Destination Wednesday: All Roads Lead To Galena, Eventually

BHTP_DistressedLogo_Circle_PMSGalena, Ill., is high on the list of scenic fall destinations, but be warned: If you’re planning a trip to Galena from any starting point other than Chicago, take the sporty car; leave the minivan home. The back ways to the historic red-brick river town twist through steep hills and ravines on shoulderless roads that change names at a whim, when they bother to carry names. Taking them at speed is a blast.

“They’re ridiculous,” Matthew Carroll, the manager at the deliciously rustic Inn at Irish Hollow, said about the roads that lead to his semi-rural location. “But pretty, aren’t they?”

“Ridiculous” is seldom used otherwise to describe Galena, which offers more types of autumn scenery than there are ice-cream flavors in the stores along Galena’s carefully preserved Main Street.

Galena has ridden the river-town rapids. In the 1850s it was the lead-mining center of the Midwest, bigger than Chicago and home to the chief customs house for Mississippi River trade. Steamboats plied the Galena River and Ulysses S. Grant ran the leather store. After the Civil War the railroads came and Galena boomed again.

When the river filled in, the diggings petered out, and the railroads faded away, Galena fell on hard times. A 1937 flood devastated the downtown and led to construction of a floodgate at its west end. So the city of Galena is actually one big gated community surrounded by other, more obvious gated communities.

“In the ‘60s the city fathers had a choice with Galena, whether to open up downtown for redevelopment or preserve the buildings,” said Kathy Bookless, a Realtor with Galena’s Eagle Ridge Realty. “The mayor said, ‘Galena is a gem; it only needs to be polished.’ From then on Galena went the preservation route.”

Most of downtown was placed on the National Historic Register in 1969, and the antique stores, craft shops and tourists moved in.

Restrictions on electric signs and facelifts have given Galena a timeless look that’s going to stay that way. Only the tenants have changed. “There are more good restaurants and fewer antique stores: that’s about it,” said Pete Stryker, a second-home owner from Chicago. Hip eateries like Fried Green Tomatoes, O’Dowd’s Irish Pub and the Perry Street Brasserie are the new face of downtown Galena.

Despite the upscale touches, Friday afternoon in Galena is still family time. Couples push strollers, motorcycles burble down Main Street, and according to local Realtor Andrea Kenna, “it seems like there’s a parade all the time.” On cue the homecoming parade trundles down the street, with fire engines screaming, kids throwing candy and the band playing the theme from Star Wars.

Outside of downtown sprawl golf-and-housing developments like the massive Galena Territory, but it never feels overdone or oppressive, in part because of the terrain. Steep hills and winding roads can hide the developments and shelter a perfect getaway, literally around the bend.

It seems a cliché, but Galena has something for just about everyone: sandtraps at sunrise for the golfers, wild turkeys in the hollows for the outdoor types, boutiques for the shoppers, funky foods for the foodies, history for the historians (Grant’s home is a popular landmark), and red wine on a porch swing for everyone else. There isn’t a lot of downside.

“We just got a Wal-Mart,” said Bookless. “Also, there are no malls, no Marshall Field’s – though I guess there are no Marshall Field’s anywhere anymore – and some people from the city simply can’t handle that.” While Galena offers four robust seasons, summer can get steamy in the valleys and touristy in town. Also, the scenic winding roads of autumn are not nearly as much fun in winter.

Fall is the season to fall in love with Galena, and here’s how you do it: Trundle down the river roads from Minneapolis, follow the river north from the Quad Cities, or take the backroads from Chicago or Milwaukee. Smell the air, heavy with leaf smoke and the musk of drying cornstalks. Take in the golds and oranges, broken by the occasional black-and-gray of a weathered barn or fencerow. Buy a pumpkin from a roadside stand and a piece of pie from a small-town cafe. If you’re smart, you’ll bring the fast car.

Author: Kit Kiefer

As content engineer for Berkshire Hathaway Travel Protection, I have one of the world's great jobs. Not only do I get to write about travel, but I get to edit the work of fantastically talented contributors from around the world. Plus I get all the maple syrup I can drink.