Steepletop

I had a great experience at Steepletop with a very informed, very passionate guide (and I was lucky enough to be on a private tour). I did the combo tour of the house and grounds; when I called to reserve my spot, I was told this was the best way to visit, and I can’t help but think she was right. The house itself is somewhat small but the outdoor space is substantial.
Most of my traveling is for literary tourism and I aim to visit as many author homes as possible. Often, I’m disappointed because the tour makes it seem like any old house, rather than the home of an author. This tour guide was sure to highlight Edna St. Vincent Millay’s life, her relationships, and her work. It was much better than what I call an «inventory tour» («This is a chair!»). I even enjoyed the outdoor walking, though I’m not usually interested in gardens and plantings. This tour made those details seem relevant, rather than just pretty things. Oh, and the most important part: She read poetry! I mean, why visit a poet’s home if you don’t hear poetry?
The price was a bit steep — which I’m sure is at least partially due to the need for income despite relatively small visitation numbers — and it really is in the middle of nowhere. It was a tad long (especially because I stayed to watch the film) and some folks might be overwhelmed by the bugs during the outdoor portion. Still, I think it was worth the trip and the fee.

Steepletop was poet Edna St Vincent Millay’s home before she passed away in 1950. According to the nice man we spoke to here, the Millay Society opened the house and grounds up to the public in 2009-​ish. What’s here now is the house itself, which is only open for guided tours, the gardens, a small historical gallery with the poet’s family tree, photographs, and heirlooms, and a Poetry Trail into the woods, leading to Millay and her family’s burial site.
Admission was a bit more than I expected, but I’m not sure why (why it surprised me, that is… not why it was more than I thought). Maybe it’s just been a while since I’ve been to a historical site, but it was $ 10 to view the gallery and grounds; guided tours of the garden or the house would have been $ 16; and a combination of the two comes to $ 25. According to the website, reservations are required for the tours. Walking the Poetry Trail alone is free.
As you come up East Hill Rd from Rte 22, you’ll see the Millay Colony for the Arts on the left. That’s not it. Keep going until you see the sign for the Millay Society at Steepletop. The gravel driveway is very tight, but I don’t think they get a lot of traffic. There are signs directing you to the side of the house, where you enter and go up some stairs to the office.
My friend and I did the gallery/​grounds thing. The man working there was amazingly informative and loved to tell us everything he knew, but he was also happy to step back and let us browse on our own. The family tree that sprawled across an entire wall, though it was packed with information, seemed a little chintzy, created with printouts and typed with not always the best grammar — a bit disappointing for an author’s home. In addition to the family history, you can find books from Millay’s own collection, a piano she grew up with, a couple of garments — one real, one a replica — and a few other family mementos.
When we had fully saturated the gallery’s displays and our host’s brain, he pulled out a big cardboard map to show us the layout of the gardens. It wasn’t until then that I realized the building we were in as not the actual Steepletop house. But it was not going to be hard to find. We memorized the map (why they don’t have a version you can take with you, I have no idea) and ventured across East Hill Rd and up a soft incline to the house. All we could do was wander around the outside, but we were interested enough to do so.
The Millay Society is in the process of restoring both the house and the gardens to their previous condition, and at the moment the gardens are in an odd in-​between state where some bits are meticulous and well maintained and others are rustic and overgrown. But the swinging gates, the weather-​stained sundial and other stone features, and grassy areas like the one that used to be a circular badminton court all still have a quaint and beautiful feel, even in their disrepair. The swimming pool has seen better days. And hopefully will see better ones to come.
One intriguing stop in the garden area was Millay’s writing cottage. It’s small and musty and was the only building we encountered that didn’t have its windows blocked from the inside, so we peeked in. A couple of desks are inside, one with a pile of papers and a composition book.
The Poetry Trail is charming. It takes about 20 minutes to roam from the road to the burial area. Every so often, a passage of poetry by Millay appears on a post. The distance between poems is just right for letting the previous one sink in. Eventually we reached the burial site and found Millay and her husband Eugen Boissevain’s graves easily enough. Millay’s mother, sister, and brother-​in-​law are supposed to be there, too, but we didn’t spot them right away (and it had started raining, so we weren’t going to spend much time searching). Millay and Boissevain’s flat gravestones were scattered with leaves and fit right into the unmanicured grove.
I’m in this area once a year and might try a guided tour at some point. Whether you’re a Millay fan or just Millay-​curious, this little historic site is worth coming a little bit out of the way to check out.