Whether you’re driving, shopping or simply strolling, there are so many interesting and unique places to see around the Hamptons and North Fork. Here are some of our favorites, both on the beaten path and off.
Find more entries in a variety of 2019 Summer Superlatives categories.
Most Fragrant Farmstand
Lavender by the Bay, 7540 Main Road, East Marion, 631-477-1019, lavenderbythebay.com
Best Place to Pet a Starfish
South Fork Natural History Museum & Nature Center, 377 Bridgehampton–Sag Harbor Turnpike, Bridgehampton, 631-537-9735, sofo.org
Most Pedal-to-the-Metal Nascar Experience
Riverhead Raceway. Nowhere else on Long Island can you get the high-speed thrills of NASCAR, plus monster trucks, school bus destruction, demolition derbies and more. 1797 Old Country Road, Riverhead. 631-842-7223, riverheadraceway.com
MacGyveriest Guy
We’re pretty sure Southampton’s Gary Anderson of Anderson Tooling Co. can fix or make anything. andersontooling.com
Sea Wateriest Swim
Those in the know call it The OG, The Original Gurney’s. But no matter what you call Gurney’s Montauk Resort & Seawater Spa, call your friends after you’ve gone swimming there and tell them you took a dip in North America’s only Olympic-size ocean-fed pool. 290 Old Montauk Highway, Montauk
Most Exhilarating Elevated Stroll
You have not taken a walk anywhere in the Hamptons until you have trekked over the 2,812 feet of Ponquogue Bridge in Hampton Bays, rising up 55 feet over Shinnecock Bay and offering breathtaking views of boats and clammers below.
Most Caesars in One Spot
Find busts of 12 great Roman emperors—including Julius Caesar, Caesar Augustus, Caligula, Nero, et al.—brought here by Samuel Longstreth Parrish and first displayed in 1898, now on the grounds of the Southampton Arts Center. 25 Jobs Lane, Southampton
Premier Place to Watch Shooting Stars
Lie on your back at Shelter Island’s Crescent Beach on a dark night, long after the crowds have left Sunset Beach, and chances are you will be treated to a celestial show.
Best Place to See a Future Major Leaguer
Hamptons Collegiate Baseball games are played across the East End all summer. As of this writing, five former players are in the Show.
Cutest Dogs Roaming a Shop
Candy, ice cream and more await at this cute shop, but the clear favorites at Summer Girl are the lovable canines. 775 1st Street, New Suffolk. 631-734-5698, mysummergirl.com
Surest Location to Feel Like Tom Hanks in Big
Get your fortune told by the Zoltar machine at Stevenson’s Toys & Games…but be careful what you wish for! 69 Jobs Lane, Southampton, 631-283-2111, stevenstonstoys.com
Most Aggressive Ducks
Otter Pond, Sag Harbor—feed at your own risk!
Coolest Place to Take a Selfie with a Tank
Everit Albert Herter VFW Post 550, 390 Montauk Highway, Wainscott
Most Incredible Sunset View While on Four Wheels
Few places allow us to enjoy a sunset and sunrise at the same time, but driving westbound on Route 27, aka Sunrise Highway, at magic hour delivers an unbelievable example of why our skies have inspired so many artists to fall in love with the East End.
Best Place to Feed Birds Out of Your Hand
Elizabeth A. Morton National Wildlife Refuge, 2595 Noyack Road, Sag Harbor. 631-725-7598
Best Place to Buy a 1999 McFarlane Toys Austin Powers Mini-Me Figure and an Ice Cream Cone
This may be an odd pairing, but if you’re up for it, you’ll find it at Sugar Daddy’s Toy Store. 103 Main Street, Westhampton Beach. 631-288-3537
Most Exotic Store Pet
Seeing shopkeepers with friendly cats and dogs behind the counter isn’t a rare occurrence, but meeting Herrick Hardware owner Noel Hare’s brightly colored, 22-year-old conure named Bungee is a rare treat. Give him a whistle the next time you stop by. 41 Main Street, Southampton. 631-283-0026, herrickhardware.com
Easiest-to-Miss Stop Signs
Even a North Fork native is likely to miss at least one of the sneaky stop signs heading north down First Street in Greenport. Add a couple of parked cars and overgrown branches, and you may miss all of them.
