Last weekend I got “permission” from my family to visit a friend living in Wolcott, Vermont, on the fringe of the Northeast Kingdom.

And this time of the year the Kingdom can be spectacular with the fall foliage and the crisp autumn air.

Now this fall, Mother Nature has played a few tricks on New England, with a dry August, and a warm September. The fall has not only been late in all areas but when it came the show was somewhat muted in colors. The last few weeks have been different with temparatures being more like normal and plenty of rain. So I anticipated my journey with great hopes of having a revitalized leaf peeping trip…

Where I live in central Massachusetts the most direct route to my friend’s place would also be one of the most boring along interstates virtually all the way. But as getting to my destination was going to be part of the vacation, and I hadn’t visited the western slopes of the southern Green Mountain National Forest for awhile, I took a slower and much longer route.

I started my trip in torrential rain heading west on the Massachusetts Turnpike (Route 90) and taking the exit towards Lenox, right in the heart of The Berkshires.

Despite the rain, the colors were magnificent, a testament to the fact leaf peeping can be worthwhile even on gray overcast days. Sometimes the grayness emphasizes the contrast of colors more than on a sunny day, when shadows can hide the subtle range of yellow and reds.

The town of Lenox plays host to Tanglewood, summer home of the Boston Symphony Orchestra, and where I picked up Route 7 to head north towards Pittsfield and the highest peak in Massachusetts - Mount Greylock. This mountain has a number of literary connections, with both Herman Melville and Henry Thoreau spending much time hiking this whale-shaped hump of a mountain.

Route 7 is not a fast road as it winds around lakes and edges of parks and forests. But what it lacks in speed it more than makes up for with stunning views of the Berkshire Hills and wide vistas of open fields and valleys.

North of Greylock and close to the Vermont border is the picturesque town of Williamstown. This is always one of my favorite destinations to visit in The Berkshires. If you’re lucky you can drive slowly with nobody behind you, and savor the moment, otherwise stop shortly after the town when the fields open out and offer great views of the town and surrounding pastureland.

After Williamstown the road transported me into Vermont and through Pownal and on into Bennington, and this is where I took my first break of the trip.

Bennington makes a worthwhile stop for any trip in this region. The town is rich in history, buildings and charm. By now the rain had eased and I enjoyed walks around the town with its antique shops, cozy restaurants, and of course the Bennington Monument. For covered bridge fans Bennington has a couple of fine examples to view and they’re well sign-posted and only a short drive from the town.

For visitors a full day should be planned in the Bennington area to appreciate its attractions, but my final destination was many miles to go, and so I headed out north on Route 7 after a short break.

The section of Route 7 between Bennington and Manchester hugs the western slopes of the southern half of the Green Mountain National Forest providing scenic lookouts and wide views of mountains to come. Every now and then the clouds would break and allow sunlight to stream through and make the slopes dance multi-colored golden. On a day with more time and less clouds I’d take a detour into Manchester and visit Hildene House and then drive the Mt. Equinox Skyline Drive.

Beyond Manchester the route passes through the Dorset’s and onto Danby, Wallingford, and finally my next major stop - Rutland. Other worthwhile detours along this section include Emerald State Park and White Rocks Recreation Area. This region has a number of fine hiking trails and places for picnics. I make a mental note for a family trip to this area in the future.

I arrived in Rutland about mid-afternoon, needing a break from driving and some energy food.

Rutland is a large town sitting on the southern edge of the northern half of the Green Mountain National Forest. In the winter it’s a popular base for Killington Peak skiers, and in the summer a good place for supplies when backpacking in the forest. I found a local eatery and sat down with a coffee and my Vermont map to plan out the remainder of my drive to the Northeast Kingdom. I wanted to see more foliage and also drive through areas of Vermont I’d never visited before - but I also wanted to get to my final destination before dark and avoid any moose encounters with my vehicle… I knew who would come off the worse!

I’ll have details on the second part of my trip in a few day’s time, and it turned out to be the most scenic of the whole trip.

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

Read Part II of my trip by clicking here.

Cliff Calderwood
Executive Director
Attractions in New England Guide