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Vermont (and the Berkshires), VT
Sunday, September 28, 2025 - 5:30pm by Lolo
miles and hours from our last stop - 5 night stay
Travelogue
Day 1 - Williamstown and MASS MoCA
Williams CollegeThis trip really had legs - starting off just the two of us “Up Island” on the Vineyard, followed by the climax of 7 wonderful days in an incredible house on Edgartown Harbor with the kids and grandkids, and now the wind down driving the scenic roads of the Berkshires and Southern Vermont in search of Fall foliage.
Our first stop on our foliage tour was Williamstown, a place very near and dear to our hearts, as it was where both our sons and one of our daughter-in-laws went to college.
We took the scenic way to get there via the Mohawk Trail (Route 2), which stretches 60 scenic miles across northern Massachusetts) from Greenfield on the Connecticut River to Williamstown near the New York border.
The serpent behind the Clark InstituteMore than just a road, it's a historic and cultural corridor that offers some of the most stunning vistas in New England.
Unfortunately for us, we were a little early for many leaves to be changing.
However, it’s still a lovely drive with quite a bit of history. Long before it was a highway, the Mohawk Trail was an important footpath used by Native American tribes for trade, hunting, and travel between the Connecticut and Hudson River valleys.
In 1914, the state opened it to cars, making it New England’s first “scenic tourist route.” This transformed the trail into a popular destination for "auto-touring," with gift shops, inns, and attractions springing up along its path.
MASS MoCAWhen we got to Williamstown, we checked into the Maple Terrace hotel, along the Mohawk Trail at the edge of town.
Noting the lack of his Maple tree which is usually a vibrant red around this time, he told us that it had been a very dry and warm season, so the leaves were turning brown and falling off the trees before they had a chance to turn vibrant. Oh well, maybe things would be better further north.
MASS MoCAThe motel had a lovely garden area with Adirondack chairs where we enjoyed some wine and cheese before heading into town to find a place to have dinner.
Rather than walk along Route 2, I suggested we walk through the cemetery behind the motel. I told a very skeptical Herb that I remembered that when on a run over a decade ago, I found paths that would bring me over to the college.
MASS MoCANot trusting my fairly poor spatial skills, he reluctantly followed, but much to my relief, we popped out on Water Street just as it was getting dark. And to add to my gloating, we were right by the Water Street Grill, a restaurant we frequented often back in the day. Wow! This was a blast from the past, as we had eaten here with the boys and their friends many many times.
We had had a big lunch with the kids in Falmouth before parting, so we weren't all that hungry, so we just ordered some salads.
MASS MoCANot wanting to go back to the hotel through the dark park and cemetery, we took the less adventurous way along Route 2.
Besides its incredible natural beauty, Williamstown is renowned for its high concentration of art and culture.
MASS MoCAUnfortunately the Clark Art Institute was closed today, so before heading north to Vermont, we decided to visit MASS MoCA in nearby North Adams.
Housed in a 16-acre complex of renovated 19th-century factory buildings, it is one of the largest and most ambitious contemporary art institutions in the United States.
Through the windowInstead of erasing this industrial past, the museum's design embraces it, creating a unique environment where art and history intersect.
The museum’s huge, light-filled galleries (one nearly the size of a football field) allows MASS MoCAto exhibit large-scale, immersive installations that would be impossible to realize in a conventional museum setting.
The museum is home to several monumental, long-term installations by internationally renowned artists, including a 25-year exhibition of wall drawings by Sol LeWitt, immersive light installations by James Turrell, and major works by Anselm Kiefer and Louise Bourgeois.
The sheer size of this museum, with its interlocking courtyards, bridges, and walkways, required and deserved more time than we were able to give it, but we very much enjoyed the exhibits that we were able to see.
Now it was on to the covered bridges, country stores, red barns, and hopefully vibrant leaves of Southern Vermont.
Day 2 - Bennington Covered Bridges, Hildene, and Manchester View Hotel
Henry Covered BridgeLeaving Williamstown, he headed north on Vermont Route 7 towards the historic town of Bennington, a town rich with colonial history, artistic heritage, and the scenic beauty of the Green Mountains. As Vermont's first town, chartered in 1749, it offers a quintessential New England experience.
One of those experiences is photographing and driving over one of Vermont’s many historic covered bridges.
We found two of them in the Bennington area: the Paper Mill Village Bridge and the Burt Henry Covered Bridges, all within a short drive of each other.
