1. Windy Hill Farm

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Great Barrington, MA

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Miranda S.

Wish we had read about the unusual May freeze that ruined the apple crop and resulted in many other U Pick places in the Berkshires canceling their apple picking season and urging loyal customers to patronize their business in other ways. Unlike these reputable orchards, Windy Hill is selling bags inside their store for $16/peck. They give you a map with highlighted rows for what is ready now. Then they sent me, my spouse, a three and a five year old and our two aging parents a 10 minute walk straight up hill on a wild goose chase, essentially. They let us know there were also giant bins of pre-picked apples we could select from. The entire orchard on both sides is rimmed with "electric fence," so you can't enter anywhere but the one designated spot, which is about as far from the main store as possible. The quality of the apples was stunning. What apples there were were a yellowy-pink color and the skin was mottled and dappled. Many had holes. We let our poor kids pick some anyway because this was their first apple picking experience and they were excited (then we tossed them). Literally every single apple was trash. We wandered through row after row but no apple worthy of picking or eating could be found. And they knew that. Don't worry, we filled our overpriced bags with apples they had trucked in from some other farm not impacted by the freeze. I wish they would have credited whoevers apples these really were, because we would surely patronize them next year. Adding insult to injury, the front desk staff were terribly rude. We bought 4 cider donuts. The donut container was on the counter and it opened toward customers with bags next to it. My father-in-law went to open it and a female employee slammed it down on top of his hand, admonishing him that she would get them. Assuming the donuts were also trucked in from somewhere else since they were cold, a little stale, and a lot greasy. Nothing like those hot-off-the-presses donuts you associate with apple picking. Another female employee followed me and my children around. I guess she thought I wasn't doing a good enough job making them not touch the 7598 breakable tchotchkes they have all over the store for sale. Overall, not a friendly location for families, even under the best pretenses, but add to that the duplicitousness involved in selling goods you don't actually have and letting customers find out once it's too late (and then refusing refunds) and this place is a hard pass. Would never pick here again, even in a perfect apple season.

Apple Cider
Theresa S.

Stopped by today to get some apples! We didn't pick our own ( lazy us ) instead purchased a bag of Honey Crisp Apples all ready to go !! Lovely spot to check out if you are in the area . They have a nice green house too ! It does get extremely crowded at times and there is limit parking so you may have to park on the road . They sell delicious apple cider and cider donuts too ! Of course I had to have a donut! They are the most delicious donuts , soft inside, crunchy outside with plenty of cinnamon sugar ! YUM! The Honey Crisp apples are our favorite , juicy , crunchy sweet yet tart .. FANTASTIC!

Apple pancake
James C.

Windy hill is a true family run maple syrup operation. There are four tables and occasionally a few picnic tables outside. The pancakes are absolutely amazing and very large and well prepared. My favorite is the Apple pancake but the pumpkin pancake isn't very far behind served with their own maple syrup. This is a must go to if you want authenticity in a sugar shack. Deceiving but enticing from the first impression as you drive up. You won't regret stopping here.

Gourds
April Y.

This place is just beautiful in the fall! Windy Hill Farm was our first stop in our journey through the Berkshires. We had already loaded up on apples in Smithfield the previous day, but enjoyed walking the apple orchard and what looks like a nursery for cut your own Christmas trees. They have a fantastic selection of fall stuff: pumpkins, gourds and fun decorations. I liked wandering through the trees for purchase, looking through the flower bulbs and everything in the hoop houses. Inside, they had really cute Christmas decorations, so I had to get a couple of snow-capped evergreen tree tea lights and some beeswax pine cone candles as well. Picked up some Lee, Massachusetts, maple syrup as well! Festive, whimsical and fun!

Wonderful job on our new pool with a terrific staff!! Great selection of plants. Pleasant and cooperative people.

Planting around a new pool was terrific. Everything was done beautifully, on time, pleasant people, attention to detail. The move existing plants, trimmed trees.

Lisa E.

