The former Hat Making Capital of the US is enjoying a revival as a destination for arts and culture. It has great food, breweries, book shops, art galleries, hiking, and a spooky island housing the ruins of a 19th century castle designed by an arms dealer. Recommendations include Dia Beacon (see below), the Roundhouse restaurant, hiking Mount Beacon, and Hudson Valley Brewery.
The second largest New York State Park with lots of options for camping, hiking, fishing, picnicking, etc. We hiked the Reeves Brook Loop, which is listed as a "moderately challenging" hike online, but was described to us by park staff as "moderate to hard," which is not the same thing. It involves a daunting but doable rock scramble that calls for both hands and both feet. And you might split your jeans if you had dressed for a moderate hike. But the view is worth it!
Sasha and I have gone to a Ren Fest every year we've been together. I go for the celebratory atmosphere, the period garb, the flagons of ale, and the feeling of being in one of my favorite works of medieval fantasy. Sasha goes to make fun of people like me.