Every autumn, pumpkins seem to take over the world. They perch on porches, fill our pies, scent our candles, and lately, they’ve even taken to the water. Yes, the water. Thank you to Shanna Hatfield for posting some pics from her excursion to the Tualatan Pumpkin Regatta on FB. Shanna was in the Portland area last week for a book signing and got to go see this spectacle. I had no idea such a thing even existed! And I don’t live that far away!
So, it’s called the West Coast Giant Pumpkin Regatta where folks climb into hollowed-out pumpkins the size of rowboats and paddle across a lake. Costumes, cheering crowds, and a few wobbly mishaps included. When I first saw pictures, I thought wow! How fun! And this has been going on for over twenty years? Turns out, people will race just about anything that floats.
And that got me thinking…
What would a Victorian Pumpkin Regatta have looked like? Or a western one? Ha! Can you picture cowboys climbing into
giant hollowed out pumpkins to race? Oh. My. Goodness! After all, Victorians and cowboys alike loved a good party.
In the late 1800s, Halloween was shifting away from fright and toward fun and community. Parlors and barns were decked out for games, laughter, and just a touch of mischief. So, if you happen to be near a lake…
Imagine a genteel Victorian regatta on some fog-kissed lake. Ladies in long gowns and gentlemen in top hats politely stepping into their floating gourds while someone on the shore shouts, “Mind your crinoline, Miss Penelope!” The brass band strikes up a tune as the racers paddle madly for the prize. Probably a lace handkerchief and eternal bragging rights.
Meanwhile, the spectators sip mulled cider and play their own party games: Bobbing for Apples in porcelain washbasins, lace sleeves rolled just high enough to scandalize. Halloween Pudding, a cake baked with hidden charms in it like a thimble, a button, a ring, each foretelling one’s romantic or financial fate.
Now imagine if a few cowboys from the Old West had a pumpkin regatta! You can bet they wouldn’t be content to simply paddle their pumpkins across the water, no, siree. They’d line up their hollowed-out gourds like canoes, tip their hats to the crowd, and shout “Yee-haw!” as they raced for them with one hand on a paddle, the other keeping a hold of their hat. The race would probably turn it into a full-blown rodeo on water. I can just see the sheriff trying to keep order while the town’s blacksmith bets his week’s wages on the fastest pumpkin, and a fiddler on the dock strikes up Turkey in the Straw to spur them on. By the end of it, someone’s pumpkin would’ve sprung a leak, someone else would be fishing their boots out of the drink, and the whole town would be laughing so hard they’d forget who won.
Yeah, I’m going to have to put that in a book! Oh, sure, back in the day they had lots of games they played for Halloween and harvest time too. The mirror game, where a brave young woman peers by candlelight to see if her true love—or a skull!—appears behind her. (Personally, I’d rather take my chances in the pumpkin boat.) And then there was a parlor game played in the dark where guests were told a room was haunted, then sent in folks one by one to reach into drawers and pull out mysterious boxes. Some contained party favors; others, well, the unexpected. (Cold oatmeal makes a fine imitation of something ghostly and unpleasant, trust me.
Folks back in the day knew how to have fun around this time of year and they certainly had imagination. Whether it was a fruitcake prophecy or a pumpkin pie eating contest, it all came down to the same thing. Celebrating the harvest, sharing laughter, and finding joy in the turning of the season.
So tell me, what were some of your favorite games to play at harvest festivals or Halloween parties? I bet none of them included racing around in giant pumpkins on a lake!
USA Today bestselling author Kit Morgan is the author of over 180 books of historical and contemporary western romance! Her stories are fun, sweet stories full of love, laughter, and just a little bit of mayhem! Kit creates her stories in her little log cabin in the woods in the Pacific Northwest. An avid reader and knitter, when not writing, she can be found with either a book or a pair of knitting needles in her hands! Oh, and the occasional smidge of chocolate!


We just played regular party games, though sometimes bobbing for apples was involved. Personally, I find it gross now.
I know! Me too, Denise! My bobbing for apples days are over.
