Galena, Illinois

Galena, Illinois
#GetToGalena By Jess Keys, The Golden Girl


Jess & Neal’s Weekend Getaway Guide

By Jess Keys, The Golden Girl

A couple weeks back, my husband, Neal, and I headed to Galena, IL for a little mini getaway out of the city. We wouldn’t trade living in Chicago for anything, but sometimes, you just want to get out of the chaos and enjoy some beautiful scenery and a relaxed pace of life—Galena Country offers that, and so much more!

If you aren’t familiar with Galena, you might compare it to other similar vacation towns outside of Chicago—beautiful, with not a lot to do. Those are great in their own right, but they aren’t Galena. There are so many fun and amazing things to experience in Galena, you’d need to plan 10 different trips to experience them all!

A lot of destinations boast this claim, but there really is something for everyone here. Whether you’re planning a romantic getaway, a bachelorette party, a family vacation, outdoor adventure, girls weekend, and pretty much any other scenario you can think of, you will truly love this charming place.

Read on for more about our experience, and what not to miss while planning your trip!

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The History:

One of the qualities that surprised us most about Galena was its history. Did you know at one time, Galena was bigger than Chicago? It was actually one of the busiest ports on the Mississippi River in the 1850s! As many as 15 steamboats could dock along Water Street at the same time. Due to this fact, 85% of Galena's buildings are in a National Register Historic District!

This was one of our favorite parts of the town—the buildings that make up the town are so old and picturesque, each with their own story to tell, and built with what’s called “Galena brick”—making the downtown area one of the most charming you’ve ever seen!

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Where to stay:

The rich history and charm continues at Farmer’s Guest House, which was built in 1867 and named one of the top 10 B&B’s in North America. I love B&B’s, and I can honestly say this one is my favorite that I’ve ever stayed in!

The owners make you feel so welcome and you can tell they truly love what they do. There are tons of B&B’s to choose from in Galena, but there are a few things that really set Farmer’s Guest House apart.

First, it’s conveniently located within walking distance of Galena’s historic Main Street. The breakfast has won several awards, which is obvious after just one bite of the pecan French toast. The breakfast menu rotates every other day between savory and sweet, and is always served with delicious fresh fruit, local coffee, locally made sausage (seriously some of the best I’ve ever had) and a mimosa bar!

Second, these things are really specific, but very important: they have THE COMFIEST beds ever. Seriously, hands-down, the comfiest bed that isn’t my own that I’ve ever slept in. They have thought of every detail to make your stay as comfortable as possible, from the individual thermostats in each room, to the library of DVDs and wall-mounted TVs in every room. Sometimes, all you want to do on vacation is snuggle in bed and drink a glass of wine and watch a great movie, right? Is there anything better? I also loved that every room is named after a General’s wife, with a biography hanging outside each door—such cool little details!

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Best of Main Street:

Named "Best Main Street in the Midwest" by Midwest Living magazine and one of “America's Best Main Streets” by Fodor’s—it boasts nearly 100 storefronts, restaurants and art galleries that are all charming in their own way! You could spend days working your way through what downtown has to offer.

I’d really recommend starting at one end and working your way down to the other, but here are some of our favorites that really stood out:

Hot sauce at Galena Canning Company in Galena, Illinois

Galena Canning Company:

Don’t be fooled by this small town shop—they stock one of the largest selections of hot sauce in the entire country! Any spice lover will feel like a kid in a candy store. They also have dozens upon dozens of their own formulas—try the Kiss of Fire Hawaiian hot sauce–(you should probably BYO fire extinguisher.)

Home goods at Isabella's in Galena, Illinois


Not finding something you love in this home goods shop would be an impossible task. From gifts to tabletop items, apothecary goods, furniture and even flooring—they’ve got a well-curated collection you’ll love. DIY enthusiasts will especially appreciate the shop’s selection of Annie Sloan Chalk Paint.

Popcorn at the Great American Popcorn Co. in Galena, Illinois

Great American Popcorn Co:

Who doesn’t love an old-fashioned popcorn store and ice cream shop? They’ve got too many flavorful blends to count—our favorites were Tiger Mix and Galena Mix! You’ve never had anything quite like it!

Canned goods and pickled veggies at Grateful Gourmet in Galena, Illinois

Grateful Gourmet:

Foodies will freak over this store stocked with the coolest kitchen gadgets, canned goods, delicious local preserves, cookbooks and more. We stocked up on a few jars of pickled veggies to make Bloody Marys at home and they are delicious!

Pasta Perfetta in Galena, Illinois

Pasta Perfetta:

In the same vein as above, Pasta Perfetta is any Italian food lover’s paradise! Shelves filled to the brim with imported handmade pastas from Europe to take home with you!

Influencer Jess Keys, aka The Golden Girl, outside Vignettes in Galena, Illinois


Any and all interior design enthusiasts must pay a visit to Vignettes, which stocks furniture, textiles, artwork, decor and more. I always love picking up a home item while on vacation, so I always have a permanent reminder of how much fun we had. Vignettes is the perfect spot to do just that. Plus, their storefront is just too Instagram-worthy—a perfect (what else?) Vignette!

Beer at Gobbie's on Main Street in Galena, Illinois


Had we had more time here, this looked like such a fun spot to grab a bite to eat, but we had dinner plans later, so we stopped in for a drink on Gobbie’s expansive and comfortable open-air patio. I can’t think of a better place to stop and enjoy a beer when the weather is nice!

The exterior of the VFW Club on Main Street in Galena, Illinois


Being avid dive-bar enthusiasts, when we walked by VFW, we couldn’t NOT go in for a beer. The beer was cold and the drinks were cheap. What more could you want from the best dive bar in town?

Pizza at Cannova's on Main Street in Galena, Illinois


Where we went for dinner. Make sure to order a pizza and a pasta dish to split so you get a little bit of everything! Excellent service. If you can, snag one of the quaint, romantic tables in the window.

Pasta Perfetta in Galena, Illinois

Gold Room:

Next door to Cannova’s, Gold Room is another fun dive bar to check out for a fun game of shuffleboard before or after dinner!

A Bloody Mary at Otto's Place in Galena, Illinois

Otto’s Place:

Well-known in Galena as some of the best breakfast in town (aside from Susan’s of course), but you should be sure not to miss the Bloody Marys! Made with a special house mix and garnished with hot Cheetos, it may be the best you’ve ever had! Sit at the counter and chat with the owner, who will give you a great run-down of the history of the building and how it came to be known as “Otto’s.”

We can’t wait to get back!