- Distance from Boston: 119 miles
- Best time: May to October
- Best for: FamilyGirl's GetawayBeaches
Some beach destinations are ideal for doing nothing but enjoying the sand and sea, and Montauk, at the Eastern tip of Long Island, is certainly capable of providing such a relaxing respite. But this lively hamlet (with its historic lighthouse) located at land's end is also ideal for weekend travelers looking to kick things up a notch with some surfing, golfing, hiking, and other activities—followed by some serious eating. With its more than fifty hotels and inns and abundant restaurants, Montauk has something to offer couples, families, and even groups of girlfriends looking for fun in the sun. It's impossible to calculate the amount of seafood (fresh lobster, tuna, clams, and scallops top most menus) served here daily—you can even get in on the action with a half-day deep-sea-fishing excursion. And if your muscles ache from being a weekend warrior, you can always enjoy a seaside massage before you head home. Here's how to experience Montauk on the go. – By Donna Heiderstadt
Montauk Cheat Sheet
View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View
1Stretch your legs after your long drive or train ride by renting a road bike from Montauk Bike Shop in the center of town and cruising out to the fisherman's dock to see the day's catch unloaded. It's an 8-mile jaunt round-trip, so allow about ninety minutes for the ride.
2You're at the beach, so savor the sunset. Grown-ups weekending without kids should head to East by Northeast, a sophisticated but casual Asian-fusion restaurant and bar, where cocktails come with panoramic views of Fort Pond. If you have kids in tow but still want to enjoy a water view and delicious seafood, grab a snack at Navy Beach, where you can opt for Montauk clam corn chowder and seared sea scallops, while the Kids Menu offers burgers and fish & chips.
3For dinner, the Fort Pond area offers a number of delicious (if pricey) options. Head to Harvest on Fort Pond to dine on steamed mussels, calamari salad, grilled pizza, and more in an outdoor herb garden. Or dine at Inlet Seafood Restaurant for clams on the half shell and potato-crusted flounder; the owners are six local fishermen.
1For a classic breakfast diner experience, join the crowds at John's Pancake House on Main Street where the portions are generous and the coconut pancakes are a specialty.
2Spend your morning on the water, and catch some breaks at the top local surf spot, Ditch Plains. Newbies can take lessons with Air and Speed Surf Shop. Try fishing for fluke or striped bass (in season) on a charter fishing boat.
3Take a break from the action by enjoying a casual lunch at the Clam Bar on Gosman's Dock, a Montauk tradition since 1947. Favorites include the crab cakes and the seafood combo plate—fried clams, calamari, shrimp, and fish. Just watch out for sneaky seagulls trying to steal your french fries!
4Have your cameras ready as you enjoy an easy afternoon hike on the five miles of hiking trails at Montauk Point State Park, where you can also climb the 137 steps to the top of the Montauk Point Lighthouse, the oldest lighthouse in New York State. It dates back to 1792 (when George Washington was still in office!).
5Wind down with cocktails, live music, and terrific sunset views at the outdoor daiquiri bar at Montauket. For a family alternative, consider a friendly mini-golf competition at the 18-hole Puff 'N' Putt Family Fun Center.
6Friends should reserve a table in advance at South Edison to enjoy former Manhattan chef Todd Mitgang's delicious versions of beach classics, such as fried belly clams, local diver scallops, and seared yellowfin tuna.
7For a sweet end to the evening, grab some ice cream at local favorite John's Drive-In (695 Montauk Highway; 631-668-5515). If adults want to keep the night going, designate a driver or hire a taxi and head west on Route 27 to take in live music at The Stephen Talkhouse in Amagansett. Shows are at 8 p.m. and 10 p.m., and there's usually a cover charge.
1Stop by for an early brunch at Bird on the Roof (47 S. Elmwood Avenue; 631-668-5833), which, despite its simple décor and location behind a souvenir shop, serves up memorable omelets and eggs Benedict.
2Digest and soak up a little sun at nearby Edison Beach or end your stay with a relaxing 60-minute aromatherapy massage at the The Seawater Spa at Gurney's Inn.
3On your way back, enjoy one last taste of the briny Atlantic with a stop at Lobster Roll on Route 27 in Amagansett, where signature rolls and sliders are made with a fifty-year-old recipe. Afterward, stop in Amagansett and browse the shops at Amagansett Square.
Where to Stay
For a breezy cottage vibe—think white-on-white décor and large windows—and a relaxing ambiance, stay at Panoramic View Resort (rooms from $225/night) set on 10 oceanfront acres. Some rooms include kitchenettes.
Located in the center of town, and just a block from the beach, the 17-room Ocean Resort Inn (rooms from $115/night) offers clean, comfortable quarters (some with Jacuzzis) and friendly service.
When to Go
Summer is the best time to enjoy all Montauk has to offer—but reserve your hotel room weeks in advance for weekend travel. If you have a shark obsession (or teenage kids), you might want to schedule your visit during one of the three major shark fishing tournaments at the Star Island Yacht Club and Montauk Marine Basin to be on hand when the biggest catches are weighed and the cash prizes are awarded.
In late spring, the Montauk Music Festival features four days of performances by up-and-coming artists, and in October you can take part in the Hamptons International Film Festival and Montauk Fall Festival.
In winter, many of Montauk's restaurants and bars are closed or have limited hours, but if you love empty beaches, it can be heavenly.
How to Get There
By car from New York City: Montauk is located about 117 miles from Manhattan, and driving takes about 2.5 hours. Take the Long Island Expressway (I-495) to Exit 68 for the William Floyd Parkway and merge onto NY-27 East and follow the signs for Montauk.
By bus from New York City: The Hampton Jitney runs regularly scheduled trip from several stops in Manhattan to Montauk daily, with expanded service on weekends. The trip takes about three hours.
By train from Penn Station in New York City: The Long Island Railroad also services Montauk several times daily from Penn Station. The ride also takes about three hours.