Deer Santa Festival

Picture Pittsfield is announcing a date change of the Annual Deer Santa Festival. The fourth annual Deer Santa Festival will now be on Sunday, Dec 4, 2022 from 3 PM to 6 PM around the Courthouse Square in Pittsfield.

Photos with Santa

At the William Watson Hotel from 3 PM to 6 PM

Dance Performance

We will have a special performance from S&S School of Dance

Music and musical performances
We will have festive Christmas music playing all during the event. The First Christian Church Youth Choir will be perfoming.

Living Windows
Businesses around the Square will fill their windows with live Christmas themed displays manned by live performers from 3 PM to 6 PM

Help Decorate the Community Christmas Tree

The Pike County Art Guild will be hosting a kids Painting & Decorating from 3 PM to 6 PM on Sunday, December 4th the Pike County Art Center 130 E. Adams.

Story Book Stroll

The library is hosting a story book stroll sponsored by DOT foods on the west side of the square!


We invite any groups or churches who would like to sing carols on the courthouse steps between 3:30 and 5:00 PM. Send an email to to be on our list, please also include your song choices so we can avoid duplicates!

Live Llamas on the Square

We will have live Llamas on the Square from 3-6 PM.

Wooden Deer and Wreath Decorating Paint Party
on Saturday, November 19 from noon until 3 PM, sponsored by the Pike County Art Guild and held at the Pike County Art Center. Details and deer order form in the Facebook Event link:

Christmas Tree Lighting Ceremony

Help us kick off the holiday season by lighting the Christmas Tree at 5:30 PM.

Holiday Market

We invite any vendors to set up on the square. There will be no charge, but you must have insurance. E-mail questions to Forms can be found below. Again, there will be no charge to set up, but we do need you to fill out the forms.

Deer Santa Yard Deer Display Challenge – Deer will be on display during the festival. We had 47 deer on display in 2019… we’re hoping to grow the herd even bigger! You can purchase a blank wooden yard deer through Picture Pittsfield for $40 ($30 cost, $5 donation to the Pittsfield High School wood shop for cutting out the deer for us and $5 donation towards the Deer Santa Festival expenses). Pickup from Pikeland Motors. 118 N. Monroe St., Monday through Friday, 9 a.m.-5 p.m. Deer will be sold on a first-come, first served basis, no holds or pre-orders. When you pick up your blank deer, please pay the $40 cost by cash or check made out to Picture Pittsfield only – no credit or debit cards.

If you have a deer from previous years, you can enter it as is, or redecorate it. To enter your previous year’s deer in the display, it will be a $10 donation, cash or check made out to Picture Pittsfield. These donations will go toward Deer Santa Festival expenses and materials. The $10 is payable at deer display drop off on December 4.

Decorate your deer any way you like (family friendly, please!), give it a name, and then deliver it back to the Pittsfield courthouse square between 11 a.m. and 2 p.m. December 4 so that Picture Pittsfield volunteers can add it to the display.  Be sure to give it to a Picture Pittsfield volunteer so the proper info can be recorded for your entry into the contest. Top deer will win fun prizes! Deer need to be removed from the courthouse lawn by their owners between Sunday, Jan. 1 and Wednesday, Jan. 4, 2023.

Some of the 2019 Deer Santa Display entries.

Christmas Wreath Display at the old Red Dome Lobby

Businesses and individuals are invited to “adopt” an undecorated wreath from Pikeland Motors for $10, decorate it, and then return it for display. Wreaths will be displayed in the lobby of Madison Square (the lobby for Brewed, Reap & Sow, and Pike County Mercantile). Wreaths will be sold on a first-come, first served basis. We invited anyone who wishes to decorate a wreath to join the free Wooden Deer/Wreath Paint party at the Pike County Community Art Center on November 19. The event link is below.[%7B%22mechanism%22%3A%22search_results%22%2C%22surface%22%3A%22bookmark_search%22%7D]%2C%22ref_notif_type%22%3Anull%7D

Owners of the decorated wreaths are welcome to take them home, or Picture Pittsfield will donate the wreaths to local nursing homes and other facilities.

Letters to Santa

Between Sunday December 4 and Friday, Dec. 16, children can “mail” their letters to Santa by dropping them off at Santa’s House on the Courthouse Lawn. Any letter with a mailing address will be answered! A big thank you to the city’s front office staff for making this possible!

Letters to Santa can be “mailed” at Santa’s House on the Pike County Courthouse Lawn.

“Light It Up Pittsfield” Holiday Decoration Contest – ?

Here’s your chance to officially become the Clark Griswold of Pittsfield! Picture Pittsfield volunteers will be touring the city between 5:30-8:30 pm Friday, Dec. 16 and selecting two outdoor holiday decor winners: Business and Residential. Business are office buildings, shops and restaurants. And residential entries are decorated homes, any size and shape. Residences and businesses must be within the Pittsfield city limits. A winner and runner up will be selected in each category for a total of four winners. Entries will be judged on creativity and overall attractiveness.

Categories:  Residential (houses, duplexes, apartments) and Business (window or store front /locally and commercially owned).   Each category can win 1st Place and Runner Up.

The things judges will be looking for:

Lights – We are looking for brightness, colors, organization and movement.

Theme – We will be looking for Christmas themes. Think movies, songs, stories,  etc. 

Spirit – We are looking for the house or business that encompasses what Christmas is all about.  

Residential and businesses will be judged on a scale of 1-5 

5.  Beyond Exceptional

4.  Exceptional

3.  Middle of the Road

2.  Best Attempt

1.  Minimalist

Be sure to have all lights and animation on between the hours of 5:30-8:30 pm Friday, Dec. 17. If you would like your business or residence to be judged then please fill out this form by Sunday, Dec. 12, 2021. If you questions, you can email them to

The Deer Santa Festival was launched in 2019 as a project of the community organization, Picture Pittsfield. Area businesses and organizations host holiday activities around the community and are listed on one community calendar. The festival kicks off with a Santa Parade and Christmas Tree Lighting event the Sunday after Thanksgiving and activities continue through December.