Thanksgiving is already a big day filled with food and family, but sometimes the awkward “what do we do before dinner?” moment sneaks up. That’s where a little planning (and a few quirky tricks) can make all the difference. These Thanksgiving entertaining ideas are fun, low-stress, and just the right amount of silly.
1 | Pumpkin Tic-Tac-Toe
One year I saw this set up on the roadside at a fall festival and instantly thought, “I could do that at home.”
You just need a wooden board or even a cardboard square painted with lines, then use mini pumpkins and gourds as your X’s and O’s.
Kids love it, but honestly, adults get weirdly into it too. I once watched my uncle “strategize” like it was a chess match.
Bonus tip: spray paint half the pumpkins gold for a glam touch. It looks fancy without effort.
2 | Gratitude Jar Game
My friend once set this up and it ended up being the highlight of dinner.
Everyone wrote something they were thankful for, then later we had to guess who wrote what.
The handwriting giveaways were hilarious (my cousin “scrawls” so not only did we have to guess who wrote it but also what it said).
It became this sweet but funny icebreaker.
All you need is scraps of paper, a jar, and a pen.
Pro tip: fold them really tight so people can’t cheat and peek.
3 | DIY Photo Booth with Dollar Store Props
I saw this done on the roadside at a fall craft fair and it looked way too fun not to try.
Grab a sheet or plaid blanket for a backdrop, tape it to the wall, and toss out some goofy props like pilgrim hats, stuffed scarecrows or fake mustaches.
It sounds cheesy, but trust me, once one person starts snapping pictures everyone jumps in.
Plus, it keeps people busy while you’re still basting the turkey.
4 | Pumpkin Bowling
My mom swears she invented this back when we were kids, even though we’ve seen it about 100 times online!
If we were playing outside she use empty 2-liter soda bottles filled with just a splash of water and a small round pumpkin as the “bowling ball.” And yep you guessed it roll the pumpkin towards the “pins”.
But if we were playing inside she would use stacked toilet rolls with “ghost” faces on them, like the image above.
The pumpkin never rolls straight, which is what makes it so funny.
It’s silly, a little messy, and very Thanksgiving backyard energy.
5 | Trivia Cards at the Table
I played this game with my friends before dinner one year and you would not believe how competitive things got.
We pulled random Thanksgiving trivia questions from the internet and scribbled them on index cards.
Suddenly, people were yelling out answers like “1621!” and “cranberries!” at the table.
It gave everyone something to do while waiting on the last dish.
6 | Butcher Paper Tablecloth Doodles
I saw this set up at one of my son’s friends birthday parties and though this could be fun for Thanksgiving!
Cover the table with butcher paper and toss some markers around.
Guests doodle, play hangman, or even write little notes of gratitude.
I once saw someone sketch out the entire Macy’s parade float line-up. The best part is you can roll it up and save it after. Instant keepsake without buying anything fancy.
7 | Guess the Spice Smell Test
My mom used to set this up as a little kitchen game when we hovered too close while she cooked.
She’d blindfold us and make us sniff cinnamon, nutmeg, thyme, and even weird curveballs like paprika.
It’s harder than you think (apparently, I once called oregano “leafy dust”).
Guests love it because it feels like a challenge but it’s not too serious. All you need are little jars or bowls. Don’t be surprised if people start demanding a prize.
8 | Cozy Hot Cocoa Bar
I saw this once at a roadside pumpkin patch café and copied it shamelessly.
Line up mugs, cocoa mix, whipped cream, sprinkles, even crushed cookies.
People love customizing their drinks and it feels like a treat before the main meal.
9 | Turkey Trot Mini Walk
My friend drags us out for this every year, and at first, we all groaned.
But a quick walk around the block before the feast actually works wonders.
We laughed, shared stories, and even stopped at a neighbor’s yard where they had a giant inflatable turkey.
It’s such a small thing, but it creates a pause before all the chaos. If the weather’s chilly, hot apple cider in travel mugs makes it even better.
10 | DIY Pumpkin Piñata
I’m a big fan of papier-mâché pumpkins stuffed with candy and little toys.
