NY Daily News Highlights Beacon as Day Trip to Escape City
So if you're going to do this, I recommend that you pack a picnic and enjoy it on the lawn of Dia (if you're allowed...I've done it, but not sure if it was acceptable or not). If you're driving, pick up your picnic at Homespun or Crumb. Each will give you a delicious selection of sandwiches, quiche, and soup. Homespun also offers a peppy selection of cheeses.
If you want to go simple but good deli sandwiches, stop at Suppa's Deli for friendly, fast service and drinks and chips. If you need picnic food, just up a few blocks is Key Foods which pretty much has everything you might need.
Then...after your walk through Dia:Beacon, come back to Main St and browse the shops! Pick up a trinket at Dreams in Plastic, shop a collection of Etsy designers at Clay Wood and Cotton, browse designers of jewelry and home goods at Global, get a cute yoga top from Mountain Tops, and this is just the beginning. There are more shops on thus end of town, and then more on the East end, near the mountain. Be sure to hit Echo (boutique and toy store), and her neighbor, a hat shop.
This is one day trip. Looks like you'll have more day trips up here to Beacon that will all be different!