Travels with Bonnie: Lake Willoughby in the Fall

Lake Willoughby, Vermont is a great fall destination and there are so many great ways of getting there from the border area around Derby Line and Derby Center:

The shortest route from the border area is to take Vermont Route 5A/105 through East Charleston to the junction where 5A turns south and 105 continues eastward. Turn south onto 5A and it brings you right to the Willoughby Lake public beach at the northern end of the Lake.

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Starting in Orleans, Route 58 takes you west all the way to 5A just a hop-skip-and-jump north of the Lake. 58 is scenic with lots of twists and turns to keep riding interesting. Exceptional views of the Willoughby Gap towards the 5A end.
Or, from Orleans take Route 5 to Barton (just a few miles) and get on Route 16 (other end of town, piece of cake). Route 16 is a very enjoyable ride past Crystal Lake just outide of town and then many twists and turns later right to the Lake Willoughby public beach and parking lot.

While IMO 58 has the most scenic views of Willoughby Gap, the scenery along 16 is even more compelling by virtue of being in your face. But beware of distractions for its twists and turns are in general more demanding than those of 58.
The full Monty is to take Route 111 out of Derby Center (green on map) to Seymour and then Island Pond (via a portion of Route 114, which goes up to Norton VT). At Island Pond catch 105 west to Westmore Road and take a left. You're going uphill, uphill, uphill, on gravel road, not too much loose, and then you go over the peak and fall on an observation point, where you can park and take in the magnificent Lake Willoughby and its spectacular shores. All asphalt down from there on Hinton Hill Road right to the Lake, take a right then take a left at the beach and take 16 to Barton where you'd go north on 5 just a bit before taking Maple Hill Road with its great views and then continue down the hill when it turns into Water Street; near the bottom of Water Street take a right on East Street until you soon come to sort of a "Y" then veer left over the river onto Tarbox Hill Road which becomes Frog Hill Road just before the stop sign at the intersection with Hinman Settler Road. Hineman Settler Road takes you all the way back to the start at Derby Center.

As you can see by the map, a trip between the Stanstead border area and Lake Willoughby has many possibilities for interesting routes through beautiful scenery.