5 Must-See Spots in the Hudson Valley’s Orange County

As the WPDH Orange Invasion comes to a close, we’d like to thank all the great folks in Orange County for having us and letting us invade your businesses. It’s been a fun month, and it was great to meet so many listeners and to hook them up with prizes. In return, as an Orange County native, I would like to share my favorite historic Orange County sites.

Museum Village on Route 17M in Monroe.

This was an absolute favorite of mine, and whenever we had out of town guests with kids, we’d head to Museum Village. It’s a living history museum where people dress up in 1800s garb and do demonstrations in 1800s rooms and shops. It was so cool, and I’m pretty sure we always left with candy and goodies from the gift shop.

Washington’s Headquarters on Liberty Street in Newburgh.

Even though I grew up right there, I didn’t actually come to appreciate Washington’s Headquarters until I was a teenager. Getting to tour the building and the grounds almost makes you feel as if you were there back when George Washington was there. There are tours and celebrations throughout the year, including a huge Presidents Day Weekend celebration.

The New Windsor Cantonment on Temple Hill Road in New Windsor.

There’s always something going on at what we used to call “The Cantonment.” Tours, military reenactments, and it’s also the home of the National Purple Heart Hall of Honor.

The Brotherhood Winery in Washingtonville

It’s the oldest operating winery in the United States. They actually made their first commercial vintage in 1839. The Winery has tours, tastings, special dinners and beautiful grounds. It’s a great place to get a taste of early Orange County. And wine, of course.

West Point.

Visiting West Point has changed quite a bit in the years following 9/11. When we were teenagers we could just drive in, walk around the grounds, hang out by the river. That’s not how it is these days, and for good reason. But there are still tours, a visitor’s center, and a great museum. If you want a true feel for Hudson Valley History, don’t skip a trip to West Point.