Woodstock, VT

Hannah’s family visited the remote town of Woodstock, Vermont many years prior to our most recent outing, opting to stay at the beautifully lavish Woodstock Inn. Today, however, the price of a room now bordered on absurd. So we set our sights on the highly rated B&Bs in the area, and The Jackson House Inn was a clear winner. Expensive in its own rite, the establishment’s gorgeous new bathrooms and delectable breakfast were worth the price of admission. Even still, we chose to visit during the winter months in an effort to both avoid the crowds and enjoy the stunning snowy scenery.

Our itinerary included everything from an open sleigh ride through Billings Farm, a self guided walking tour / shopping spree through downtown Woodstock, and a not so quick stop at a glassblowing factory. We would certainly recommend Billings Farm, although be prepared for the smell in the milking department. Start with the 20 minute movie in the visitor center – it provides a good history of the area – and check out the upstairs exhibit if you have time. If you’re visiting in the winter, be sure to jump on line for the sleigh ride. It’s a quick trip around the farm, but a wonderful way to enjoy the countryside. Don’t forget to stop by the farm house during your visit as well. If you’re traveling with kids, try to attend one of the many demonstrations they offer, such as butter making. (It’s more entertaining than it sounds!) There are walking paths nearby, which would be a nice addition to almost any trip. Unfortunately, the 20 degree weather made that an adventure we decided to skip.

The retail opportunities in Woodstock are extensive. We loved Danforth Pewter and the Vermont Flannel Company. Everything’s made either on the premises or right down the street. The general store was fun as well, and contained a number of surprising, high quality merchandise such as Peterborough baskets. Unfortunately, the staff was disinterested and not very helpful.

On our way back to Boston, we stopped at the Simon Pierce factory and restaurant, a fantastic operation including a glassblowing workshop, 5-star restaurant, and expansive shop. Plan to wait for lunch – the restaurant does not take reservations – but the wait is worth it. Almost the entirety of the dining area looks out on the waterfall that powers the generator below. When you’ve finished your meal, be sure to stop by the “seconds” section of the store. The works are fun to browser and there are usually some great deals to be had.

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