Hand-painted night scene of the Woodstock square at Christmas by Ashley Ann: a lit clock tower, garlanded gazebo, and a couple crossing the snowy square

There's something special about a small-town Christmas.

The glow of twinkle lights on quiet streets.

Familiar faces, and traditions that bring people together year after year.

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Ethereal Confections · Woodstock, Illinois

Christmas on the Square

25 days of chocolate · $100 · ships in November

The Square is lit. December is coming.

Twenty-five mornings of chocolate, waiting behind twenty-five doors.

Take a walk around the square

What's behind the doors

Twenty-five mornings of chocolate

December 8

The Six O'Clock Alarm

Flavor to be revealed

December 16

The Gazebo Waltz

Flavor to be revealed

December 12

First Step's a Doozy

Flavor to be revealed

And 22 more behind closed doors

Unveiled one morning at a time — and doors 24 & 25 stay secret until you open them

The open Christmas on the Square calendar: twenty-five starry blue drawers with hand-lettered gold numbers

A keepsake box, built for tradition

  • 25 hand-crafted confections, one for every morning
  • Gluten-free, dairy-free, and plant-based
  • No-melt shipping guarantee — it arrives perfect, or we make it right
The Christmas on the Square box: Ashley Ann's hand-painted night scene of the Woodstock square

The art of the square

Painted for our hometown

This year's calendar wears an original by Ashley Ann, a local artist and designer who creates hand-drawn pieces inspired by small towns, quiet moments, and meaningful traditions. Her work celebrates community and the beauty found in everyday life.

The scene is our home: Woodstock, Illinois — the town square that starred in Groundhog Day. If the clock tower and gazebo look familiar, you've seen them at the movies. Come December, the square is at its best: community, creativity, and connection, shining brightest during the holiday season.

The last lit window

Christmas on the Square Advent Calendar

$100.00 Reserve today · ships in November

Twenty-five hand-crafted confections behind twenty-five starry doors, in a keepsake box painted by Ashley Ann. Reserve yours today and it ships to your door in November — in time for December 1st.

Our advent calendars sell out every year. Reserving now is the only way to be sure.

Reserve yours now — your calendar ships in November. Gifting? Ship it straight to them at checkout.

Christmas on the Square Advent Calendar · $100.00 Reserve Yours Now

Good to know

Questions, answered

When will I be charged?

Today. Reserving your calendar is a full purchase — that's how we guarantee your box in a small-batch run.

When does it ship?

Calendars ship in November, in time to open drawer number one on December 1st. You'll get tracking the moment yours is on its way.

Will the chocolate melt on the way?

No — every calendar ships under our no-melt guarantee, with cold packs and insulation whenever the route calls for it. If anything arrives less than perfect, we make it right.

Is it really gluten-free, dairy-free, and plant-based?

Yes — like everything we make. Every confection is gluten-free, dairy-free, and plant-based. Full ingredient and allergen details are included with your calendar.

Can I send it as a gift?

Absolutely. Enter their address at checkout and we'll ship it straight to them. Ordering for several people? Place separate orders, or reach out and we'll help.

Can I cancel or return my reservation?

Advent calendars are made in one small batch, so all reservations are final. If something's wrong with your order, write to us and we'll take care of you.

Coming this December

Every December morning, a new door opens here.

Once the calendars ship, this page becomes the square's daily countdown — a story behind every door. Be there when the first one opens.