15 Unique & Fun Things to do in Long Island, New York

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The following list of things to do in Long Island is brought to you by New Yorker, Aurie Ceylon from hey, it’s aurie! Read on for some of her top Long Island must-dos.

Pop quiz: What do you get when you mix 3 bodies of water, 2 counties, and one big duck?

Long Island, of course

My friends, let’s just state the obvious: Long Island is New York’s best kept secret. 

Yes, of course New York City is the best place in the universe (says the completely unbiased New Yorker!), and upstate has its rustic charm, but there’s nothing quite like the nautical mystery of the Empire State’s favorite island… or, technically, peninsula. 

Comprising two counties – Nassau and Suffolk – There is something to match everyone’s cravings and quirks. Long Islanders joke that they never have to leave because they have everything they need to thrive year-round, and I have to say without a doubt that it’s true! As a native Long Islander, I had childhood friends who hadn’t left their home peninsula in years. Years! 

The scenic views, the outstanding food, the endless pop-up festivals and fairs… What more could you need? 

And, I know what you’re thinking… Long Islanders must run out of stuff to do eventually, right? Surely, there is a limit to the number of quirky, mysterious, historic, and even spooky adventures, right? Wrong, friends. Don’t let the Long Island Expressway fool you; this nautical waterfront peninsula is jam-packed with action and intrigue. 

Unsure where to begin? Don’t worry, I’ve got your back.

Stick with this citified Long Islander as I walk you through the top 15 things to do on Strong Island.

Save this List of Things to Do in Long Island for Later!

You’ll be very glad you did.

1. Explore Oheka Castle

Yes, a castle. No, we’re not in Europe. Welcome, friends, to OHEKA.

Fun fact: OHEKA is said to have inspired F. Scott Fitzgerald’s The Great Gatsby!**

Growing up, I thought OHEKA was only reserved for soirees hosted by Long Island’s upper echelon or destination weddings that aired on TLC. Only in recent years did I learn that not only is this historic estate a fully functional hotel and restaurant, it’s also a private residence that offers guided tours of almost every nook, cranny, and trellis! 

Quick History Lesson: OHEKA was once Long Island’s most desirable “party mansion” and the second largest private residence in the United States! The events were said to be legendary, with guest lists that included Hollywood starlets, North shore aristocracy, and even international politicians. Sadly, after the original owner died, OHEKA’s glamorous beginnings came to a screeching halt. OHEKA was later used as a military academy and then a retirement home before it was left abandoned. Fortunately, a developer purchased and reinvigorated the home, returning it to its former splendor! OHEKA is now back to being a popular site for weddings, private events, and even film sets for Hollywood. 

The good old days have returned, huzzah!

What to do at OHEKA: Not looking to tie the knot? Me neither. But, don’t worry, there’s plenty to do at this luxurious estate besides nuptials. Stroll the grounds in your Sunday best before dining at OHK Bar & Restaurant for brunch, lunch, dinner, or drinks. Afterwards, feel free to explore the intricacies of the home. Take a guided walking tour, or go rogue and do your own exploring. Just, don’t get lost! This house is much bigger than you might think. 

Click here to start planning your OHEKA adventure!

2. Check out The Big Duck

The big… what? Yes. It’s exactly what you think it is. 

What (and why?) is The Big Duck? Located in Flanders, New York, The Big Duck is a ferrocement (or a building made of reinforced mortar or plaster). This Long Island oddity was created by duck farm Martin Maurer in 1931 as a way to bring business to his struggling farm. Originally used as a quirky (and adorable) shop for ducks and duck eggs, The Big Duck officially closed for business in 1984. It was added to the National Register of Historic Places in 1997, and is now a gift shop and tourist attraction for all willing to make the trek.

Fun Fact: Christie Brinkley lent her voice for the welcome tape, which plays for visitors in the gift shop! Click here to learn more about The Big Duck.

