Overlook Mountain – Woodstock New York

Treadmill Rating (out of 10):  4 out of 10
Distance: 5 miles round trip
Max Elevation: 3140 feet
Elevation Gain: 1400 feet

Photo By David C. Wickers

The stunning views of the Hudson Valley abruptly sloping up into New York’s Catskill Mountains attract many hikers each year. So spectacular are the views that the mountain inspired many of the works of the 19th century Hudson River School of painting.  From the center of the Village of Woodstock, NY, take Rock City Road (which turns into Meads Mountain Road) to the trail head, which is located directly across from the Karma Triyana Dharmachakra Budhist monastery. Follow the gravel, red-blazed Overlook Spur Trail up the seemingly endless slope for 1.6 miles and you will reach the first treat of this hike: the ghostly ruins of the Overlook Mountain House. The once-luxurious hotel could accomodate 300 guests when it was built in 1871. It burned down and was re-built, only to burn down again. Another attempt to re-build was abandoned in the 1920s for lack of funds. The ruins hold such attractions as a stairway to nowhere, and trees have grown within the once-lavish interior. Continue your trek upwards at a now less-challenging incline to the summit, at 3140 feet. Climb the historic fire tower at the top, and then follow a narrow trail behind the information cabin to a rock ledge with a terrific view. Unpack your lunch and sit for awhile on the edge of this great cliff. You will find inscriptions chiseled in the rock memorializing hikes a centrury and a half ago. Before or after your hike, tour the galleries and shops in the artists colony of Woodstock, which lent its name to the famous concert 43 miles away in Bethel, NY. You can buy Tibetan prayer flags (think Everest) in town or at the monastery.
 

DIFFICULTY RATING
While power hikers are frequently seen doing they’re daily routine, this trip rates as moderate to strenuous for most people. Expect to take rest breaks on the way up.
 

ELEVATION STATS
This is a roughly five-mile rountrip hike. Allow about three hours hiking time, and another few hours at the ruins and summit. The summit is at 3140 feet, with an elevation gain of 1400 feet from the trailhead.
 

HOW TECHNICAL IS THE HIKE?
This is a non-technical hike (uphill walk) along an unpaved road. Care should be taken if you choose to explore the ruins. Common sense should keep you intact.

WHO CAN DO THIS HIKE?
While I’ve seen people pushing strollers up this trail, they have always looked very unhappy. Backpackers love this hike, as camping is permitted at a distance from the trail. Just about anyone who likes to walk should be able to do this hike, although they may mumble and grumble after awhile on the way up.

WHEN SHOULD I GO?
This hike can be done year round, although it is more difficult in snowy winter months. Aside from deer, you may see bears, and I was once rattled at by a rattlesnake — the area is home to Timber Rattlesnakes.

Photo By David C. Wickers

TRAINING ADVICE
Hikers should be in reasonably good shape. As with Woodstock itself, the mountain has little to no cell phone reception. Hence, no one will hear you scream.

GEAR LIST
Bring at least two bottles of water, lunch or snacks. In cold months, bring a thermos with hot tea or soup and dress appropriately — mountain weather can change drastically. Bug spray is helful in warmer weather. Walking sticks are helpful, and a camera invaluable.