As development slowly crept into the Hudson Highlands around the turn of the 20th century, efforts were made to preserve the area but it was not until the State of New York tried to relocate Sing Sing Prison to Bear Mountain - so named for its resemblance to a bear in repose - that conservation forces truly mobilized. Railroad magnate E.H. Harriman and others donated land and vast sums of money to save the Highlands and in 1910 Bear Mountain-Harriman State Park was dedicated. Within five years it was hosting more than one million visitors per year and 100 years later more people come to the state park, New York’s second largest, than Yellowstone National Park.
Harriman is one of the best parks around for all-day hikes with your dog - the first segment of America’s most famous trail, the Appalachian Trail was carved across Bear Mountain in the 1920s. There are more than 200 miles of marked hiking trails through Harriman State Park and many more in adjacent Bear Mountain State Park. Even so, the crush of visitors can be so great that designated hiker-only parking lots fill up quickly. Arrive early or face difficult access to trailheads in good weather.
The Timp Hike is a popular introduction to the Hudson Highlands, starting directly on Route 9W that runs along the Hudson River opposite of Jones Point, just south of Bear Mountain. The trailhead is an unpromising break in the weeds just south of the parking lot but things pick up once your dog negotiates the awkward, rocky steps in the early stages of the journey. The hike splits into the Ramapo-Dunderberg Trail (red blazes) and Timp-Torne Trail (blue blazes). From here, heading up the red trail, you break out to views of the Hudson River and roll up and down mountains through boulder foundations until the Timp, a peak overlooking the interior of the Highlands. Climb back down the Timp and return on the blue trail to complete a rewarding 9-mile loop.
In general, the hiking in the west region of the park is more paw-friendly. Dirt trails move through forests with little understory and long sightlines. The trails crisscross often and there is plenty of up-and-down hiking. It is not unusual to have tagged four or five small peaks in a two-hour trip. Make sure to find a trail map before heading out. Oh, and dogs aren’t allowed in park campgrounds so you’ll have to leave and come back each day of canine hiking.
Take Palisades Interstate Parkway north of I-87.