Image by Hoard11 from iStock

3. Visit Montauk a.k.a. “The End of the World”

Every summer, thousands of New Yorkers flee the city for the white, sandy shores of East Hampton. But, I’ll let you in on a little secret: If you skip the Hampton Jitney and keep driving towards what is referred to as “the end of the world”, you’ll end up in a coastal village reserved for the true Long Islanders. No fussy parties or celebrity sightings. Just peaceful, pebbled shores and a quiet, maritime town that is rich with history (and lobster!). 

Located on the South Shore on the “tail” of the Long Island fish, Montauk is a breath of fresh air for those of us who are ‘over’ the upscale vibes of the neighboring beaches.

Fun Fact: Montauk is the easternmost point in New York State! It’s been nicknamed “the end of the world” for its vast and seemingly endless views of the ever-ominous Atlantic Ocean. 

What to Do in Montauk: Without a doubt, you must check out New York State’s FIRST lighthouse! Commissioned by President George Washington and completed in 1792, the Montauk Lighthouse was the first public works project in the United States! Built on the edge of a rapidly eroding cliff, it is the perfect historical segue for all nautical thrill-seekers. Check out this well-preserved relic, which is now protected by the Montauk Historical Society. 

Don’t forget to pop into the Montauk Lighthouse Museum! Click here to get a virtual tour of the Montauk Lighthouse

NOTE: Looking to stay overnight? Book a room at the oh-so-historic Montauk Manor.

Image by enzol from Pixabay

4. Get Boozy at Macari Vineyards

Wine o’clock, anyone? 

It would be a severe oversight to talk up the best parts of Long Island without mentioning one of my favorite delights: The wine! Take a drive further out east and you will find yourself overwhelmed by over SIXTY wineries and vineyards in Suffolk County.

For the sake of keeping this list reasonably succinct, I’ll list one of the most popular to date: Macari Vineyards. Located on 500 acres of gorgeous Mattituck waterfront, this family-owned vineyard and farm has been in business for over half a century. Visitors can take in the outstanding views while sampling wine by the glass, flight, and even snack on charcuterie! 

Feeling rosé? Macari Vineyards also offers a private rosé tasting lunch suite! This experience includes learning the history of the vineyard, a guided tasting of the top 5 wines, and a curated charcuterie and lunch spread prepared by Chef Lauren Lombari. 

P.S. – You can add on a rosé tower!

NOTE: For New York City-dwellers looking to check out more than one North Fork winery, this Long Island winery tour is definitely for you.

Image by Jill Wellington from Pixabay

5. Shop Til You Drop at Roosevelt Field

Calling all ‘material girls’! This is the mall to top every mall you’ve ever been to in your entire life. Yes, I am biased.

Roosevelt Field is the largest shopping mall on Long Island, the second-largest in New York State, and the tenth-largest in the NATION! 

With beautiful wraparound windows and stunning skylights, it feels like more of an indoor metropolis than your standard shopping mall. With over 200 specialty stores and a food court to rival the streets of NYC, it’s easy to spend an entire day getting lost in retail therapy. Located in Garden City in Nassau County, it’s accessible for city-dwellers and Long Islanders, alike. 

Fun Fact: Before it was converted into a shopping mega-mall, Roosevelt Field was an airfield for famous aviators including Amelia Earhart, Wiley Post, and Charles Lindberg!

Click here to learn more about Roosevelt Field Shopping Mall 

Image by gonghuimin468 from Pixabay

6. The Enchanted Sunken Forest at Fire Island

Ready for a mystical woodland anomaly? Look no further than the oh-so-enchanted Sunken Forest on Fire Island. Located on the largest center island on the south shore of our favorite peninsula, Fire Island’s Sunken Forest has been called “a rare ecological community” and has been ranked as “globally rare”, meaning there are few remaining occurrences of sunken forests around the world!

What (and how?) IS the Sunken Forest? Mainly composed of American Holly, Sassafras, Juneberry, and other hardwoods, this 50-acre fecund mystery might seem like your average forest. But, here’s the secret: the varied and mature trees that make up the forest will never grow higher than the sand dunes that surround it. So, when you’re walking through the forest, it feels as if you are “sunken” behind the dunes. Get it? 

What to do at Fire Island’s Sunken Forest: Hop on the Sayville ferry and explore the Sunken Forest on your own (for all of you woodland adventurers), or take a park ranger-led tour. 

