TV
New York’s Path Through History Weekend, June 14-15, is the perfect chance to explore the stories that shaped our favorite region, Long Island. Suffolk County is brimming with landmarks that tell tales of innovation, war, whaling, wine, and even... a duck-shaped roadside attraction. Here are 10 must-visit destinations for history lovers of all ages.
For even more ideas, visit our Arts & Culture page.
1. Grumman Memorial Park – Calverton
Celebrate Long Island’s aerospace legacy at the site where Grumman built and tested jets for the U.S. Navy. Stand beneath the legendary F-14 Tomcat and discover how local innovation helped power American air supremacy. Free and outdoors.
Did you know? The F-14 Tomcat was featured widely in the 1980s classicTop Gun.
2. Lt. Michael P. Murphy Navy SEAL Museum – West Sayville
Explore the legacy of Long Island-born Navy SEAL and Medal of Honor recipient Lt. Michael Murphy. This interactive museum honors America’s soldiers with powerful exhibits and personal stories that speak to courage, sacrifice, and honor.
3. Explore New York’s Oldest Town – Southold
Southold, New York’s oldest English town, is rich in coastal history and rustic charm.
Climb a historic lighthouse and learn about the ferry lines that once connected Long Island to ports across the Northeast. Set on a scenic bluff with panoramic Sound views, this event adds depth to a daytrip steeped in maritime history. Plus, check out their Special PTH Weekend Event: “Going Places: Ferry Companies of the Long Island Sound” (June 14)
Did you know? The Horton Point Lighthouse Nautical Museum is only open seasonally from Memorial Day weekend through mid-September, so visit while available
Just a few miles away lies Long Island Wine Country, blending rich history with bold flavor. At The Old Field Vineyards, the first vineyard was planted in 1974, when it was just farmland known as “The Old Field,” offering years and years’ worth of agricultural history in the roots. Mattebella Vineyards crafts sustainable small-batch wines on a family-run property. Visiting Long Island Wine Country, home to over 60 wineries and vineyards, is the perfect way to toast centuries of tradition in every glass!
Did you know? “The Old Field” is mentioned in Southold records as early as 1660!
4. The Long Island Museum – Stony Brook
A Smithsonian affiliate, this museum tells the story of Long Island’s 19th-century transformation. Wander historic buildings, explore the renowned Carriage Museum, and catch the Triumph of Nature: Art Nouveau from the Chrysler Museum exhibition. Dads and grandfathers enjoy free admission on June 15.
5. The Whaling Museum – Cold Spring Harbor
Discover how Long Island’s seafaring towns once fueled a global industry. Learn about whaling ships, tools, and tales of high-seas adventure at this dynamic, family-friendly museum. Free admission for dads June 14–15.
Did you know? The whaling scene was developed by Native Americans in the Woodland Period of 1000-1640 AD. The Native Americans then taught the first settlers how to hunt whales.
6. George Washington’s Culper Spy Ring – Route 25A
Follow the path of America’s first spies along historic Route 25A, where George Washington's inner circle gathered intelligence for him during the Revolutionary War, and led to a victory against the British. Finish your self-guided tour with a stop at Twisted Cow Distillery in East Northport and toast with their “Culper Spy Ring Rum.”
Did you know? In five years of delivering messages, not a single spy was caught by the British.
7. Suffolk County Freedom Trail – Various Locations
The Suffolk County Freedom Trail is an interactive online trail with 46 sites that honors sites and stories tied to African American history and the fight for freedom. Visit historic homes, churches, cemeteries, museums and more to learn about the legacy of resilience and resistance dating back to the 17th century, on the same ground we walk on today.
8. The Big Duck – Flanders
Quirky? Yes. But also a bonafide landmark on the National Register of Historic Places! Built in 1931 to promote ducks and eggs for sale within, this 20-foot-tall concrete duck is a tribute to Long Island’s once-thriving poultry industry. Today, it’s a beloved roadside stop with a visitor center full of feathered history and souvenirs.
9. Discover Montauk’s Deep Blue History – Montauk
Montauk, nicknamed “The End of The World” for being LI’s easternmost point, isn’t just a beach destination; It’s one of Long Island’s most historically layered communities. The region was once home to the Montaukett Tribe, whose legacy shaped the region. As you delve into the history, you’ll uncover its transformation from Indigenous land to WWII military base, to resort town for presidents and celebrities. The Montauk Manor was built in 1926 and ran through Prohibition, and Montauk’s rich fishing scene (think anything from cod and haddock to sharks and tuna) earned it the title of “Fishing Capital of the East.”
Did you know? Montauk is said to have inspired the famous movie, "Jaws," which celebrates its 50th anniversary this summer.
At the tip of the peninsula stands the iconic Montauk Point Lighthouse Museum, commissioned by George Washington in 1792. Camp Hero State Park served as a strategic World War II military base with bunkers, radar towers, and Cold War secrets still embedded in the dramatic cliffs that surround the area. Don’t miss the historic Montauk Yacht Club, established in 1929, which once hosted Gilded Age elites like the Vanderbilts and the Astors, remains a symbol of the town’s timeless maritime charm.
Did you know? Netflix’s original series, Stranger Things, is said to have been inspired by the military conspiracy theories around Montauk’s Camp Hero.
10. Vanderbilt Museum & Planetarium – Centerport
Experience the opulence of the Gold Coast at William K. Vanderbilt II’s waterfront estate. Tour the mansion, explore deep-sea specimens in the marine museum, or gaze into the stars at the planetarium.
Did you know? The mansion, called “Eagle’s Nest,” originated as a small cottage and expanded into a 24-room Spanish-Revolution style mansion.
