Woodstock is to me quintessential Vermont, but with an upscale touch. Or maybe more than just a touch - everything *is* upscale here. The town is located in a lovely valley between the Green Mountains and the border to New Hampshire in central Vermont. With a population of about 3,200 it has the right size for a place to spend a few days on vacation - you'll find everything from great lodging, superb restaurants, shops, museums etc.
Be prepared that the main road going through the town, US 4, is quite busy. Vermont doesn't have a lot of East-West connecting roads and this is one of them.
The town looks back at a history of about 250 years. As the highly dignified seat of Windsor County since 1766 it prospered well. People built many grand houses, especially around the town's common.
The town is still wealthy nowadays and it shows. The Rockefellers and the Rothschilds own estates in Woodstock and the surrounding countryside.
We visited Woodstock in early October 2007. The foliage was not in full swing yet, but it was a good start. I'd characterize the landscape as rolling hills - no frightening mountains, no endless flat ground either. Lovely. I wish we'd had one or two more days there; two nights was definitely not enough.