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Writer's pictureAmy Laskye

Holiday Proposals in Galena: A Week to Remember

The holiday season in Galena is always magical, but this week was particularly special as two incredible proposals unfolded—each uniquely tailored to reflect the couples' personalities and love stories. I’m so thrilled to share these heartwarming moments with you.


A Window to Forever Proposal: Zach’s Story


The window at Massbach Ridge Winery

The first proposal of the week was one of adaptability and creativity. Zach had originally planned his big moment outdoors, but when the weather took an unexpected turn, we had to think quickly. That’s when inspiration struck: why not incorporate Galena’s cherished Living Windows event into the proposal?


With just two days to replan, I reached out to the wonderful team at Massbach Ridge Winery. They graciously agreed to be part of the surprise, offering their beautifully decorated window as the perfect backdrop. Zach popped the question as part of the Living Windows display, with festive lights and holiday cheer all around. Adding an extra layer of emotion to the moment, both Zach and his fiancée’s mothers were just outside the window, watching the magic unfold.


The combination of creativity, community, and family made this proposal truly unforgettable. It’s a memory that the couple will cherish forever—and so will I!




 


An Intimate Afternoon Proposal at Galena Cellars - Justin's Story


A gentleman proposing to his girlfriend at Galena Cellars Winery in downtown Galena, IL
Galena Cellars Winery

The second proposal of the week was equally enchanting, set in the charming ambiance of Galena Cellars Winery. The soon-to-be groom chose the third-floor tasting room for his big moment, a cozy and romantic setting. Midday light streamed through the windows, casting a warm glow as he asked the love of his life to marry him. With the room all to themselves, the intimacy of the moment was breathtaking.


To make the day even more special, I had recommended Goldmoor Inn for fine dining the evening before, and Fried Green Tomatoes for their celebratory dinner. Both spots are iconic in Galena, offering the perfect mix of elegance and comfort for such a momentous occasion. We captured some stunning photos at these locations to round out their unforgettable day.



Planning Your Perfect Galena Proposal


These two stories remind me why I love what I do. Helping couples create one-of-a-kind proposals is such a joy, and Galena offers so many beautiful venues and experiences to make your big moment truly extraordinary. From wineries and historic inns to holiday events and scenic vistas, the options are endless.


If you’re planning a proposal and need ideas, be sure to check out my blog for inspiration. And if you’re feeling stuck or want help designing a unique experience, I’m here for you. Together, we can create a moment you’ll both treasure forever.


Congratulations to these two amazing couples on the start of their forever! Here’s to love, laughter, and the magic of the holiday season! ❤️




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