Travel Back in Time in This Illinois Town Full of Lincoln Lore, Kraft Cheese, and Midwestern Kitsch

This may come as a surprise to some, but Illinois isn’t entirely dominated by Chicago’s skyscrapers and sky-scraping deep-dish pizzas. Beyond the sprawling confines of America’s third largest metropolis, the Prairie State is home to a wealth of bucolic towns and surprisingly legit hiking destinations, all of which are a scant few hours away. Galena is one such place.

Located on the northwesternmost corner of Illinois, near the Mississippi River and the Iowa border, it’s a breath-of-fresh-air town that’s the antithesis of Chicago in many ways. While only a three-hour drive, Galena feels more like a three-century drive with its preserved-in-time architecture, fertile farmland, and deep history covering everything from US presidents to Kraft Cheese. That innate charm is what draws travelers and transplants alike.

“In returning to our Midwestern roots, we quickly fell in love with the picturesque charm of Main Street and the many unique small businesses,” explains Geoff and Alex Arroyo-Karnish, husbands who moved to town in 2019 from Manhattan, and opened Galena Bakehouse in a renovated antique store during the pandemic. For them, the draw was the win-win proximity to beautiful nature and the innate inclusivity they felt from locals. “Galena feels more inclusive and welcoming than most traditional small towns,” they add. “In 2021, we created the first annual Galena Pride Picnic, a family-friendly event that was well attended by people from Galena and the surrounding communities.”

It’s that sense of welcome and Pride that drew the couple to Galena, and it’s the natural backdrop that keeps them—and so many others—inspired. “Galena is a beautiful town surrounded by rolling hills and gorgeous countryside,” says the pair. “When we first walked the town's half-mile Main Street, we couldn't see and visit everything in just one day, and that impressed us. There is truly something for everyone, whether you love outdoor adventures, local wineries, history, shopping, or delicious food.”

From its old-timey lore and old-fashioned ice cream parlors, to progressive events, outdoor beauty, and bald eagles soaring overhead en masse, Galena feels utterly worlds apart from Chicago. Make the trek and see, sip, and taste for yourself.

3 hours from Chicago
2 hours, 50 minutes from Milwaukee

A stark contrast to Chicago’s shiny towers and even shinier Bean, Galena is the town that time forgot—and we mean that with love. It’s nice to hole up someplace that feels of a simpler era—one filled with un-ironic barn dances and ice cream parlors. The downtown area still looks the way it did in the 19th century, replete with brick walkways and buildings listed on the National Register of Historic Places. Much of this is on full display along Main Street, where more than 100 businesses—from candy counters and wine bars to restaurants and toy stores—are nestled inside original buildings from the 1800s.

Beyond shopping and snacking, history is everywhere in Galena. This is particularly prominent with its Presidential lore, as the town was famously home to President Ulysses S. Grant, whose former abode is managed by the Illinois Historic Preservation Agency, and is available for tours. President Abe Lincoln also had Galena ties, including a famous speech he made from the DeSoto House Hotel. The Victorian-style inn is the oldest operating hotel in the state, and Lincoln impersonators still host old-timey dinner theater events on the property, complete with chicken Fricassee and apple pie—Lincoln’s favorites. For more historic eats and sips, check out Mulgrew’s Tavern & Liquor Store, one of the oldest bars in Illinois (in operation since 1921), famed for its cheap beer, foot-long chili dogs, and slot machines. Then there’s Council Hill Station, an 1850s general store-turned-saloon, with live music, country breakfasts, and barn dances held every weekend in the summer.

Some history is downright cheesy—and again, we mean that with the utmost love. Like the fact that Galena is not only home to President Grant, but also Kraft cheese. Everyone’s favorite neon-orange cheese product was born in the tiny suburban town of Stockton, and the company’s all-American lore is on full display at the Stockton Heritage Museum. The pint-sized museum has an exhibit that tells the story of J.L. Kraft & Bros. Co., who opened its first cheese plant and began delivering milk from local dairies to the facility via horse-drawn wagon. Nowadays, museum visitors can snap selfies with one of said wagons, gain inspiration from Kraft-inspired cookbooks, and learn everything you’ve ever wanted to know about the invention of Velveeta.

