Doggin’ in Montauk, New York

For many canine hikers the late winter and early spring months are the choicest cuts of the hiking year. Popular trails that have been choked with fair-weather traffic are blissfully clear and inviting, especially for a dog that enjoys stretching his legs. And your dog loves the crisper air he finds on these hikes

Such is the case in Montauk, at the very end of Long Island, New York. Once primarily a bustling fishing and whaling center, the eastern end of Long Island is now the summer playground of New York City. But a drive that can take a congested half-day in June is scarcely a two-hour, clear-sailing excursion in April.

Heading across Long Island on the Montauk Highway, as you clear the Hamptons and arrive in Montauk you encounter first the centerpiece of outdoor adventure here – the thousands of unspoiled acres of diverse habitat in the Hither Woods area. Canine hiking crosses maritime forests, open grasslands, walking dunes and over two miles of beaches.

Many of these splendid trails carry names derived from tales of Indian lore. Talkhouse Trail remembers a famous 19th century Montauk Indian known for his singular ability to walk long distances. Legend says he could walk from Montauk to New York City in a single day. Indian Jumps Trail recalls a time when two Montauk men were in love with the same woman. The loser for her hand killed the other and in his death throes the dying man took three great leaps leaving depressions along the edge of the trail.

Hither Hills is known for its unique vegetation: Russian olive trees, wild grapes, berries and more. You’ll also see huge boulders carried from New England by glaciers and deposited like marbles in the dunes. Along the northern Napeague Bay, a band of 100-foot sand dunes known as the Walking Dunes, literally saunter across the shoreline from west to east.

At the end of the island you will find two parks welded together. The grounds of Theodore Roosevelt County Park once supported America’s first cattle ranch when the nation’s earliest cowboys drove cattle herds to graze on Montauk’s downs in 1658. Following the Spanish-American War in 1898, vice-President Theodore Roosevelt brought his band of victorious Rough Riders and 28,000 soldiers to quarantine after seeing action in the disease-contaminated tropics. Take your dog to explore the Big Reed Pond nature trail system on three interconnected loops that showcase a variety of ecosystems from tidal marsh to upland hardwood forest. The sandy, paw-friendly trails reach out to the bay in Block Island Sound and gentle waves for easy canine swimming.

Next door is Montauk Point State Park, home to the venerable Montauk Point Lighthouse, commissioned by George Washington in 1795, at the very tip of Long Island. The lighthouse is surrounded by cobbled beaches and massive breakwater chunks of stone that you can negotiate carefully with your dog for a memorable walks. Traditional trails lead to fresh water ponds, including the “bottomless” Money Pond, said to be the hiding place of gold from pirate Captain William Kidd in 1699. Kidd buried loot at more than a dozen Long Island locations before his capture and execution in 1701 for the crime of bopping an unruly sailor over the head with a wooden bucket, supposedly killing him.

Also in the park are trails along the Atlantic Ocean leading into Camp Hero, a former military base. The area was used as a Revolutionary War practice site and was formally established as a coastal defense installation during World War II. Now open for limited use (mostly hiking), Camp Hero features pristine maritime forests, natural freshwater wetlands and dramatic vistas from bluffs rising from the Atlantic Ocean. Our dogs are welcome on this shoreline and to poke around the bunkers and batteries that remain in the demilitarized base.

No canine hiking trip to the the eastern end of Long Island can be complete without a visit to some of the most beautiful beaches on the eastern seaboard. Not only will you find most of these beaches empty and dog friendly this time of year but back in the Hamptons you can expect to find a place to park – something that would be unthinkable in just a few weeks.

Doug Gelbert is the author of over 20 books, including The Canine Hiker’s Bible.

To subscribe to his FREE Newsletter on hiking with your dog and receive a copy of Rules for Dogs in 100 of the Most Popular National Park Service Lands, visit

In the warmer months he leads canine hikes for tours, guiding packs of dogs and humans on hiking adventures. Tours, ranging from one-day trips to multi-day explorations, visit parks, historical sites and beaches.

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