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You are here: Home / Travel & Destinations / Windy Hill Farm & The Red Lion Inn, Stockbridge, MA

Windy Hill Farm & The Red Lion Inn, Stockbridge, MA

October 3, 2008

Well, well, well, where have we all been? I guess it’s that time of year again for our annual visit to Stockbridge, MA. This is the time I usually get a gift certificate to the Red Lion Inn for my birthday. It’s a great excuse to drive up to the Berkshires to go apple picking at Windy Hill Farm and eat a nice lunch at Red Lion.

The thing is…you have to be really careful about the weather when it comes time to go apple picking. There is a tendency for rain in September and October, prime apple picking months. If you plan too far in advance, there is a chance you will be rained out. Actually, the best way to go apple picking is just by driving around on a nice day and unexpectedly drop in on a local orchard. I have done that many times. Or, it can be something that you wake up and decide to do, if you are close enough to an orchard.

We got semi-lucky and went on a day that was cloudy in the morning and sunny in the afternoon. It was breezy and cool, perfect for what we were doing. Amazingly enough, Stockbridge was full of people on a Thursday. I thought it would be nice and empty. I guess leaf peeping is more popular than I thought.

Here are some photos of our time at Windy Hill Farm.

Windy Hill Farm from behind

Windy Hill Farm from behind - further up the hill

Windy Hill Farm - up and over the orchard

Windy Hill Farm - walking up the orchard

Windy Hill Farm - apple tree

Windy Hill Farm - apple tree


Windy Hill Farm - apple

Bag of apples

Windy Hill Farm - pumpkins

Some kind of Holly bush, I think

Trees changing colors in Autumn


We had a really good time picking apples. Since it was Thursday, we got the Wednesday, Thursday special of only $16 to fill up two big bags. I thought that was pretty good. We also got a big pumpkin, some hot cider and a donut.

After that was all finished, we drove about a mile up Rt.7 to the Red Lion Inn for some lunch. This was a pretty funny meal. I ordered five plates of food. I though the salads were…well, just salads. I didn’t know they were an entire lunch for one person. After I got done ordering, the waitress just looked at me. I was like, “What, is that too much?” She said that it was fine. I just told her that we would wrap anything we had left over, which we did. It was fun.

After we were done eating, we walked upstairs to visit the room we stayed in over Christmas and to see the library we spent some time in. That was fun too. We then rode the elevator downstairs to leave out the back door.

I really like that place and I have to say that Autumn is probably the best time to go.

Related posts:

  1. Lee, Stockbridge, Great Barrington and Beyond
  2. Great Barrington, Stockbridge, Lenox and Lee, Massachusetts
  3. Pumpkin Picking in the Berkshires – Stockbridge, MA
  4. Pick-Your-Own Apples at Cayford Orchards in Skowhegan, Maine
  5. Thanksgiving at the Red Lion Inn

Filed Under: Travel & Destinations

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