Our Story

The Apple Holler Story

The Mighty Glacier

Although several generations of the Flannery Family have been living, working, and playing on this 78-acre farm for over 30 years now, there is an even longer and stronger history that guides Apple Holler. The magic of Apple Holler started thousands of years ago, with the sun rising over the Great Lakes and the rich soil being created by the mighty glacier. It’s the pristine water from the ancient Inland Sea, the magic, and excitement from the air on warm summer days and crisp autumn nights. 


It’s all about the simple joys of childhood and savoring the present moment with those who matter most to you. In telling you “the Apple Holler story,” we hope that you will get a little taste of the age-old tradition and magic that make our family farm so special. 

Cows and Berries

Stretching as far back as the early 1900s, the land now known as Apple Holler was a working dairy farm. You would have seen grasslands, rows of field corn, and, of course, lots of cows. The main building that houses the restaurant, country store, and bakery was originally the farm’s milking barn.

In the year 1970, a man named Clayton bought the farm. He did not want to raise cows; he had a different vision for the farm. Clayton wanted to grow an apple orchard. He planted hundreds of apple trees and several kinds of berries. He then named the land Berry Lea Farm and invited people to visit and pick apples and berries. He owned the farm for almost 20 years.

A Family Business

In 1987, newly-weds Dave and Vicki Flannery bought the abandoned orchard. In that same year, the Flannerys refurbished the old milking barn and transformed it into the cozy red barn restaurant that has crafted delicious bakery and mouth-watering, down-home cooking ever since. The Flannerys went on to plant thousands of apple, peach, and pear trees as well as a pumpkin patch in 1993, rejuvenating the old orchard. While growing this small family farm and business, Mr. and Mrs. Flannery also focused on growing their family, eventually raising five children who would all go on to work, play, and make their childhood memories at Apple Holler.

Apple Holler Red Barn

Making Memories and Traditions

What the Flannery Family and Apple Holler Team are perhaps proudest of, is how much Apple Holler has grown and changed throughout the years- just like the many families and friends who have created their own life-long memories here. Upon entering the 78-acre orchard today, you are engulfed by over 30,000 thriving fruit trees. The booming orchard offers over 50 different varieties of apples, peaches, and pears.

The Story Continues

So come on out and visit us as you and your family become a part of history as you experience all of the exciting entertainment at this icon of southeastern Wisconsin and northeastern Illinois. We can’t wait to see you at Apple Holler, where you can pick your own memories all year long!

We strongly believe that the care we put into our family farm is returned to us and those who visit in the form of delicious tastes, beautiful sights, and lasting memories. Through a bit of hard work and a whole lot of love, we hope to pass this tradition on to future generations of our family and yours. We invite you to join us as the Apple Holler story and your own continue to unfold.

– Dave and Vicki Flannery, stewards of the land