If you have time and patience, you can carve any photo onto a pumpkin! I like to do awesome characters from my favorite shows. This year it was Gaten Matarazzo, he plays Dustin on "Stranger Things", this instructable will be made using the pattern of him.
This takes a long time, so I try to spread it out over 3 days (yes, 3 days!) Don’t do it too early ahead of time though, this is a real pumpkin and once it’s cut it will begin to rot. When I’m done, I spray the inside and out with a disinfectant spray, or a bathroom cleaner spray with bleach (whatever I have on hand.), to keep the mold at bay. Even so, it really won’t last much longer than a week. If it’s warm where you are, you might try to keep it in the fridge when it’s not on display.

Step 1: Choose Your Photo

The first day, I work on the photo for the pattern. You can google an image, or upload your own photo. Make sure you choose a photo with lots of contrast. Take it to your photo editing software; I use PhotoShop. (My picture was actually a composite of 2 different photos that I put together and fixed up a bit; I wanted him with the opened mouth smile while wearing the hat, and I also deleted the background…) Make the photo as large as possible to fit your pumpkin.

Step 2: Make Your Photo Black and White (Desaturate) and Posterize

Make the photo black and white, (In PhotoShop go to: Image –Adjustments-Desaturate) You then play with the contrast, (In Photshop go to: Image-Adjustments-Brightness/Contrast, sliding the button until it looks the way you want and press ok.) Depending on how much work you want to do, you could go with just black and white. Remember, anything black with remain untouched, it is the white that will be cut through and removed (I like more detail in my pumpkins, so I have shades of gray in mine, those will be cut into different depths of the pumpkin flesh.) If you would like to do more detail then you will need to posterize it; this will show you the picture with a few shades, I like about 5,- black, white, and 3 shades of gray). (To Posterize in PhotoShop go to: Image-Adjustments-Posterize. Type 5 in the Levels box that pops up, press OK.) This should make your photo with 5 clear levels of gray scale. Look at your picture; make sure you don’t have any black parts completely encircled by white, as the black piece would just fall out. Edit if you need to. I like to then tint the whole thing orange. (You don’t have to do this; it makes it easier for me to visualize what my pumpkin will look like...) (To tint in PhotoShop go to: Image-Adjustments-Color Balance-. Move the top slider to Red and the bottom slider to Yellow, press Ok.)

Step 3: Print and Prepare Pattern and Pumpkin

Print at least 3 copies. The one you tape to the pumpkin will end up ruined, so you’ll need another to work from, and a spare just in case. I put clear packing tape on the back of the pattern, since you’ll be pricking the outlines with a pin, this helps prevent the paper from getting too soggy from pumpkin juice.

Slash around the edges of your template. Remember you have to make it fit onto a rounded shape.

Wash your hands well and clean your pumpkin; I use disinfectant wipes on it. (Bacteria causes it to rot sooner.)

Step 4: Collect Your Tools and Supplies

Things you will need:

Lots of time and patience(!)

Tools and Supplies:

I’ve collected a lot of different tools over the years, but these are my main tools:

Pointy xacto blade (for cutting around lines) (or any sharp craft knife, I even got a whole set with different blades at the dollar store.)

Flat square blade (for planing)

Clay loop tools, one large (for thinning the inside, and for scraping off the skin of very large areas) and one small (for skinning smaller areas) (I have others in my set, but those 2 are the main ones.

A large safety pin or other sharp pointy thing (for poking holes like to make eye highlights or other tiny areas of light)

Pin cushion with pins (for pin pricking the pattern)

Thin Serrated pumpkin carving knife (the kind you see in the stores, this is only used to cut out the bottom.)

Large spoon or pumpkin scoop (for gutting the pumpkin)

Bowl (for guts and shaved bits.)

Newspaper bag or long rubber gloves (keeps your hands and arms clean when gutting.)

Photo

Clear packing tape (for waterproofing pattern)

Masking tape (taping pattern to pumpkin)

Large Pumpkin (fairly large and smooth with a flat side will be easier)

Disinfectant wipes (to clean the pumpkin)

Newspapers or old sheet (to protect the area.)

Paper Towels (for clean up)

A computer and printer (for finding and printing picture)

PhotoShop or similar software (for editing photo)

Paper (to print your pattern on

Scissors (for slashing edge of pattern)

Pumpkin light (I got it at the dollar store. Or you can use a bright flashlight or even a light bulb on a cord) (Candles are just not bright enough.)

