On the road again: Galena, Illinois

by | Dec 2024 | Voices & Series

A few years ago, I picked up a book entitled “20 Great Weekend Getaways” published by the Midwest Living folks. The front cover features a gorgeous 19th century village tucked in the side of a of a hill. Dozens of brick buildings and church steeples jut out amongst the treetops.

The picture intrigued me enough for Jackie and I to plan a road trip to find this historic gem. The town of Galena, Illinois is located a hundred miles northwest of Chicago. About an hour north of Chicago, you pick up the two-lane US-20, which winds through rolling hills and small villages.

Galena is an old lead mining town. In its heyday, the town was also a stopover over for steamboats detouring off the Mississippi River for a short cruise up the Galena River. Galena was the home of President Ulysses S. Grant, and his original home is open to tourists.

Civil War era mansions and downtown buildings have not changed much in the past 150 years. The mines dried up and the steamboats stopped coming, which caused the town to languish and remain almost untouched for decades.

Galena’s vintage buildings now house dozens of restaurants, antique shops, bookstores, boutiques and over 40 bed and breakfasts.

Weekends in Galena are packed with visitors from all over the Midwest. In fact, a downtown shop owner informed us that next to Chicago, Galena is the most visited town in Illinois.

We visited Galena on a Halloween weekend. This was great for entertainment but almost impossible to find a place to stay. We found a reasonably priced small room in a bed and breakfast built in the 1850’s on a Thursday night but were told there was nothing in town available for the weekend. After checking at several other places around town we ended up driving to Dubuque, Iowa on the west side of the Mississippi.

We stayed in The Mandolin Inn, a restored Edwardian mansion. The hostess was not thrilled that we knocked on the door at 9 p.m without a reservation but found a room for us. The place was fabulous. The hostess told us that Kevin Costner had recently rented the whole place for a week. He was in town for an anniversary reunion of the Field of Dreams in nearby Dyersville. Being a big baseball fan, we made the 20-mile trip to Dyersville and found the field, house and barn exactly as it looked in the movie.

Halloween weekend may be the busiest weekend of the year in Galena. There is a lighted tethered balloon show on Saturday night followed by a two-hour parade. The parade highlights include flames shooting from the hot air balloon baskets mounted on floats. The shadows from the flames dance on the fronts of the buildings as the floats wind through the packed downtown.

Friday night we had dinner at the Log Cabin on Main St. The restaurant has been open since 1935 and specializes in hand-cut Angus beefsteaks. We were told that members of ZZ Top had dined there after an area concert.

We spent our time shopping in great stores, riding bikes along the Galena River Trail and touring the historic neighborhoods overlooking the town. We ran into a lady raking leaves and asked her when most of the houses on her street were built. She informed us that the majority were built between 1830 and 1860. She then pointed across the street to a somewhat unassuming old brick house and proclaimed, “That is the house that President Grant grew up in.” His bigger home downtown is the more celebrated one that was given to him after returning from his presidency.

If you are willing to drive a few extra miles, spend a long weekend in Galena and experience one of the great small towns in the Midwest. You will not be disappointed.

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