I’m with Denise about the regular games; this was mainly at school. Outside of school was trick or treating; for us that only involved treats. I do recall tapioca pudding being used at summer camp in skits; nowadays that would gross me out (why nausea was part of a skit at summer Bible camp is a mystery). Boba tea is a much more pleasant use for tapioca.
Kids love gross things. Then we grow up Mary and it’s all ewwww!
We did all the normal Halloween games but I am up for racing those pumkins around the lake!
I know, I’d love to try it too!
Good morning Kit! I enjoyed this article. And can’t wait on that book! The hayrides were always fun! And the haunted house. I remember the baked goods were delicious!
Best wishes!
Haunted houses are always fun, Tracy!
I played most of my games at the school carnival for my kids. I do like the hayride. I liked trick or treating when I was a kid and taking my boys when they were little.
I’ve never been on a hay ride, Linda. They never used to interest me. I wouldn’t mind going on one now.
I like watching kids try bobbing for apples. I do also enjoy hay rides but only if not too hay-y as I am allergic.
Allergies would put a damper on a hay ride, Debra. I don’t blame you for not wanting too much hay involved!
I don’t think I have ever heard of pumpkin boat racing.
I hadn’t either, Bridgette. I’d love to see a pumpkin regatta. I guess I’ll have to wait until next year.
I have never heard of pumpkin racing but your story sure made me picture it. Lol. It sounds like a lot of fun!
Yes, I am definitely going to have to put something in a book, Barbara. And of course use cowboys. One of them would forget to take off his spurs and start poking holes in his pumpkin. Okay, it would have to be a really thin pumpkin. But still…
When I was young we would go out trick or treating, my older brothers would actually throw eggs around, we did have chickens and around this time of year it seemed like the chickens weren’t laying many eggs, but they actually were. We used ro have alot of fun on Halloween. When my 2 kiddos were growing up we would take them trick or treating and they would also have carnivals here in town and also haunted houses, we all really loved doing that. When my grandchildren were young we would also take the trick or treating and they would also pass out candy and we would also go to the carnivals. It sure sounds like the pumpkin races were alot of fun, I enjoyed reading your post, Thank you for sharing about these fun things they used to do. Have a great day and week.
That’s hilarious about your brothers, Alicia. I bet your parents just couldn’t figure out why the chickens weren’t laying as well during that time of year!
Sounds like good clean fun. I especially love imagining cowboys in a pumpkin race and can see the sherif having to keep order. When I was growing up we always have Halloween Carnivals at school and had fun games like the cake walk, bobbing for apples, and others that I can’t remember. It has been too long ago. Thanks for reminding me of days gone by when things were safer and more fun.
I love cake walks. In my little town they do cake walks in the grocery store! There are painted squares on the floor throughout the store, and they start playing the music at random.
I never really went to a Holloween party or Harvest . I do enjoy going to our local Apple Butter Fest. It’s huge with all types of fall décor handmade and apple butter of course made fresh all day long.
That sounds like great fun, Carrie! I love those little festivals!
No pumpkin regattas here. We have in the past bobbed for apples, but used a wash tub. Unless you are able to get the stem in your teeth, you must pin the apple to the bottom to get a good bite in it to bring it up. A good way to drown you or your competition. We also would hang apples by a string to catch with just your teeth. Not easy unless you work as a pair and wedge it between you. We replaced that one with large marshmallows. Less dangerous and easier to catch by yourself. We would have face painting, scarecrow making, and wreath or centerpiece making. Pumpkin decorating either by cutting out a jack-o-lantern, painting it, or decorating it with fabric, flowers, and whatever else they wanted. For Halloween, we would have touch boxes. Cooked, cold, oiled spaghetti for innards, Peeled grapes for eyeballs, a piece of fur, a cauliflower head for a brain, and cold oatmeal for lungs or shock value. The suggestion of what they are touching is sometimes worse than the actual feel….or not. Anything to have fun and an enjoyable time.
No pumpkin races, but definitely hayrides and bonfires and mulled cider and doughnuts!