Upon entering the sixty acre orchard, you are engulfed by over 30,000 dwarf apples trees with the choice of over 30 varieties of apples in addition to pears, peaches, pumpkins and sugar snap peas. In the main building you can peruse a diverse selection of delicious bakery, deli items, unique gifts and home-made pantry items and proceed to enjoy a home-style meal in the friendly and comfortable setting that reminds one of Grandma’s farm kitchen.

This down-home setting, that is a regular meeting place for thousands of families and friends, has not always been what it is today. This Wisconsin treasure has taken many forms throughout the years. It has taken many decades of hard-working and dedicated individuals to create the special atmosphere that so many have come to love and enjoy.

During the first half of the 20th century, the land we now know as Apple Holler was a working dairy farm spanning over 80 acres, which was later reduced to 73 ½ acres when the interstate was built. The main building that now houses the endearing restaurant, Country Store and bakery was once the milking barn. The aged, wooden floor of the Country Store is the original floor from the days of the cows (don’t worry, all of the “gifts” the cows left behind have been since cleaned up for many years).

In 1970, Clayton berry purchased the barn and the surrounding land and began planting apple trees and in the fall, sold the apples as well as deli items in a little shop he created in the cow barn. At this time, the orchard was known as Berrylea. In 1987, Dave and Vicki Flannery took over the cow bar and converted it to a restaurant. In 1993, the Flannery first began planting thousands of fruit trees. Over the years, they have continued to plant trees and expand what is now known as Apple Holler.

Each fall, thousands upon thousands of families and friends make their way out to Apple Holler to enjoy the fall festivities including apple, pear and pumpkin picking, hayrides and many exciting outdoor attractions in the Family Farm Park, but fall isn’t the only time folks enjoy coming out to have a great time “down on the farm”.

The restaurant, with its down-home cooking, is open year-round for breakfast, lunch and dinner, as is the Country Store, bakery and deli. In the winter, folks enjoy private horse-drawn sleigh rides through the snow-covered orchard. The Red Barn Theatre stays busy all year long with the delightful musical productions in the intimate and personal setting. Family fun is always in season, with wonderful children’s theatre productions and activities for field trip groups as well as families.

It doesn’t end there. Apple Holler also boasts mouth-watering pig roasts, picnics and catering, sugar snap peas and peach picking, many special holiday events and prime rib buffets, gemstone mining, The Golden Goat Bridge, mazes and SO MUCH MORE!

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”!