Spectacular nursery with a friendly and helpful staff...Head in and pick up some pint baskets for Blueberry picking as we did today. Abundant amount of berries are ready to be picked, half making it into the small green baskets and half right into your mouth. It's fun to see and taste the many varieties, the smaller ones tending to be sweeter and more flavorful but the larger ones being juicer. Peaceful hilltop, netted in though there will be some buzzing now and then. We headed right for the Co-op and bought some quality yogurt to top with our yield. Go early or later on a hot day as the sun can be relentless... Prices are roughly 4.25 a pint for 6 or more and 3.75 a pint for 12+. I think this is one of the best seasons that I have seen and the blueberries are fantastic. Great for kids, great place to smooch without the kids.

Bushes sold to us - wanted 4'. Hearts what we got!

Terrible customer service. We purchased a number of bushes and they sold us the wrong size for the space after much discussion with salespeople. The owner Dennis was rude and nasty and very disreputable. He refused to even exchange them for the correct size although it was totally the fault of his sakes jets on who was nit very knowledgeable. Stay away! Buyer beware.

A view from behind the shop, the hills are hidden under the fog.
Julia E.

Despite reading some poor reviews, I had a great experience here. I spent time chatting with the women behind the counter and some folks outside and they were all very pleasant. I was here strictly for a nursery visit. The plants all looked very healthy and the displays that were set up are beautiful. They had a small selection of hand picked houseplants inside of the store that you could tell were very special. We left with a double blood root (that is incredibly hard to find), a hanging fuschia, and 2 houseplants. I didn't feel like the plants were overpriced for the quality that they were. Stop by here and take a look for yourself.

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8 years ago

Nice nursery stock but pricey. The employees in the shop are just plain rude. Will not be back.

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12 years ago

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15 years ago

Fun place! Get there early to avoid some of the crowds. The staff was friendly and helpful. And of course the apples are delicious!

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Review Highlights - Windy Hill Farm

“Head in and pick up some pint baskets for Blueberry picking as we did today.”

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Hilltop Orchards

Hilltop Orchards

(187 reviews)

$$

This small cider/winery is an excellent stop on your tour through the Berkshires. They have some…read moreinventive ciders and wines that don't follow the "rules" of flavor profiles. Using grapes shipped from CA and mixing with apples crown on site, this small batch operation is a delightful stop. Specifically, I want to shout out our wine guide who took us through several of their wines. She made our experience there memorable with her amazing personality, charm, and humor. The space is small but offers a variety of options to hang out and enjoy their wines and ciders - inside by the fireplace, outside on the screen porch, or outdoors on the patio. We loved our time at Hilltop and hope to return.

The place is rundown and I think the people writing positive reviews must have been too intoxicated…read moreto notice the unfortunate state or affairs and the people who run the place are neglecting the orchards. The "vineyards" were sad and disheveled, and the apple orchard looked worse very seriously neglected. The apple trees were very old, untended to and rotting, the trails were poorly maintained, the parking was a disorganized, and the grounds looked like nobody was taking care of them. The amount of junk round the building is staggering, not a place you want to buy food or drink from. The "food" is not fresh or made onsite it's just overpriced groceries. We only stayed here because my daughter had been so excited and we had traveled out of our way to get here. We made the best of it, but I could hardly find enough decent apples to fill the bag we had already purchased. Many of the apples had dark, greenish spots all over them: a fungus that you can see my photos. When I asked, "Do you still have pick-your-own?" it was because the trees looked practically empty from where we were standing. Walking through the orchard confirmed that impression: there was very little worth picking. We were there during prime apple season where all other orchards are overflowing with apples; even so we went to the very farthest trees at the back of the orchard; rotten, fungus, and very few trees producing fruit. I should have read past all the drinking reviews to the heart of the matter: unkept place absolutely do not go here. Looking around, the whole place is run-down and neglected. Honestly, I felt sad for the trees and grape vines. This was an overpriced, incredibly disappointing experience. If you're looking for somewhere to drink wine, maybe you'll have a different experience. But for apple picking, I wouldn't recommend this place to anybody. An absolute mess, and I won't be back, it was the worst orchard experience I've ever had.

Windy Hill Farm - gardening - Updated October 2026

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