Food

Deer Mountain Inn
The restaurant at the Inn is great. The chef, Ryan Tate, earned a Michelin star at his Manhattan restaurant, creatively named Le Restaurant. (He’ll be cooking for our wedding reception, too.) There’s a relatively simple Inn menu and also a big tasting menu that requires a reservation, and either way you won’t go wrong grabbing dinner here before the welcome party.
Tannersville
Downtown Tannersville is cute, and people like the two Mama’s Boy establishments, one a pizza joint and the other a burger spot. There’s also Twin Peaks Coffee & Donuts and some other cafes and markets in Tannersville. About 10 minutes east down the main drag there’s a fancier market and deli called Circle W, designed for country-going city people like us. These are all great places to for a quick bite.
Phoenicia
About 20 minutes south, this small town is home to both the famous Phoenicia Diner and the equally famous Sweet Sue’s, known for its fantastic breakfast pancakes.
Slightly Farther
Woodstock and Kingston are each about 40 minutes away, and each has its own selection of cute, excellent, appropriately city-meets-country places. But the big-deal, New American, farm-to-table, trés Brooklyn destination restaurant around here is Peekamoose, about 40 minutes away in a town that is somehow still called Big Indian. No doubt some of you are already planning an excursion.

Activities

The waterfall that inspired both the area’s name and the Hudson River School of painters, Kaaterskill Falls is a short drive away and a lovely place to go for a little hike. But be careful: According to the Times, this is dangerous place to take selfies (though we’ve done so successfully).
The home and studio of Hudson River School painter Frederic Church is 40 minutes away, right across the Hudson in Greenport. It’s an impressive house, a National Historic Landmark, and a State Historic Site that claims to be one of the most visited sites in New York.
This remarkable sculpture park is its own work of art. Harvey Fite, a Bard professor, bought a disused quarry, used its stone in his pieces, and then transformed the space itself into a Land Art work that complements the pieces. It’s pretty cool.
The nearest big town, Saugerties has some cute shops and restaurants and, for some reason, a Woodstock museum. (Max Yasgur’s farm was in Bethel, 90 minutes away.) Be sure to check out the lighthouse, on the Hudson riverside.
This sprawling, open-air museum is more than an hour from Deer Mountain, so it's perhaps an ambitious day trip. But it's right off the New York Thruway, so it could make an excellent detour on your way up or back from Tannersville. Heading north to Deer Mountain, take Exit 16. Heading south, take Exit 17. Either way, pack a lunch, follow the signs, and be sure to take the obligatory photos under Menashe Kadishman’s "Suspended."
Forty minutes from Deer Mountain, Woodstock is, well, Woodstock. It’s worth checking out and has plenty of places to eat, but expect plenty of tie-die and crystal among the vintage shops, galleries, and boutiques. We liked the Station Bar, a dive in an old train station, filled with vintage tchotchkes.
Apparently the longest, fastest, and highest zipline in North America — and the second largest in the world — is at Hunter Mountain. Please don’t injure yourself while selfie-ing here, either.
And here is the Deer Mountain Inn Exploration Guide of area activities, including other, more ambitious hiking options.