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Travel: Spend a weekend in Woodstock

Travel: Spend a weekend in Woodstock

A favorite of my late-spring trips is one I took a couple years ago to the northwest Chicago suburb of Woodstock, Illinois. Our accommodations were at an adorable bed and breakfast called the Cherry Tree Inn. I didn’t realize it when the trip was first arranged, but we would be staying at a famous place — it’s wasn’t just any bed and breakfast. It was a movie star.

The Cherry Tree Inn was featured in the 1993 movie "Groundhog Day," starring Bill Murray. I was staying with a group of fellow travel writers and one of them stayed in a room that appeared in the movie. Several other spots in Woodstock were also part of filming.

The community could just not be any more charming. It was absolutely the perfect Midwestern town for a feature film. It’s one that would be an appropriate setting for every Hallmark holiday movie. Woodstock is listed on the National Register of Historic Places, is recognized as a Distinctive Community Destination by the National Trust for Historic Preservation, and was named a Preserve America Community by the White House.

We spent one evening enjoying dinner at the Public House of Woodstock. It also happened to have made an appearance in "Groundhog Day" as the pub where the characters made a toast to world peace.

It sits on the downtown square where a park is situated in the middle (also featured in the movie) which is surrounded by small shops and eateries where you could easily spend a full day shopping, sipping and dining. Among our stops were Ethereal Confections for a chocolate tasting, Blue Eagle Pottery and Silver Prairie Natural Soap Company where we watched a soap-making demonstration.

I marveled at the Woodstock Opera House, also on the square, which just adds to the 19th century charm. I wish I’d had time to take in a movie at the nostalgic Classic Cinemas Woodstock, which has an amazing mural on a wall beside it that highlights Woodstock’s history and famous connections, and includes an image of Bill Murray. By the way, they still celebrate the city’s part in the movie with an annual Groundhog Days festival.

We left the downtown square for a bit and spent part of our time on a fun experience of getting lessons on playing steel drums and other instruments at Culture, Arts & Music.

We also did some shopping and dining in some area communities, and it was so nice to end each day at our home base back at the Cherry Tree Inn, where we couldn’t resist spending a little time on the inviting front porch. The hosts are amazing cooks and we were stunned at the beautiful gourmet breakfasts they presented.

The final stop on our last day before heading home was at the Loyola University Retreat and Ecology Campus for a hands-on cooking class, where we made the most amazing homemade pasta. I still dream about that meal. We also got a tour of the gardens, which was fascinating.

For more info on the area, visit and visit


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