you make the correct turn at the fork, you end up at a rocky, boulder covered beach. If you’re into birds, many different kinds exist in here. Can’t say that I’ve seen any exciting ones but then again I’m not much of an avid bird watcher.

9. Mashomack Preserve

It’s a bit of a drive and a boat ride over to it but once you get there, you’ll understand why it’s one of my favorite places. Located on the southeast tip of Shelter Island is Mashomack Preserve. 12 miles of coastline and 2,300 acres full of animals, creeks, and woods are open for exploration whenever. Five different trails means five different types of hiking fun. It’s worth the hour and a half ride and I’m sure your parents would be more than happy that you finally left your couch.

10. Old Westbury Gardens

Not to confuse it with Oheka Castle, which has gone mainstream since Kevin Jonas got married there in 2009 and Taylor Swift recorded her music video for Blank Space there, Old Westbury Gardens is one of Long Island's Gold Coast mansions. Everything about it just screams Jay Gatsby. It’s picture perfect and full of history. Built in 1906, it consists of everything you would want in a house during the early 1900s. While you’re there, make sure you explore the gardens in their entirety. Hidden gems can exist inside of hidden gems.