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If you are looking for the quintessential all-American town, I found it for you. It’s Galena, Illinois. Located about a 3-hour drive west of Chicago, this adorable little town is charming and delightful. It’s a great weekend getaway anytime of year, but I especially love it in the winter. There is nothing more enjoyable than the drive out to Galena. It’s literally farm land the entire time and the rolling hills are breathtaking.
I’ve actually been doing holidays in Galena since I was in high school, so it’s a long standing tradition in my family. Back in the day we went with my grandparents and rented a house. Now I go with Mike, my parents and my sister’s family. We typically spend Thanksgiving at Eagle Ridge in Galena. We rent a home for the weekend and enjoy a slow-paced weekend together.
While it is a small town, it actually has tons of things to do and see. Keep reading to see how to spend the Holidays in Galena.
Where to Stay
There is no shortage of super cute places to stay in Galena. The majority of the places are decorated with farm like details and cozy comforts. The accommodations scream winter scene, especially when it’s snowing out. This makes holidays in Galena even more special.
Eagle Ridge Resort and Spa
This is where we have been staying all these years. On the property, which they call the territory, you can rent homes, condos or stay at the lodge in a traditional hotel room. Tons of options for accommodations, just pick one that is right for you. The territory is beautiful, and full of adorable houses, rolling hills and working farms with tons of animals.
Bed and Breakfast Options
Galena is known for their charming B&B’s and they have plenty to offer. While I’ve never stayed at a bed and breakfast, I do think they are very charming. Most of the ones in Galena are set in old mansions dating back to the 1800. The historic charm is something to marvel at.
Airbnb or VRBO
You can also find great accommodations on these sites too. Here’s a tip, if you want to stay in the Territory, search for the location as “The Galena Territory, Guilford Township”. You can also find condos near downtown Galena, which is perfect if you are planning on wine tasting all day so you can walk back home.
What To Do
Shopping in Downtown Galena
The downtown area is the All-American Downtown, which charming little local stores scattered down main street. It truly is from another time. I enjoy the friendliness of the store owners. We actually talked to the gentleman at the Great American Popcorn Co. for 15 minutes. You don’t realize how interesting strangers could be until you actually stop and talk with them. The small-town vibe is one of the best parts about spending the holidays in Galena. Be sure to check out my favorite shops on Main Street.
My Favorite Food Shops In Galena
Rocky Mountain Chocolate Factory
My Favorite Small Boutiques In Galena
Vingettes of Galena – A home store with modern and traditional furniture. Every time I go in the store I want to take something home with me.
Something Special – Hand painted pottery that will take your breath away. The details on each piece is amazing, and you can tell that love and labor went into each piece.
Poopsies – Whether you have kids or are just a kid at heart, you have to stop into Poopsies. A modern day toy store that will have you wishing you were 10 again.
Simply Elegant – A Chicago-like boutique with woman’s clothing, high-end home goods, and furnishings. Spending hours in this store will inspire you to re-do your home.
Winter Activities
Winter is the best time to head to Galena. You can cozy up in front of a fireplace or walk around the town and take in all the Christmas decorations. It’s snows frequently there so it’s a great place if you want a true winter scene. Whether you love the great outdoors or prefer to enjoy winter with a glass of wine inside, there is plenty to do to get you into the winter spirit.
Skiing at Chestnut Mountain Resort
Galena Territory Christmas House Tours
Take a Tour
Galena has tons of tours centered around the town’s deep history. Whether it’s visiting Grant’s Home or taking a trolley around town, you will for sure learn something new. Here are some great tours to take in Galena.
Where to Eat
Vinny Vanucchis – Great italian spot in downtown Galena
Durty Gurts – Delicious burgers and chili, great for lunch or classic pub food. We eat here every year, it’s a tradition!
Fried Green Tomatoes – Italian restaurant featuring a twist on classic dishes.
Otto’s Place – From breakfast to lunch and brunch, Otto’s has you covered.
Desoto’s House – This classic bed and breakfast has three dining options to meet all your needs.
So there you have it, my ultimate travel guide to spending the holidays in Galena. Looking for more holiday travel posts? Have you check out my travel guide to Quebec City, it’s a must see if you are planning a winter trip.
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