Every August since 1855, the town of Middlefield, Massachusetts has held the Middlefield Fair. It’s hosted by the Highland Agricultural Society. There are tractor pulls and pie eating contests and agricultural contests. Fun for all ages!
Glendale Falls, a Trustees of Reservations property, is located in Middlefield. Glendale Falls is one of the tallest waterfalls in Massachusetts, cascading 160 feet. The surrounding forest includes hemlock, birch, and beech. There is a trail to the bottom of the falls, which is the best vantage point to view the falls.
One little-known fact about Middlefield: Martha Stewart spent her childhood in Middlefield, and her first weekend home was on Clark Hill Road. Here is a link to a lovely article with memories of her Christmas holidays spent in Middlefield. An excerpt is below:
“On Christmas morning we strapped on our cross-country skis and followed Andy’s freshly cut trail into the hollow. We skied all the way to Glendale Falls, then found our way home and ate a big breakfast of pancakes, local maple syrup, and bacon. The Christmas ham was in the oven, and the plum pudding was steaming atop the stove. Our friends from the village arrived to have Christmas dinner with us. Their two children, Anna and Bo, played with Alexis and exchanged presents and told each other stories of the woods and winter. After frolicking outside until they were almost frozen, the children wrapped themselves up in blankets and whispered by the fire.”