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Tulips surrounding a water fountain in the Atrium Cafe.

Road Tripping from Galena to Chicago

Family Fun

3 Days 164 Miles


Galena, Oregon, Grand Detour, Dixon, Chicago


A vibrant downtown, too-many-to-count bed and breakfasts and three wineries keep me coming back to Galena, just about the perfect small-town getaway in my book. Come autumn, it will be just us girls at Eagle Ridge Resort and Spa; then skiing at Chestnut Mountain in the winter with my husband. On this rambling, back roads trip to Chicago, I’m flying solo.

Day 1:

Classics Rediscovered

  • Busy town

Wanting to make the most of my time, I stay in the heart of historic downtown at the 1855 DeSoto House. Don’t be fooled by the quaint lobby, this place has modern conveniences, including free wifi. I like to park the car (gratis) and walk. The majority of the 100 or so shops, galleries and restaurants (no chains here!) line Main Street, just outside the landmark hotel. Some of my favorites: Lulu’s for artsy clothes, Poopsie’s for handmade jewelry and kitschy gifts, Fritz and Frites for from-scratch onion soup, Rocky Mountain Chocolate Factory for extra-thick English toffee and just about any store with the word Galena in its name.

Day 2:

Back Road Byway

  • Aerial shot of Lowden State Park.

South of Rockford, the state’s third-largest city with its own museum campus, the Rock River follows State-2, a scenic two-lane that leads to inspiring views, state parks, historic sites and pretty little towns. Less than seven miles apart, Lowden and Castle Rock state parks offer plenty of picnic spots, hiking trails and photo ops. On the bluff, overlooking the river, a 50-foot tall statue of Chief Black Hawk peeks between tree branches. In Oregon, a block off the main street, I breeze through Conover Square. The two-story former Schiller Piano Factory houses cute shops, tuned ready-to-play vintage pianos and antiques. Resident-potter Reed Bakken shapes, glazes and fires his porcelain and stoneware at Slip and Slurry Pottery. At Cook’s Collection, I eyeball gadgets I didn’t know I needed, like a pickle picker and collapsible colander. A little more time and I’d sign up for classes from Linda Hinkelmann, owner of Basket Beginnings.

Going Green Spotting a billboard for John Deere State Historic Site in Grand Detour, I feel a surge of the old childhood awe for giant, green machines. Not far down the road, a white picket fence surrounds nearly a whole city block where John Deere, a blacksmith by trade, settled in 1836. Guides lead tours of a replica of the surprisingly rustic workshop where his prairie-conquering plow was born. The neighbor’s house serves as a gift shop. No giant tractors and plows, but plenty of cute toy ones. 

Day 3:

Treasure Hunt

  • Ladies showing their latest purchases to each other.

More nostalgia trips in Dixon: Ronald Reagan’s two-story white clapboard boyhood home and the Lincoln Highway (State-38), the first coast-to-coast route. Zig-zagging through wide residential streets, I spot hand-painted red-white-and-blue “L” signs on telephone poles. From the Mississippi River to the Chicago suburbs, the road, now a National Scenic Byway, meanders by 40 towns. In Franklin Grove, an original marker stands in front of the Lincoln Highway National Association’s two-story limestone building. It’s a good place to pick up info about what’s ahead. On the way out, I snap a picture of the marker, less than two dozen remain in the state. Now that I know what to look for, I spot a marker in a verge, a mural on the side of a brick building in Creston and a gazebo in a DeKalb park.

100 Shops!

A string of turn-of-the-century towns dot the Fox River just west of Chicago—one more irresistible than the next. Pretty neighborhoods of historic homes surround downtowns lined with all sorts of appealing shops and restaurants. A combination endless boutique and ultimate ladies-who-lunch spot rambling through a white mansion in Geneva, The Little Traveler might be the most seductive of all. Treasures from all over fill 36 rooms. Pulling myself away from the incredible jewelry department, I head to the sunken Atrium Cafe. A model in sleek black Capris and a fuchsia jacket slinks by, part of a daily fashion show. Note to self: bring girlfriends. Outside, I wander up and down tree-lined South Third Street, stopping at other favorites: The Paper Merchant, Cocoon for home accents and trendy clothes at the Meeting Place. With one bite, The Latest Crave becomes a new fave. Mile-high icing tops cupcakes in to-die-for flavors: key lime, lemon, red velvet, blackbottom and more. I go with carrot. Yum!

Long known as the antiques mecca, neighboring St. Charles is busy reinventing itself as a complete weekend getaway. A redone riverfront is taking shape with the historic Hotel Baker anchoring green spaces and an entertainment district. Century Gardens District on the east bank proves some things only get better with time. The dozen or so turn-of-the-century homes now hold shops. Must-stops: Town House Books & Cafe with local authors works; Stonehouse on Cedar for antiques and simple objects and Panache, a well of fabulous, one-of-a-kind jewelry made from vintage buttons, plus art and clothing, in an 1850 farmhouse.

I brake for discounts! Uh, oh. I planned to breeze on into Chicago in Aurora but all those drivers heading for the exit apparently know something I don’t. Who can pass up Chicago Premium Outlets and its literally acres of bargains? Not me. Luckily there are plenty of lodging choices nearby, too.

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