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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.
Day 4 - Hike and wander around Manchester
Lye 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!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 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 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 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.
Day 5 - Hike to the Mount Olga fire tower in Molly Stark State Park and Shelburne Falls
Setting off on the Mt. Olga TrailThis was it. The final day of what had been a fabulous 2 ½ week nostalgic trip back to some of our favorite spots on the East Coast, with the highlight being a full week with our sons, wives, and grandkids in a beautiful home on Edgartown Harbor on the island of Martha’s Vineyard.
Not that we had any choice, but we were pretty ready to get back home to Sonoma Valley, where we hoped to see the fall foliage colors of the grapevines in the wineries near our home.
But, this trip still had some fun things to do and places to visit.
Climbint the Mr. Olga fire towerAfter leaving Manchester, we drove Route 30 to connect to Route 100, but this time, we went south rather than north. Then when we got to Route 9 (and scenic Vermont Road), we turned east to get to Molly Stark State Park, where we planned to do the highly acclaimed hike to the Mount Olga fire tower for panoramic views of the fall foliage below.
From the Visitor Center we set out on the trail which immediately led us through a beautiful forest of spruce and fir trees.
Already I liked this hike so much better than the previous day’s hike to Lye Brook Falls, because the terrain was less rocky and rooty, so I could actually look around me rather than constantly down at my feet so I didn’t trip.
View from atop the fire towerWe took the loop in the recommended clockwise direction, which was steeper than the longer descent - not that either way was too steep with a total elevation gain for the hike was only 617 feet over 2.1 miles.
At 0.7 miles, we took the short spur trail to the summit of Mt. Olga, upon which the steel fire tower lookout tower sits. It was closed for repairs for a while, but fortunately for us, it was now open for climbing to the top.
Top of the fire towerThe original purpose of this tower was to serve as a watchtower for spotting wildfires. It was staffed by a fire lookout, who would scan the surrounding landscape for any signs of smoke.
This method of fire detection was used until the 1970s, when modern technologies like aerial patrols and satellite imagery became more common for fire detection. So, today it’s purpose is purely recreational.
What goes up, must come downWhen we arrived at the fire tower, there were two women waiting at the bottom waiting for their husbands to come back down, as they were not comfortable climbing up
As long as I can hold onto a railing, I have no problem, so Herb and I did not hesitate to make the climb to the top.
The climb consists of a series of metal stairs that wind their way up the interior of the tower's frame, with railing to hold onto along the way. Unlike some fire towers that can feel very exposed, the stairs on the Mt. Olga tower are enclosed by the steel framework, which provides a sense of security as you ascend.
The Bridge of FlowersThe final flight of stairs led us through an opening in the floor of the 7’ x 7’ observation cab, where we were treated to a stunning and uninterrupted 360-degree panoramic view of the Berkshires of Massachusetts, the Green Mountains of Southern Vermont, and even Mount Monadock in New Hampshire.
Unfortunately, as I mentioned earlier, the foliage was a bit of a dud this year because of the dry weather and warm nights, but it still was very pretty.
Bridge Street BridgeGoing down a fire tower is always a bit scarier than going up, but as long as we took it slow and held onto the railings, it was no problem.
To complete the loop, we headed back down the spur trail and continued on the main Mt. Olga Trail, which took us through the woods and into the park's campground area, completing the loop.
Historic district from the Bridge of FlowersFrom there, we continued on to our final destination, Shelburne Falls, along the Mohawk Trail in Massachusetts.
Nestled in the rolling foothills of the Berkshires in Western Massachusetts, Shelburne Falls is a picturesque village, uniquely situated with the Deerfield River flowing through its center.
Where there are rivers, there are bridges to cross them, and Shelburne Falls has two of them, standing nearly side-by-side, each of which serves a distinct purpose.
Reflections from the Bridge of FlowersThe Bridge of Flowers is Shelburne Fall’s most iconic landmark. Once a trolley bridge, in 1929 it was transformed into a stunning public garden creating a breathtaking floral walkway over the Deerfield River. From April to October, this 400-foot pedestrian bridge is adorned on either side with a vibrant and diverse array of flowers, vines, and shrubs, attracting visitors from around the world.
The Iron Bridge, also known as the Bridge Street Bridge is a truss bridge built in 1890. It runs parallel to the Bridge of Flowers and is the only way to get a car across the river.
Reflections from the Bridge of FlowersThe first thing we did when we got to town was to stroll across the Bridge of Flowers, but it was so crowded with a tour group that we decided to try again later when we could at least get a decent photo of the flowers.
The other major attraction in the village is the glacial potholes, a collection of 50 smooth, circular pools carved into the metamorphic rock of the Deerfield riverbed, just below the falls.
These “potholes” range in size from 6 inches to 39 feet in diameter, which make it the largest of its kind in the world.
Glacial PotholesDespite their name, the "glacial" potholes were not directly carved by glaciers. Instead, they are the result of a long and powerful process of river erosion that began around 14,000 years ago as the last glaciers retreated, creating a massive flood which produced a torrent of water carrying sediment (sand, pebbles, larger stones), which got trapped in small cracks and depressions in the riverbed. As the powerful current spun these trapped stones in a whirlpool-like motion, they carved out the smooth, deep, cylindrical potholes we see today.
Back when we were here in 2012, we were allowed to actually walk on and explore the potholes, but since then, for safety reasons, direct access to them has been restricted.
Reflection under the Iron BridgeThe only way to view them now is from an observation deck at the end of Deerfield Avenue, just below the hydroelectric dam and Salmon Falls, just a short walk from the Bridge of Flowers.
So after lunch at the nearby Salmon Falls Cafe, we had to satisfy ourselves by gazing down at them from the observation deck.
It was just after 3 o’clock so we were able to check into our accommodations at the Blooming Inn, an historic 1852 Victorian house, which would be our home for the night.
Blooming InnEach of the four rooms at the Inn are individually decorated, with antique furnishings as well as modern amenities like a private bathroom (although it was across the hall), Wi-Fi, A/C, etc.
We were in the 2nd floor Balcony Room, which I found out later was the most sought after room in the whole Inn, because it had a private balcony, which we did take advantage of that evening with a pre-dinner glass of wine.
While the Blooming Inn doesn't offer a traditional cooked breakfast like many Inns do, it has a very well-equipped self-serve coffee and tea station, along with toast, English muffins, and various spreads in a downstairs dining area.
The Blooming Inn parlorI felt like we had stepped back in time. The village itself is a designated historic district, with well-preserved 19th-century architecture that gives it a timeless New England charm.
After our wine on our coveted balcony, we took a stroll through the historic district, with its well-preserved 19th-century architecture that gives it a timeless New England charm.
A toast to an awesome vacationOur dinner reservation at the West End Pub was on the other side of the river, so we walked once more across the Bridge of Flowers. What a different experience it was than this afternoon when we were shoulder to shoulder with a tour group. We pretty much had the bridge to ourselves and the lighting was perfect.
After taking a few photos, I noticed that Herb was shooting down at the River itself, capturing the reflections of the historic buildings along the shoreline.
Ahh..Now that was even more interesting than the shots of the real thing.
That evening we had a wonderful dinner at the West End Pub, known for its cozy and upscale pub atmosphere, delicious food, and stunning views of the Deerfield River and the Bridge of Flowers.
What a great way to end a fabulous 40th Anniversary trip!
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