My top recommendations for activities (other than hanging out at home on our huge sofa) would be the hike around Lake Minnewaska (park at the upper parking lot and look for the lake loop) or the Undercliff/Overcliff (both a 15 min or less drive). If the weather permits, go tubing in Phoenicia. For little towns to explore, check out High Falls, Rosendale and Woodstock. A slightly larger town that offers a lot is Kingston. Go wine shopping at the Kingston Wine Co., have a glass of wine at Brunette, enjoy Polish tapas at Lis Bar, drink a coffee at Outdated, enjoy the bookstore/bar/cafe Rough Draft, grab a killer cocktail at Stockade Tavern, and shop at Clove & Creek and Hops Petunia. Click here to discover more hiking trails.
For dinner, check out The Spy (as for the room with a fireplace) or Egg’s Nest (has outdoor seating in the summer) in High Falls. For brunch, Hash in Stone Ridge is a must but Kitchenette in High Falls is also great. For drinks with or without food, check out the brewery and restaurant Rough Cut, do a cider tasting and eat wood oven pizza at Westwind Orchard, and the brewery Arrowood Farms.
It’s fun to go food shopping at Saunderskill Farms in Accord and the Davenport Farm Stand in Stone Ridge (they both have sandwiches, salads and all kinds of fun local stuff to buy). You can also pick up pierogis from Helena's Specialty Foods in Kerhonkson (run by an awesome Ukranian family).
If you need more serious groceries, I recommend going to Emmanuel’s in Stone Ridge and the wine shop next door. The Applestone Meat vending machines are open 24/7 and sell awesome locally raised meats of all sorts. Check out Twilight Acres for flowers and little gifts. The High Falls Food Co-op is open to everyone and has great health-food options, prepared foods and the world’s best key lime pie.