The Apple Holler Story - Family Farm & Orchard | Apple Holler

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 and tradition that guides Apple Holler. The magic of Apple Holler actually started thousands of years ago with the sun rising over the Great Lakes and the rich soil created by the mighty glacier. It’s the pristine water from the ancient Inland Sea and the magic and excitement in the air on warm summer days and crisp autumn nights. It’s in the simple joy 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, named the land Berry Lea Farm, invited people to visit, and pick apples and berries. He owned the farm for almost 20 years.

Apple Holler ExteriorA 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.

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 20,000 thriving fruit trees. The booming orchard offers over 40 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

Now Picking: Yellow Da Rosa, Rosalee, Cameo, Jonathan, Macoun, Cortland, Golden Delicious, Red Delicious, and Crimson Crisp Apples

Find out what we're picking next and get notified of upcoming events:


In order to ensure the health and safety of our guests and staff while having an enjoyable time on the farm, Apple Holler has implemented the following procedures:

  1. Face Masks Required: Face masks are required when coming indoors at Apple Holler, except when eating at your dining table. Face masks are also required outdoors at Apple Holler when social distancing is not possible.
  2. Vaccinations: Vaccinations are highly encouraged.
  3. Showing Symptoms? If you, someone in your party, or someone with whom you have recently come into contact with are showing symptoms of COVID-19, please do not visit our farm. Return home and follow the CDC guidelines.
  4. Keep Your Distance: Stay a minimum of 6 feet (preferably more) away from other visitors and staff at all times.
  5. Wash Your Hands Thoroughly When You Arrive: Please use hand sanitizer & hand washing stations (indoor & outdoor) upon arrival and often. We have dispensers placed for your convenience.

We are committed to keeping your family, our family, and our employees safe. There remains an inherent and elevated risk of exposure to COVID-19 in any public place where people are present and we cannot guarantee you will not be exposed. Regular sanitizing, access to sanitizer and handwashing, and daily health checks of our employees are just some of the precautions we are taking.