It’s Apple Season again

We started out for Woodstock, IL in search of apples. Our family is no stranger to farms – it’s one of our favorite fall activities. In addition, these days we are getting especially close to nature, with few other options available. Luckily, Illinois has no shortage of farms, even near Chicago. Moreover, each offers something different, appealing to both kids and adults.

Our main goal was to find an apple farm with a great apple crop, plenty of space for social distancing, and a few extra attractions nearby. When you’re setting out for an hour-long drive, it’s nice to have a plan. So when I discovered that the small but famous town of Woodstock was close to All Seasons Apple Orchard, our destination was set!

Woodstock, IL

However, the trip to Woodstock isn’t short – it took us about an hour to get there. Located about 50 miles northwest of Chicago, Woodstock is a town every local loves to talk about, especially when it comes to the movie that made it famous: Groundhog Day. Yes, the 1993 popular flick with Bill Murray and Andi MacDowell was filmed right here. In the movie, Woodstock stood in for Punxsutawney, Pennsylvania, where Groundhog Day is a huge annual celebration. Remember the story? The day repeats itself over and over again, mixing comedy, frustration, and a bit of romance.

Stepping into Woodstock’s town square feels like stepping into the movie. You’ll find the same bar, theater, shops, and cafés featured on screen. Lately, as our own days start to feel repetitive, it all seemed especially fitting. Perhaps that’s why Woodstock reminded me of a small European town – old architecture, cozy atmosphere, and the way historic buildings surround the central square.

Next, start your visit with lunch at Public House, located next to the Courthouse on Woodstock Square. We were lucky to visit on a warm day and enjoyed our meal outdoors. Inside, movie memorabilia decorates the walls, and you can even pose with a little groundhog cutout. Afterward, we caught part of the Farmer’s Market, one of the best in the region. It runs from May through October and features delicious foods and live music. The café lunch was excellent, and the people couldn’t have been friendlier.

In fact, I loved the town’s historic charm. Woodstock is listed on the National Register of Historic Places and has been recognized as a Preserve America Community by the White House. For instance, two architectural highlights stand out: the County Courthouse (built in 1857), right beside the Public House, and the Woodstock Opera House (built in 1889). Fun fact – Orson Welles staged his first play there, and the summer troupe once included Paul Newman, Tom Bosley, and Shelley Berman.

The square remains the heart of the town. As you can imagine, Groundhog Day is a major annual celebration here, featuring a chili cook-off, dances, movie screenings, guided tours of filming sites, and, of course, the famous prognosticator announcing the season. As we explored the square, it truly felt like walking through scenes from the Bill Murray and Andi MacDowell classic.

And to top it off, we found Ned’s corner and the exact spot where Phil kept stepping in the puddle.

It was a lot of fun and inspired us to re-watch “Groundhog Day”. The locals were incredibly kind, eager to share stories and point out movie landmarks. It was refreshing to see how vibrant the downtown still is—and how well the historic square has been preserved.

All Seasons Apple Orchard

From Woodstock, All Seasons Apple orchard is just a short 15-20 minute drive. We arrived early in the season, hoping to pick my favorite, Macintosh apples. After buying our apple bags, we decided to walk to the orchard and take the hayride back. The path was clearly marked, wide, and short enough that even toddlers could handle it. Plus, there was plenty of space for social distancing.

Along the way, we passed tall corn stalks, perfect for a photo stop. Once at the orchard, staff directed us to the best rows for picking. Definitely follow that advice, since some varieties aren’t ripe yet, while others may be past their prime.

Bring or rent an apple picker! Many of the best apples grow higher up, catching more sunlight. My kids loved using the picker to reach the top branches. Don’t forget to sample the apples! There is something special about eating the apples right off the trees, something very basic and enjoyable.

Finally, after filling our bags, we took the hayride back – an easy way to carry everything and a quintessential part of the farm experience. Of course, no orchard visit is complete without apple cider and cider donuts, and All Seasons doesn’t disappoint. They’re fresh, warm, and perfect to enjoy outdoors at the picnic tables, often with live music playing nearby.