Each fall there comes a time when most of the trees have lost their leaves and those that remain have turned dull and lifeless. The wind nips, foretelling winter's bite. Skim ice creeps out from pond edges, and trail sections that were muddy all summer crackle underfoot. It's tempting then to pack away hiking gear until next year. But some less timid souls have a trick or two up their sleeves, a simultaneous embrace of the darkening days and extension of the hiking season. As Halloween approaches, try these hikes to areas known for tragic histories and spooky legends, to put a spring in your step—and perhaps a chill up your spine.

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For more ideas of trails with spooky histories, see "Hike with Ghosts."

Sleepy Hollow
Tarrytown, N.Y.

Each year about this time, Nestor Danyluk, a trip leader with AMC's New York-North Jersey Chapter, digs up his notes on nineteenth-century writer Washington Irving. Danyluk, a professional landscape historian, heard a talk several years ago on the origins of Irving's scary tale, "The Legend of Sleepy Hollow." It identified a real Ichabod Crane, who may have served as the model for the hapless schoolteacher chased down the road to Tarry Town one dark night. Especially interesting to Danyluk, it also identified the possible headless Hessian soldier of the story and model for Ichabod Crane's unrequited love (a young woman of Irving's acquaintance), both allegedly buried in the same cemetery. The speaker "spun an incredible yarn," Danyluk says. "I didn't even want to check his facts—I just wanted to run with it."

Danyluk and co-leader Paul Brunn tell this and other stories each fall as they lead an annual hike from the Tarrytown train station through the town and the cemetery, stopping at the Dutch Reformed Church where Irving is supposed to have first heard some of the stories he later immortalized. "The sequestered situation of this church seems always to have made it a favorite haunt of troubled spirits,” Irving wrote. “The dominant spirit … that haunts this enchanted region, and seems to be commander-in-chief of all the powers of the air, is the apparition of a figure on horseback without a head."

It gives new meaning to hiking in the shoulder season. Hike at your own risk.

Doodletown and Harriman Mine
Hudson River Valley, N.Y.

This year on the Sunday closest to Halloween, Tom Parliment will lead his thirteenth annual trek to the abandoned town of Doodletown. Doodletown was inhabited for 200 years, from the 1760s to the 1960s, but little remains of it now beyond cellar holes and old road beds—and three cemeteries. Parliment has researched the town and guides the ghost-town ramble, pointing out, for example, the spot on a road where in 1777 British troops marched through, taunting local patriots.

Sometimes hikers arrive for Parliment's Halloween trek in costume, though he notes it can be hard to hike five or six miles in a witch's hat or wizard's cape. He occasionally slips away from the group to don a ghoul mask, but the hike typically ends by mid-afternoon, leaving plenty of time for other tricking and treating. In spite of the morbid subject, or perhaps because of it, the hike has a reputation as a matchmaker: Several couples first met on the hike. Perhaps there's something in the air beyond spirits.

Danyluk and Brunn also lead walks through Doodletown and nearby Harriman, site of a former iron mine, now also abandoned. Danyluk has heard that Doodletown may be a twist on an old Dutch phrase, Dood Tal, for "dead valley." If so, it is, as he says, the ultimate irony: "There are a thousand people in Doodletown, and all of them are dead."

Bash Bish Falls
Mount Washington, Mass.

Called the most spectacular waterfall in Massachusetts, Bash Bish Falls plunges 60 feet into an icy green pool. The falls take their name from the story of a young Mohican woman who protested her innocence when accused of adultery, but was nonetheless bound to a canoe to be sent over the falls. As the time for her punishment approached, the story goes, a ring of bright butterflies circled her head, she broke free of her restraints—and threw herself over the falls. The infant daughter she left behind grew into womanhood but took to brooding at the top of the falls. Eventually she, too, dove to her death, followed by a white butterfly. Some say that on moonlit nights you can make out a woman's shape behind the falls.

Mount Chocorua
Albany, N.H.

A father's grief, a friend's revenge, and a dying man's curse combine in a tale that adds the weight of myth to some verifiable facts that swirl around this popular White Mountain summit. In the early eighteenth century, when the rest of his tribe relocated to Canada, a young man named Chocurua stayed behind in their traditional lands. Father of a young son, he became friends with a settler, Cornelius Campbell, whose son was a similar age. While Chocorua was away, his son ate poisoned meat meant for a bothersome fox and died. The grief-stricken father believed that his son had been poisoned deliberately. Enraged, he killed Campbell's family while Cornelius was working in the fields. In some versions of the story, Campbell shot Chocorua at the top of the mountain that now bears his name. As Chocorua lay dying, he cursed the white settlers. For many years, the people of Albany believed in Chocorua's curse, even after some of their poor luck with crops and cattle was tracked to an excess of lime in the groundwater.

Chocorua is far enough north that any hike in late fall will be sure to bring a chill. Find information on climbing Chocorua in AMC's White Mountain Guide and White Mountain Guide Online.

Greenleaf and Lakes of the Clouds Huts
White Mountains, N.H.

In Passport to AMC's High Huts in the White Mountains, author Ty Wivell tells the story of Ben Campbell's heavy soles. In 1980, after serving as Greenleaf's hutmaster the year before, Campbell was named hutmaster at Lakes of the Clouds Hut. Tragically, he died climbing in the Scottish Highlands a few weeks before he could take up his new position. To honor his love of the mountains and the huts, Campbell's family delivered his hiking boots to Greenleaf Hut. Over several years, the Greenleaf croo reported hearing boots thumping in the night and finding Campbell's boots in different parts of the hut. Eventually the boots were delivered to Lakes of the Clouds Hut, where their soles have been quiet ever since.

If you want to stay at the once-haunted Greenleaf Hut, the full-service season continues until October 15; Lakes of the Clouds Hut is closed for the winter season.

Full moon and new moon hikes
Haunted hikes don't necessarily need a scary back story. Sometimes just changing the lighting shifts the mood. Jean Plough, a trip leader for AMC's Delaware Valley Chapter, schedules a hike every month of the year on the Saturday closest to the full moon—except this October, when it's a new moon hike on Saturday, October 29. (October's full moon rises on the eleventh.) Or test your soles on All Hallow's Eve, the night that the membrane between the living and dead is supposed to be at its thinnest.