As evidenced by the surplus of candy counters and soda fountains, Galena is a wholesome wonderland for families and kids. For food and activities alike, most everything in this quaint town caters to visitors of all ages—except maybe the wineries and wine bars, of which there are surprisingly many. Particularly, Galena is a sweet tooth paradise, teeming with old-timey ice cream parlors and candy shops, including the 50-year-old American Old Fashioned Ice Cream Parlor and Candy Carnival for all your taffy, popcorn, and mini donut needs. For shopping, Gabby’s Gifts is a quirky spot filled with kid-friendly knickknacks like puzzles, toys, and childrens’ books, while the P.T. Murphy Magic Theatre is sure to be a hoot with its silly theatrics and close-up sleight of hand. One ongoing activity that’s fun for the whole brood is Live at the Plaza, held every second and fourth Thursday of the month at Green Street Plaza through August. The free events offer something for everyone and all ages—live music, food, extended hours in nearby shops, and other performances, all with different themes like Educator Appreciation and LGBTQIA+-centric Amazing for All.

In Chicago, outdoor recreation is typically limited to urban beaches and drinking cocktails on rooftops. In the quieter, wide-open terrain of Galena, however, outdoor activities are a bit more bountiful. Hiking and biking opportunities can be found throughout the town’s parks, forests, and prairies, including the nearly nine-mile long Galena River Trail, Apple River Canyon State Park, and Casper Bluff Land & Water Reserve, where you can traverse trails and theorize about ancient Native American effigy mounds in the Earth.

With waterways criss-crossing the region, there are plenty of aquatic options to choose from too, including fishing on Lake Galena (just be mindful that bald eagles might provide some competition, since Illinois is home to the second largest wintering population outside of Alaska). Or you can rent kayaks or paddle boards from Nuts Outdoors, offering guided jaunts on the tranquil Galena River. After exploring Galena by land and water, it’s time to buckle up and hit the sky—Long Hollow Canopy Tours provides adrenaline-pumping zip line tours through Tapley Woods, at speeds up to 40 mph and heights that reach 75 feet.

In terms of epic all-natural Americana, it doesn’t get much mightier than the Mississippi River. The iconic waterway traverses the western border of Illinois, along the edge of Galena and the state of Iowa, so naturally such a major body of water is going to provide some staggering scenery. Visit the riverside Chestnut Mountain Resort for a choose-your-own-adventure of Mississippi-adjacent activities, from the Soaring Eagle Zipline to mini golf courses and an Alpine slide that zooms down the banks of a forested palisade to the shores of the river. The resort also provides Mississippi River cruises, for an informative guided immersion into the river’s ecosystem and wildlife.

Golf is another mainstay activity in Galena County, as the lush region boasts some of the most meticulously manicured greenways in the Midwest. There are 11 courses in the area, ranging in size and scope from leisurely nine-hole courses to championship-level courses for the seasoned golf pro and/or masochist. Standout options include the Apple Canyon Lake Golf Course, with nine holes weaving by canyons, hills, and bluffs, and Lacoma Golf Course, a veritable Disneyland of golf that’s grown from a nine-hole course in 1967 to a 45-hole complex consisting of three different courses, plus a driving range, full practice facilities, a pro shop, and a bar. If you’re looking to try something a little more novel and a little less rage-inducing, try your hand (or your foot) at FootGolf, a soccer-golf hybrid at Eagle Ridge Resort & Spa. Essentially, it looks like a jumbo version of golf, with soccer balls in place of golf balls, and over-sized holes and flags to aim for.

Since literally any outdoor activity is improved by the presence of goats, Galena is a veritable paradise of cute outings with hooved critters. Hoof It Goat Treks does exactly what their name promises, taking guests on leisurely guided hikes through prairies and forests with baby goats in tow. For adults, the company also provides goat trek/wine tasting combos, wherein hikers can stroll the forest with a glass of wine, followed by a tasting of wine and goat cheese (naturally).

Goat yoga is another popular local pastime, best experienced with Galena Goat Yoga on Silver Linings Farm. Each 45-minute session, the perfect combination of stretching and snuggling, provides yoga mats in an air conditioned studio. Or if you’d prefer something more relaxed, the studio offers hour-long coffee breaks in a furnished corn crib with pastries and about a dozen goats. The company also provides private goat events, in case you’d really like to take your bachelorette party to the next level.

