SOLD OUT: Overlook Mountain House Winter Hike: Woodstock, NY – 5 Miles/Moderate+

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  • 03/20/2021
    8:45 am - 6:00 pm


By far one of the best views of the Hudson Valley you will ever see and a trip back in time to 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 of in downtown Woodstock for food, drinks and to check out the hippies! (indoor dining is still and option upstate)

How it works:

  • Register and we will send you very specific info on where to meet and what to bring.
  • You may take Metro North, Amtrak or drive to meet the group at the Poughkeepsie Train station at 10:40am.
  • Your guide will pick you up in Poughkeepsie and bring you to all the activities.
  • You will be back on the 6:50pm train at the latest.


  • 10:40am pick up at Poughkeepsie Train Station
  • Pick up lunch at local Deli if you did not bring your own.
  • Travel to Woodstock and Overlook Mountain
  • Hike for about 90 minutes before stopping at the top for lunch.
  • After hike we will stop for hot chocolate and snack at a local bakery.
  • Depart for train.  5:50pm or 6:50pm at the latest depending on how the group manages the hike and time in town.

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 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

Cost: $70 includes ($60 VIP Members): transportation to and from the Poughkeepsie Train station, park fees, guide fee’s, taxes and gratuities.

Not included: Lunch, Train fare,  (you may also drive to meet the group at the train station)

Covid 19 Protocols:

  • Please do not come if you have been exposed.  You may cancel up to one week for a refund.  Within one week you will be given a credit to use for selected events.
  • We will take temperatures when you arrive.
  • Event limited to 6 people so there is space for everyone to be safe. We will be traveling with 6 people in an 8 passenger SUV.  That gives a space between each person.  Windows open and heat blower on.
  • Face masks must be worn while within close proximity..


Can I come alone?  Yes, 98% of those attending this event normally register on their own. You welcome to bring as many non member guests, friends & co workers as you’d like, just make sure to register for the number of people that you want below. Our staff will be ready to greet you and introduce you to others whether you are on your own or with guests.

Do I need a ticket? We will have your name on our list.

Dress Code:  Dress for the weather check The National Weather Service ONLY  (they do not alter forecast for advertising)  New Paltz NY Location.

How will I find the group?  We will send you a confirmation email with exact locations, contact info and names of those who are hosting the event when you register. We will send follow up emails as we get closer, usually the night before or morning of.

Ages: 21+  Most of our events attract 20’s -40’s although some events can skew younger or older (50’s) depending on the event. Some events are clearly age specific as indicated.   If this is an issue for you contact Dave at the address below and we can usually give you a very accurate idea of what to expect.

Who Comes to These?: Our activities attract NY Professionals from all backgrounds and professions who are looking to expand their social circles.  You will also find others who are looking to learn something, network for business, try something they have never done before or enjoy something they love doing but can’t get their friends to do. There may also be some people looking to find that someone special who share a passion for the same activities (but don’t make this the sole reason you come out).

Questions?  If you want to know how many people are coming, what the ages are likely to be, the gender breakdown or the overall vibe of the event before you register, contact Dave Cervini at or call 212-873-2256.

What if the weather impacts the event?  We will determine if the event will happen about 24 hours prior to the start.  You will be notified as soon as we know.  We usually send updates as well

This event is nonrefundable unless the event is canceled or rescheduled.

By registering for this event you take full responsibilities for your actions and agree to conduct yourself accordingly.




or Drive to Meet the group at PK Train Station, New York, Poughkeepsie


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