Are you looking for holiday drawings and art for everything from Valentine’s Day in February of each year, to the stroke of midnight on New Year’s Eve? What about lessons on how to correctly write the name of each festive day: from apostrophe use to capitalization? You’ve come to the right place!

My name is Lillie, and I’m an artist and English teacher who delights in hand-illustrating holiday art, as well as explaining the punctuation and spelling rules that trip up adults and kids alike. I’ve been working on a growing compilation of holiday articles that I’ve compiled below for your enjoyment and education. Enjoy!
Holiday Drawings, Art, and Lessons
See fun, cute holiday drawings and art, plus lessons on how to correctly write the names of each of these festive days. Many of the articles here have free activities showing how to create illustrations for each special occasion.
New Year's Eve
Is it "Happy New Year" or "Happy New Years," or "Happy New Year's?" What about the capitalization and apostrophe? Find out here, assisted by two fluffy monsters...
Valentine's Day
There are lots of confusing rules around the capitalization and pluralization of the February 14 holiday, Valentine's Day. Get the whole run-down in this hand-illustrated article... with the help of a friendly octopus!
Pi Day
Pi Day is celebrated on March 14 because the mathematical symbol Pi stands for the number 3.141592... which is an irrational number that goes on for forever. This article has a free downloadable printable coloring activitiy for "Pi-lentines" -- cute Valentines for Pi Day!
St. Patrick's Day
See time-lapse drawing videos and happy art to celebrate St. Patrick's Day in March, plus a lesson on how to correctly write the name of the holiday.
Easter
Drawing a colorfully decorated Easter egg can be a wonderful activity for the spring holiday, and this tutorial and time-lapse art video can show you -- and any kids in your life -- an easy way to do it.
Father's Day
Ready to celebrate dads this June? But wait -- is the apostrophe written as "Father's Day," "Fathers' Day," or "Fathers Day?" Find out here, along with the interesting reason why.
Christmas
Want to draw Santa for a December holiday activity, or maybe just an adorable Santa hat? Here's how...
Seasons
While seasons are not technically holidays, they're time periods in which festive days fall, and in order to write them correctly, you'll need this surprising lesson on whether or not to capitalize the first letter of spring, summer, autumn, and winter!
Holiday Drawings, Art, and Lessons, in Sum
So which holiday drawings, art, and lessons in this round-up is your favorite? I’m partial to Pi Day, myself, because I enjoyed doing it with my students, but the shamrock in my St. Patrick’s Day piece has also stolen my heart. Cute little clover!
So what new holidays should I illustrate and add to this growing list? Should I begin getting into international, world holidays, or bizarre and obscure ones? I’m open to anything that would go well with my whimsical style of cartoon drawings, so feel free to add your requests to the comments section below! Do share…
Want more? Check out my instructions for a healthy gingerbread house-making activity!

The author and artist, Lillie Marshall, is a National Board Certified Teacher of English who has been a public school educator since 2003, and an experienced Reiki practitioner since 2018. All art on this site is original and hand-drawn by Lillie. She launched DrawingsOf.com Educational Cartoons in 2020, building upon the success of her other two sites, AroundTheWorldL.com (established 2009) and TeachingTraveling.com (founded 2010). Subscribe to Lillie’s monthly newsletter, and follow @WorldLillie on social media to stay connected!