What do we do when the weather hits the 50s in the middle of January? Get out and explore, of course! On a whim, we decided to venture out to one of our neighborhood towns, Woodstock, Illinois. Located about 50 miles northwest of Chicago, the small town of Woodstock oozes small town charm. Their claim to fame happens to be the location of where they shot the movie Groundhog Day starring Bill Murray(Phil Connors) and Andie McDowell. In fact, if you have a free afternoon, I encourage you to get your stroller and walking shoes then just walk around. Heck, if you’re in the mood you can follow in the footsteps of Phil Connors. We did and had a fun time!

Groundhog Day Walking Tour – O the Places We Go Style

Download a map and make your own trip. There are 15 sites listed, but we weren’t able to see everything. We did see about half of the items and spent a few hours enjoying the square.

Woodstock Opera House aka Pennsylvania Hotel (121 Van Buren St.)

Also known as the Pennsylvania Hotel where Rita stayed, the Woodstock Opera House was our first stop. Although there was no official tour listed, we asked if we could look around. They happily obliged. The Woodstock Opera House is famous for a few things including the first appearance of Orson Welles. It also serves as a historic landmark and is listed on the National Register of Historic Places.

Woodstock Square Park aka Gobbler’s Knob (SW corner of Woodstock Square Park)

In the movie, Woodstock Square Park is the official site where the festival took place and the prognostication was made of six more weeks of winter. This cute little square has a monument dedicated to those fallen, a bandstand, and benches for sitting. Perfect for grabbing coffee or lunch and sitting and enjoying nature.

Woodstock Square aka Gobbler’s Knob

Center of Woodstock Square Park is the location of the Band Stand Dance

Go ahead and dance like Phil and Rita at the bandstand.

The Old Courthouse aka location of the bar scenes from the movie (101 N. Johnson St)

Old Courthouse at Woodstock Square

Much to his dismay, Phil isn’t able to get home with talks of a blizzard on the way. He heads to the bar to drink his worries away. The bar is actually in the Old Courthouse. In 1974, the building was issued landmark status in the National Register of Historic Places. Now, it serves as a restaurant, Old Public House, an art gallery, and studio.

Cool fact: The Old Courthouse is located in the exact center of McHenry

Taqueria La Placita aka Tip Top Cafe (108 Cass St.)

Taqueria La Placita aka Top Top Cafe

Taqueria La Placita is where Phil and Rita grabbed coffee. Also, in front of the restaurant is the famous puddle Phil steps in.

Woodstock Theater aka Alpine Theater (209 Main St.)

Remember when Phil catches a flick in costume?

Royal Victorian Manor (Cherry Street Inn) 344 Fremont St

I would have LOVED to peruse inside but alas I only have an outdoor picture from when we did a drive by. This is the cute bed and breakfast that Phil Connors (Bill Murray) stayed at. If you have your heart set on staying here, you’ll have to wait until next year. They are sold out for 2017.


These weren’t in the original walking tour, but we totally suggest adding them to your itinerary.

Expressly Leslie, 110 S. Johnson St.

  • Vegetarian food. Say what?! Really? As we were walking around the square my husband first spotted this vegetarian joint, Expressly Leslie. The smell alone was all we needed to order falafel wraps and a falafel plate. Oh, was it good! My normally picky 4-year-old kept saying “Yum” in between bites. It was delish! I highly recommend it.

Read Between the Lynes, 111 E. Van Buren St.

  • If you’re a fan of books, coffee, ice cream and candy (ALL of my favorite things) a stop to Read Between the Lynes is a must. The shop features two sections. On one side you’ll find books, books, and more books including a super adorable section for kids with a tree.

Cool Tree at Read Between the Lynes at Woodstock Square

  • The other side you’ll find coffee, chocolate, candy and ice cream.

  • Kids looking to read up on Groundhog Day? Consider this the perfect stop for all those Groundhog Day – books, shirts, and more.

Woodstock Square - Read Between the Lynes Groundhog Day Books

Visit the surrounding neighborhood.

You’ll see all sorts of cute and charming homes.

We Wish:

We didn’t get as much time to explore as we wanted. Here’s my bucket list for when we come back.

Bucket List:

Award-winning farmer’s market
Smoothie at Expressly Leslie’s
Yogurt at YoFresh Yogurt Cafe
Shop at the boutique shops surrounding the Square.
BBQ at BBQ King
Find a vintage shop or take more time to explore Sparrow’s Nest, a thrift store closeby
Catch a flick at Woodstock Theatre

Is there anything else you would add?

Bottom Line:

Do yourself a favor and visit this charming town with its rich history and gorgeous Victorian architecture. Believe me, you’ll want to come back again…and again…..and again….

Nitty Gritty:

Website: www.realwoodstock.com is an awesome reference for what to see and do in Woodstock. I actually wished I saw this earlier! Another great website to learn more about the Square and its history –> woodstockil.gov
Parking:  Free parking surrounds the square. In addition, there are plenty of parking lots within walking distance from the square.

For more information on the downtown historic square, here’s a neat little pdf of the history of the buildings that surround the square.

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