Thrifted Halloween Painting Trend: Upcycling an Old Painting into Halloween Art

With Halloween right around the corner, I thought I would share a recent project that I've been working on.  The thrifted Halloween painting trend hit the scene hard last year.  The idea is to head to your local thrift store and find an old painting that you can upcycle into Halloween art.  I saw a lot of people doing this last year by adding subtle ghosts to landscape paintings and they all turned out so well.  It has taken me a year to get around to it, but I'm glad I finally jumped on board.  It was a fun project to complete. And while my results are definitely less subtle than a few ghosts scattered into a landscape, they are also most definitely Halloween-esque.  Let me show you. 

So I headed to my local Goodwill over the summer and snagged two canvases, both were by the same artist and they were both folk art. I saw the smaller canvas first and immediately knew exactly how I could turn it into Halloween art.  Then I spied a similar larger canvas, and I became convinced that it was meant to be.  I grabbed both pieces and headed to the checkout.  Honestly, both pieces of art have sat in storage for months, but I recently remembered them and pulled them out.  After a little debating, I decided to start on the larger piece first.  

This is what the canvas looked like when I began.  Nothing in particular about this canvas screamed Halloween.  On the contrary, it is a very traditional folk art, with lots of barns and houses, little Amish people, and horses pulling wagons.  But in the back of my mind, I knew what it could become. 

And here are some of the details from the original art. 

Notice the bright orange sun and yellow sky.  I knew that would have to be the first thing I changed. 

I also immediately knew that I would have to adjust all the bright white picket fencing.  

Notice too all those quilt squares painted on the buildings and barns.  I knew I would have to come up with a plan to change those as well. 

But it was all the little people scattered around this painting that excited me.  I adored this little lady hanging out her quilts, and the mom and daughter to her right.   I had a pretty immediate idea of how I would use all these people in a Halloween painting.  And I'll bet you are thinking the same thing. 

But my first order of business was to get the basic color scheme corrected.  I chose a dark blue for the sky and made that sun into a much bigger yellow moon. Then I adjusted all of the trees and bushes to reds, oranges, and yellows to replace all the bright green that we started with.  I also made all of the previously white picket fencing black.  

With those basic changes completed, I was finally able to move on to the fun part- converting all those little people into my Halloween cast of characters.  

The very first character I started on was the little fellow on the bicycle in the center of the painting.  I took one look at him and decided he HAD to become the Wicked Witch from the Wizard of Oz.   And with a few easy updates, he did.  

Here's the before and after. 

Since the bicycle already had a basket, it only made sense to add little Toto in there as well.  But this was only just the start.  

Next up was the little character on a tricycle.  I thought to myself, what character would be riding a tricycle?  And I knew it had to be a clown.  Here's that transformation. 

Then the inspiration struck for my favorite little lady hanging out the laundry on the line.  I thought I could make her into the main Sanderson Sister, Winifred, and naturally the little socks hanging on the laundry line turned into witch's stockings.  I covered all the quilts in white until I could come up with an idea.  The white actually sparked the idea that two of them could be plain white sheets/ ghosts and then I just turned the last one into a Halloween colored quilt with a few random patches.  I couldn't leave this little scene without coming up with a costume for the dog, so I made him into a pumpkin. 

Then I remembered the two ladies behind my little clown who were folding a quilt.  And I thought they should be the other two Sanderson siters, Sarah and Mary.  And I just turned their quilt into a sign that reads Hocus Pocus. So now all of the Sanderson Sisters are present and accounted for. 

Longtime blog followers may remember that The Harris Sisters paid homage to the Sanderson Sisters a few years ago.  

And it just kind of snowballed them there.  I incorporated all sorts of Halloween characters and costumes, some of which are specific to costumes that my little family has worn over the years.  Others are nods to some of the Harris Sisters' costumed endeavors, while others are just easily recognizable Halloween characters.   The biggest challenge was finding costumed characters recognizable enough that you would still be able to recognize in miniature form.  This is a large canvas but there is A LOT of subject matter in it, making each individual character around 2 inches tall if they are in the forefront, and closer to only an inch tall (or less) for those in the background. 

Here is a look at some of my favorite Halloween characters from the scene.

This little guy raising the flag in the forefront of the scene became Fred Flintstone. 

This was a nod to the year my family dressed as the Flintstones, which incidentally turned out to be the coldest Halloween on record.  We froze ourselves, but we looked good for this one photo.  

I turned a couple of tiny little characters into Woody and Jessie from Toy Story. 

This was a throwback to our Toy Story Era, when we dressed as Andy's famous toys back in 2018.

And remember that sweet mother and child?  I turned them into Snow White and a bunny, two things that may not seemingly go together. 

But there was, in fact, one Halloween I dressed up as Snow White. 

And Lexi wanted to be a rabbit. 

And these may win the prize for some of the smallest characters in this painting.  There was actually nothing in this space originally, but I wanted to include Raggedy Ann and Andy so I added them in this space. 

Of course, this was a nod to the year that Lexi and I dressed as those famous rag dolls all the way back in 2016. 

I turned this little guy into Harry Potter.

Our family has dressed as characters from Harry Potter for the last two years in a row.  Here is Lexi as Hedwig, Harry Potter's snow owl, from two years ago. 

And as the zany but loveable Luna Lovegood last year. 

I decided to turn a couple more characters into Dorothy and the Scarecrow from the Wizard of Oz to tie into the Wicked Witch I had already incorporated. 

And you may remember that The Harris Sisters all dressed as Dorothy a few years ago when we made our own trip down the yellow brick road. 

And I could not call this a Halloween transformation without adding my all time favorite Halloween characters, the Peanuts gang.  Did you notice the little boy and girl flying kites in the original painting?

They became Charlie Brown in his ghost costume (I had a little trouble with the scissors) and Lucy in her witch costume.  The kids with the kites were originally running in the church yard.  I felt like this area was screaming for a graveyard so I also added one and a few ghosts too. 

As for the kites themselves, I could not rest until I incorporated Snoopy flying on his doghouse.  So he became a kite, pulling a sign saying "Welcome Great Pumpkin".   And if you look closely, you will find Linus heading to the pumpkin patch on the left with his blanket.  That little detail was my daughter's idea. 

So this project really took on a life of it's own.  I worked here and there on all the little details over the course of about a month transforming all the little houses, people, and animals into their own sweet Halloweentown.  I added lots of pumpkins, candles, ghosts, lights, and signs throughout the scene to make the transformation complete.  Here is a look at the final finished painting. 

And here is a final look at how it all started. 

This was such a fun project and I would absolutely recommend.  But if you are a little hesitant to give it a go, I would definitely say don't start out as ambitious as I did.  Maybe working a few ghosts into a landscape is probably the better place to start.  And this trend doesn't have to just start and end with Halloween.  It might be fun to do something similar for other holidays or seasons.  In any case, next time you pass your local thrift store, I hope you will take a peek at the thrifted art and see what calls to you.