A perfect weekend for wine and history is a stay at the Thayer Hotel at West Point.  This historic hotel is located on the grounds of the US Military Academy at West Point with breathtaking views of the region.  They are offering a Sip and Stay Package to introduce you to the history of West Point and a little wine tasting afterward.  
Your stay will begin in the Thayer Hotel’s Zulu Time Rooftop Lounge with amazing views of the valley while you sip a complimentary glass of wine.  Then wake up the next morning and have a nice breakfast in MacArthur’s Riverview Restaurant.  After breakfast you will begin your guided tour of West Point.  
While I never had a guided tour of West Point, I will tell you the history and architecture are amazing.  I spent many years at West Point during football season as a teenager exploring the grounds on my own.  Fort Putnam was one of my favorite places to hike for the day.  Unfortunately I never made it the museum, but will have to do that soon.  

After your tour of West Point you will be taken to Palaia Vineyards to end your day wine tasting and enjoy a  complimentary cheese plate.
The Sip and Stay package begins at $239 midweek and $259 weekend.  For more information on the package click here.

One important note: When staying at Thayer Hotel you must bring proper government issued identification for everyone in your party.  You have to enter the grounds of West Point and go through security check to reach the hotel.