By Jim Grayson, Special to OnMilwaukee   Published Nov 03, 2017 at 6:01 PM

Don't sleep on Galena, a delicious little city tucked into the northwest corner of Illinois.

Anchored to the north by the Wisconsin border and about five miles east of the Mississippi River and Iowa, it’s only 170 miles (under three hours driving) via Madison and a truly delightful destination for a restful weekend – plus the route that gets there is lined with gorgeous rolling hills.

A sleepy locale it is not. There’s a wide assortment of activities including dining, eating, drinking and playing. You won't be disappointed.

The centerpiece of Galena is the appropriately tagged Main Street. Yes, every town has one, but the generic name belies the uniqueness of this one. It’s a Norman Rockwellian scene in small town Americana, in the near literal heart of the country, charming with cobblestone streets, strikingly attractive mansions, haunted tours and pub crawls throughout its downtown, and omnipresent trolley rides.

Our visit took place just after Labor Day, and the air had a fall crispness – a beautiful day for sure, but I can’t help wonder that the scenery would be postcard-spectacular during a gently falling, fluffy snowfall, too. Having seen the city bustling in summer previously, it was kind of surprising to hear that September and October tend to be Galena’s busiest times of the year.

Main Street carries the nickname, "the Helluva Half Mile," which is a clever play on Chicago's magnificent mile. Be forewarned that there is little true resemblance to the Windy City place, pace and sheer space (not to mention the size of crowds). But there's no slight intended; Galena’s primary shopping, dining and drinking district has treats galore – 101 businesses in all – making a slow strolling walk a joy. There’s actually a no "chains" ordinance that creates and maintains the city’s unique ambience with an interesting array of antique shops, galleries and boutiques.

A family would have a swell time in Galena, maybe even for a full week, but it has a romantic feel that makes it ideal for couples of all ages. On the weekend that my wife and I spent, a "Ladies Getaway Weekend" was in full force and the town wore that well too.

If you want to enjoy and engage with Galena’s natural beauty, there’s plenty of opportunity besides the rolling hills on the drive there. The Galena River sits beside downtown and includes a nearly nine-mile hiking trail. The river seems to be consistently dotted with canoes, kayaks, jet skis and pontoons. And for the really adventurous, hot air balloons are a popular choice.

There’s a ski hill nearby, Chestnut Mountain Resort, that obviously bustles with visitors headed down the slopes in the winter, but also features biking, zip lines and Segway tours in the summer. It’s neatly tucked amongst the hills overlooking the Mississippi River.

Possibly the most heart-pumping exercise, though, may simply be walking the steps from Main Street skyward (at least it felt that way). We participated in the Heroes for History Stair Challenge, aka "5K on STAIRoids," which included a really nice, touching 9/11 tribute and raised donations for Galena Area 1st Responders and the Galena-Jo Daviess County Historical Society. The race began with a hearty walk up nearly 200 steps (the more than 200 participating signed up for one lap or seven). It was a really cool event, and Milwaukee should consider something similar on the lakefront.

And far as lodging, we stayed at the DeSoto Hotel, the oldest operating hotel in Illinois – dating to 1855 – which features 55 graciously decorated Victorian-style rooms. Its history is impressive, recounting former President Abraham Lincoln delivering a speech in 1856 and Ulysses Grant tabbing the hotel as his presidential campaign headquarters later in the 1800s. It’s a delightful place, located in the heart of downtown.

President Grant’s presence is felt further with a 3,300 square foot vacation home, available for guided tours, located just on the other side of the Galena River. The 18th U.S. President and Civil War general called Galena his vacation home during his presidency. It’s a worthy venture, especially if you’re a U.S. history buff!

We previously stayed at the Eagle Ridge Resort and Spa, about seven miles east of Galena. With its four golf courses (63 total holes) and guest rooms that were recently renovated, the spacious, pretty surroundings provide a solid option for an intimate getaway, a grander celebration or a company retreat.

Drink and dining

  • Galena Cellars Vineyard and Winery is a downtown gift shop, patio and tasting room (you’ll get an extra treat and wine insight if you happen to be served – special callout! – by either Ben or Marion the Bubble Lady). But if you want the full winery experience, travel to the vineyard about 10 miles outside of town for a spectacular, relaxing view from their wraparound porch. While our trips have included numerous Galena Cellars pit stops, the area includes four wineries and two breweries that I’m guessing are worth sampling too.

  • Farm-to-table is a hot dining trend, so maybe a Farm Tour might make an earthy, interesting activity. It’s called Agritourism, formally defined as "any agriculturally based operation or activity that brings visitors to a farm or ranch," and Galena has a couple options: Beyond the Barn Farm Tour and another option opening in 2018.
  • Fried Green Tomatoes is our top choice for eating, featuring a signature dish of spaghetti and meatballs that's the best I’ve ever tasted. But the kitchen does nearly as well with other Italian fare, seafood and steak. Vinny Vanucchi's, the Victory Café and a host of other café and ice cream options hold their own also.
  • The website says it best about Galena Canning Company "old-fashioned goodness with gourmet flair! And most of all fresh." It offers a huge variety of salsas, pasta sauces, barbecue sauces, chilis, relishes, pickles, hot sauces, mustards, jams and jellies, fruit butters, syrups, toppings, flavored oils and vinegars – with free samples galore. It’s always crowded. Milwaukee Third Ward would kill with one of these.
  • The owner of Myrtles Pies creates and bakes 240 pies each weekend. They’re delicious ... enough said.


  • In a town that likes to play up that it's mysterious and haunted, of course they're going to have a magic show and "master magician. The popular P.T. Murphy Magic Theater is a great show at a reasonable price.

This town has character and nearly every business plays some part in creating their version of "historic, days-of-yesteryear cool."

Galena attracts visitors mostly from Illinois, Wisconsin and Iowa, but does well with folks from Minnesota, Indiana and Missouri, too. There’s a resemblance to Door County, Lake Geneva and Mackinac Island, so if those were previous destinations that satisfied, then Galena will tickle your fancy, as well.