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04/25/2026
8:45 am - 6:50 pm
Overlook Mountain Hike & Woodstock Adventure
Experience one of the most spectacular views in the Hudson Valley while taking a step back in time at the abandoned Overlook Mountain House Hotel (1824–1923) in historic Woodstock, NY.
This hike is definitely a workout, but the incredible views and fascinating ruins at the summit make it well worth the effort.
After the hike, we’ll head into downtown Woodstock for food, drinks, and a chance to explore the town’s famous artsy and hippie culture.
How It Works
Register for the event and we will send you detailed instructions on where to meet and what to bring.
Your guide will pick up the group in Poughkeepsie and provide transportation to all activities.
We will return you to the station in time for the 5:50 PM or 6:50 PM train at the latest.
Itinerary
9:59AM – Pick up at Poughkeepsie Train Station
Stop at a local deli to pick up lunch if you did not bring your own
Travel to Woodstock and Overlook Mountain
- Hike:
• Approximately 90 minutes up the mountain - 5 miles roun
• Lunch break at the summit with incredible views and the historic ruins - 60 minuted down the mountain
After the hike:
• Stop in Woodstock for food and drinks
• Explore the town before departing
Return to Poughkeepsie for the 5:50 PM or 6:50 PM train, depending on the group’s pace and time spent in town.
How Difficult Is the Hike?
The hike follows an old carriage road that climbs steadily up the mountain.
• Difficulty: Level 7 out of 10 (due to the incline)
• Terrain: Wide, easy-to-navigate path
• Duration: About 90 minutes up and 90 minutes down
The incline will definitely get your heart pumping — and you probably won’t need to go to the gym the next day!
About the Overlook Mountain House
Perched high above the Hudson Valley, the Overlook Mountain House Hotel (1824–1923) was once a grand Catskills resort. Today, the haunting stone ruins remain and offer one of the most dramatic viewpoints in the region.
Cost
$85 per person ($75 VIP Members)
Includes:
• Transportation to and from Poughkeepsie Train Station
• Park fees
• Guide fees
• Taxes and gratuities
Not Included:
• Lunch
• Train fare
(You may also drive and meet the group at the train station.)
Can I Come Alone?
Yes! About 98% of people attending our events register on their own. These events are designed to be social and welcoming.
Dress Code
Dress for the weather. Please check The National Weather Service forecast only for the most accurate information:https://www.weather.gov/ Use New Paltz, NY as the location when checking the forecast.
Hiking shoes recommended
Ages
21+
Questions?
If you’d like to know how many people are attending, the typical age range, gender breakdown, or the general vibe of the event, feel free to contact:
Dave Cervini
dave@newyorksocialnetwork.com
212-873-2256
Weather Policy
We will determine whether the event will proceed approximately 24 hours before the start time. You will be notified as soon as a decision is made, and updates are usually sent in advance.
Refund Policy
This event is nonrefundable unless it is canceled or rescheduled.
Liability
By registering for this event, you acknowledge that you participate at your own risk and take full responsibility for your actions, and agree to conduct yourself accordingly.