Overlook trail guide

If you are to hike on the Overlook trail in Woodstock, New York, then you have come to the right place. The famous trail is well-known for its refreshingly countryside feels which is a great get-away from the busy city known as the Big Apple. Moreover, it offers a chance to take invigorating strolls through the big woods.

Overlook trail
The Overlook Mountain House was a secluded retreat during the Catskill tourism boom. Source: Getty Images

The Overlook trail has been renowned as a source of inspiration to artists for centuries. Both painters, photographers and writers have considered it an escape for creative retreats. Mount Overlook has features such as the Catskill Escarpment range, which forms a beautiful silhouette of glaciated mountains beginning on western Hudson River. Read on to know its background, directions, rules and regulations and more about Overlook.

Background about Overlook Mountain in Woodstock NY

According to the locals, people living in the surrounding area are friendly to visitors of the mountain. The Overlook Mountain trail is an old gravel road that is approximately 4.6 miles if go up the steep mountain and come back down. When you get to the top of the mountain, it has an amazing view alongside the historic fire tower.

Trail guide for Overlook Mountain

  1. From the parking area and sign in at the kiosk
  2. Start walking up the trail road and keep at it
  3. There I a bend with old ruins of former Overlook Mountain house but its advisable to keep off the place, although it is quite a sight to behold
  4. After the hotel ruins, you will spot a well-marked fork so you go right as you head into the Overlook Summit
  5. To the left you will find the big fire tower which you can choose to climb for more fun
  6. After the fire tower, there is a small ranger station and to the right of it, there is a short trail back to the cliffs of Overlook Mountain which provides an amazing view
  7. Go back down the way the trail goes


The Overlook Mountain Catskills is accessible from NYS Thruway (Exit 19) in Kingston (Route 28). Take Route 28 west approximately 6 miles to a right on Route 375, then eventually a left onto Route 212 to the Woodstock Village Green. At Village Green, make a right on Rock City Road in the center of town, continuing past the 4 corners intersection to Meads Mountain Road. The parking lot is to the right about 2 miles up Meads Mountain Road.


If you are looking for reviews on your potential hike to Overlook Mountain trail Woodstock, New York, there are several resources that might assist you. Some of them are:

  • Yelp reviews on the hike destination and experience
  • Reviews on LocalHikes.org by previous hikers
  • An Overlook Hotel write-up by HudsonValleyRuins.org
  • If you’re looking for refreshments after the hike, there is an official Woodstock restaurants page

Featured activities in Overlook Mountain Trail


Biking is allowed on Meads Mountain Road to Overlook Fire Tower trail and continuing on to the Overlook Turnpike Primitive Bicycle Corridor.


Although there are no set camping sites, primitive camping is allowed as long as its 150 feet away from the nearest road, trail or water body. Also, if you plan to camp for more than three nights or in a group of more than ten, you might need the permission of a forest ranger.

Hunting and trapping

General information on these activities include safety tips as well as rules and regulations on the how-to. It also includes links to seasonal tips on the same.

Rules, regulation and your outdoor safety

  • It is advised to practice the leave-no-trace principles to minimize human impact on natural resources and be respectful of other users.
  • All users of Overlook wild forest must follow all land use regulations and follow all outdoor safety practices for their own safety and to protect the environment.
  • For your benefit, avoid going inside the ruins of the former Overlook Mountain House.
  • There is a privately-owned tower for which the dirt road is maintained and it is recommended to respect this private property.
  • Hiking groups of more than twenty people require a temporary revocable permit from the land manager.

Tips for hiking the overlook mountain

  • It is advised to carry a bug spray to protect from mosquitoes and check for possible ticks after the experience
  • Keep an eye out for rattlesnakes as they are a common to see. They are the most venomous snakes in New York and can grow up to four feet long.
  • If you are bringing a pet, be sure to keep it on a leash
  • Check the forecast beforehand so as to adorn the appropriate gear

Renting a car in the Catskills

Although walking may be a great way to experience Mount Overlook, getting a car may be less tiresome. Also, it may give you a chance to explore more than just Overlook Mountain wild forest. Most of the hotels, trails and attractions are barely within walking distance and public transportation isn’t an efficient way to get around.

Tours in the Catskills

Woodstock NY Rock n’ Roll Tour

This is a historic tour that includes walking music and takes place in Woodstock, New York. It offers privileges such as the company of a roll and rock guide as well as getting an insider’s view of the Bears Ville Center Complex.

3-Day Zip Lining & Waterfall Hike in the Catskill Mountains

This is an amazing experience that provides the chance to see the New York greenery from an incredible top view. Also, the zip line is the highest, fastest and the longest in North America as well as the second largest in the world.

Hudson River Sightseeing Cruise

This cruise should be on your top list of activities to engage in Woodstock. It provides clear views of historic lighthouses, waterfront mansions as well as other remarkable sites aboard the Rip Van Winkle 90-minute cruise. Moreover, the journey has the company of the knowledgeable staff as you see some of the most fascinating views.

Other New York hikes

  • Anthony’s Nose Hiking Trail- it is a decent hike that offers sweeping views of the Hudson Valley and Bear Mountain State Park from the top.
  • Mount Marcy – It is a challenging hike that takes you to the highest peak in New York at 5,344 feet. You’ll need to hike it vertically but it is definitely worth it.
  • Mount van Hoevenberg – This is a steep trek that ends with a panoramic view of the Adirondack High Peaks Region.
  • Bull Hill Full Loop – It provides scenic views of the NYC skyline from the top and is beautiful for a hike.

New York travel insurance

It is advisable to get a travel insurance when visiting New York, mostly medical insurance. Be sure to get it from a company that has a large network and offers both short-term and long-term coverage. Also, the cover should cushion you if you’re traveling for a long time as well as cover, you in your home country.

FAQs about overlook mountain trails

How long does it take to hike Canyon Overlook Trail?

The trail can take upto an hour to hike. It is a one-mile trip and therefore not a long distance.

Is Canyon Overlook easy to hike?

The Canyon Overlook is easy as it is only a mile long walk. Also, it has a parking space that is near the canyon itself, making it easy to navigate.

How long is Overlook trail Beaver Creek?

The trail takes more than 4 hours to hike it. Most people who take it classify it as challenging but equally rewarding.

How difficult is Canyon Overlook trail Zion?

Although the trail is short, it is barely easy. The path emerges on a hilltop covered with pillars of eroded stone.

The Overlook trail is one of the more moderate hikes in New York. It has stunning views when you get the top of the mountain and the fire tower which you can climb to get the aerial feel of Catskills. The Overlook Mountain Woodstock is perfect for a stretch and simultaneous adventure.