An all-encompassing guide to the East End
A quality guide to Montauk from our friends at Montauk Yacht Club. Hey, they even helped us put the distance of each location back to the Yacht Club—thoughtful folks. Don’t forget to bring $13 bucks to see Joe at the lighthouse. The other things to know:
How to get to Montauk
Long Island Rail Road (LIRR)
Taking things a little slower seems to be a theme here at Whalebone HQ. And traveling by train is a nice excuse to do just that. Snag a ticket from New York to Montauk via the Long Island Railroad (LIRR), crack open the book that’s been on your bedside table for the past six months and don’t forget to look out the window a few times.
The Jitney
Another more environmentally friendly way to catch a ride from Manhattan to Montauk–and pretty much anywhere else in the Hamptons. The world is your oyster with this one. But maybe save the oysters for after the bus ride.
BLADE
If you’re really feeling fancy, there’s nothing quite like Blade service to set the tone for your trip. A hop, skip and a jump from Manhattan to Montauk Airport (KMTP) with shuttle service to Montauk Yacht Club (MYC).
Surfing
Ditch Plains Beach, Montauk (2.6 miles from MYC)
Ditch Plains is an ode to simpler days. Home to some of the best waves this side of the Mississippi and a mean burrito courtesy of the legendary Ditch Witch food truck. Head out to the break yourself or watch your friends wipe out from the comfort of the sand. Dogs welcome, which means you can finally snap that shot of your pup doing a hang-ten.
Recommend a surf excursion wherever it’s working (boards and transport) with lessons all set up by local pro, Pat Fallon.
Hikes & Views
Shadmoor State Park (2.2 miles from MYC)
Quite possibly home to the best aerial views of the Atlantic Ocean, Montauk has to offer year-round. We’re talking about the stuff of movies here. It’s worth noting that snowshoes or skis are ideal for any winter treks to the park’s shoreline cliffs. Pack a lunch, pick a trail, and start walking.
Recommend walking in the park in the morning with coffee.
Hither Hills State Park (6.9 miles from MYC)
Right at the entrance of Montauk, you can’t miss this one. A solid choice of accommodation for the campers of the group. Or make it a day trip if you’re not into waking up to the sound of waves hitting the shore and the sweet smell of salty air. We’ll leave it up to you. Plenty to do here with sandy beaches, swimming, biking, camping, and hiking–all in one place. But you’re gonna need to leave the pup at home for this outing.
Cocktails, Beach & Sunset
South Edison Beach (3.3 miles from MYC)
An ideal spot if you pack your birthday suit instead of a swimsuit. Hey, it happens to the best of us. Thankfully South Edison is within walking distance to the shops in town. There isn’t a ton of parking at the beach itself, but if you find a spot in town the walk is easy peasy.
The Montauket (2 miles from MYC)
Located on Fort Pond, right up the road from Navy Beach, sunsets in Montauk don’t get much better than the ones you’ll witness at this local watering hole. Parking is pretty limited, so bikes or alternative transport are going to be your best bet at getting a front-row seat to watch mother nature’s light show over Gardiners Island.
Recommend a sunset cruise around Gardiners Island.
Coffee
Left Hand Coffee (3.1 miles from MYC)
The go-to spot near the center of town for the individual, right- or left-handed, that prefers to be well-caffeinated before starting the day. Coffee, cold brew, lattes–all of the above plus some.
Beer
Montauk Brewing Co. (3.2 miles from MYC)
Fact: Montauk wouldn’t be Montauk without beer–beer from Montauk Brewing Co. beer if we’re getting specific. You’ll find a range of seasonal offerings (big fans of the Surf Beer over here at Whalebone HQ) and staple brews here. Craft beer fans–welcome to paradise.
Restaurants: Quick Breakfast / Lunch
Anthony’s Pancake House (3.2 miles from MYC)
An old-school diner that screams pure Americana and serves up some of the fluffiest pancakes on all of Long Island. Maybe even the world. Almost as good as the pancakes is the primetime viewing opportunity of hungover humans after a night out on the town. Pro-tip: Sit at the counter for a better view of the entertainment and quick seating.
Happy Bowls (3.4 miles from MYC)
Owned by a local family of surfers, Happy Bowls is a solid choice for water lovers looking to meet like-minded folks over the best PB&J bowl you’ll find on the Atlantic Seaport. They offer a few takes on a traditional acai bowl, plus a build-your-own, and a few great smoothies.
Montauk Bake Shoppe (3.2 miles from MYC)
No need for maps here, just follow the sweet wafts of coffee, fresh bread, and crispy pastries thanks to the fact that The Montauk Bake Shoppe produces its baked goods on the premises. Tip: Try the jelly croissants. You won’t regret it.
Goldberg’s Bagels (8.8 miles from MYC)
Hear us out. NJ bagels are great. But Goldberg’s might just give the Garden State a run for its money. The Montauk location has flagels (flat bagels–arguably better than the traditional version) and some other non-circular breakfast fare to satisfy everyone in the group.
Joni’s (3.1 miles from MYC)
Next door to Left Hand Coffee. Stock up on grab-and-go breakfast, smoothies on your way to the beach or a few sandwiches for post-surf munchies. Plenty of gluten-free and vegan options to keep everyone happy at this local staple.
