Upcoming Events

To easily RSVP for our events, please visit our Facebook Event Page. Events may be cancelled depending on government orders with regard to the global pandemic.

Date TBD: Sassy Stitches Cash Mob: Help Picture Pittsfield support our locally-owned businesses! Join us for our next Picture Pittsfield Cash Mob! We are going to “mob” Old Sassy Stitches, and pledge to spend money there. We’ll have giveaways, specials and a party atmosphere as we have fun, eat and shop!

Sept. 22: Fall Equinox Courthouse Glow: Picture Pittsfield and the Pittsfield Lodge #790 Ancient Free and Accepted Masons are hosting an informal event at the Pike County Courthouse starting at 6:30 p.m. Tuesday, Sept. 22, on the west side of the courthouse. During the equinox, or first day of fall, the setting sun hits the courthouse just right and the center of it “glows” orange. This event will be canceled if the sun isn’t shining.

Oct. 17-18: Fall Pickin’ Days on the Square: Picture Pittsfield is hosting Fall Pickin’ Days booths and activities on the Pike County, IL, Courthouse Lawn on Saturday, Oct. 17 from 9 a.m.-5 p.m. and Sunday, Oct. 18 from 9 a.m.-4 p.m. This is part of a county-wide event. If you are a vendor who would like booth space for this event, click here.

Nov. 29: Deer Santa Festival Kickoff: Parade and Christmas Tree Lighting Ceremony on the Square 3-6 p.m. around the Pittsfield Square.

• Santa’s Parade from 3-3:30 p.m.
• Photos with Santa from 3:30- 4 pm. at William Watson Cafe
• Ornament Decorating from 3:30-5 p.m. – Kids and kids at heart can decorate a shatter-proof ornament to hang on the community tree on the courthouse lawn. Sponsored by Picture Pittsfield and the Pike County Art Guild.
• Christmas Tree Lighting Ceremony at 5:15 p.m.; this will be done on the evergreen tree on the west side of the courthouse lawn.
• Christmas carols from 5:15 p.m. until 6 p.m.

We can use the community’s help:

• If you are interested in having a float in Santa’s Parade, contact Brandy Myers Gratton at (217) 617-2656 or by emailing bmyersgratton@yahoo.com.
• If you are part of a choir that would like to sing a few Christmas carols, please contact Picture Pittsfield President Jessica Guthrie to get on the schedule and submit your song list (as lovely as it might be, we don’t need six “Silent Nights” in a row.) Contact info below.
• If you are a business owner on or near the Pittsfield square, we’d love for you to be open that afternoon/evening with Christmas decorations outside, Christmas carols playing, etc. There will be a lot of hungry families at 6 p.m., so restaurants may want to have some yummy dinner and dessert options. We’ll be happy to add you as a co-host to this Facebook event and promote any specials you’ve got going on.
• If you are a vendor who would like booth space for this event, click here.