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Cliff Calderwood is a travel writer living in rural Massachusetts. He writes extensively about New England where he has lived for the last 27 years with his family and dogs.

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An October Trip to Northern Vermont - Part II

fall foliage green mountains imageThis is part II of my recent journey to northern Vermont and the Northeast Kingdom.

If you remember part I was where I explored from The Berkshires in Massachusetts and followed Route 7 north to Rutland in central vermont.

While I really wanted to continue my fall foliage exploration on the western side of the Green Mountains I realized this would have to be another journey as I was growing concerned with traveling through the Kingdom in darness.

This is hunting season and the moose and deer are hyper-active after dark this time of year.

So from Rutland I picked up Route 4 east and cut over towards Interstate Route 91. This section of Route 4 is highly scenic as it traverses through the Killington area following Route 100 South briefly to West Bridgewater before heading over to Woodstock. On certain dates in October the Killington Skyship takes you to the summit for wonderful fall foliage views from its 4,235-feet peak.

Route 4 follows the picturesque Ottauguechee River as it winds through villages and farmlands outside the Woodstock area. It’s not a fast route but worth taking slowly anyway to enjoy the Vermont rural feel.

Woodstock is a popular destination for many, especially in October. It has a much photographed covered bridge right off the village green and a number of well-preserved buildings on the square. Most people find a parking spot on or near the square and walk around town to enjoy the atmosphere and take a few pictures.

The Woodstock are includes a number of attractions such as Billings Farm Museum, Marsh-Billings-Rockefeller National Historic Park, and of course Quechee Gorge.

Getting through Woodstock today was slow but the weather had cleared and it was a chance to refresh my memory of the place as I made my way to White River Junction to pick up the last major and long part of my journey on Route 91. The rain of the previous week had turned the fields an Irish green so common to see in this area of Vermont in the fall.

This was my first trip on Route 91 north beyond White River Junction, and it proved to be captivating. On a few occassions I almost lost the sensation I was in a car as the Connecticut River Valley spread out before me and I could see both Vermont and New Hampshire communities along the river.

The drive provided memorable foliage scenes as I moved towards St. Johnsbury as this area had reached peak, and had even moved beyoond peak away from the river region.

I reached St. Johnsbury still in plenty of daylight and turned west on Route 2 towards West Danville where I picked up Route 15 west. These towns and villages are in Caledonia, one of the three counties that make up Vermont’s Northeast Kingdom.

While my drive takes me along the southernmost extreme of the Kingdom its reputation is evident even here. The roads between villages seem longer and the blending with the wilderness evident with the onset of sunset it does seem well-named as a Kingdom.

My final destination takes me through Hardwick and then continuing on Route 15 to my final destination of Wolcott. I saw the sign for Cabot Creamery Tours in South Walden, and then the famous Fisher Covered Bridge approaching Wolcott. The fall foliage was past peak in this area and the leaves were well into their dropping phase. But I knew just a few hours drive south they were still waiting for peak.

This is the way it is in New England during the fall season - in October if you want to see peak you just have to be flexible and drive around and you’ll see it happening in some town or village throughout the region.

I had a wonderful day’s journey reaching northern Vermont, and I hope you have a chance to sample some of the places I’ve described and make time to get off the interstates and explore the backroads of Vermont.

This completes my journey log and you can read the first section of my Vermont trip by clicking here.

For more suggestions on things to do in the area check out my Vermont vacations page by clicking here.

Cliff Calderwood
Executive Director
Attractions in New England Guide



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  1. [...] Read Part II of my trip by clicking here. [...]

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