Located less than ten miles from nearby Killington, Pittsfield is a tiny historic town (less than 20 acres in area) nestled in the Green Mountains. Both the mountains and the area’s rivers provide plenty of year-round outdoor activities for residents of the town and the surrounding area. The town is named after the Pittsfield, Massachusetts town of the same name, which in turn was named after William Pitt, the 1st Earl of Chatham and Prime Minister of England in the middle 1700s. Pittsfield was first settled in 1786, with the farmland used mostly for grazing livestock, and many of the original farmhouses and barns still remain. Pittsfield is one of the thirteen Vermont towns that were completely cut off by flooding when Hurricane Irene roared through in 2011.
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What to Do In and Around Pittsfield
Pittsfield is located on scenic Route 100, which is one of the more popular routes to view fall foliage. Thousands of visitors arrive each year to take in the riotous explosion of golds, reds, oranges, and ambers.
Pico Mountain is one of Vermont’s tallest mountains, and Pico Ski Resort is one of the state’s most popular ski resorts. This totally smoke-free resort offers snowboarding, downhill skiing, cross country skiing, snowshoeing and much more. The resort also offers classic tree skiing, cruising and carving trails. There are 57 trails, 265 skiable acres and a vertical drop of almost 2,000 feet. There’s an indoor climbing center and several restaurants too.
Another popular area ski resort, Killington Resort, has year-round activities for the entire family, including skiing, snowboarding, ice skating, hiking, golf and mountain biking, not to mention all the fun things to do at their Snowshed Adventure Center! There are several restaurants and bars to help keep your energy up.
Once the snow melts, head to a river and go tubing! Contact a local area tubing tour company for slow and easy tubing on the Vermont River, Tweed River, and White River. The rivers are great for fly fishing too! You can also play a few rounds at the White River Gold Club or the Green Mountain National Golf Course.
Gifford Woods State Park is one of the few old-growth hardwood forests left in the state and is close to the Appalachian and Long Trails, Killington Peak, and Pico Peak, making it a hiker’s dream. Access the Appalachian Trail from the park or hike the Kent Brook Trail, a short loop trail through the hardwood forest. In the spring enjoy colorful wildflowers, and when the weather turns cooler, it becomes a popular viewing spot for gorgeous fall color.
The hike to Thundering Falls is one of many scenic hikes along the Appalachian Trail in the area. A multi-use, out-and-back trail, it’s less than half a mile long and is used year-round by bird watchers as well as hikers, bikers, and joggers. Along the hike, you’ll enjoy the lovely views of the surrounding mountains and green valley before you hit the peak. The falls are spectacular, with 140 feet of water cascading down over the rocks.
Nearby Historic Attractions
Take a step back in time with a visit to the nearby Stockbridge Common Historic District. Centered on the town common and Maplewood Cemetery, this historic town has several well-preserved 19th-century buildings, including the 1826 Union Church.
The President Calvin Coolidge State Historic Site in nearby Plymouth includes a visitor’s center, the Coolidge Homestead (where Coolidge lived as a child and took the oath of office), a historic one-room school house, a general store, the Farmer’s Museum, and more. Be sure to visit the Plymouth Cheese Factory (started by Coolidge’s father) for tours and yummy samples.
Vermont Vacation Rentals in Tiny Pittsfield
Barn-style vacation homes with iconic gambrel roof lines, alpine-style cabins, and rustic mountain retreats are just a few of the types of Vermont vacation rentals you can choose from. Nestled up against the mountain side, these vacation homes step down the slope and have large decks and balconies that are perfect spots for dining al fresco or just enjoying the beautiful mountain view.
Many of our rentals feature open floor plans, and stone fireplaces or wood stoves to keep the chill off during those chilly mountain nights. Typical amenities include Wi-Fi and large flat screens, and fully equipped kitchens that come with everything you’ll need to keep everyone fed, including microwaves, toaster ovens, tea kettles and coffee makers. If you’re planning on doing a lot of skiing or hiking, be sure to choose one of our Vermont vacation rentals with a private sauna or hot tub—you’ll be glad you did!
Give us a call for suggestions for places to dine out or more things to do while in Pittsfield or in the Killington area. We’d love to help you with your Pittsfield, Vermont vacation plans.