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Natural Awakenings Westchester / Putnam / Dutchess New York

Dog Hiking Service Available in Westchester: Dogs are picked up, hiked off-leash where possible and then dropped back off at their homes.

How do you get seven dogs running through the woods back on their leashes? Just ask Evelyn Osmak or Michele Drella, experienced hikers and pet sitters who have combined their skills to offer dogs the chance to do what they love most: play in the great outdoors.

Osmak, of Pleasantville, NY, and Drella, of Mt. Kisco, NY, are bonded and insured and have been members of Pet Sitters International since 2011. The longtime acquaintances had been hiking together for a year and a half before they incorporated their business, Take a Hike NY, this past summer. “Dog safety is our number one concern,” Drella says. “And we have plenty of first-hand experience, being dog owners ourselves.”     

She says clients’ dogs are picked up, hiked off-leash where possible and then dropped back off at their homes. Daily excursions last two to three hours and are offered five days a week. In-home pet care and weekend hikes are offered by appointment seven days a week, including holidays. Drella says she and Osmak post pictures and videos to their website several times a week. “Most of our clients are into a more holistic approach—not just for themselves, but also for their dogs,” she says. “A whopping 95 percent of our clientele do yoga—the owners, that is. Although we have plenty of pictures of downward-facing dogs, too!”

New customers can tag along on the first hike if they wish. For more info, visit or call Michele Drella at 914.582.7337.