Recommend breakfast catered by Joni’s (local staple).
Restaurants: Lunch / Dinner
Showfish at Montauk Yacht Club
Focused only on the freshest locally-sourced ingredients, Showfish presents a unique take on east-end dining that embraces fresh fish, farm-to-table vegetables, and unique culinary concoctions cooked to serve in a stunning seaside setting.
The Dock (1.1 miles from MYC)
The Dock serves exceptional food six days a week. Just not on Mondays. What they might lack in personality and charm they more than make up for with locally caught and sourced daily specials. Regardless of the giant plasma TVs everywhere and screaming kids running around, this place might have the best peanut butter pie dessert special on the planet.
Things to do (other than the beach)
Hamptons Fly
Take “flite” with the most highly awarded electric hydrofoil in the world! You haven’t truly taken in the stunning sights of Montauk until you’ve glided 2 feet above the water on a Fliteboard! The amazing instructors of Hamptons Fly will guide you through how to operate the board, and before you know it, you’ll be soaring above the water.
Take a Fishing or Sailing Charter
Montauk claims to have more world saltwater fishing records than any other port in the world. Which is why you shouldn’t be surprised to see the words “Fishing Capital of the World” on the welcome sign as you enter Montauk Harbor.
- Sail Montauk offers a myriad of options for all interest and experience levels.
- John Waters (General Manager of Safe Harbor Montauk Yacht Club) fishing charter boat recommendations: Gianna Helena Charters, Masterpiece Charters, My Mate Charters.
The Montauk Lighthouse (6.0 miles from MYC)
Starting to lose the will to lather on another layer of sunscreen at the beach? Try the Montauk Point Lighthouse Museum for a change of pace. Located next to Montauk Point State Park, the iconic lighthouse has no shortage of unforgettable views and rich heritage.
Recommend taking a tour with lighthouse keeper Joe Gaviola.
The Ranch (3.5 miles from MYC)
The Ranch—the birthplace of the beloved white condiment. Kidding. But worth the stop for anyone with a passion for awe-inspiring art in the setting of the great outdoors. A great place to get a peek at the Andy Warhol Estate across the street too. Visits are by appointment only, so be sure to call ahead.
Rent a Moke
There’s something special about cruising along the coast in a doorless with some good tunes cranked on the radio. Enter the Moke. A small, pastel-colored electric car that emulates summer island vibes. Head over to Sole East in Montauk or Blue Mar in Southampton to grab one.
Spa day at The Seawater Spa at Gurney’s (6 miles from MYC)
Pamper yourself for the day.
Take a tour of Wölffer Estate Vineyard (22.4 miles from MYC)
Just 30 minutes south and you’ll find yourself at Wölffer Estate Vineyard in Sagaponack sipping on a bottle of their Summer in a Bottle Rosé.
Recommend taking a tour of Wölffer Estate with art gallery owner and collector Adam Lindemann.
Montauk County Park (formerly Theodore Roosevelt County Park)
Recommend an afternoon barbecue here.
Ride Horses at Deep Hollow Ranch (3.5 miles from MYC)
Recommend horseback riding to the beach from the oldest cattle ranch in the United States.
Relax at Montauk Yacht Club
Recommend hanging out at the nighttime fire pits with DJs Manuel Peláez Arranz and Oli Benz or a live band on Saturday night.
Golf (1.9 miles from MYC)
Practice your putting at Montauk Downs State Park Golf Course. One of the top 10 courses in the country, this 18-hole course was designed by Robert Trent Jones, Sr. and just so happens to be the location of a special something put on by yours truly come June. Sign up for The Golf Thing 2023 here. It’s all in the hips.
Whale watching
These gentle giants are a sight to see. Hang out with the Coastal Research and Education Society of Long Island to make sure you’re doing things safely for yourself and the whales.
Mountain Biking
Get lost on the tracks at Hither Hills. Ocean views for days.
Workout
New York Pilates (3.5 miles from MYC)
Starting in New York City, this cult fitness joint has made its way to the Hamptons. Ocean and pond views from the private patio make for possibly the most peaceful ab-busting workout you’ll ever get. Book ahead of time.
Shopping
The Boneyard
A great place to read magazines. And drink some coffee. And pet the yellow dog. And buy a t-shirt or two.
Cynthia Rowley (3.5 miles from MYC)
Mrs. Rowley considers herself a local so good chance you’ll run into her if you take the train out to Montauk. She’s been surfing in Montauk with her family for years, and the same could be said for her boutique.
Bontemps Montauk (3.1 miles from MYC)
Everything in this store screams salty air and sandy beaches. Think: East Coast meets South of France.
Destination Haus (3.2 miles from MYC)
The destination if you’re looking for home design inspo. With a curated selection of works from artists around the world, you’ll find some real gems here whether it’s furniture or glasswork.
Wyld Blue (3.6 miles from MYC)
For those on the hunt for luxury vintage fashion, this Montauk spot should be on your itinerary. Next-level.
Candied Anchor (3.3 miles from MYC)
The candy shop you wish you had in your hometown growing up. And probably today if we’re being honest with ourselves here. Packed with nostalgic Americana candy straight out of the 60s.