Paper Mill Covered BridgeBoth were classic Vermont covered bridges - long, narrow picturesque barn-like structures, painted barn-red with a gabled roof, set on a foundation of stone abutments.
Their sides are covered with weathered, vertical wood siding, often with one or two small, square windows cut into them to allow slivers of daylight to pierce the dim interior.
The entrance, known as the portal, is a prominent arch or rectangle, often topped with a sign listing the bridge's name, its clearance height, and the year it was built.
Hildene EstateThey are very difficult to photograph without either falling into the stream or getting poison ivy in the bushes that surround them. Instead of shooting the bridge straight-on and only showing its portal, the best vantage point is to move to the side so you can still get the front portal, but one of the sides of the bridge as well, giving it a sense of depth and dimension.
A surprisingly significant number of cars drove through the bridges when we were there. These were not just pretty to look at, but the necessary means of crossing streams and rivers.
Hildene EstateAs each car drove over the wide plank floorboards of the bridge, we could hear the rumbling and creaking under the weight of the car.
Before continuing on to Manchester, we stopped for lunch at a place in Bennington called Ramunto’s Brick Oven Pizza. You can always tell a place is going to be good when it’s crowded with local workers.
From there we left Route 7 and took the more scenic Route 7A through the picturesque town of Shraftsbury before stopping at Hildene, the magnificent former summer home of Robert Todd Lincoln, the only surviving son of President Abraham Lincoln.
The home is perched on a promontory with breathtaking views of the Battenkill Valley, nestled between the Taconic and Green Mountains.
View from our balconyThe name "Hildene" comes from the Old English words for "hill" and "valley with stream."
Visitors can tour the meticulously preserved 24-room Georgian Revival mansion, which is furnished almost entirely with original Lincoln family furniture and personal belongings.
Dinner at Thai BasilWe had already toured it several times before, so we chose instead to stroll through the beautiful grounds surrounding the house, the highlight of which is the formal garden, designed to resemble a stained-glass cathedral window.
The pattern is created with privet hedges, and the "panes" are filled with a vibrant mix of annual and perennial flowers.
Then it was on to the Manchester View Hotel, our home for the next three nights. We would use it as a base camp to explore the various scenic drives through Southern Vermont.
Our room had a private balcony with lovely mountain views and a real-wood fireplace to cozy up to in the evening. Very nice!
We had dinner that night at Thai Basil, a charming and cozy restaurant in the heart of Manchester, Vermont, offering authentic Thai cuisine.
Day 3 - Scenic Drive on Vermont 100, Rutland, and the Southern Vermont Art Center
Along Route 100Today we drove another one of Vermont’s scenic roads - Route 100, a scenic byway that stretches for over 200 miles, winding through picturesque villages, past rolling hills, and alongside crystal-clear lakes and rivers.
Our first stop was the famous Vermont Country Store in Weston, a nostalgic, old-fashioned general store with an eclectic collection of everything from clothing to home goods, to toys and gains. I remember about 30 years ago not being able to tear the kids away from this store.
SVAC horse canvasI actually remember what Tommy bought - a fighting nun hand puppet with a habit of fighting for what is right. Called the Punching Nun, it was activated by levers inside its habit, which made its arms punch like a heavyweight boxer. He absolutely loved it.
Our original intention was to drive all the way up to Stowe, another 2+ hours (each way), but the leaves just weren’t colorful enough to make all that driving worth it.
SVAC sculpture gardenInstead we drove as far as Killington, and then turned West of Route 4, stopping in the town of Rutland for what turned out to be a fabulous lunch at a place called Roots.
This lovely, elegant restaurant was tucked away in an alley, which we were only able to find by asking someone. I had a delicious Scallops Salad.
From there we continued west along 4, and then Route 30 back to Manchester.
Cozy nightBefore going back to the hotel, we stopped at the Southern Vermont Art Center, set on a picturesque 100-plus-acre campus at the foot of the Taconic Mountains.
The SVAC features a variety of exhibition spaces as well as the largest sculpture park in Vermont. creating a unique fusion of art and nature.
By far my most favorite work was a statue of a horse covered with paintings by Leonardo da Vinci, Magritte, Van Gogh, Vermeer, Monet, Munch, Michelangelo, Degas, Klimt, and more.
That night back in our very cozy room at the Manchester View, Herb made a fire (real-wood not gas), and we cozied up with some wine.
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