Kids went wild trying to break it, and adults couldn’t stop cheering. It’s the kind of unexpected fun that makes people talk about “that one Thanksgiving” for years.
If you’re not crafty, just grab an orange balloon and wrap it in tissue paper. Still works.
11 | Thanksgiving Bingo
My friend came up with this and it was genius.
She printed bingo cards with squares like “someone mentions football,” “pie is mentioned,” or “uncle falls asleep.”
Throughout the day, people secretly marked their cards.
Suddenly, we were all stifling laughter when Aunt Karen launched into politics (yep, that was a square).
It’s sneaky, funny, and keeps the vibe light. Just don’t make the prizes too serious, or the competition gets cutthroat.
12 | Pumpkin Painting Station
I saw this at a kid’s Halloween party and thought, “Why not at Thanksgiving?”
Set out small pumpkins, paints, and brushes.
People end up painting everything from classic faces to weird inside jokes.
It’s also great because it entertains kids without screens. Plus, the pumpkins double as instant décor guests can take home!
13 | Pass the Story Game
My mom always loved this one.
You start a Thanksgiving story with a single line (“The turkey escaped from the oven…”) and each person has to add to it.
It never ends well – last year, our story ended with the turkey going on a space mission to Mars!
It’s goofy, creative, and requires zero prep.
People surprise you with how ridiculous they get. It’s something that is great for both kids and adults to get involved in!
14 | Scavenger Hunt Indoors
I saw this roadside at a church fall fair, and the kids were racing everywhere looking for hidden leaves and candy.
You can do the same inside by hiding mini pumpkins, little notes, or even clues that lead to a silly prize.
Adults get into it more than you’d think, especially if the clues involve food.
I once hid a piece of pumpkin pie under a box lid and nearly caused chaos. Simple but surprisingly fun.
15 | The Compliment Circle
One Thanksgiving, my friend suggested we go around the table giving one compliment to the person on our left.
At first, everyone groaned. But then it got kind of emotional in a good way. People started saying oddly specific things like “You make the best cornbread” or “You always drive me home when it rains.”
It felt genuine, and it stuck with me. It’s one of those Thanksgiving entertaining ideas that doesn’t cost anything but lingers.
16 | Thanksgiving Charades
This one can be a lot of fun if you have a goofy group of friends who need entertaining! This is just charades… but Thanksgiving.
Think along the lines of having to act out things that are associated with Thanksgiving. Friends of mine played this once and they were acting out things like “cranberry sauce” and “post football nap” and it was hilarious.
Doing it at Thanksgiving is perfect because it doesn’t take much space or props. Just scribble words on slips of paper. The sillier, the better.
17 | Dessert Decorating Contest
My mom always let us decorate pies or cookies with whatever sprinkles and toppings we could find.
It always turned into a competition, with one cousin trying to “out-design” everyone else.
One year, someone made a whipped cream “mohawk” on the pumpkin pie.
Guests love getting hands-on, and you end up with desserts that look half-artistic, half-disastrous. Either way, it’s memorable.
18 | Old-School Board Games Out
I saw this idea roadside outside a thrift store where they had shelves of vintage board games, and it clicked.
Dust off the classics like Sorry!, Clue, or even a deck of Uno cards. Suddenly, the whole house feels cozy and retro.
I once brought out Connect Four, and people played for hours while the turkey roasted. Simple, nostalgic, and it works for all ages.
19 | Thanksgiving Pictionary
My friend did this last year, and let’s just say his attempt at drawing a turkey looked more like a cactus.
But that’s the charm. Everyone laughs at the ridiculous drawings, and it breaks any lingering awkwardness.
All you need is a whiteboard or paper.
Throw in Thanksgiving-themed words like “pilgrim hat” or “mashed potatoes.” I promise the drawings won’t make sense, but that’s half the fun.
20 | Candlelit Storytelling
One year I saw this done roadside outside a little harvest festival tent.
They turned off the lights, lit a bunch of candles, and had everyone share a quick story or memory from past Thanksgivings.
It felt oddly magical.
Doing it at home makes the room cozy and gives everyone something real to connect over. Plus, it’s a calming way to wind down after the games. Even the kids hushed up for it.
