Labor Day Weekend Bucket List: Experience the East End Like It’s Your Last Time Here

Add Hamptons and North Fork experiences to your summer bucket list
Add Hamptons and North Fork experiences to your summer bucket list!

Summer comes to its unofficial end with the arrival of Labor Day weekend on the East End, but as whispers of “Tumbleweed Tuesday” fill the air, you suddenly realize there are aspects of summer that you’ve yet to experience. Fear not, you still have a few days, but the clock is ticking…

Montauk Point Lighthouse, Photo: David Taylor
Montauk Point Lighthouse, Photo: David Taylor

Climb the Montauk Lighthouse
It’s not every day you can climb to the top of a National Historic Landmark. Now here’s the question—have you actually done it this year? Or ever? If you want Montauk’s ultimate water view, it’s time to start counting. One, two, three…75…99…137…. Now share that selfie!

Get Lost in Sunflower Fields of the North Fork
You’re driving along and suddenly,there they are. Fields awash in the colorful burst of bright yellow-orange of sunflowers as far as the eye can see. It happens every August, a sure sign of summer’s home stretch, and only Mother Nature knows how long they will last in all their glory. Stroll through the maze at Sidor Farm in Mattituck before they’re all gone for another year!

Can you catch the biggest striper in the state?
The ultimate fishing pole dance! Photo: Ann Kosche/Hemera/Thinkstock

Bring Home a Striper
Get your head out of the gutter—that’s not a typo! Though fall is prime season for catching striped bass in local waters, the grail fish can still be had if you know what you’re doing. Talk to your local tackle shop about the best locations and bait to pull in keeper bass (that’s at least 28 inches long south of the George Washington Bridge) and hogs. We’re hearing live eels floated at night in Shinnecock Inlet are doing the trick, but it’s technically not impossible surfcasting at ocean beaches. Just make sure you have a license. And if things go poorly, you can always turn your focus toward bluefish, which always deliver a mighty fight, if not the most delicious dinner.

One More Southampton Social Club Saturday (and Thursday, Friday and Sunday) Night
The premier nightlife spot in the Hamptons has four straight days—wait, make that nights, through September 1—of DJs to send off summer in style.

Live It Up at a Lobster Bake on the Beach
Sink your toes in the sand, let the sound of the surf wash over you, and dig into the summery smorgasbord of lobsters, oysters and clams at the Beach Club at Gurney’s Montauk Resort & Seawater Spa.

Maidstone Club golf course
Maidstone Club golf course

Play a Round of Golf
The East End is dotted with world-class golf courses, and not all of them are private. Tag along with a friend who’s lucky, or rich, enough to be a member of the Maidstone Club, the Bridge or five-time U.S. Open host Shinnecock Hills, among others. Or enjoy nine or 18 holes at a public course, like Montauk Downs, Sag Harbor State Golf Course, Shelter Island Country Club, Poxabogue in Bridgehampton or Indian Island and Cherry Creek in Riverhead.

Sail with Polynesian Inspiration
Climb aboard the first U.S. Coast Guard Inspected Passenger Sailing Vessel built on the East End of Long Island and cruise around the waters of Montauk aboard the MonTiki catamaran. You may even get the chance to go for a swim.

Go Clamming
Grab some buckets (and your paperwork, of course), floats to keep them buoyant, even a floating cooler, if that’s your thing. Whether you use a rake, your toes or dig down in the sand on your hands and knees, chances are you’ll be pulling up some tasty quahogs (Atlantic hard shell clams).

The Malayan tiger (Panthera tigris jacksoni), Photo: © Photo by Joel Sartore/National Geographic Photo Ark (
The Malayan tiger (Panthera tigris jacksoni), Photo: © Photo by Joel Sartore/National Geographic Photo Ark (

Visit National Geographic Photo Ark
World-renowned wildlife photographer and conservationist Joel Sartore created the Photo Ark project to document every species living in the world’s zoos and wildlife sanctuaries, inspire action through education, and help save wildlife by supporting on-the-ground conservation efforts. So far he has visited 40 countries in his quest to create a photo archive of global biodiversity—you need only visit the Southampton Arts Center to see more than 100 of his portraits of birds, fish, mammals, reptiles, amphibians and invertebrates.

See the Hampton Designer Showhouse
Summer in the Hamptons means style, and nowhere is superior interior style on display quite like it is within the walls of the Hampton Designer Showhouse, this year benefitting Stony Brook Southampton Hospital. This gathering of myriad design masters all under a single roof at 66 Rosko Lane in Southampton is wrapping up its 19th year over Labor Day weekend.

Madoo bridge
A view at Madoo, Photo: Barbara Lassen

Meander at Madoo
The natural beauty of the East End is rarely more magical than during a stroll amid the gorgeous gardens and installations of this glorious conservancy set on an enchanting 2-acre landscape in the heart of Sagaponack.

Toast Summer at Sunset Beach
This Shelter Island hot spot always brings a bit of glitz and glamour to the island surrounded by islands—wanted or not is a matter of opinion—and does do its name proud with a summertime sundown show. You can show your local cred by casually mentioning, drink in hand, that the stretch of sand you’re looking out over isn’t actually named Sunset Beach, but rather Crescent Beach.

