Nestled in the rolling hills of northwest Illinois, Galena is a charming city known for its well-preserved 19th-century buildings, vibrant downtown, and rich history. Sometimes referred to as the “city that time forgot,” entering the flood gates truly feels like entering another century. A weekend in Galena promises a perfect blend of relaxation, exploration, and history, along with a plethora of photo ops, making it an ideal getaway. We’ll share our detailed Galena 3 day itinerary to help you plan the perfect 3 days in Galena.
If you have never heard of Galena, you may be wondering why we’d suggest visiting a small town in corn country. Here are a few reasons. Galena has been called one of the cutest or most beautiful towns in America by World Atlas, Jetsetter, Travel & Leisure, and Expedia. It has been named one of the most romantic towns in the US by NBC News, and New York Travel Guides. It has been said to have one of the prettiest Main Streets in America by Readers Digest and Country Living.
But there is more to Galena that its charming cityscape. The city lies in what is called the Driftless Area, a small section that for some geologic reason escaped the glaciers of the ice age. Having never been plowed flat like the majority of the Midwest farm country, the region is known for grassy hills, forested ridges, karst geology, and spring-fed waterfalls. Not only is this a pleasant surprise in the midst of the breadbasket, it also fills the area with outdoor activities.
In the area surrounding the city, there are at least a dozen state parks, preserves, and recreational areas that include hiking trails, mountain biking, kayaking, swimming, and cave tours. There is even a ski resort about 30 minutes away! You’ll also find several ranches with horseback riding, u-pick orchards, and farms that provide excursions and weekend stays. When I took my grandchildren for a weekend farm stay, it was only 20 minutes from downtown Galena.
Galena has long been a popular destination for those in the upper Midwest, its quaint allure remains a hidden gem for many. It may seem a little out of the way, but the time it takes to get there is absolutely worth it. A weekend in Galena makes a wonderful getaway for couples, girls trips, and even families, and that will only scratch the surface. It also makes a refreshing overnight stop when traveling US Route 20, or the Great River Road.
How to Spend Your Weekend in Galena –
Read on for your guide to making the most of this picturesque town, a photo perfect 3 days in Galena. We wrote this with an actual Friday to Sunday weekend plan, so be mindful that some businesses and attractions will have different availability if you visit mid-week.
As for our meal choices, there are dozens of restaurants in the Galena area. We have chosen those that are among the best and well loved, and those that feature delicious farm to table goods from the local area. In addition, there is a surprising ethnic variety for such a small city, and we have opted to take advantage of that.
Lastly, I must forewarn you, and apologize, as when we visited last my grandson carried the camera most of the time, so most of our photos are from the younger perspective. We have supplemented with a some creative commons shots as well.
Getting to Galena
Galena is conveniently located in the northwestern corner of Illinois along US Route 20, otherwise known as the General Ulysses S. Grant Highway. (Incidentally, this is the longest highway in the US, running from Boston all the way to Newport, Oregon.) It is it easily accessible, but primarily by car. If you’re visiting other Midwest cities, it’s about a 3 hour drive from Chicago, Milwaukee, or Des Moines.
Alternatively, you can fly into the Dubuque Regional Airport, which is just a 30-minute drive from Galena, and rent a car for the short trip. For those coming from farther afield, both Chicago’s O’Hare International Airport and Midway International Airport offer rental car services for the drive to Galena.
Where to Stay in Galena
Galena offers a variety of lodging options, from historic bed and breakfasts to modern hotels. Here are some top choices:
- Jail Hill Inn: This luxury bed and breakfast offers spacious suites and top-notch amenities. The historic building, formerly a county jail, provides a unique and memorable stay, and frankly, it’s just beautiful.
- DeSoto House Hotel: Located in the heart of downtown, this historic hotel dates back to 1855 and offers elegant rooms and a rich history. Its central location makes it easy to explore the city, it’s family friendly, and has an inhouse lounge.
- Irish Cottage Inn and Suites: For those who prefer to be a bit outside the center of town, but close to the action, this Irish cottage boutique style, at the edge of town may be right. The location includes an pub, which will be one of our suggested dining locations, and live entertainment on weekends.
