On your (scenic) meandering journey to Woodstock, cross the Connecticut River on bridge from Hanover, NH, to Norwich, NH. (Sidebar: Dan & Whit's store in Norwich is something to experience, but this trip isn't going there now) Pass under the Interstate, and turn Left on Route 5 South. Drive about a mile or two on Route 5 South, and look for Jericho Street on the right hand side. Drive up Jericho Street, which goes up and over a lovely long hill. Jericho Street ends at the junction of Route 14 and the White River.
Turn right (north) on Route 14. Drive on Route 14 for about a mile (?) and look on the left hand side for a bridge that crosses the White River. This will put you on the Quechee/West Hartford Road. Drive up this road (it actually heads southwest, but it is upwards) about a mile or two and look for Joe Ranger Road on the right. Turn Right on Joe Ranger Road. There are some lovely views -looking over pastures toward the hills between VT and NH) on the right hand side of this road shortly after beginning this road. Joe Ranger Road is a dirt road, but it is well maintained. This road ends in Pomfret, and actually crosses Cloudland Road just before it ends at The Pomfret Road. You could take a left on Cloudland Road (also a dirt road), and end up in Woodstock, or you could take a left on The Pomfret Road, and also end up (after you turn left at Teago) in Woodstock.
If that is more of a meander than you had planned, I'll suggest a shorter detour. Rather than taking Route 4 from Quechee to Woodstock, take the more scenic River Road. If you've already seen and "done" the Quechee Gorge, you can avoid that congestion by turning right at The Fat Hat store.
This corner comes up quickly, just as you round a bend (as you are headed West on Route 4). Just before this turn, you'll pass the Mobile Station across from the I89 exit, the country store (?), and a lawn mower/snow blower shop. Turn right at The Fat Hat, and continue down Main Street into Quechee (a very pretty road ). Notice that the Ottauquechee River is on your left. KEEP THE RIVER ON YOUR LEFT. Stay on this road as you drive past Simon Pearce and thevillage of Quechee. About a half mile after you drive through the town, there is a fork in the road...take the left hand fork. STAY WITH THE RIVER. You are now on The River Road. You will drive past the Quechee Club clubhouse and then on towards Woodstock. About 4 miles past the clubhouse, you need to slow down...the road narrows as it dips down towards the river. At the bottom of the road, you will see the Taftsville covered bridge with Route 4 on the opposite side of the river. You do NOT want to get onto Route 4 at this point, you want to take the dirt road into Woodstock. Remember, KEEP THE RIVER ON YOUR LEFT. So, if you want to stop and take pictures of the covered bridge, do, but take the dirt road...you won't regret it. It is my favorite drive...I try to do it every day.
Keep that river on your left, and you'll end up in Woodstock. You'll even pass the start of the oftmentioned Cloudland Road.
I hope you have a wonderful time, and that I haven't been so longwinded that you're already home again!
Hope I'm not too late in posting this!