Click here to learn more about Fire Island’s Sunken Forest

Image by 12019 from Pixabay

7. Fish & Sip at Atlantis

(Alright, not the real Atlantis). 

Located in Riverhead, the Long Island Aquarium (formerly my favorite title: “Atlantis Aquarium”) is the small-town aquatic vibe that you’ve been looking for. The intimate, homey feel of this ‘boutique-style’ aquarium will trick you into believing that you’ve stepped through the looking glass and into an underwater kingdom of wonders.

As a Long Island kid who spent many weekends at Atlantis, I’m here to tell you: This aquarium is a small but mighty Long Island must-see. Aside from the sea lions and stingrays (and the stellar gift shop!) the Long Island Aquarium’s calendar is chock full of engaging and interactive events and exhibits for kids and adults to explore.

What is Fish & Sip? Exactly what it sounds like. For ticketed entry, visitors are welcome to join the aquarium’s fish & sip after hours spectacular, which features more than 20 wineries and craft breweries from Suffolk County. Sip on wine and munch on snacks as you take in the aquatic splendors of Long Island Aquarium.  

After all, what’s more fun than exploring an aquarium at night? 

(“Night at the Aquarium”?)

Click here to learn more about Fish & Sip

Image by congerdesign from Pixabay

8. Vanderbilt Museum & Planetarium

Vanderbilt, as in… The Vanderbilts? 

Yes, as in THOSE Vanderbilts. 

Located on a 43-acre plot on the North Shore of Suffolk County, the Vanderbilt Museum and Planetarium is basically your Long Island two-for-one special. Spend the day exploring and marveling at the Vanderbilt home and museum, then at nightfall pop into the planetarium for a metaphysical adventure through the solar system. The Vanderbilt museum was listed on the National Register for Historic Places in 1985 and includes marine and natural history exhibitions, a curator’s cottage, a seaplane hangar, a boathouse, gardens, and more. 

Quick History Lesson: The Vanderbilt mansion, or “Eagles Nest”, was the summer home of William K. Vanderbilt II, grandson of ‘OG Moneybags’ Cornelius Vanderbilt. Originally built in 1910 as a small cottage, Eagles Nest was later expanded into a 24-room Spanish Revival mansion, which visitors can tour today! The Vanderbilt Planetarium was completed in 1971, and includes various timed performances, including a laser show!

Fun Fact: Eagles Nest was BUILT to be home and a museum! Along with being a homestead for the Vanderbilt family, the home was built to include expansive museum space for William to show off his natural history and cultural specimens collected during his travels. Exhibits include a memorial wing, a habitat wing (complete with taxidermy!) and more. 

Click to learn more about Vanderbilt Museum & Planetarium

Image by Brandi Day from Pixabay

9. Zipline at Long Island Adventure Park

Let’s take a quick break from the Long Island history and cultural oddities. Why not… climb a tree? 

Long Island Adventure Park is a self-guided, tree-top adventure for all of the stubbornly independent thrill-seekers (ahem, me.)! With 203 treetop platforms connected by (thrillingly wobbly) bridges, and 14 trails color coded by difficulty level, it’s easy to imagine spending far too many hours physically exerting (or, perhaps overexerting?) yourself. 

Go with friends, family, or on your own. There’s a little thrill in it for everyone. 

Did I mention there are 49 ziplines???

Fun Fact: I grew up down the street from the wooded plot of land that would later become the Long Island Adventure Park! When they started construction, we weren’t sure what they were building, but now it has become a major tourist attraction! Every time I go home, I am shocked to see the packed parking lot for this treetop adventure course!

Click to learn more about Long Island Adventure Park

Image by rickyoumans from Pixabay

10. Small Town Vibes in Port Jefferson

Calling all witchy, nautical, small-town-lovers: This is the place to beat. Think Mystic Pizza meets every Hallmark movie ever made. 

Don’t let the Starbucks fool you, this place is adorable. 