View from The Halyard at Sound View Greenport
View from The Halyard at Sound View Greenport, Photo: Barbara Lassen

Sit for a Sunset Dinner on the Sound
Watch the sun go down from the deck at The Halyard at Sound View Greenport while locally sourced seasonal fare keeps summer on your plate just a little longer. May we suggest you start out with a We Are All a Little Mad Here—a quirky cocktail of Hendrick’s Summer Solstice, Lavender, Elderflower and Pineapple.

Gravitate to Gosman’s Dock
Put whatever talk you have heard about any kind of sale out of your mind for now. Instead, embrace the nostalgia of grabbing lunch Topside, a steamed lobster at the Clam Bar, or even just an ice cream cone, strolling the shops and sitting down to watch the boats come and go at this special spot in Montauk history.

Drop a Line Off the Ponquogue Bridge Fishing Pier
Make sure to keep an eye out for kayakers, divers and other aquatic entertainment seekers.

Lobster Roll aka Lunch
The Lobster Roll aka Lunch, Photo: Oliver Peterson

Hit the Lobster Roll Trifecta
You have entered the Napeague Stretch, aka Lobster Roll Country, which means there is only one meal on your mind…times three, if you’re going to consolidate a season’s worth of the handheld local dish into one day. Start with a classic from The Lobster Roll aka Lunch, then cross over for the creamy version at the Clam Bar, and finish with the latest addition to the roster, a roll from the new Morty’s Oyster Bar.

Wine Down Summer
If only we could keep summer in a bottle all year long and let it out in little bits whenever the notion strikes… Time to raise glass at summer’s final Wölffer Twilight Thursday (August 29), Sunset Friday (August 30) and Sunset Saturday (August 31).

See a Different Kind of Toy Story
Before two-year-olds were given tablets to play with, there were these magical things called toys that all the kids would play with and cherish. Sag Harbor Whaling & Historical Museum’s Toy Story exhibit transports children and parents to a simpler time, featuring dozens of toys, dolls and board games from the 19th and 20th centuries, as well as modern paintings for sale that explore the themes of childhood and playtime. The show runs through September 5.

View from Shelter Island
View from Shelter Island, Photo: Oliver Peterson

Sail Around Shelter Island
Hop aboard a yacht or a Sunfish—the vessel is not as important as the journey it will take you on.

Take in a Labor Day Art Show
Admire the artwork showcased in the Southampton Artists Association’s Labor Day Show. Canvases, sculptures and photographs created by East End artists line the walls of Southampton Cultural Center’s Levitas Center for the Arts. Your friends are sure to be impressed that you spent your Labor Day weekend looking at fine art.

Commission Some Artwork
The Westhampton Beach Festival of the Arts packs the Great Lawn across from St. Mark’s Church with stunning sculpture, jewelry, paintings, photography and mixed-media works. While an outdoor art fair is enticing enough, this one encourages you to commission your dream piece from the artists, adding a level of bespoke service that is just so “Hamptons.” The festival runs August 31 from 10 a.m.–6 p.m. and September 1 from 11 a.m.–6 p.m.

Catch the Summer Farmers Markets
Most farmers markets don’t stick around all year, so you need to shop smart on Labor Day weekend. Make sure to hit the markets at Good Ground Park in Hampton Bays (ends Thursday), in East Hampton (ends Friday), in Springs (ends Saturday) and at Shelter Island Historical Society (ends Saturday).

Sag Harbor Cinema restored
Sag Harbor Cinema restored, Photo: Oliver Peterson

Be Cinematically Charitable
eBay for Charity hosts a Tumbleweed Tuesday extravaganza featuring 60 artworks by renowned artists on display at Sag Harbor’s Sara Nightingale, Julie Keyes and Grenning galleries from 2–8 p.m., as well as an art reception at Sylvester & Co. Modern General from 5–7 p.m. Each piece is part of an online auction that’s raising funds to help Sag Harbor Cinema re-open its doors this fall. The Page restaurant will have a cash bar, free popcorn and hors d’oeuvres flowing from 5–10 p.m., with an additional auction offering gift baskets, a MacBook Air and more.

Experience Mimosa Monday
For more than 30 years, many Hamptons locals have celebrated the end of summer, and the change in population, at the annual Mimosa Monday bash on Sagg Main beach in Sagaponack. Ring in the new, or old, paradigm with good friends, good vibes and some champagne and OJ in the sand on Monday, September 1.

Camp Hero in Montauk
Camp Hero in Montauk, Photo: Oliver Peterson

Visit Camp Hero
Back in the public eye thanks to Stranger Things and the debut episode of Travel Channel’s Strange World, which delved into the creepy legends and government conspiracies surrounding this defunct military base, Camp Hero in Montauk is a must-see, whether you’re a true believer in a tinfoil hat or a serious history buff. Walk the grounds to see defense facilities, gun emplacements and, of course, the massive SAGE radar tower—all perched atop the bluffs.

Paddle the Peconic
Riverhead’s Peconic River makes for an excellent day on the water. Set off in a kayak, canoe or stand-up paddleboard (SUP) and explore the beautiful Peconic Estuary on trips of various lengths, depending on your skill and available time. All routes are pretty relaxing and easy going. No white water here, just a lovely day.

Visit our online calendar at for more events and experiences this weekend.

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