Freeport, IL

Bikes & Brews

An unforgettable day trip to Stephenson County

I was on the hunt for a great destination. The target? An unforgettable day trip in a rural setting. You know—the kind where you leave early, pack in a great itinerary and return home late but completely refreshed. A destination close enough we wouldn’t spend the whole day driving and could instead focus on the trip itself.

Driving through Northern Illinois over the last year, I happened to notice signs for the Jane Addams Trail. Friends mentioned that the area was known for great gravel rides, and a quick Google search uncovered Freeport, a popular place to access the Tutty’s Crossing trailhead in Stephenson County, IL. As an added bonus, the area also had three breweries and a winery within 10 miles of the trail. I was sold! A day of biking and breweries sounded like the perfect itinerary.

A day of biking and breweries sounded like the perfect day trip itinerary.

Tales of the trails

It didn’t take long for me to round up a group of friends with the promise of a good ride and great beer. The Saturday morning of our trip we loaded up around 7AM and began the 90-minute drive to Freeport. Our trailhead was easy to find off Highway 20, and we drove through Freeport’s downtown shopping district as we approached our mark. My friend Jane, who was more interested in the breweries than the biking, was intrigued. She opted to hang out at 9 East Coffee and check out the boutiques and antique shops instead of pushing the pedals.

The rest of us unloaded our bikes and gear to hit the trail. Our goal was to reach Orangeville, just a few miles shy of the Wisconsin state line and a 29-mile journey roundtrip. Brad was a little concerned about the distance, but the miles flew by! The natural beauty of the area created a peace that kept us silent a good portion of our ride. We had a chance to sneak up on a sandhill crane perched in nearby Richland Creek and saw several species of birds in the canopy above us. While the trail itself was mostly flat, we were impressed to encounter over 20 bridges that crisscrossed over the Pecatonica River and nearby creeks. There were a number of marked stops and restrooms along the route which made for a comfortable journey.

We returned to Tutty’s Crossing nearly three hours later, recharged by the beauty of our ride and famished from our workout. We met Jane and found she had done some scouting around town. She led us to Pub 219, a restaurant just across the street from the trailhead that featured a promising menu. We were glad to find a table outside in the noon sunshine and quickly placed our orders. We each ordered sandwiches, some opting for the very tempting varieties of grilled cheese. I selected the traditional grilled cheese with Havarti and Cheddar and was amazed by the flavor pairing it produced.

Shopper’s delight in downtown Freeport

As we enjoyed our sandwiches, we told Jane of the wildlife and rock formations we encountered on our ride, and she filled us in on her adventures in Downtown Freeport. After sampling pastries and coffee at 9 East Coffee, she had noticed the window display at Flair Hair Boutique across the street and decided it was worth a stop. At Flair, she mentioned her interest in additional shops and was directed to the nearby Swank & Mercier and Royal Oaks Antiques for vintage merchandise. Jane proudly showed us the dress she purchased at Flair and her new sunglasses and earrings from Swank & Mercier. Judging by her many shopping bags, it was clear that her wandering had been a success.

In her newly established role as a tour guide, Jane mentioned swinging by a dessert stop before leaving downtown. The Union Dairy Farms & Ice Cream shop was eye-catching, a jewel in Downtown Freeport. Its 50s-style diner charm enticed us to enter and try one of their 52 flavors of fabulous ice cream or choose from their long list of sundaes. Still plenty satisfied with my lunch, I chose a single scoop of butter pecan in a waffle cone. The girl behind the counter kept piling on ice cream—I didn’t know if I should remind her of my single serving or just let her continue! As we exited to eat our treats outside, we saw an impressive-looking statue. The plaque explained that this was the site of the second Lincoln-Douglas Debate in the1858 Illinois senate campaign. My inner history buff was thrilled—we came for ice cream and found a piece of history in the process!

Cheers to day-trip beers

Re-energized by our sugar high, we trekked the three blocks back to the trailhead, loaded up and traveled about a mile to our first brewery destination. Generations Brewing Company is housed in a modern building with an expansive door that opens to the patio. We each picked a selection of samples and complimented the staff on the variety of flavors and styles. My personal favorite was the Pretzel City Amber with its beautiful red color, but Sam preferred a seasonal brew, Jelly Donut, with its light, tart cherry flavor. Our introduction to Stephenson County brews was off to a delicious start and we were eager to see how the vineyards compared.

Famous Fossil Vineyard

It took us less than 10 minutes to arrive at Famous Fossil Vineyard and Winery, and we stopped to snap photos of the picturesque country view surrounding the winery. As the wine aficionado of our group, Sam was most looking forward to this stop. While she might have entered as the primary consumer, we all left as great fans of Famous Fossil’s wines. The Illinois grapes created a clean, refreshing flavor in the LaCrescent and a bold, robust taste to Fossil Rock Red. The beautiful atmosphere and distinct wines not only made it worth our trip but also warranted a few bottles to take home!

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Wishful Acres Farm & Brewery, situated just down the road, was a building in stark contrast to the modern stylings of Generations. The brewery and tasting room at Wishful Acres was in a striking red barn with lovely accents and charm. We were pleased to find that the owner and brewer himself, Nate Peterson, was our host, and he helped us to choose our samples according to our described preferences. Since beers here are produced in small batches, the varieties on tap are always changing, but we found an option for all palates. Being the responsible friend he is, Brad opted to be our driver and found that Wishful Acre’s root beer was equally tasty!

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Our final stop brought us back out to Highway 20 and to the Lena Brewing Company. The style of this brewery looked like a blend of the previous two—a contemporary feel near a big, red barn! As we entered, we snagged a table on the patio and were immediately hit with the wonderful aroma of Rafter’s Restaurant next door. A full day of enjoying beverages makes you hungry! Our hostess informed us we could place an order for appetizers from Rafters and also brought us a list of brewery staples and limited-edition brews. After placing our food order for a haystack of fried onions and BBQ nachos, our attention was back on the beer. I elected to go straight for the glass this time and, at the suggestion of our hostess, chose the seasonal favorite, Perfect Situation. The gang was also ready to settle into one glass over our appetizers and chose the lighter 38 Hefeweizen and the fruity flavors of Drunkleberry. No one was disappointed.

What a difference a day trip makes

As we all piled back in for the ride home, we were awash with sensations. We were, once again, full and satisfied with great food. We had packed in a day of great adventure, great tastes and great company. The car ride back was filled with laughter and happy chatter as we revisited stories of the day—the natural beauty, the amazing people, the incredible flavors and the fantastic memories that we made here. What can I say? Stephenson County left an impression on this crew and it won’t be long before we’re back for another unforgettable day trip.

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