Travel Guide: Galena, Illinois

This may be only my second travel guide, but I have been to Galena, Illinois more times than I could count! It all started way before my mom even graduated high school. My grandparents purchased a home in The Galena Territory (home to Eagle Ridge Resort & Spa), and the rest is history. Well, history in the making. My family has big love for this little town, and when I was in high school, we built our own family home that overlooks the Shenandoah horse stables — perfect for viewing fireworks on 4th of July! Needless to say, I’ve spent a lot of time here, and these are my absolute top picks for exploring one of my favorite towns!

Where to Stay in Galena

Galena has a ton of places to stay when you’re in town, but here are a few options that I have found to be the best!
Beautiful hotel located in the heart of the territory. You can expect your standard resort treatment here. We usually pop by their Woodlands Restaurant or Paisano’s Pizza on our first night in town for a quick bite to eat.
The Irish have quite the presence in Galena as local business owners, and the Irish Cottage’s hotel front looks straight out of the streets of your small town in Ireland. Enjoy a great stay and an even better pub!
With AirBnB on the rise, there’s no question that renting your vacation home is an awesome route to go to make you feel like you’re in a home away from home. The Galena Territory has a bunch of rental homes to select from that are great for large groups or a more affordable getaway.
A stunning resort half-way up to Chestnut mountain and nestled along the river with a strong European vibe. A truly breathtaking and upscale place to stay with owners that give care to each and every person arriving to stay with them. Hospitality at its finest.

Where to Eat in Galena

As Chicago’s Pasta Queen (TM), you know I need to get my Italian fix when I’m out of town. I have been going to Vinny’s for as long as I can remember! The salad is one of my favorites all-around – just the perfect dressing. And did I mention the garlic bread? It’s insanity. Most of the items on the menu are delish, but I always go with my favorite – Chicken Vinito.
Much like their resort as a whole, Goldmoor Inn takes fine dining to another level. If you’re looking for a special occasion meal in Galena, this is the place to go. We got the watermelon and burrata salad, beef wellington, filet mignon, and chocolate pot de creme…and I’m still day dreaming about it. Be sure to get a seat near a window if you’re going around sunset.
This restaurant was an accidental discovery while on the quest for a tasty dinner. As someone whose been coming to Galena since I was a baby, I rarely stray from the favorites, but this has now joined my favorites! Not only that, it’s been the only place I’ve ever eaten beef stroganoff, which I must order every time. 111 Main is perfect for lunch or dinner with American food in a charming historic building.
This place is known for it’s handcrafted sandwiches and cocktails. Each and every item at Embe is homemade, and it is above and beyond delicious. I can honestly say the best pulled pork sandwich I’ve had in Illinois reigns from Embe, and my parents will specifically go just for their bread pudding!
Now it’s been quite some time since I’ve been here, but it’s definitely one of the top restaurants in Galena. Quality food, amazing variety. You are sure to have an excellent meal here.

When to Stay in Galena

4th of July
What’s more patriotic than spending a weekend in the land where President Grant lived? Nothing much, honestly. Galena goes buck wild for 4th of July – LITERALLY! I’m talking multiple planned activities, but the grand show of them all is the annual rodeo and fireworks display. It’s an absolute must!
Columbus Day Weekend 
In it’s annual tradition, the Galena Country Fair hits town during this weekend. It’s perfect for if you have a 3-day weekend from work or with kid’s having time off from school. Check out the crafts and food vendors and enjoy Galena’s most beautiful weekend filled with Fall foilage. Keep in mind – parking DOES get crazy most holiday weekends, so be sure to research parking or shuttles before heading to town.
Galena is a HUGE Halloween town. Maybe it’s the paranormal activity that happens around town, or maybe it’s the big parade they through every year! The whole town gets involved, and there’s masks and costumes as far as the eye can see!
Labor Day Weekend
I love visiting during Labor Day Weekend as the final send off of summer. The town is still booming, but not as busy as the other big holiday weekends. It’s the perfect end to the summer in the wilderness.
Any ol’ Weekend
Honestly, when it comes to being in nature, close to a quaint Americana town with great shopping, food, and activities…any ol’ weekend would do. If you’re planning a Bachelor/Bachelorette Party or other big celebration, this would probably be your best bet, so you’re not competing with the crowds!

What to Do in Galena

Fishing, Hiking, Horseback Riding
Like your regular old tampon commercial, you can do it all in Galena. (For reference hahahahaha: https://youtu.be/cQuc5Y5k6mE)
Goats seem to be a hot trend nowadays, and it’s no surprise that Goat Yoga has taken off in Galena! I, personally, have tried this in Denver and had an AMAZING time. If you’re looking for some zen mixed with playful animals, this is definitely something for you.
Galena is FULL of amazing history. Around every corner you’ll find a historic landmark, story, or tale of the past. Check out President Grant’s House, explore the Dowling House or Belvedere Mansion, or simply ask any local about their favorite Galena story.
Believe it or not, Galena is known for more than meets the eye. There’s a variety of ghost tours to choose from, and I highly recommend taking one at nighttime! It’s a whole different level of tour that will make you feel more connected to the town, whether you believe in spirits or not!
Believe it or not, there IS in fact a mountain in Illinois, and if winter sports are your thing, this is the place to go! Skiing and snowboarding are available in its winter season to enjoy, and during the summer you can race down the hill in toboggans or check out the zip line! Regardless, you’ll want to grab a cozy drink and snacks in it’s old school restaurant overlooking the gorgeous mount.
There so many fun gift shops on the Galena Main Street. Anything for silly gifts and toys, antiques and priceless items of the past, to your regular tourist garb. Not to mention my favorite stop, the Galena Garlic Company.

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