For the 50+ Traveler

I’ve long been fascinated with population growth. And there’s probably no greater study in population growth than these two cities on the east and west ends of northern Illinois -- Chicago and Galena. In 1840, Galena was the larger city, a bustling town near the Mississippi River with more than 10,000 residents. Today? The city of Chicago has 2.9 million residents, and Galena, at the last census, claimed 3,429 residents.

That’s just one thing that makes this such an interesting road trip. Had things gone differently 150 years ago -- had a port on the Mississippi River been deemed more important than a port on Lake Michigan -- then this road trip might have been from the bustling metropolis of Galena in northwestern Illinois to the tiny town of Chicago on Lake Michigan. But that’s not what history chose, and so Chicago’s downtown was replaced by skyscrapers while Galena’s downtown looks much as it always has.

This road trip has a history as well, since Chicago residents have long chosen Galena as a weekend getaway. As Chicago grew well beyond Galena’s size and Galena’s main industry (lead mining) began to fade, Galena became a vacation destination for people in Chicago looking to escape the hustle and bustle of the city.

Whether you live in Chicago and are looking for a weekend road trip or are just visiting Illinois, the long-traveled journey from Chicago to Galena has much to offer.

The skyline of Chicago, Illinois.


We'll start in Chicago, the third-most-populous city in the country, where you'll have your pick of things to do, places to go, and delicacies to enjoy.

For starters, here’s how to spend a great Saturday and Sunday in the Windy City. Looking for a place to get that iconic Chicago photo? This list has you covered. And if you’re in the mood for something a bit off the beaten path, consider one of these activities you didn’t know you could do in Chicago.

For a true taste of Chicago, you’ll need to try a slice (or two) of the city’s world-famous deep-dish pizza. Not up for pizza? Chicago also offers great hot dogs, ethnic eats, and plenty of outstanding restaurants.

Honestly, you could spend a week in Chicago and not see everything. But it’s time to hit the road. From downtown Chicago, take Interstate 90 toward Rockford to begin your journey.

A steamboat on the Fox River in Elgin.


Along the western edge of the Chicago suburbs you’ll find the Fox River. This river, which runs from Wisconsin to central Illinois, is the main downtown attraction for many western suburbs, like McHenry to the north and Saint Charles and Geneva to the south. Near the center sits the town of Elgin.

The downtown area is the big attraction in Elgin. Exit Interstate 90 at State Street (Illinois Route 31) and take it south to downtown Elgin. Cross the river at East Chicago Street and explore the downtown area and the parks by the river. There are several great lunch spots here and much to explore. Visit the cultural center and then walk out to Walton Island Park, which sits on islands in the middle of the Fox River.

The entire Fox River Valley is a great spot, so if you have time, you can explore the cities up and down the river. Some of these communities are known for their architecture, so look for local house tours that will allow you to see the insides of some of the historic homes in the area.

Murals in downtown Belvidere.


The next stop along Interstate 90 is the town of Belvidere, just outside of Rockford. If my wife and I were planning on traveling from Chicago to Galena and taking our time (taking two days to get there), we’d probably do it like this: Leave Chicago in the morning, have lunch in Elgin, have dinner in Belvidere, and then spend the night in Rockford. It doesn’t take that long to drive to these locations -- the drive time from downtown Chicago to Rockford is only 1.5 to 2 hours -- but you’ll need lots of time to explore.

And Belvidere is a great stop along the way. If you’re a fan of murals on the sides of brick buildings (like you’d see 100 years ago), then Belvidere is your place -- it’s known as the City of Murals. The local arts council maintains dozens of murals in the community, and a drive through downtown Belvidere will reveal many of them. Just make sure to drive in both directions!

The town of Rockford, Illinois, along the Rock River.


Rockford is one of the largest cities in Illinois. Chicago and its suburbs make up nearly 70 percent of the population of the entire state, but of the outlying areas, Rockford is the largest, with 330,000 people living in the city and the surrounding suburbs. Because of that, you’ll find more to do here than in any other spot between Chicago and Galena. If you plan on making this a two-day road trip (even though you’re only 90 minutes from Chicago), Rockford is a good stopping point.

There are two downtown areas in Rockford on either side of the Rock River. Both sides have plenty of options for dining and entertainment. The city is home to minor league hockey (the IceHogs) and baseball, and there are several breweries.

On our last visit, we spent an evening at Prairie Street Brewing Company right on the river. We sampled the beers and enjoyed a nice meal right next to the (surprisingly wide) Rock River. Perhaps Illinois should be known for its rivers, because we’ve encountered them on every stop on this road trip.

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A little U.S. history on my way back to Chicago.

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If you’ve heard of Freeport before, it’s probably because of the town’s high-school mascot -- the Pretzels! That’s the main reason you need to stop here on your road trip -- Freeport is Pretzel City, USA.

Freeport is a medium-size town (home to around 25,000 people) and is very similar to some of the other towns on this list. There’s a river near the downtown area with parks and trails surrounding it. You can visit the Lincoln-Douglas Debate Square where Abraham Lincoln and Stephen Douglas once debated. And, of course, you’ll need to stop by the Pretzel City Shop (or one of the bakeries) downtown so that you can say you had a pretzel while in Freeport.

Maybe you’ll even want to stop by the local high school and check out the stadium. Its name? The Pretzel Bowl.

Apple River Canyon State Park in Illinois.

Apple River Canyon State Park

Perhaps you’re a bit tired of driving and feel like a stroll through the woods, or even a picnic. A good spot for that would be Apple River Canyon State Park. As you head toward Galena from Freeport, turn on Illinois Route 78 toward Warren. After about 6 miles, you’ll turn left on East Canyon Road, which will take you directly into the park.

It’s a very small park, situated in a small canyon carved out by the Apple River. But it was a nice place for my wife and I to stretch our legs, have a picnic lunch, and then take a post-lunch stroll on one of the loop trails (all are less than a mile long).

As you leave Apple River Canyon State Park, you’ll take Canyon Park Road back to U.S. Route 20. The rest of the way to Galena is the most scenic part of the drive. This section of road looks nothing like Illinois! The rolling hills will remind you of Kentucky or maybe Virginia. I was born in Illinois, and I like to tell people that the two most scenic drives in the state are the Great River Road outside of Alton and U.S. Route 20 between Elizabeth and Galena. Have your camera ready!

Historic main street in Galena, Illinois.


Galena is our final destination, and it’s a great place to spend several days.

As I mentioned at the beginning of this piece, Galena is a town with decades of history. Ulysses S. Grant lived here for part of his life, and when he ran for president, his campaign office was located on Main Street in Galena.

Speaking of Galena’s Main Street, it’s often included on best-of lists, and once you come upon it, you’ll see why. There are charming shops, restaurants, and art galleries as far as the eye can see.

But there’s much more to do in Galena aside from strolling the vibrant Main Street. I chronicled many of those things in this article. I’ve visited at least a half-dozen times, and each time I find more interesting things to do. We’ve visited in the winter to go skiing, and we’ve visited in the summer for the Fourth of July. It’s the perfect getaway spot -- and the perfect end to our road trip.