Escape Chicago for a Weekend in Oshkosh Wisconsin

From the winding country roads and outdoor adventures, to the breweries and art scene, Oshkosh, Wisconsin, has much to offer.  The Wonderland exhibit at the Paine Art Center and Gardens in Oshkosh caught our attention in particular, so we decided to visit for the weekend. We rented a cabin near Green Lake and planned on exploring the surrounding area.

Oshkosh With Kids

We drove up from Chicago on a Saturday morning. The 170 miles went quickly despite some construction near Milwaukee and we arrived in the town of Ripon in time for lunch. A quick Google search pulled up the Knuth Brewing Company, a microbrewery with a wood-fired pizza oven and locally-sourced menu. We decided to park and then enjoy lunch before checking into our cabin.

Escape Chicago for a Weekend in Oshkosh Wisconsin and surrounding Green Lake


As we parked the car just off Main Street, we stumbled upon a historical car show. What a perfect introduction to this small town! Folks from all over the region came to show off their lovingly maintained vintage and creatively chopped contemporary cars. My daughter Avi was delighted by the singing purple people eater perched in the engine block of a purple car. After checking out a few of the vintage wheels, we finally made our way to lunch.

Knuth Brewing Company is a casual place, offering a wide variety of local staples. Favorites include the pretzels with caramel and mustard, veggie wood-fired pizzas, generous salad plates and a large selection of proprietary beers. We shared a humongous hummus plate, a sausage, tomato and mushroom pizza, and some gooey soft pretzel bites before heading back in the car.

Escape Chicago for a Weekend in Oshkosh Wisconsin and surrounding Green Lake


We rented a cabin called Two Creeks Farm, which is located just off the shore of Green Lake. The cabin is situated on 40 acres of rolling prairie, bounded by forest and farmland. The 3-bedroom home was perfectly sized for our group which included two families with one toddler each. Two of the rooms had queen sized beds and the third featured a bunk bed. All of the bedrooms had plenty of space for a spare cot or crib if needed. The spacious kitchen was well stocked with the basics, and the living and dining rooms had abundant space to spread out.

Once settled, Avi wasted no time in exploring the rolling prairie. A wide path had been cut through the waist-high grasses, providing access to the small pond on the property. The air was dense with pollen, goldenrod and coneflowers catching the late afternoon sun as two great blue herons flew overhead. Avi also stumbled across a snake nest that had clearly just vacated itself of newly hatched snakelings! The fall colors were just beginning to blaze to life, creating a scenic backdrop for exploring and enjoying our time at the cabin.

The terrace just off the main entry of the cabin features a set of adirondack chairs, perfect for enjoying a morning coffee while the fog burns off the fields. We didn’t have to walk far to discover some fruits ready for harvest. A concord grape vine growing just off the main floor bedroom was ripe for snacks. We were completely in love with Two Creeks Farm.

Escape Chicago for a Weekend in Oshkosh Wisconsin and surrounding Green Lake


Green Lake is known for hosting all kinds of outdoor activities, from fishing and boating, to swimming, cycling, and more. Despite the variety of options, we decided on a toddler-friendly activity at Pineapple Hill Orchard a few miles up the road.

We were anticipating a typical family run orchard with apple trees, a pumpkin patch and some cider donuts. Boy were we surprised! We pulled into one of the most beautifully lush garden landscapes I’ve ever seen set around a Cape Cod style home and outbuildings. There were dusky rose hydrangea, Mexican sunflowers, dahlias and herbs were riotously jostling for attention. Owners Greg and Barb Becker greeted us warmly, and while they explained that they don’t have a “U-Pick” facility, they’d be happy to show us their orchard.

We followed Greg out to the Empire orchard, mystified at the tiny trees bearing dozens of fruits. Greg explained that the pruning and training method they used allowed for more branches to get sunlight, creating an abundance of fruit on each tree. It certainly didn’t look like a traditional apple tree, but the fruit we sampled was phenomenal. The skin dusky at first pluck, we learned to buff the natural waxes off the apples and enjoyed the sweet, juicy crunch. We purchased a few varieties in the shop (as well as a caramel apple, of course), and eventually made our way home to turn those Macintoshes into some fabulous pies.

Escape Chicago for a Weekend in Oshkosh Wisconsin and surrounding Green Lake


The following morning dawned rainy: perfect for a day of museums in Oshkosh, located only 30 minutes away. Upon arriving at the Paine Art Center and Gardens, we were stunned at the beauty of the grounds. From the home, gardens, and interior collections to the exhibit that sparked the entire trip: the Wonderland show. The Wonderland show featured larger than life photographic prints by artist Kirsty Mitchell. Enchanted by the confluence of a fairytale building holding the beauty of the photographs, we wandered the gardens for more than an hour. The Paine is a true treasure and should be better known by not just locals in the midwest, but art lovers across the nation.

Escape Chicago for a Weekend in Oshkosh Wisconsin and surrounding Green Lake


After a quick lunch at the Fox River Brewing Company, we visited another highlight: The Experimental Aircraft Association Museum (EAA). The EAA hosts more than a half million pilots and airplane enthusiasts for two weeks in July for the EAA AirVenture fly in. The convention features an array of experimental, home built and otherwise non-commercial airplanes.

I grew up with a flight enthusiast brother and heard of Oshkosh as this mythical place for my entire life. The museum features original and model versions of some of the most famous experimental airplanes ever built. Favorites  include the Wright Brothers First Flight, a tribute duplicate of Charles Lindbergh’s airplane built to commemorate his transatlantic flight, and SpaceShipOne, the first privately built aircraft to go into outer space. The displays were truly amazing.

Fascinating for any level of interest, the airplanes are fantastic to consider from every angle. Informative videos and guides on site include a LEGO model of Paris and interactive exhibits exploring the fundamentals of physics. Our three hours spent at the museum passed far too quickly.

Escape Chicago for a Weekend in Oshkosh Wisconsin and surrounding Green Lake


Before we left, however, we took a ride to Pioneer Airport, just across the runway from the museum. For pilots under 36″ tall, Pioneer Airport features historic aircrafts and and discovery flights in biplanes and other small aircrafts. We also learned about the Young Eagles Program, which allows kids over 8 to enjoy a free introductory flying experience. We cannot wait to return!

All in all, Green Lake and Oshkosh are fantastic destinations, be it for a day trip, weekend or week-long adventure. Between city and country, there is so much to enjoy for any level of activity or age. Outdoor adventures, arts and culture, aviation and technology, food and brews – there’s literally something for everyone.

Photos by Tyler Mallory; This post may contains affiliate links. If you make a purchase after clicking one of those links I will receive a small commission.

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1 thought on “Escape Chicago for a Weekend in Oshkosh Wisconsin”

  1. Kirsten N

    What a jolly and stunning kid! she seems having so much fun. I wish I could go back her age and enjoy life like there’s no problem at all.

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