Galena 3 Day Itinerary – Day 1
We suggest arriving mid to late morning on your first day if that is an option. This allows for learning the intriguing history of this small city that once outsized Chicago. Although where you are coming from will determine the way you enter the city, we really prefer to come into town on Route 20 from the east. It is in this direction that you will descend into the valley, and have it open up before you into a view that makes a lovely first impression.
A Surprising Lunch at Little Tokyo
Who would have ever thought that you could relish a delicious Japanese lunch in a small town in the corner of Illinois, but it is true. With its minimalist Japanese decor, you’ll feel steeped in the Zen, and realize Little Tokyo is the real deal as soon as you enter. Whether you feel like a full meal of traditional favorites, a bento box, or are in the mood for sushi, the food is delicious and the fish is fresh. How they get it to Galena’s upper Midwest location seeming as if it were just caught, I have no idea, but I am glad they do.
Get to Know the City on a Trolley Tour
Start your weekend in Galena by learning the history, including its boomtown years and the slump, and the stories of its famous residents on a 90 minute tour with Galena Trolleys. These bright red family built trolleys have become a delightful part of the city landscape, and a fun photo op, but they also provide a nice way to relax, see the charming architecture, and experience some of the fine views of this hilly corner of Illinois. What’s more, you’ll learn the city history from lead mining and riverboats, to its role in the civil war while seeing the associated locations.
Dig in Deeper at the Galena History Museum
After getting an overview of this charismatic town, it is well worth your time to acquire a more complete understanding at the Galena History Museum. The exhibits there will expand your understanding of the Sauk People who once lived on the lands, the city founding and its rapid expansion and wealth, the atmosphere that brought political and military genius to fruition, and the vision which turned a dying mine town into the attraction it is today. It is said that Galena has had the highest per capita rate of military Generals than any other US city, with no less than 9 Generals calling the city home. It’s worth learning about!
Savor the Classic Galena Dinner at Log Cabin
Savor your first dinner at Galena’s first steakhouse, the family run Log Cabin Steakhouse, which has served up hand-cut aged steaks on its downtown corner since 1937. It is almost required that you eat here on one of your 3 days in Galena, so why not the first. Almost everything about the Log Cabin screams classic Americana from its rustic decor with the lantern chandeliers, to the quintessential steakhouse menu, and even the vintage cocktails, although the chef spices it up with some dashes of Greek inspired offerings. A bone in ribeye alongside a Log Cabin old fashioned will have you feeling right at home for your weekend in Galena.
Evening Entertainment – How About Magic?
Don’t let all that food put you to sleep because after dinner it is time to be bewitched and mystified. Walk one block over to Hill Street to get your blood flowing again, to what has been called the best show in Galena, the P.T. Murphy Magic Show. An extremely rare find for anything outside a major city, Master Magician Murphy puts on an up close and personal performance in his intimate 24 seat theater, getting the audience involved in the humor, illusions and sleight of hand. Don’t be surprised if you’re called to the stage to assist, but you’ll love the show either way.
Nightcap at Baum Bros?
If you’re feeling spellbound by the first day of your weekend in Galena, and the magic, and aren’t quite ready to call it a night, walk around the corner to Baum Bros Public House. You can pick your poisons, from craft beer to wine, but the stars of the pub are the craft cocktails created with their own locally distilled spirits.
Galena 3 Day Itinerary – Day 2
Day two of our weekend in Galena will be spent exploring the downtown area, and primarily Main Street. Many people across the Midwest travel to Galena for this experience. I assure you, it will be crowded by mid-morning, so we suggest getting up early, to see a quieter side of things before breakfast, and the crowds.
Early Morning Walk?
As a frequent traveler one of the things you learn right away is that hours just past sunrise are the best time to see most cities and destinations, and Galena is no exception to this rule. Early risers will find the quiet streets in a beautiful glow.
It is also the perfect time to explore the river front greenway and cross the footbridge into Grant Park where you can see the Blakely Rifle and the Civil War Monument. The bridge is located behind city hall, and if you wish to make your route a circle, there is another bridge a few blocks to the north, at Meeker Street.
