Recently, Branden and I took a trip to Galena, Illinois, and it was the perfect romantic getaway! If this post inspires you to travel to Illinois, make sure to check ahead for up-to-date events, exhibits and opening hours at any attractions.

Located about two and a half hours from Chicago, Galena is an amazing escape from the city and a charming compliment to a larger vacation through Northwest Illinois. Picture this: a once bustling port city along the Mississippi River turned into the busy city dweller’s respite, complete with stunning two-story, historic brick buildings crafted out of a unique brick called Galena Brick, plus cozy B&Bs and delicious farm-to-table restaurants. It’s no wonder Galena’s Main Street was named “Best Main Street in the Midwest” by Midwest Living magazine. It feels like you’ve stepped into a Hallmark Christmas movie.

While this was my first visit to Galena, I can see why people come season after season. The drive in from Chicago has some of the most beautiful forest-lined roads, perfect for fall leaf lovers. In winter, they have snowshoeing at Casper Bluff Land & Water Reserve. The Reserve features more than 85-acres of Mississippi River bluffs, rich with historical and Native American archaeology, plus natural wonders like birdwatching. The spring brings festival after festival, and summer offers warm days and even a hot air balloon race!

Working with the Enjoy Illinois team, we crafted the perfect itinerary filled with delicious foods (dreamed up by local Illinois makers), picture-perfect wine tastings, adventurous and relaxing horseback rides, and even a spooky ghost tour! 

Here is a peek at our trip and my recommendations, based on this awesome itinerary on


The Goldmoor Inn

The Goldmoor Inn

The Goldmoor Inn is located on the Goldmoor Estate overlooking the Mississippi River, which makes for the perfect backdrop for a beautiful view of the sunset. With over more than 30 years of hospitality, everything from the service to the food had an extra touch of luxury. It was stunning and serene, and the perfect way to start off a romantic getaway. Dinner here was delicious and the views were unreal!

Timmerman’s Super Club

Timmerman’s Supper Club was our next dinner spot. The view was also spectacular and overlooked the Mississippi River. Are you starting to see a common theme? Galena is all about great food and beautiful views. All the dishes were familiar favorites with a twist, like baked French onion soup and stuffed mushrooms with crab and cheese. One nice addition: you can add lobster or crab legs to any entree. I had some of the tastiest Fettuccine Alfredo here!

Log Cabin Steakhouse

Log Cabin Steakhouse

The Log Cabin Steakhouse is a Greek steakhouse and we definitely recommend it! With close to 1,500 reviews on Tripadvisor, and a 5-star rating on nearly all of them, be sure to make a reservation and call ahead because they are very popular. Our server Zack was amazing, and the food was top notch. What makes this place so special is that it has an old school vibe, and yet feels current and modern.

The saganaki (flaming cheese) here is the BEST I’ve ever had. You also need to try the Grasshopper for dessert! This mint ice cream drink was the cherry on top of such a delicious meal.

Breakfast & Coffee

Galena loves breakfast and so do we! The first morning we dined at Otto’s Place; they had some of the best breakfast potatoes. And the next morning, we filled up at Big Bill’s Sandwich Shop and Coffee Bar, where we loved, loved, LOVED their pancakes!

Coffee at Big Bills

For a coffee break, I recommend Galena Bakehouse. Everything they make is made from scratch and has a limited supply (they never have to throw away food because it always sells out). They had so many delicious pastries, quiches and danishes, as well as Argentinian empanadas. Plus, and maybe most important first thing in the morning, the coffee there was perfect. They also offer picnic basket rentals where they fill a picnic basket with all the goodies you’d need for the perfect lunch out and provide a list of more than 25 beautiful locations in Galena for your outing. We definitely want to try that next time!

We also stopped by Bread + Vine for some lunch. We had the Caesar salad, charcuterie board and truffle fries (my fav!). You also need to try the Nutella croissants here. They were so good I’m telling everyone you can’t plan a trip to Galena without having them!

Great American Popcorn Co.

Last on our food tour was the Great American Popcorn Company. Thank me later, but you definitely want to stop here and try all the flavors. The cheddar popcorn was my favorite and I just had to bring a few bags home


As you’re planning your trip to Galena, know that it is a small town with a very long Main Street with everything you could want up and down the street. From shopping to restaurants and really fun bars for nightlife, Main Street is filled with more than 125 different stops and is a can’t miss when visiting. Find one parking spot and be prepared to walk and shop, walk and sip, and walk and snap photos of all of the beautiful, historic 1800’s era buildings. Here are some of my favorite things we did and would highly recommend:


There are so many fun outdoor activities in Galena, from e-biking along the Mississippi river to kayaking the more gentle Galena River, you’ll have tons of ways to work up a sweat. We went kayaking with Nuts Outdoors, and I’m so proud I didn’t fall into the river. This is definitely a bonding activity on your romantic getaway- where you can laugh and connect on a different level than you can at a restaurant or in the city. The adventure guides at Nuts Outdoors will help set you up with your equipment, point out the best paddle route, and explain how to kayak in an easy and fun way.

Horseback Riding

Located about 10 minutes from downtown Galena, Shenandoah Riding Center is great for beginner and experienced horseback riders. They hand-pick the best horse for your skill level and temperament, making sure you and the horse are the perfect match for your trail ride. I made friends with Stella the horse; she was so sweet! There is nothing like getting out in the country, and horseback riding is such a soothing way to experience the meadows and woodlands of Galena, and let the city hustle melt away.

Candle Making

The Scent Workshop in Galena

If you are looking for a more leisurely, indoor activity, try creating your own scented candle at the Scent Workshop. My husband and I got to sort through all of their scents, find the ones we liked, and mix together our own unique fragrance-infused candles. My favorite combination turned out to be a blend of white peach, almond and pomegranate.

Wine Tasting at Galena Cellars

Get ready to be on cloud WINE. We picked up eBikes from Nuts Outdoor and pedaled along the 12-mile trail to Galena Cellars Vineyard and Winery Our rental included a free glass of wine and a pick up at the vineyard, so we didn’t have to pedal back to town. Galena Cellars has a wide variety of wines from bold reds to bright roses and even a sparkling gris. Tasting our way through the Galena Cellars Vineyard was the ultimate romantic activity.

Galena Trolley Tour

Hop on one of Galena Trolley Tours bright red historic trolleys and take a tour of the city. Learn all about how Galena became the town it is today and even visit the home of Ulysses S. Grant and the Belvedere Mansion — the jewel of Galena with its 22 rooms and Gone with the Wind-style curtains.

Night Life

Guided around Galena by candlelight and a seasoned lively storyteller, our skin crawled as we heard about the ghosts and dark histories of Galena on our Haunted Galena Ghost Walk. This tour was so fun and we got to hear and see a different side to the city. We also saw the fabulous P.T. Murphy, a master magician who put on such a fun and exciting magic show that my husband and I are still talking about it.


There are so many cute places to stay in Galena and the town is very well known for its bed and breakfast spots. We loved the Irish Hollow Inn, an opulent and luxurious inn set on more than 500 acres of rolling hills and located only about 15 minutes from the heart of Galena. It was both beautifully decorated and so cozy. Add a spa treatment on your last day before your check out to leave feeling totally refreshed and relaxed.

A big THANK YOU to Enjoy Illinois for having us and for such a wonderful experience.

We can’t wait to come back to Galena! We loved it here!

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