Quick History Lesson: What is now referred to as the Village of Port Jefferson was originally inhabited by the Setalcott First Nations people. In the 1650s, the land was sold and divided by local settlers and later developed into a shipbuilding village, which brought in profits and residents through the 18th and 19th centuries. When the town was officially incorporated in 1963, Port Jefferson was rebranded into a quaint and nautical tourist hotspot. Today, this incorporated village has become one of Long Island’s most desired attractions for both tourists and prospective residents for its breathtaking views, small town charm, and fresh fare. To this day, it remains a real estate gem, with intricately adorned Victorian “painted ladies” and massive cliffside mansions.

What to do in Port Jeff: Hop on the double decker train or cruise in on the ferry to Port Jeff terminal. Spend your day tooling down the main street, sampling homemade ice cream and shopping for trinkets and used books OR take the scenic route up the winding residential roads. Marvel at the historic homes, then grab dinner at one of many waterfront restaurants, where you’ll feast on fresh seafood or classic American cuisine. Take in the sunset on the pier and pretend you’re the star of your nautical rom-com. 

If you don’t head home with a North Shore necklace and a bag of old fashioned fudge, you did it all wrong. 

Click to learn more about Port Jefferson’s upcoming events

11. Live the Teddy Life at Sagamore Hill

Attention to my fellow history lovers, specifically those who are intrigued by the mysterious private lives of the U.S. Presidents: You must go to Sagamore Hill.

Quick History Lesson: Sagamore Hill (now a national historic site) was the home of America’s favorite U.S. President and nature conservationist – Teddy Roosevelt. A native New Yorker, Teddy Roosevelt spent his childhood summers in Oyster Bay, and in 1880, 22-year old Teddy purchased 155 acres of land on Cove Neck, a small peninsula just north of Oyster Bay. He built a large Queen Anne style home on the land and lived in the 22-bedroom home until his death in 1919. In 1962, Congress declared Sagamore Hill a National Historic Site!

What to do at Sagamore Hill: Visitors can take guided tours of the interior of Teddy Roosevelt’s home (complete with original furnishings!) or walk the grounds, free of charge. Visitors can also check out the Theodore Roosevelt Museum. 

Click to learn more about Sagamore Hill 

Image by Kirkikis from iStock

12. Downtown Abbey Dreams at Hempstead House

No, we haven’t traveled back in time to Season 1 of Downton Abbey.

Yes, y’all. This is still Long Island. 

Welcome to Hempstead House.

Built in 1912 and located on the North Shore in Port Washington, this 50,000 square foot sprawling estate is a waterfront WONDER. Did I mention that it contains not one, but TWO CASTLES? 

Quick History Lesson: Howard Gould, son of railroad tycoon (yes, tycoon) Jay Gould, built Castle #1 to be a replica of Kilkenny Castle. The original name of this Downton Abbey lookalike was Castle Gould until Howard sold the house in 1917 to Daniel Guggenheim, who changed the name to Hempstead House. In the 1920s, Hempstead House was a hotbed for summer soirees, performances, and exhibitions. Today, it is back to its former glamor and is available for mansion tours, hikes, walks, picnics, and more. 

Fun Fact: Why are there TWO castles? After Castle #1 was completed in 1912, it turns out it wasn’t all that the Goulds had hoped for. They didn’t like the house and decided to build Castle #2 to use as their living quarters! Talk about expensive taste. 

Click here to learn more about Hempstead House

13. Get Some Scents at Lavender Bay

Have you ever been surrounded by 17 acres of French Lavender? Neither have I, but after learning about Lavender by the Bay, I’m going to have to make the trip. 

What is Lavender by the Bay? Established in 2002, this family-owned farm is the perfect blend of agriculture and artistic sensibilities. Located on the North Fork in Suffolk County, Lavender by the Bay has two locations (East Marion and Calverton) that offer stunning views (and scents!) of endless fields of French Lavender. Visit the farm in July and be captivated by over 18,000 blooming bulbs!

While you wait for Lavender season, check out the shop! Browse in-person or online and you’ll be overloaded with lavender salts, soaps, honey, pillows, and more!

Do I already have 3 bunches of dried lavender in my online shopping cart? Absolutely. 

