Forever Cherished: Most Rated Cultural & Historical Sites Not to Be Missed

Long Island isn’t all bagels, traffic, and endless property taxes—it has some significant history and culture under the radar. While everyone’s too busy bickering about the best pizza or complaining about LIRR delays, they’re missing some incredible landmarks that tell the real story about this island we call home. If you’re a history buff, a weekend warrior, or you just need an excuse to leave the house, these must-see spots will make you appreciate the real Long Island. And even if they don’t, at least you’ll get some good Instagram photos.

1. Old Westbury Gardens: Living Like a Vanderbilt as Close as You’ll Ever Get

Did you ever dream about living the life of Gatsby, minus the tragedy, the parties, and the tragic ending? Old Westbury Gardens lets you do that. This massive 200-acre mansion belonged to financier John S. Phipps, who had the wealth to turn his backyard into a fairy-tale come true, Europe style. Nowadays, we mere humans get to come visit, take tours, hear concerts, and stroll leisurely through the garden. Want to impress a date or be the center of your own period drama? This is the place to go.

2. Sagamore Hill – Where Teddy Roosevelt Showcased Presidential Biceps

Long before Roosevelt was wrangling bears (at least, most likely, and making headlines), he had his home in Oyster Bay. The man himself spent his most influential years living in the "Summer White House" that is Sagamore Hill. This isn’t your typical, dusty antiques-ridden home—Roosevelt’s personality infuses the entire place. From the hunting trophies to his towering library, the house yells "power move." And it’s got hiking trails and beaches to boot, so you can take a breath of fresh air with a side of history.

3. Montauk Point Lighthouse – Simply because George Washington said so

If it’s good enough for George Washington, it’s good enough for you. Montauk Point Lighthouse, authorized in 1792, is New York’s oldest lighthouse, the ultimate “I told you so” to those who complained that Long Island had no history. Hiking up, you get nutty ocean views, and up there, you can learn about the legends and wrecks that make Montauk’s rocky shoreline mysterious. And, bonus: some credit Montauk with having been the inspiration for *Stranger Things*, so you might not be imagining the sense that the government’s watching you when you go visit.

4. Vanderbilt Museum & Planetarium – From a Rich Man’s Passion to a Cultural Treasure

What do you do when you're obscenely wealthy in the early 1900s? You build a mansion, collect oddities, and eventually turn it all into a public museum. That’s exactly what William K. Vanderbilt II did in Centerport. Part mansion, part museum, part planetarium, this property has taxidermy animals, marine specimens, and ancient artifacts, to name a few. And if viewing ancient oddities isn’t your thing, the planetarium’s space shows are a good reason to stop by. And the views on the property are next-level gorgeous.

5. Gold Coast Mansions: The Equivalent to Hollywood Homes on the Gold Coast

Ever questioned where the families with the old money on Long Island showed off their wealth? The **Gold Coast Mansions** on the North Shore are the setting for *The Great Gatsby* in real life—think Oheka Castle, Sands Point Preserve, and Glen Cove Mansion. Some are tour-able, party-able, and even overnight-able if you're feeling the urge to live the high life for a day. Others are restricted, but you're welcome to drive by and dream about the way your life would change with a few hundred million dollars in your bank account.

6. Parrish Art Museum – Because the Hamptons are Not Just About the Rosé

We all think the Hamptons are all about pricey beachfront mansions and influencers taking selfies with their brunch, but real ones know that it’s also home to the **Parrish Art Museum**, a sleek, modern gem dedicated to the display of American artists. The building’s architecture alone, sleek and minimalist, makes the visit worthy, but the rotating exhibits and permanent collections make it a must-see for the artsy set. If you're done with the beach and pricey coffee, this is where you go to be cultured.

7. Fire Island Lighthouse – The Original GPS System

Prior to Google Maps, sailors relied on landmarks like the **Fire Island Lighthouse** to avoid wrecking their ships. This towering black-and-white tower, built in 1858, has seen its share of action. Climb the 182 steps to the top for views of the Atlantic, Fire Island, and beyond. And yes, it’s a climb, but at least you’ll be worthy of those beachside cocktails afterwards.

The Last Word: Long Island History is Hipper Than You Think

Listen, we all get it. Everyone thinks about the LIE traffic, the strip malls that never end, and the horn-blasting drivers who think it’s an Olympic sport when they think about Long Island. But beneath the facade, there’s a wealth of interesting and rich history in its mansions, its lighthouses, and its museums. Whether you’re a life-long resident on the island or a visitor, these cultural and historical attractions prove that Long Island’s much more than bagels and beach jams. **So, What’s Your Favorite Long Island Landmark?** Do you have a go-to historic destination? Do you know a secret gem that isn’t receiving the attention it deserves? Leave a comment and let’s debate it—because, let’s be real, no conversation about Long Island is complete without a little bit of disagreement. And if you’re considering planting your roots close to these timeless wonders, **Dean Miller’s got you covered.** Want a home that places you squarely in the center of the best that Long Island has to offer? **Get in touch with us today—before it all gets even pricier.**