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48 Hours in Galena, IL

September 1, 2020 2 Comments

48 Hours in Galena, IL

September 1, 2020 2 Comments

A couple days prior to the weekend, a friend asked if we’d be interested and able to spend the weekend with them in a rental home in Galena, IL. They’d previously planned the weekend trip with another couple, also our good friends. Sadly, there was a family emergency that left them unable to go and we ended up taking their place. Given those circumstances, we were excited to visit a new town and spend time with our friends but our hearts were with the ones who weren’t able to be there. She is the biggest supporter of our blog from day one and the world’s nicest person. (Love you guys!)


This may have been one of the first trips where we’ve had no part in the planning and it was refreshing. Lucky for us – our friends who planned this have great taste and picked a great town and rental home!

The home is located in the Galena Territory, a residental community about 15 minutes outside of downtown Galena. It’s a sprawling area, with hills and valleys, prairies, woods, walking trails, large yards and beautiful homes. There’s a golf course and resort, plus recreational area for the homeowner’s that includes a swimming pool, general store, and restaurants.

Rental Home near Galena, IL

The rental home was perfect for our three families – there were 6 adults and 6 kids, aged 7 and under. The home had a huge yard, private firepit tucked in the backyard, hot tub, screen porch and large deck, along with plenty of space inside and out. The layout of the home is always helpful to us so here is what the two floors contained:

  • MAIN LEVEL
    • Open-concept living room, kitchen and dining room
    • Walkout to screen porch and deck (gas grill)
    • Master bedroom with Queen + en suite bathroom (with shower)
    • Queen bedroom
    • Shared full bathroom
  • LOWER LEVEL
    • Lower-level living room and ping pong table, walkout to back patio with a hot tub
    • Queen bedroom
    • 2 Twin bedroom
    • plus TWO full bathrooms

Interested in this home? Here is the VRBO.com link:
Sweet Retreat – 4 bedroom, 4 bathroom home in Galena Territory


Our friends and their two young kids arrived a day earlier than us and had lunch at the Highland Restaurant in the Galena Territory. That evening, they had takeout pizza from Cannova’s and said it was good.

The next morning, they booked a “goat trek” at a local enterprise called Hoof It in Galena. There are a variety of different treks, including private and group bonfires – see the website for more. They were given a goat on a leash, a tour guide, and they set off on a short kid-friendly (and stroller-friendly) hike with the goats. Their 3-year-old loved playing with and feeding the goats, and they recommend this as a fun activity to do outdoors with kids in Galena!


We arrived that afternoon and spent the day and evening at the rental home. We hadn’t seen our friends since February and it had been even longer since our kids had played together. Half the fun for the kids is exploring a new home, so there were many games of hide & seek played and lots of fort-building. Dinner that evening was prepared by our friend Kurt – absolutely delicious steak and shrimp tostadas! (Maybe he’ll share the recipe with us…). We finished out the night playing Codenames and having drinks on the screen porch.

The next morning, the moms headed out to explore the downtown area. It’s too difficult with that many people, especially young kids and during COVID, to walk around together. Plus, moms needed to get their shopping fix… alone. 🙂

Downtown Galena – a shopper’s dream!

We drove into town and it was our dream! Blocks and blocks of historic buildings along Main Street – shops, restaurants, and other local businesses. We could’ve easily spent an entire day wandering in and out of the shops. We found some cute gifts for family members and friends, then grabbed an outdoor beer and appetizer at Galena Brewing Company.

Appetizers and beverages from Galena Brewing Company

One of the great things about Galena, at least now, is that part of Main Street is gated off to cars and the restaurants have set out picnic tables and provide outdoor service in the streets. Overall, the entire city was very Covid-conscious and we felt very comfortable with it all.

That evening, we had a campfire at the big firepit in the backyard and stayed up too late… again! We also hit up the hot tub after the kids were in bed. It was a very quick trip but so good to see our Chicago friends again and let our kids run and play together after so much time has passed.

We can’t wait to get back to Galena and pick up where we left off! It’s probably so pretty during the fall, and imagine it’s got to be like a Hallmark movie during the holidays! Fortunately for us, a different friend is in the process of purchasing a rental home in Galena and we’ve already called dibs! So stay tuned… more trips to come.


If you like reading about our weekend getaways, you may like the following posts from past trips:

Crane Lake, Minnesota

Tent Camping in Northern Wisconsin

Manitowish Waters, Wisconsin (+ a day trip into Michigan’s U.P.)

Eagle River, Wisconsin in winter

Boulder Junction, Wisconsin in fall

Plus, you can always check out our “Places” tab for more ideas on day trips, weekend getaways, or longer vacations. We love getting time to explore new towns and cities and love sharing with you all!

2 Comments

  • Julie Page September 27, 2020 at 1:35 pm

    Hi Sara and Katie! I love following you guys on all your adventures!! We are planning a day trip to Galena next Saturday with our senior dog. We just purchased a dog stroller for him as he is really struggling to get around these days. I’m hoping if he is zipped into his stroller that the store owners will be fine with us bringing him in. What are your thoughts? Did you guys see a lot of dogs in town or in any stores? Thanks in advance for any info you can provide! Julie

    • Sara October 16, 2020 at 6:59 am

      Hi Julie,

      That’s a great question. I don’t remember noticing many dogs. I think its worth a shot though! Let us know how it goes!

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