Hey BigDog,
I myself live in the Woodstock area also, a little town called Reading. There are several things to do in the area. For lodging it might be a bit cheaper to stay in White River Jct. As the area offers chain hotels. From there you can drive through Quechee to get to Woodstock. In Quechee Simon Pierce is a cool place to check out. They blow glass there and also have a great restaurant. You may also want to stop quickly and check out the Quechee Gorge. These are both free things to do. In Woodstock there is the Billings farm museum that may be something to check out. Woodstock is a quaint town that is great to stroll through. If you are into covered bridges there is the Taftsville bridge which is between Quechee and Woodstock. Woodstock offers a covered bridge in town and another west on Route 4. If you go out route 4 you may want to go a little further to Killington Resort and take a ride up the Mtn. on the gondola. The ride on 100 south is beautiful and there are several small towns that you will go through. Weston offers the bowl factory and the famous Vt. Country Store.
If you decide to go east to Windsor- The Birthplace of Vermont- there are several things to do there. Harpoon Brewery, Another Simon Pierce but a modern version of the one in Quechee, The American precision museum, Our Nations longest covered bridge. The Windsor/Cornish covered bridge, which spans over the Ct. river. And if you are into smoked meat just down the road from the American Precision Museum and the covered bridge is a place called Green Mtn. Smokehouse. They are a USDA processing facility, but you can purchase their delicious goods in the small retail store out front. They received the Yankee Magazine Food award for Best Bacon in New England. Sooo.. as you can see you have lots of fun options. The only thing I would suggest is to go online and check to make sure what you want to see is open as we are going into the shoulder season.
Enjoy your time and safe travels.
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