Population 546

Photo: Jasmine Lee.

If you’re looking for a cushy resort town filled with massive infinity pools, Uber golf carts, prime rib buffets, and excessive amounts of tiny umbrellas behind every bar, this may not be the place for you.

Pittsfield, Vermont falls under the “off-the-beaten-path treasure” category. On any given day, you’re likely to stumble upon a Bikram Yoga retreat, destination wedding, world-class mountain bike path, or Spartan Race (a series of badass obstacle races that range in distance — from 3 miles to 26.2 — and difficulty). That is to say, Pittsfield is not for the lazy traveler. And we love that.

Within easy striking distance of Killington ski resort, White River, and Woodstock, outdoor activities run rampant around here. It’s the perfect place to live that off-the-grid lifestyle without sacrificing things like epic showers and delicious food.

How To Do It Right

  • If you’re traveling with a group of friends, try and book rooms at Amee Farm Lodge, or the “White Barn” at Riverside Farm. If you’re into being all romantic and stuff, give the farm’s “Bride’s Cottage” a shot. (Sadly, you can’t sleep on the covered bridge, according to our friend who may or may not have tried.)

Riverside Farm. Photo: Amee Farms.

  • Make your way to the General Store, the only store in town, to stock up on supplies. Hint: Order the Black Bear Sandwich, stat. The selection of local craft beer is also impressive. As is the syrup. And the Vermont snack bars. Okay, we may have overdosed.
  • Visit Clear River Tavern. It’s rumored to have invented the “jump shot” in pool.
  • Prepare to be surprised by the dining options, even if you’re the most seasoned traveler. (Exhibit A? See The Backroom). Who doesn’t love decision-free dinner plans?
Photo: Marion Abrams.

The Backroom. Photo: Marion Abrams.

  • Leave your phone in your room, because cell reception is minimal (that’s a good thing!). You can Insta that shot of you being pensive on the Amee Farms porch later.
  • A lady (?) by the name of Gina Shirley composed a meaaan cabin fever playlist that sits will with trips to places like Pittsfield. Get a taste of it below.

  • Find the cottage at the top of the mountain. If you leave Pittsfield and don’t find this single-room oasis sitting humbly up high with views across Vermont, you’re blowing it. No, we’re not going to tell you how to find it — that’s part of the adventure.

For bookings and more details, visit vermontsoriginalstore.com.