I would do Brandon Gap (on the mountain road) over riding Rt 4 to Woodstock. We did Brandon Gap on our tour of southern vermont, we were fully loaded with camping gear. It is a very steep in places, so we had to stop numerous times, but it really isn't that far or long to climb overall. It is very nice at the top and would be a nice ride over to woodstock from there. From the gap, you get to ride 107 and then 12 to woodstock; at Silver Lake, you get the option to take Stage Road down to the town, which was a very nice road, maybe one of the best I have ridden in Vermont anywhere.