The Berkshires: An Itinerary of Things to Do

Photo-Illustration: The Strategist. Photos: Courtesy of Hopie Stockman

Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations and itineraries possible. In this recurring series, we find those people who’ve done all the work for you and have them walk us through a particularly wonderful, especially well-thought-out vacation they took that you can actually steal.

For her honeymoon, Hopie Stockman, the co-founder of L.A.-based textile brand Block Shop, wanted to give her Texas-born husband, Rad Furniture co-owner Russell Hill, a tour of her childhood stomping grounds in New England. They started with a long weekend in the Berkshires. She’s visited the area a dozen times, starting with trips with her family when she was a kid, and says even though every season has its own magic, fall is “heaven.” Here, Stockman shares a hiking trail that’s been traversed by literary giants, an excellent Shaker-inspired restaurant, and a spectacular place to listen to classical music.

When doing a Berkshires weekend, fly into Boston and land before five so you can get to your hotel before dinner. It’s a two-and-a-half-hour drive to the region. Before leaving the city, I always stop at Flour Bakery (12 Farnsworth Street), a local chain that has a location on the wharf near the airport. The baked goods and sandwiches are yummy and filling enough for the drive but won’t ruin your appetite for dinner. Leaving Boston at the end of the day on a Friday, the traffic will be horrendous, but just grit your teeth and get through it. Once you’re out of the city, it’s easy.

Coming from L.A., I have minimalism fatigue. I don’t want blond wood and brass accents. I want sagging ceilings and exposed beams. The Inn at Kenmore Hall (1385 State Road) is a 1792 home that Frank Muytjens, the former head of menswear at J.Crew, and artist Scott Edward Cole carefully restored — note the original banisters, moldings, and millwork. We stayed in room three, which has a fabulous giant freestanding porcelain bathtub and ochre candles you can light so you feel like you’re in a Brontë novel while you soak. I wanted to spend a week there. But you have to like dogs — they have a sweet vizsla, Dutch, who wanders through the hotel.

After checking in, we went straight to Tanglewood (297 West Street), the summer home of the Boston Symphony Orchestra, which is in residence through November (James Taylor also regularly does gigs there). The performances take place in an open-air concert hall (the Koussevitzky Music Shed) with indoor seating and seats on the surrounding lawn, where you can set up anything from a small blanket to a table topped with a tablecloth, cloth napkins, and a candelabra. We used our jackets and scarves to make a little music-listening nest and had pizza and beer we picked up there. You can also order a picnic basket ahead of time through the Tanglewood website and it’s waiting for you when you show up. After you eat, lie down on the grass and let the music wash over you. When you get home, text Scott what time you want your coffee.

Every morning at the time you requested coffee, there will be a light tap on the door, but when you open it, no human is there, just a beautiful silver tray with coffee and milk. After coffee, head downstairs to the dining room, where, like everything else in the Inn,…