Overlook Mountain House Fall Hike: Woodstock, NY – 5 Miles/Moderate+

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  • 10/08/2022
    9:00 am - 7:00 pm

Take a trip back in time and see one of the best views the Hudson Valley has to offer during the peak of the fall foliage at the abandoned Overlook Mountain House Hotel (1824-1923) in historic Woodstock, NY.

This hike is a workout, but worth it for the views.

Following the hike we will stop in downtown Woodstock for food, drinks and to check out the hippies!

What to expect from the Overlook Mountain House Fall Hike:

  • Our chauffeur driven van will meet the group near Penn Station at 9am.
  • We will drive to Woodstock, NY for the hike to Overlook Mountain House.
  • When we reach the top we will sit for lunch overlooking the valley.
  • After the hike we will stop in the town of Woodstock to have a bite to eat, relax and check out the hippies!
  • Our van will drop you off back near Penn station at or around 7pm.

Cost:  $150 ($140 V.I.P. Members) includes: round trip transportation with professional driver to and from the city and all attractions.

Not Included: Lunch.  Bring your own or we will stop along the way to pick up food.

How hard is the hike? This hike is an old carriage path straight up the mountain. It is at a constant incline that will keep your heart pumping for 90 minutes up and 90 minutes down.  It is a level 7 out of 10 only for the incline otherwise the terrain is easy to navigate. You won’t need to go to the gym the next day!

About Overlook Mountain House Hotel: MH History


Can I come alone? Yes, most guests do! It’s a great way to meet new people.

Dress Code:  Dress for the weather. Casual and comfortable. Hiking shoes recommended.

Ages: 21+

What if it rains?  We will determine the night before.  If the hike is canceled or rescheduled you may switch to the new date, use this trip as a credit or get a refund.

Questions? Email Dave Cervini at dave@newyorksocialnetwork.com or call 212.873.2256, M-F 10am to 4pm.

Nonrefundable unless canceled.


Looking for more adventures outside the city? Click here.





COVID-19 Protocols: In accordance with current city and state protocols vaccination status is not mandatory for this event.  However, we do ask that participants act in a responsible manner and do not attend if feeling ill, showing symptoms or have been recently exposed.  Mask wearing is optional unless the venue or city has mandated that.  Everyone should respect the comfort levels of others as we transition into this next phase of socializing in the Covid era.

This event is nonrefundable.  If you have tested positive for Covid and cannot attend, we will do our best to provide you with credits to select future events with a copy of your positive test results. Please note that due to the cost involved in some activities credits may not be used for the event you missed.







254 West 31st, near 8th, New York, New York, 10001


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