Vermont RT 100, and Beyond for the Day
We experienced a little bit of everything, flatlander style
“Except for a few, everybody in Vermont is a flatlander.”— Don Keenan
“Pick a place, and let’s go,” my husband Carl said.
“Road trip! Are you sure you don’t mind? You’re on the road all the time,” I replied, trying not to sound too excited. He’d just given me carte blanche to plan a trip to anywhere, within reason of course.
I took out a map of the US and taped it up on the wall next to the dining room table. I stared at it. The Gulf Coast was too hot and wet, the West Coast was too far away unless we flew; and the Midwest was stifling and well, flat.
New England—Vermont
888.4 miles from our front door to destination: Stowe, Vermont.
Vermont in the summer is well known for its maple syrup, covered bridges, green mountains, craft beer breweries, and waterfalls with swimming holes.
Vermont is also known for their cider and fried doughnuts, and Ben and Jerry’s ice cream factory, complete with a graveyard that honors those flavors considered dead. The agriculture is mainly dairy; and Montpelier is the only state capital that does not have a McDonald’s. None of these particularly held any interest to me—I don’t like dairy, eat fried food, or fall prey to Quarter Pounder’s with Cheese, no matter how starved I am.
Vermont Route 100
We took Route 9 from New York into Bennington; and then further east to Wilmington, to pick up VT Route 100 to travel north to the more-affordable Morristown, just outside of Stowe a premier destination resort area.
Vermont RT 100 is the north/south 216 mile highway located in the south/central part of the state. It’s one of the most scenic byways in New England.
We booked a room for four days and three nights through AirBnB in an authentic farmhouse in Morristown, less than 10 miles from Stowe. It would serve as a hub to explore across the rest of the state.

We made several stops along the way. We wanted to get a feel for Vermont’s past; and to see some of the postcard perfect red barns, white houses, and rolling green hills. The route gave us an opportunity to explore a bit of history, some culture, a little bit of shopping, and a glimpse into the Green Mountains.
Bennington
Blue Benn Diner
Our first stop was a visit to The Blue Benn Diner. It is a 1940s authentic railcar that opened its doors back in 1948. What drew us to it was the menu and its long history and reputation for being consistently in the top 10 of its kind in the country.
The diner offered beyond traditional (chocolate chip and raspberry pancakes, soy sausage, lox sliders, butterscotch pie, and homemade Indian pudding); and the price was right: affordable for two, under $40, with unlimited refills.
We counted over a dozen out-of-state license plates from as far away as Colorado and Oregon as we pulled into the parking lot. It was packed and we didn’t want to wait for a booth so we squeezed into two empty seats at the counter. The seats were tiny, or my butt was big compared to the ladies of the 40s and 50s.
Carl had a Farmer’s Omelette with sweet potato fries and I had the lox sliders—the food upheld their reputation.. The coffee was a bit weak for me. Carl liked it; he’s a trucker, and not choosy. Our breakfast was well worth the time and money spent; next time I’ll order green tea and sit in a booth.
Bennington Museum (Grandma Moses)
Anna Mary Robertson (Grandma) Moses) (1860-1961) was born in upstate New York, and didn’t pick up a paint brush and start painting pictures and murals for the first time until she was 77 years old.
She is known as a primitive painter. Grandma Moses is self-taught; and her work is created from using her imagination and memory only. One of the reasons I wanted to see her work was to understand how one captures the imagination from mind directly onto paper. It isn’t as easy as it sounds.

Before Grandma started painting pictures there were signs she may have been a suppressed artist.
In 1900 she was asked to help paint the inside of her sister’s home. Grandma painted one room green with a pink ceiling, and another one blue with another pink ceiling. Eventually all the rooms were (each) painted a different color with complementary colored ceilings throughout the house.
When she baked pies she decorated the holes with spruce or greenery for a personal touch. Cakes and cookies were topped with her handcrafted unique flowers, birds, or children at play. She used raspberry juice or vegetable dye to color frosting; she didn’t like white frosting on cakes or cookies.
At 77 Grandma could no longer continue to sew and knit yarn pictures due to painful arthritis. Her sister suggested she try painting. She was delighted to find she was quite good at it, and (accidentally) found a new career that eventually paid good money. She was never attached to her work enough to hold on to it.