Right in step with Galena’s obsession with all things Americana, the region is rife with old-timey fairs. Like the Elizabeth Community Fair, a summertime spectacle of dairy shows and fantasy truck pullers, which, entering its 103rd year, puts the “old” in “old-timey.” This is followed in August by the Jo Daviess County Fair, the longest-running consecutive fair in the state. In operation since 1860 (for reference: that’s just four years after Lincoln made his balcony speech at the DeSoto Hotel), the all-ages event features carnival attractions, a beer tent, a derby, a pageant, and—curiously—a mud volleyball tournament. It all culminates with the Galena Country Fair in October, a weekend chock full of fudge, jumbo baked potatoes, walking tacos, and pork chop sandwiches.

More fall fun can be had at the annual Warren Pumpkin Festival, an old-fashioned lineup of tractor pulls, carnival rides, vintage car shows, and of course, pumpkin-themed games and snacks aplenty. This is followed in late-September by the 14th annual Fall Harvest & Art Festival, hosted by Galena Cellars. Despite being a wine-centric event, kids and adults alike get to stomp their own grapes—though the latter are the only ones able to enjoy the fruits of their labor. There’s also live music, pumpkin painting, horse-drawn carriage rides, and local art for sale. And let’s not forget Oktoberfest. This year’s fete, taking place October 5, kicks off with a cannon blast, the annual tapping of the keg, a wiener dog race, and naturally, live polka.

For a town with a population of a few thousand, Galena’s dining scene impresses with its array of restaurants and its mix of old and new, from adorably dusty saloons to a queer-owned bakery slinging empanadas and Argentinian cheese bread.

Considering the town is surrounded by farmland and fresh water, it’s not surprising that much of its restaurants are seasonally driven and locally sourced, like blackberry pork rib-eye and free-range chicken piccata at Fried Green Tomatoes, or bourbon-marinated tenderloin tips and Illinois wines at Woodlands Restaurant & Lounge. Bread and Vine is an on-the-nose bistro that specializes in two classic comforts: carbs and wine. It also has one of the most eclectic menus in town, offering French hot dogs alongside Roman-style pizzas, pork belly bao, coconut margaritas, and a French-leaning wine list.

The belle of the ball when it comes to local fine dining, though, is the Goldmoor Inn, a historic manor-like hotel that applies a modern interpretation to its farm-fresh fare. Dine at the chef’s table overlooking the kitchen and feast on a veritable omakase of whatever the kitchen is cooking up that day, interspersed with samples of daily specials and interactions with the cooks, who according to the website, “talk candidly about the joys and stresses of professional cooking.” If all that wasn’t insider-y enough, diners can even sleep in the kitchen (basically)—the Chef’s Quarters is a hotel room located directly above the kitchen.

In the morning, rise and shine at Galena Bakehouse, the sunny cafe owned by Geoff and Alex Arroyo-Karnish. “We love serving our scratch-made pastries and coffee drinks to both the local community and the many visitors,” they say, citing everything from Argentinian cheese bread and cinnamon rolls to glazed almond coffee cake, beef picadillo empanadas, and oatmeal cranberry cookies. “It has been such a dream to bring this showcase of love to this very small town and to have them welcome all of it.”

To drink, it’s all about stemware here, as Galena is Illinois wine country. Oenophiles can visit Massbach Winery 30 minutes away in Elizabeth, or pop into the tasting room on Main Street. Fergedaboudit Vineyard & Winery is another local staple, located in Hanover, which is also home turf for Rocky Waters Vineyard & Winery, perched on 25 acres of fruitful vineyards. Back in town, Champagne on Main is a bubbly wine bar with plenty of shimmer—from the twinkling chandelier to the flutes of Champagne.

In case you can’t snag a res for the bedroom over the Goldmoor Inn kitchen, fear not. The chateau-esque resort has plenty of other ornate rooms and suites to go around, each complete with two-person whirlpool tubs and complimentary breakfast delivered to your doorstep, along with cottages and log cabins that Lincoln surely would have loved. And speaking of Lincoln, you can rest your head where he made his speech in 1856, in one of the 55 Victorian-style rooms at the DeSoto.

Another cozy hideaway is the Inn at Felt Manor, an estate from 1850 that Arroyo-Karnish’ first managed upon their move from Manhattan. Today, accommodations at the tranquil property include the rustic-chic Coach House, the equestrian-themed Stable Studio, and the Manor itself. While the latter is temporarily closed for renovations, the historic property boasts five suites with views of downtown Galena.

Or, for something decidedly less decadent and old-timey, the Palace Campground is a state-of-the-art playground for RVs and tent campers, complete with above-and-beyond amenities like mini golf (and glow-in-the-dark mini golf on select weekends), heated swimming pool, wagon rides, and an arcade.

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