We took a three-day mystery ride, and if foliage season has you thinking about a road trip, you might want to steal the idea. Jay had been talking for a couple of years about getting out to the Berkshires, ever since a day trip he took with our oldest son, Marshall. The only detail I had to go on was that one of their stops back then was an estate belonging to some famous sculptor, that Marshall’s friend Ben Perrett works there. That clue was the whole plan.
We usually go to Newport, so that’s what I told him this time — a few days in Newport, something to look forward to after a hectic stretch. Except I hadn’t booked Newport at all. I’d found an Airbnb in Western Massachusetts instead. The idea was simple: track down the mystery estate, hit some art galleries, and see some of Western Mass.
Santarella Gardens turned out to be the name of the Airbnb — in Tyringham, MA (set your GPS for Lee, MA if you want the shorthand — you’ll recognize the area as home to Tanglewood and the Norman Rockwell Museum). It’s under two hours by car: winding mountain roads, wide-open farmland with cows, some houses beautifully kept, some that clearly needed some love.
We got there just after 3 PM. Check-in wasn’t until 4, so I’d packed a picnic. Jay asked twice on the drive whether we were taking a roundabout route to Newport — when you’re not the one driving, I guess you stop paying attention to where you actually are. All he knew was he was on a three-day vacation. It wasn’t until we were sitting under the Terrence F. Curtin Pavilion in Tyringham, eating lunch, that he finally asked where we were. I told him: the Berkshires, where he’d been asking to go for a long time.
I knew we were close to the Airbnb, so I pulled over to check the GPS. Jay looked up and said, “Wow, check out THIS place.” Turns out that place was our Airbnb. It looked a little like Santa’s Village —he saw a two-story turret that used to be a grain silo, tucked into the Berkshires like something out of a storybook. Here’s the Airbnb listing if you want to see it for yourself — they call it the Enchanted Tiny Tower.
The Enchanted Tiny Tower is round, with a spiral staircase running up the outside wall. A handful of other buildings share the property, each one its own kind of unusual. Behind us was a duck pond, with a path through the woods — nicely landscaped, ducks included. It was the smallest Airbnb we’ve stayed in — 350 square feet, spread over two floors — so packing up to leave meant sending Jay upstairs. There wasn’t room for both of us to move around at once.
Santarella sits right in the middle of Stockbridge, Lenox, and Lee, which makes it a good home base if you’re willing to drive a few hours west for foliage season. That’s Tanglewood and Norman Rockwell Museum territory — plus two other places we visited: Chesterwood and The Mount.
We visited Chesterwood, in Stockbridge, which was the summer home and studio of sculptor Daniel Chester French, the same French who sculpted The Minute Man in Concord and the seated Abraham Lincoln at the Lincoln Memorial in Washington, D.C. French bought the property, then a 150-acre farm, in 1896, and had his studio built by his friend, architect Henry Bacon, who later designed the Lincoln Memorial itself. It’s now run by the National Trust for Historic Preservation, with tours through the residence, studio, and gardens, plus woodland trails and a mountain view from the studio piazza.
We caught up with Ben Perrett, our oldest son Marshall’s friend, after one of the guided tours. He’s now the Buildings & Grounds Manager there, and he walked us through how he got the job — his predecessor had held the role for 48 years, so when the position finally opened up, Ben had already picked up certifications in landscape architecture, construction supervision, and a few other fields to make sure he’d be qualified when it did.
On our last day, we brought a picnic to the grounds of The Mount, in Lenox — the estate Edith Wharton designed, built, and lived in herself, at the turn of the century. Wharton was the first woman to win the Pulitzer Prize, and she used what she knew about architecture and landscaping to lay out the Georgian-style mansion and the formal European gardens around it. Today it operates as a cultural center, with tours, lectures, and outdoor sculpture on the grounds.
If you’re from the area and still like to go leaf peeping, this would make a great overnight field trip. Share photos if you visit cool places!