“Do you ever get attached to any of your work?“ asked by President Richard M. Nixon, at an awards ceremony honoring her.
“I spend enough time painting them, and I like the money” Grandma said, smiling
Studying and seeing the intricate details, perspective, and balance that she used, up close astounded me; remember she was self-taught.
Weston
The Vermont Country Store.
I was yearning for glimpse of the past. The country store opened in 1946 and was dedicated to old, new, and hard to find.
Toys like Rock'em Sock'em Robots, Desktop Derby Horse Racing Game, and Gumby and Friends Bendable Pals lined the shelves. My favorite find was a reproduction of the 1965 Mystery Date Game board set. It reminded me of my favorite TV show back then, The Dating Game.
We strolled down aisles and aisles of eclectic products from past and present. And, according to the elderly saleslady who assisted us, there were over 6,000 under this one roof. We believed it.
Carl bought me a special addition cow calendar—I love to pet cows so he thought this was a great souvenir—we chose a hunk of maple fudge to eat on the road; a pair of mustard yellow merino wool socks that caught my eye, and two big jugs of maple syrup.
The Vermont Country Store showcases a once held American hard-work ethic, a certain polite, yet friendly and helpful attitude, and a sense of community.
Unusual of note in Vermont
There were no advertising billboards littering the highway beauty. Vermont doesn’t allow billboards anywhere in the state.
And the cows and surrounding dairy farms were clean. I never knew cows could stay clean.
I watched both sides of the highway for over 80 miles and couldn’t find dirty cows in muddy pastures. For the record, there were no dilapidated barns, or paint peeling from the pretty houses along the road, either. It was by far, the most perfect picture places I’d visited, that housed people, of course.
Vermonters are probably the most considerate drivers on the road. They don’t tail gate. When there is a four-way stop you practically have to motion for them to take their turn, otherwise they’ll sit there all day; unlike Michigan drivers who barely stop, and say “F**k it, I’m going,” whether they have the right-away or not.
We stopped in Rochester to take a peek inside The Little Red Barn Vintage Store. I’m not a vintage clothing person but kept an open mind because the place was cute and they had a large selection of unique finds.
We detoured off VT 100 to VT 125, and headed up the mountain pass of Middlebury/Lincoln Gap to see our first waterfall with a swimming hole and catch a little hiking time on a short trail through the forest.
Middlebury/Lincoln Gap
I found a portion of Long Trail where I was certain we couldn’t get lost. Carl has a great sense of direction, I don’t. I try and stay on marked trails but past experience told me to stay mindful up here, these woods were thickly treed, unlike my past hiking in Michigan, California, or Nevada.
We hit the trail for a short hike. Less than a mile in we ran into Strange Dude, who sat sprawled out on the middle of the trail with his pack, staring into space while stroking a hunting knife. It’s pretty weird to encounter another human in the middle of nowhere and not either say hello, issue a nod of the head, something, anything. Nope, not this guy. The hair on the back of my neck raised. Carl was already grabbing my arm and turning me around to head back. Even his cheerful self had a bad vibe.
We found a swimming hole, but it was getting late in the afternoon. We passed on the swimming and headed down the twisty, tree-lined road into Warren, caught the 100, and drove up through Stowe, to Morristown.
We grabbed some snacks and local craft beer at a roadside bar, checked in with our hostess Julia, and unpacked; thrilled with our new digs.
We got our suits on, grabbed our goodies for happy hour, and hit the swimming hole in our new backyard. Julia was happy to report there were no snakes or leeches, but plenty of bull frogs and birds.
And we called it day.
(I’ll follow up with more on Vermont at another time—but suffice to say the first day supposed all our expectations, and we’ll be returning again, someday soon.)
See you next week!
Vermont sounds gorgeous! I was happy to hear about the clean cows. Makes me feel better about milk and ice cream coming from happy cows.
This sounds like a fun trip Patti! I am particularly fascinated with the story of Anna Mary Robertson (Grandma Moses). Based on what you said, she started painting at the age of 77, loved it, and earned an income from it. What a life! This is a reminder that age is not always the barrier that we think it is.
PS: Happy belated birthday Patti! I'm sending lots of love, hugs and blessings. 🙏🏻🙏🏻💗💗