Most Blair Witch Experience
Hither Hills State Park. Wandering around the woods is scary enough for some people, but when you stumble upon a bizarre series of polls with carabineers connecting black nets to a mysterious box and microphone, it’s likely to have even the toughest among us running for an exit while avoiding possible tripwires and other traps. 176 Montauk Highway, Montauk. 631-668-2554, parks.ny.gov/parks/122
Hippest Hangout for Vinyl-Loving Hipsters
If there’s one thing hipsters love, it’s vinyl records, which is why Innersleeve Records is full of them. The super chill store buys, sells and trades cassette tapes, CDs, records and music memorabilia. Guitars, amps, cables and instrument accessories are also available for purchase or rental. 199 Main Street, Amagansett, 631-604-6248, innersleeverecords.com
Easiest Place to Dig Up an Artifact
Havens Beach in Sag Harbor has been turning up all sorts of vestiges of days gone by since the dredging around Long Wharf last year. The estimated 8,500 cubic yards of dredge spoil was dumped at Havens, and along with sand and muck, historians and amateur treasure hunters have found all kinds of objects from the past, including old coins, bones, musket balls and more. Havens Beach Road, Sag Harbor
Most Photogenic Vintage Gas Pumps
Opened in 1847, the Springs General Store is a throwback to a bygone Hamptons where artist and neighbor Jackson Pollock once traded a painting for groceries, and residents could buy milk, get gas and send their mail all in one place. The trio of Gulf gas pumps dried up ages ago, but they still stand as a reminder that the past is not forgotten in this part of town. 29 Old Stone Highway, East Hampton. 631-329-5065, springsgeneralstore.com
Coolest Way to Cover Up a Bad Tattoo
What better way is there to cover up an embarrassing tattoo than with another, much cooler tattoo? Natives with Ink specializes in intricate designs, delivering both fresh ink and expert cover-ups. 40 Montauk Highway, Southampton. 631-740-7354, nativeswithink.business.site
Most Miniature Hamptons Buildings in One Place
Hamptons Mini Golf, 668 County Road 39, Southampton, 631-283-2158, hamptonminigolf.com
Most Likely Place to See the Buffalo Roam
North Quarter Farm, 1950 Roanoke Avenue, Riverhead. 516-647-1146, eastridinginc.com
Best Place to Channel Stranger Things
Montauk’s Camp Hero, the now-defunct military spot where the government conducted strange experiments, served as the inspiration for Netflix’s hit supernatural series Stranger Things. The show takes place in the 1980s in a small Indiana town where sinister science experiments gone wrong cause extra-dimensional monsters to run amok, but its working title was Montauk.
Best Place to Play Classic Pinball on a Rainy Day
The Clubhouse in East Hampton has several classic pinball machines to play, as well as a ton of fun arcade machines. 174 Daniels Hole Road, East Hampton, 631-537-2695, ehitclubhouse.com
Most Magical Way to Explore Montauk
Sailing Montauk’s Catamaran Mon Tiki. There’s nothing quite like sailing the expansive waters off Montauk on the majestic Catamaran Mon Tiki. Launching daily from Gurney’s Star Island Resort & Marina, tours offer a tranquil, unforgettable experience with breathtaking views of the Montauk Lighthouse, the beautiful coastline and more. 32 Star Island Road, Montauk. 631-668-2826, sailingmontauk.com
Richest Hiking Habitat
Affectionately known as the Jewel of the Peconic, Shelter Island’s Mashomack Preserve is an expansive, 2,039-acre wonderland of woodlands, fields and 11 miles of coastline. Take a long walk and enjoy the view. 79 South Ferry Road, Shelter Island
Biggest Hess Truck Collection on Display
Twin Forks Moving & Storage, 11 Tradesmans Path, Bridgehampton, 631-725-7700, twinforksmoving.com
Most Adoptable Guinea Pigs
In addition to cats and dogs, the Southampton Animal Shelter Foundation also has guinea pigs and other pets available for adoption. 102 Old Riverhead Road West, Hampton Bays. 631-728-7387, southamptonanimalshelter.com
The Perfect Wave
Montauk’s Ditch Plains offers a can’t-miss summer break, possibly even the most consistent in the state. This beach’s cobble rock reef bottom doesn’t change like the sands at other local spots, making the waves almost always the same. Bring a longboard to conquer the slow, mushy waves, perfect for the novice. True shredders will have to hunt along the coast and find the best break on any given day. 18 Ditch Plains Road, Montauk
Best Secret Back Road to Bypass Traffic That Only Locals Know About
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