Enjoy Breakfast at Charlie’s Place
You’ll find Charlie’s Place Eatery on Main Street, directly across from Log Cabin. It’s a great morning spot with its traditional cafe atmosphere, with expansive windows letting in lots of light. The menu features all the breakfast preferences from skillets and omelets, croissants and wraps, sandwiches, eggs, breakfast meats, pancakes and waffles. Plus you find some upscale features such as benedicts and country gravy combos. I suggest the strawberries and cream waffle for a sweet treat, and the meat lovers skillet for something savory.
Shop and Explore until Your Feet Wear Out!
Galena’s Main Street is one of the most charming and eclectic in the entire US. Midwesterners travel to the city to do nothing other than explore the mosaic of boutique shops, art galleries, craft studios, along with the intermittent vineyard salons. You’ll find a little bit of everything along this 7 block stretch of historic buildings along Main Street, including specialty foods and spices, toys and gifts, jewelry and clothing, as well as home furnishings and antiques. There are no less than 50 different emporiums along Main Street each with its own distinct atmosphere and goods.
Intermingled with all of these shops there are also a number of tasting rooms, most featuring wines produced at local vineyards across the Driftless Area. For those who like things a little more effervescent, there is also a champagne tasting room too. And for those who prefer a non-alcoholic drink, there is even a craft root beer shop where you can sample a flight.
For those who are concerned about tiring, there are plenty of intermittent benches along the street, including the one where you should have your photo taken with the General Grant statue. You’ll find public restrooms located at the City Hall building and at the foot of Hill Street. Don’t forget to explore the nooks and crannies of the street, which includes a couple stairways to upper city streets, and greenspaces.
My grandchildren say I can’t forget to tell you about the Blacksmith Shop at the end of the street. Actual trained blacksmiths work the forge, and demonstrate the craft live, explaining as they go.
They also say that Kandy Kitchen, where they had a heyday, is an essential stop!
Make a Choice for Lunch
Everyone we know has spent at least one whole day exploring Main Street, so, we suggest stopping for lunch right along the strip. There are numerous restaurants and eating establishments dispersed among the boutiques, and you’ll have no problem finding one that suits your taste. In fact, you’ll be spoiled for choice. I recommend continuing our ethnic exploration and trying either Italian at Vinnie Vanuchi’s or Mexican at Campeche. If we could squeeze in one more meal during our 3 days in Galena, I would say enjoy them both.
Italian Fare at Vinnie Vanuchi’s
Located in the middle of Main Street next to the Ulysses S. Grant bench, Vinnie Vanuchi’s has a fun Italian vibe, with it’s red and white checkered table cloths and grapevine wrapped rafters. The lunch menu includes appetizers and “sangwiches,” as well as full meals of all your classic Italian favorites, such as lasagna, manicotti, fettucine alfredo, and chicken marsala. I’m a fan of the baked seafood Italiano.
Mexican at Campeche
Located at near the north end of Main Street, near the Blacksmith Shop, Campeche features a red brick, more industrial atmosphere, bright tiles and artwork in primary colors that give it the Mexican feeling. Named for the founder, “grandma’s” Gulf-side hometown where the recipes originated, Campeche features traditional south of the border choices, with some extra seafood options, and breakfast picks. Don’t miss the fried ice cream!
Need to Get Out of Town? Try Hoofing It.
You may spend all day exploring downtown Galena, and if so, we understand. Many people spend multiple days doing so. However, if you need to break up your time in the shops, Hoofing It Goat Treks is an fantastic, playful and relaxing adventure for your weekend in Galena, and one that is completely unique. Visitors embark upon a 1 hour woodland trek with a guide and a friendly family of goats who love petted and make wonderful walking companions. Treks are offered at 3:30 and 5:30 on Saturdays. The farm also offers both wine and musical treks with the goats.
Satisfy your Taste for French and German at Fritz and Frites
Fritz and Frites, with their slogan, “A little French… A little German… A little bistro,” has been called the best restaurant in Galena by many. As the slogan suggests, the menu is an interesting collection of both French and German specialties, almost like eating in Alsace. You’ll find that the decor of the restaurant emits the resonance of a French cafe, with it’s black and white tiled floor and framed paintings. But when it is time to order you can mix and match, from pate, escargot, and brie, to schnitzel, spaetzle and sauerbraten. Personally, I am partial to the cassoulet.
