I love visiting Downtown Woodstock with it’s charming square complete with historic buildings, amazing architecture, and cobblestone streets. Plus, don’t forget the number of restaurants and cute independent shops! During the holidays, the downtown area steps it up and really does make everything extra special. Read on to see all the holiday fun  in store for families in Downtown Woodstock.

Fun fact: They filmed Groundhog Day here and you can actually take a walking tour and walk in Bill Murray’s footsteps.

READ MORE: Find more holiday activities to add to your holiday calendar.

Meet Santa

During the holidays, Santa is normally found at Santa’s Hut. During this particular holiday season, they’ve had to move him to the Stage Left Cafe inside the Woodstock Opera House.  I was actually very impressed with how organized and safe the entire process was. Make sure to reserve free timed tickets here. We arrived a bit early and asked if we could see him earlier. They were nice enough to squeeze us in! While we waited, we scoped out all the decorated Christmas trees. (see below) After Santa’s little helper checked us in, the kids were escorted to a bench in front of Santa and Mrs. Claus safely behind the plexiglass. Such a cute setup!

See Santa safely, go on a pickle scavenger hunt, see all the festively decorate Christmas Trees, view the holiday lights, and just simply enjoy the charming downtown area.

See Santa safely, go on a pickle scavenger hunt, see all the festively decorate Christmas Trees, view the holiday lights, and just simply enjoy the charming downtown area.

Christmas Tree Walk

A stop at the Woodstock Opera House is a must on any regular day, but during the holidays they have their Annual Christmas Tree Walk with trees decorated by different organizations.  This year’s theme is “Home for the Holidays.”

See Santa safely, go on a pickle scavenger hunt, see all the festively decorate Christmas Trees, view the holiday lights, and just simply enjoy the charming downtown area.

Go on a Scavenger Hunt…for the Pickle

As one of our advent activities, we learned about the legend of the pickle. Then when I saw that the town of Woodstock had a Legend of the Pickle scavenger hunt, I was so excited. What a fun way to tie in what we learned! It’s a bit of a challenge since you need to first need to unscramble the names of the businesses. Once that’s done you have to search for the pickle at each place. Once you find it, have an employee sign your card.

 

We did it all for the pickle – the Pickle Craft Ornament!

Tip: To get the prize, you’ll need to visit 20 spots. A majority of the places can be found right around the Square.

Go shopping

The best part about the hunt was getting to see all the businesses we normally would have never seen. So many cute shops!

See Santa safely, go on a pickle scavenger hunt, see all the festively decorate Christmas Trees, view the holiday lights, and just simply enjoy the charming downtown area.

Get Coffee (or Tea)

As you know, I love my coffee. Make sure to stop by Ethereal Confections, a bean-to-bar chocolate shop, for their yummy coffee or hot chocolate. Psst. They even offer delectable hot cocoa bombs! Another spot for coffee is Caesaroni’s Cafe or the shop adjacent to Read Between the Lynes, a super adorable independent bookstore. If you’re a fan of Alice and Wonderland and tea, you’ll absolutely love Casting Whimsy. Looking for sweet treats? The Sugar Circle has yummy cinnamon rolls.

 

Walk around

Don’t miss the mural by the movie theater. Go around the corner to find the groundhog Woodstock Willie . In fact, you may see the Woodstock mascot all over town.

See Santa safely, go on a pickle scavenger hunt, see all the festively decorate Christmas Trees, view the holiday lights, and just simply enjoy the charming downtown area.

See the Square all lit up

Unfortunately, we had to leave right before dark and didn’t see the lights. The pictures look breathtaking!

Final thoughts

For all the holiday feels, make sure to spend time in downtown Woodstock. See Santa safely, go on a pickle scavenger hunt, see all the festively decorate Christmas Trees, view the holiday lights, and just simply enjoy the charming downtown area.

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