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You are here: Home / Travel & Destinations / Great Barrington, Stockbridge, Lenox and Lee, Massachusetts

Great Barrington, Stockbridge, Lenox and Lee, Massachusetts

October 4, 2009

On Thursday of last week, we decided to head up to the Berkshires for some apple picking. Every year, we end up going too late and are rushed by the end of the season. Of course there are still apples to pick, but many of the varieties are already gone. This year, we thought it would be a good idea to go apple picking not too early, but not too late.

I think we’ll stick with going at the end of the season. There is one reason for this…the Honeycrisps are ripe. I guess the Honeycrisp is a late season apple, because there were “Not Ripe” signs all over the place where these particular trees were. It’s funny because I tasted a few and they seemed fine to me. I grabbed about 15 of them. I have a feeling they will ripen up just fine. Just so you know, the Honeycrisp is the biggest and best apple there is. They are huge.

We go apple picking at a place called “Windy Hill Farm Nursery Orchards & Garden Center.” I think that’s the official name. We just call it Windy Hill. It’s located on 686 Stockbridge Rd in Great Barrington, MA and really is a great orchard. They have hot cider inside and plenty of apples and pumpkins to choose from. I’m guessing when I say there are about 15 different types of apples to pick. We have been visiting this orchard during Autumn for about five years now.

The only problem is…it’s a little far away. I was thinking out loud on the way back from our exciting day when I said, “I think this is the last year for Windy Hill.” I got a funny look. I continued, “It’s just too far away. I can’t see driving for almost two hours to head up to the Berkshires when there has to be plenty of good orchards around where we live.” It’s true, there are tons of orchards around here, but we really like to make a day out of it. We don’t want to just run over to Glastonbury real quick, grab some apples and leave. That seems more like a chore. 45 minutes away is a good distance for an apple orchard. That way, we get to visit some town that we hardly ever go to and it makes the whole thing more fun. I like that. So, next year, I think we’ll head up to the “Quiet Corner” somewhere. I am sure Pomfret has an apple orchard. After all, Pomfret is an area full of beautiful rolling hills, a perfect place for apples to grow.

Thursday was fun. Not only did we visit Windy Hill, we also visited Yankee Candle in Stockbridge to gather a nice assortment of Autumn smelling candles and tarts. It wasn’t my idea to go there, but being the accommodating companion that I am, I agreed that it was a good idea. Now, every time I go downstairs, I think there is an apple pie or pumpkin bread in the oven. It’s really not fair.

Besides apple picking, another goal that I had for Thursday’s trip was to head up to Lenox to check out a really nice country house/hotel called Blantyre. I have heard great things about this place and wanted to see it first hand. I am always on the hunt for the next marvelous Thanksgiving or Christmas dinner. The visit was supposed to be a surprise. I wanted to drive to Lenox in stealth mode and quickly turn into the Blantyre driveway. My plan was foiled when I got lost…again. For some reason, Lenox is in something like a spiderweb vortex. It seems like every road going into the town is identical and has the same left turn. Each time I go there, I find myself making the same mistakes, over and over and over. This time, it took a confession and use of the GPS to find our destination. It really wasn’t any big deal because I am used to my surprises being ruined due to lack of preparation.

When we finally made it to Blantyre, we were very pleased by what we found. There is a really long driveway that leads to a large English house type structure. It is secluded and absolutely feels like another land. I can’t compare it to Europe because I have never been there, but if I had been there I am sure the Blantyre would feel just like it. It was kind of like Robin Hood was going to walk out of the woods.

We walked through the front door and found a really upscale and formal cluster of rooms. We visited the main room, the music room and the dining room. I also peeked out to the terrace and the front lawn and gardens. It was better than I had imagined. (Don’t worry, I have pictures)

A woman came out to greet us and answered all the questions about holiday dining that we threw at here. We gave the desk gentleman my name for a return call after they had the menu and arrangements set up. We walked out and strolled around for a while and took some photos.

After we left Blantyre, we decided to head down to the Prime Outlets in Lee, MA. I had this strange desire to get slippers. I know, I know…I am a big burly man. What in the world do I need slippers for? Well, this Winter, I am not fighting cold feet. I do it every year and it’s just not going to happen this time.


We arrived at Prime Outlets and were disappointed by the lack of selection of slippers. The slippers that were there were all made from leather and cost close to $50. They also had no thick hoodies or sweatpants to be found. This isn’t the first time we have walked away empty handed from this joint. I guess it was a good idea while it lasted. By the way, I picked up a nice pair of slippers in Walmart yesterday for $11. I also got a pair of sweatpants for $10. That’s what I’m talkin’ ’bout. This is simple house gear, mind you.

Lastly, we headed back to the Red Lion Inn in Stockbridge for some lunch. This is quite the tradition each year to settle us down after some good apple picking. We even got the clover leaf on top of our Guinness.

Here are some pictures of our exciting day up in the Berkshires. The weather was good when we arrived, sprinkled a little bit while we were picking apples and then cleared up again. All in all, it was a good day – minus the slipper thing.

Windy Hill Orchard in Great Barrington, MA

Windy Hill Orchard in Great Barrington, MA


Simon the house cat at the Red Lion Inn in Stockbridge, MA

Entrance to Blantyre in Lenox, MA

The Music Room at Blantyre in Lenox, MA

The main entrance room at Blantyre in Lenox, MA

The patio area at Blantyre in Lenox, MA

Half of the building at Blantyre in Lenox, MA

The other half of the building at Blantyre in Lenox, MA

Tennis courts at Blantyre in Lenox, MA

The grounds at Blantyre in Lenox, MA

Related posts:

  1. Lee, Stockbridge, Great Barrington and Beyond
  2. Windy Hill Farm & The Red Lion Inn, Stockbridge, MA
  3. Pick-Your-Own Apples at Cayford Orchards in Skowhegan, Maine
  4. Pumpkin Picking in the Berkshires – Stockbridge, MA
  5. Autumn Apple Picking In Connecticut

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