Need a Little Evening Entertainment?
If you aren’t ready to call it a night yet, walk a block down to experience the local nightlife at Miss Kitty’s Grape Escape. Known as a “wine and martini lounge,” we don’t have to tell you what the club is known for, but it is described as a lively bar with a welcoming atmosphere. They feature live local music on Thursdays, Saturdays and Sundays, with an occasional Friday show thrown in.
Galena 3 Day Itinerary – Day 3
Today we will venture out of the downtown area, and learn about some of the movers and shakers who originally put Galena on the map, including President Ulysses S. Grant. No weekend in Galena is complete without a visit to his home. After that, we will experience a couple other attractions that make the city unique among small towns, and maybe even get out on the river if time allows. We’ll wrap it all up with a knock-out farm to table dinner.
Are You Up for Another Morning Walk?
If yesterday’s walk started your day off right, and you think another is in order, this time I suggest investigating West Side Sculpture Park. If you are lodging downtown, it will take 15 to 20 minutes to walk to the park, or you can drive, if you just want a good morning stretch. Founded by metal artist John Martinson, the small park features fun sculptures crafted of welded steel and repurposed junk, scattered within a wooded area of short grassy trails. The sculptures are colorful and creative, evoking the imagination. I love the Eyeful Tower.
Feel Like Home with Breakfast at Otto’s Place
Known for its locally sourced farm fresh ingredients and homey atmosphere, breakfast at Otto’s features something for everyone, and it can’t be missed during your 3 days in Galena. You’ll feel like you’re having breakfast in your grandma’s kitchen. And while she was a good cook, she probably didn’t serve up pork belly, goat cheese, or homemade pop-tarts, and she probably didn’t offer cocktails for those who hit the bar a little too hard the night before. Whether you want a classic country breakfast like biscuits and gravy, or something fancier like coffeecake skillet or frittata, you’ll be satisfied.
Discover Lifestyles of the Rich and Famous
We mentioned it before, but Galena has been the home of more Generals than any other US city, and at one time. It was also the source of great wealth, and many men who grew to great influence spent a part of their lives living in the city. Others, such as Abraham Lincoln, never lived in Galena, but he visited on more than one occasion.
Get to Know a Great Man at Ulysses S. Grant Home State Historic Site
After breakfast head on up the hill to the prominent Ulysses S. Grant Home State HIstoric Site. As a enthusiast for Presidential homes and locations I may be biased, but I believe the home tour should not be missed. The beautiful Italianate home was a gift to General Grant, for his victory in one of the bloodiest wars in US history. It was the General’s home until his vie for the Presidency, and his sitting home during his Presidency. It was also here that his children spent much of their formative years.
Home tours are led by well-educated and dedicated docents, who care deeply about the former President, his mark on history and his legacy. All but the most studious historians will learn something on the tour. This is where I learned that although a huge persona, President Grant was only 5’8” tall, a fun fact I like to share, among many other things.
The tours are family friendly, although due to the structure of the home, not accessible. I took my grandchildren and although they were not completely absorbed in the guide’s information, they found plenty of fascinating things to look at and discuss. I suggest taking the first tour of the morning at 09:00.
Once through the home, don’t miss the little string of historic buildings behind the home, including the replica general store and the gift shop. If all are open at the time of your visit, we enjoyed the unique miniatures display featuring the pets of every American president, and the signature China used by each family in the White House.
Also, at the bottom of the steps near the parking lot is an early Galena historic marker, and small log cabin. The markers explain the earliest pioneers of the area, and the difficulties they endured. We found it fascinating but hard to grasp that a family of 8 had lived in this tiny home, and we were all reminded just how good our lives are.
Move on to Belvedere Mansion
After completing your exploration of the Grant Home, continue over to the Belvedere Mansion and Gardens, referred to as the finest Italianate Mansion in Galena. The home is known for its opulence and refinement, a true display of a life of comfort in the mid-1800s.
