Pumpkin Picking in the Berkshires – Stockbridge, MA

Another one of my favorite things (again) is to visit Stockbridge, MA. It’s a small town located in the Berkshires…in between Lenox to the North and Great Barrington to the South. Here is a great website to learn more about the Southern Berkshires.

There are some really cool attractions in Stockbridge, one being the Norman Rockwell Museum, two being the Red Lion Inn and three being the Windy Hill Nursery. We have yet to visit the Norman Rockwell Museum, but have graced our presence at the other two.

Late September is the best time to go up. The weather is still good and it’s sweater in the morning, t-shirt in the afternoon temperature. Perfect for pumpkin picking. If you are into finding cool places for apple picking and pumpkin picking, you surely know of finding the wrong places. You know the ones…little trees in open, field-like settings. When you find the right one, you need to hold on to it, no matter the distance. That’s what we did here.

Windy Hill is a nice, large tree seasonal setting. Inside, they offer hot cider, donuts and all the apples you could imagine. Outside, they offer a nice hillside full of apple trees…about 20 different varieties. You can pick to your heart’s content. Right outside the building, they have a good variety of plants, flowers and plantings. They also have tons of pumpkins.

We picked up a few nice ones for carving later. You can really hang out here for quite some time, if you have it. We wanted to go north on Rt. 7 a few miles into the town of Stockbridge to eat dinner at the Red Lion Inn.

Stockbridge offers a very small main street setting with a few shops to browse through. You can get all that cool stuff you remember from childhood vacations, such as rock candy and taffy. A walk up and down both sidewalks worked up our appetite for some good dining. Before going in, we usually check out the back of the Inn. It shows the enormity of the building. There is a rich history of this structure, which I share below. The first time ever visiting this town, we ate lunch in the back courtyard, so there is sentimental value.

One thing you have to remember about the Red Lion Inn…if you want to eat in the main dining room, you must dress appropriately – a suit or comparable for the females. I am stressing this for the guys, because we are usually the ones with the issues. If you don’t have the right clothes, you can eat in the tavern part of the inn, downstairs. We have seen people turned away from the dining room time after time. Dining at this Inn is an experience. It brings you to another place and makes you want to stay for much longer than you can. Wine…candles…food and a good time. After eating, a nice break on the front porch sitting in a rocking chair is sooooo relaxing.