Desk lamp (you need a good light to see the faint pin pricks)

Band aids (I learned from experience that I tend to get blisters where my fingers rub the tools, so I put band aids on my fingers ahead of time to prevent that.)

Disinfectant spray (To help keep the mold away.)

Step 5: Gut Your Pumpkin (Or Not)

I don’t even gut the pumpkin just yet; I do that halfway through,but you can do it first if you want to. I don’t cut out the top, I cut out the bottom. I just use the standard serrated pumpkin tool; the thinnest one I could find. Then gut it with a big spoon and smooth the inside out. (I like to put a plastic newspaper bag over my hand and arm so I don’t get pumpkin guts all over me.) You’ll want the flesh to be no more than an inch thick. (The thinner it is, the more light will show through.) If it is thicker, you’ll have to thin it out from the inside. (You don’t have to thin the entire pumpkin, but just the side that will have the design.) You can use a spoon, but I found a large clay loop tool works really well. Scrape it around the inside and peel off the flesh.

Step 6: Tape Pattern to Pumpkin

Use masking tape to tape your template to your pumpkin on the flattest smoothest side. (I like to pin the picture on through the highlights in the eyes, (the white dots), to prevent it from moving while I’m smoothing it and taping it down. There will be wrinkles, but don't worry about it.

Now, yes this takes forever, so prepare your carving space. Since I’ll be sitting a long time, I like to sit on my comfy couch. I cover it with an old sheet and make sure that any cracks are covered so I don’t lose any tools down them. I lay an old towel on me and cradle the pumpkin in my lap.

Step 7: Prick the Pattern

You then will be pricking the outlines with a pin, (or even just sticking pins in it and leaving them there.) Yes it’s tedious but the more pin pricks the better the transfer. Follow all the outlines of the different shades, poking holes through the template and into the pumpkin. (Make sure you get them all, as once you peel off the paper, it’s nearly impossible to match up again.) Some (less important) parts you may want to cut right through the paper into the pumpkin with the xacto blade.

Peel off the paper. (Don’t panic! You will have transferred the picture with tiny pin holes, even though it doesn’t look like it. Just look closely.) Sometimes bits of paper and dried pumpkin juice are left behind, that’s ok; just wipe it off with a disinfectant wipe or even a wet paper towel.

Step 8: Cut All the Outlines

I’m right handed, so it makes sense to start on the upper left so your hand isn’t rubbing all over the cut parts. Get your non wrecked template and compare it up close to the same parts on the pumpkin with the pin holes. (Remember, anything that is black will remain untouched orange pumpkin skin, so try not to poke it or scratch it because once you put the light in it will show through.) Using your xacto knife, follow the dots with the blade, cutting lines like a “dot to dot” coloring book. (Yes, it will “bleed” pumpkin juice; just dry it off with a paper towel.) Remember you won’t be cutting all the way through on most of these, so don’t go very deep.

(I usually gut my pumpkin now after cutting all the outlines, but it doesn't really matter.)

Step 9: Cut Out White Chunks

Now that you have all the outlines cut, it’s time to start cutting at different depths. I like to start with the parts that are white. These are the only parts that will be cut entirely out and removed. I trace around the cut part deeper and deeper with the xacto blade. If the flesh is thicker than the blade, I usually switch to a craft knife that has a breakaway blade and just extend it fully and kind of saw through it carefully and remove the chunk, sometimes depending on size or shape, I will remove it in pieces.

Step 10: Planing to Get Different Shades

To do the different shades, you need to first remove the orange skin. First go around the edges again with the pointy blade and cut a little deeper. Then I use the blade that is square and flat (rather than pointy) to kind of plane off the skin. The lighter the shade, the deeper you need to go. Then just plane off the pumpkin meat little by little until you get it smooth, but don’t go all the way through.

You might be thinking, “Oh dear, this is looking terrible; I spent all this time….” Again don’t panic! It just does not look that great in the light of day!

Step 11: Check Shades With the Light Inside

You can check to see the shade to see if you need to thin it more by turning off the room’s light and sticking the pumpkin light inside. Towards the end when I just need to adjust the shades, I even work in the dark (with the light inside) shaving bits off (with the small clay loop tool or flat blade) until it looked right.) Do this for all the different shades, there will be different levels for each shade.

Step 12: Spray With Disinfectant Spray

When you are all done, take it outside and spray it inside and out with disinfectant spray to keep mold away, (don't forget the bottom).

Step 13: Step 12: Light It Up!

Put your pumpkin light in it, (don’t use a candle, it’s not strong enough anyway). Once you turn off all the lights and put your pumpkin light inside, it comes to life!