The home was built for J. Russell Jones, a diverse man of stature who played a role in many significant events. At the time of its construction, Galena was larger than Chicago, and viewed by many as the center of trade in the Mississippi Valley. Russell’s contributions to the times are best left summarized by the current owners of the Belvedere Mansion.
“J. Russell Jones became a man of means and stature from humble beginnings to the Belvedere Mansion on the east side of the River and on to Washington and the cities of Europe without a formal education or affiliations of means. His time in Galena was the serving ground for his later years of service to his country from US Marshal, to Chairman of the Republican Party, to businesses of steamboats, cotton and railroads. He was instrumental in carrying support for Grant’s campaign and triumph during the Civil War and Grant’s eventual place as President of the United States. His friendships are the hallmarks of a life well spent. We are proud to be the stewards of his legacy.”
Take Pleasure in an Irish Lunch at Frank O’Dowd’s Irish Pub and Grill
For those of you longing to visit Ireland, you’ll get a small taste at Frank O’Dowds, located allt he way at the top of the Hill on US Highway 20. I have visited a few Irish pubs, and Frank O’Dowds feels like it could sit out back at the Cliffs of Moher or the Giant’s Causeway. Once you learn the furnishings were handcrafted in Ireland, it is no longer a surprise, and you’ll enjoy this little jaunt on your weekend in Galena. You can go light with a soup, salad or sandwich, or dig into some true Irish specialties, including fish and chips, bangers and mash, shepherds pie, or chicken and stout gravy.
Get to Know the Spirits on a Distillery Tour at Baum Bros
A little further along Highway 20 you’ll find Baum Bros Distillery. While craft breweries are found in almost every city these days, distilleries are a bit more rare, and Baum Bros is even more unique as it produces four different spirits, bourbon, vodka, gin and moonshine, in seven total varieties. A tour takes you inside the operation to discover the processes of milling, mashing, fermenting and distilling. Not only will you find the process and equipment fascinating, you’ll be suffused in the sights, sounds, and smells of the process, and top it all off with a tasting. Tours are offered at 1:00 and 3:00 on weekends.
Back to Town or Out in the Open with Nuts Outdoors?
If you made the 1:00 distillery tour, or that was an option you would rather not participate in, you may want to finish up your downtown perusing. Shops are open until 5:00, so you have a few more hours to do so. If you would rather see a little more of the natural side of Galena, consider renting an electric bike, or kayak from Nuts Outdoors. Nuts offers 2 hour bike and kayak rentals, from near the downtown area. The Galena River Trail is the perfect place to explore by bike, and you an depart right from the shop. If you prefer to kayak, you can rent all the supplies, and be dropped right at the river for launch.
Relish Dinner at Fried Green Tomatoes
End your trip with a bang, with dinner at Fried Green Tomatoes. Another contender for the best restaurant in Galena, the choice of many, it is another essential during your 3 days in Galena. With its rough hewn stone on one side and wall-paper on the other, it has a more luxurious than atmosphere most of the other restaurants, with the feeling of being on the town. Know for its Italian-inspired comfort foods and steaks, the menu goes far beyond that offering with surprises such as charcuterie boards, beef carpaccio and ahi tun salad. As for me, the sea scallops with sweet pea pancetta risotto and the Chilean sea bass with olives and roasted tomatoes are meals to write home about.
Sadly, Your Weekend in Galena Has Come to an End
After dinner, it’s time to head home. Unfortunately, Monday morning beckons. As you travel home, you can reflect on the delightful experiences and memories made in Galena.
A weekend in Galena, Illinois, offers a perfect blend of historical exploration, culinary delights, and outdoor activities. From the rich history of Ulysses S. Grant’s home to the charming streets of downtown and the serene landscapes of Horseshoe Mound Preserve, there’s something for everyone. Whether you’re savoring a meal at a local restaurant or enjoying the live music scene, Galena promises a memorable and enriching getaway. Plan your visit today and discover the timeless charm of this beautiful city.
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About the Author
You know me, Roxanna Keyes, sometimes referred to as FoxyRoxyK, the founder of Gypsy With a Day Job. I was 50 before I really began to experience all the world has to offer. I really don’t want you to wait so long!
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