Home » 2025 Martha's Vineyard & Vermont

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 CollegeWilliams 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 InstituteThe 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 MoCAMASS 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 MoCAMASS 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 MoCAMASS 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 MoCAMASS 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 MoCAMASS 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 windowThrough 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 BridgeHenry 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 BridgePaper 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 EstateHildene 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 EstateHildene 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 balconyView 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 BasilDinner 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 100Along 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 canvasSVAC 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 gardenSVAC 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 nightCozy 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.

Day 4 - Hike and wander around Manchester

Lye Brook FallsLye Brook FallsRather than taking another long drive, we decided to hang out around Manchester for the day, starting off with a hike to Lye Brook Falls, a very popular hike to a waterfall, that begins at the end of the Lye Brook Access Road.

The trail starts off on a wide, flat path before entering a mixed hardwood forest. From there, we followed an old logging railroad before the trail began to gradually climb on much rockier terrain.

We crossed a few small streams and muddy places before coming to a fork where we took the one to the right, which led us on a spur trail to the falls. This section of the trail narrowed and hugged the side of a hill, with some interesting rock faces and running water.

I found a red leaf!I found a red leaf!At 2.3 miles, we arrived at Lye Brook Falls, one of the highest waterfalls in Vermont, cascading approximately 125 feet down a series of tiers.

Before we started on the hike, Herb had looked to see if there were any Geocaches along the way, and found that there was one near the falls.

For those of you fellow travelers unfamiliar with geocaching, very briefly, it is an outdoor treasure-hunting game, in which people hunt for geocaches that have been hidden by someone. All these hidden caches can be found on the Geocaching app.

Participants, like us, then select a Geocache nearby to hunt for and then navigate to its GPS coordinates using a GPS device or smartphone with a geocaching app to navigate to the cache’s location. The Geocache App tells you how far away you are from the “treasure,” and when you walk, it tells you how many feet you are away from it. It also gives clues about where it is hidden.

Colorful leaves in a streamColorful leaves in a streamThe geocaches themselves are waterproof containers (ranging from tiny little containers to ammo boxes) that contain little trinkets for trading—items that you would just throw away if you found them in your house, but for some reason feel like treasures after having gone through so much trouble trying to find them. I have a box of “treasures” I felt worthy of saving in my wall unit.

If you find it, as we did, you sign a logbook. If the cache contains small trinkets or "swag," you can trade items, taking something and leaving something of equal or greater value.

It might seem silly, but it’s a global phenomenon, with millions of geocaches hidden in over 190 countries.
Herb beat me to it this time

Geocache successGeocache successThen we retraced our steps back to the car for a total of 4.6 miles and 934 feet of elevation gain. It was a nice way to spend a morning.
Later that afternoon, we went back into Manchester and stopped in Orvis to look at fly fishing rods and the very well-stocked Northshire bookstore.

In the “Readers Park” on the outdoor patio of the bookstore, we came across a metal sculpture of Thomas Jefferson that brought back so many memories for us. It used to stand in front of the old Jelly Mill, a once cherished and iconic destination in Manchester, which was sort of a gift shop on steroids - a multi-level emporium housed in a sprawling, renovated dairy,barn, that you could get lost in for hours wondering through their eclectic array of goods.

Thomas Jefferson statueThomas Jefferson statueI’m not sure who loved it more - my 80-year-old mother or my then 10 and 12-year old boys.

The point of my diversion is that the Thomas Jefferson statue outside the Northshire Bookstore used to stand in front of the old Jelly Mill.

On one hand, Jefferson holds a model of a church, and on the other, a government building. This is intended to represent the principle of the "balance of church and state," a concept deeply rooted in Jefferson's writings and political philosophy.

The rest of the statue continued some of Jefferson’s most famous quotations.

This was our last night in Manchester, so it was quite nostalgic to bring us all the way back some of our earlier visits when we used to come here with our young sons and my Mom and Dad.

Tomorrow, we would head to Shelburne Falls along the Mohawk Trail to spend the last night of our 2 ½ week East Coast vacation.