Click here to learn more about Lavender by the Bay

NOTE: Looking to have lavender dreams by the bay? Book a room at the waterfront Menhaden Hotel.

Image by Hans from Pixabay

14. (Fall Only) Scare Your Pants Off at Schmitt’s Farms

Yes, I know what you’re thinking. A haunted house? Seriously? 

But, you’ve never been to a haunted house like this. 

Located in Melville, Schmitt’s Farms HAUNT is without a doubt the scariest haunted house on Long Island. By day, Schmitt’s farms is a family-friendly nicety, full of PG fun. Spend the day pumpkin picking or enjoying the very-cute petting zoo. Head home with a jar of Apple Butter and a blue ribbon from the pie eating contest. 

After nightfall, however, it’s a totally different scene. 

Quick History Lesson: Schmitt’s Farms HAUNT came to life in 1994 after the Schmitt brothers decided to turn their unused greenhouse into a haunted house of horror. What started as a Halloween money-making scheme quickly morphed into a phenomena that attracts thousands of Long Islanders every October. Each year, Bill and Fred Schmitt concoct new and horrifying ways to scare the pants off their guests in the ever-changing HAUNT spectacular. 

And, they do not disappoint. 

As a Long Island kid who spent her childhood at this horrific sensation, I gotta tell you it’s completely worth the hype. The actors are chilling, the grounds are vast and endless, and you’re never quite sure when the “ride” is over. 

Spoiler: There’s a guy with a chainsaw. And he’s FAST.

Click here to learn more about Schmitt’s Farms HAUNT

Image by Benjamin Balazs from Pixabay

15. (October Only) Shuck Til You Drop at OysterFest

(Yes, that was an oyster pun.)

Want to learn a super cute secret? Hop on the train to Oyster Bay and you’ll emerge in the cutest hole-in-the-wall town right on the Long Island Sound. With boutiques and cafes lining the main streets and the smell of big water in the distance, it’s easy to get distracted. But, stick with me, friends. You gotta get to OysterFest. 

What’s OysterFest? Aside from being the largest waterfront seafood festival on the East Coast, OysterFest is an annual two-day celebration of Long Island culture, centered around community, the Long Island Sound, and – you guessed it – Oysters. Under the auspices of the Oyster Bay-East Norwich Rotary Club and its Oyster Bay Charitable Fund, over 200,000 Long Islanders and visitors flock to the historic village of Oyster Bay each year for food, fun, and fellowship. 

What to do at OysterFest: Visitors are encouraged to sample the many forms of the festival’s briney mascot. Try it raw, grilled, fried, steamed, ‘chowder’-ed… the more the merrier! (I recommend trying Blue Point Oysters, if you’re jonesing for the authentic Long Island staple!) 

Not an Oyster fan? Not to worry. OysterFest serves food for every palette, including shrimp, clams, hot dogs, corn, and other traditional festival foods (yes, even funnel cake!). 

Aside from the food, OysterFest also includes live entertainment, amusement rides & games, Oyster shucking competitions, a massive arts & crafts pavilion, a craft brew tent, and more! It’s hard to imagine fitting so much excitement into two days, but – in typical fashion – Long Islanders always manage to get it done.

After hours of exploring, I headed home with a full heart and very stuffed stomach. I sampled, sniffed, and touched everything I could get my hands on, and chatted with small business owners based all around New York State. Definitely worth the train ride, and I’ll be back next year for another shucking good time! (Yes, another pun.)

Click here to learn about OysterFest!

Photo by Thomas John on Unsplash

Did I Miss Any of Your Favorite Things to do on Long Island?

Let me know in the comments so I can add more Long Island recommendations to the list!

My Go-To Travel Favourites:

🧳 Eagle Creek: My favourite packing cubes

💳 Wise: For FREE travel friendly credit cards

🍯 Honey: For finding coupons automatically

🏨 Booking.com: For searching hotels

📷 Sony A7IV: My (amazing) camera

✈️ Google Flights: For finding flight deals

🌎 WorldNomads: For travel insurance

🎉 GetYourGuide: For booking activities

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