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Can you escape the Headless Horseman??? If you’re looking for an awesome Halloween party theme, a unique Thanksgiving party, or celebrating the end to a Legend of Sleepy Hollow study, this party is perfect for you! From (semi) spooky decorations to autumnal feasts and kid friendly fun & games, they’ll have the ultimate time! Read on to check out our ideas!
DECORATIONS
The Legend of Sleepy Hollow features the schoolmaster, Ichabod, and the terrifying Headless Horseman. The Headless Horseman is actually quite a recognizable figure around Halloween as there are many decorations that feature this mystery figure! The story is also set in the autumn season, which also makes it perfect for a Halloween (or Thanksgiving) theme!
Around the Halloween Season, Michaels has a number of decorative items featuring the Legend of Sleepy Hollow as well as the Headless Horseman – Tree Buddees Headless Horseman with Pumpkin Halloween / Christmas Ornaments, 8″ Sleepy Hollow Sign Tabletop Accent, 8″ Washington Irving Tin.
And since this is of course a Legend of Sleepy Hollow Party, bring out the book (or books by Washington Irving)!!! Maybe it will inspire some new to the story to pick it up and read a few pages 🙂
THE PHOTO AREA
Photo backdrops are a great way of setting a theme and double as a nice and easy activity! Pick a backdrop that functions as decorative, add a few props to the scene and you’ve got a great place to hang out!
For this Sleepy Hollow inspired party, any Halloween or dark, autumn backdrop would work great. We’ve used this Autumn Backdrop in several of our parties! Otherwise, you could also pick up a backdrop that features a headless horseman (Halloween Backdrop Theme Photography Cemetery Headless Horseman)
Note, you don’t have to go all out with a photo backdrop stand either. Grab a few pieces of tape and an empty wall & you’re all set!
THE TABLE
Although the Headless Horseman is quite a popular Halloween figure, there isn’t too much in the way of table supplies featuring him, which may be a good thing 🙂 We actually had two tables for this party, a tween/teen table and an adult one 🙂
THE KID TABLE
We kept the kid table very simple with only a few items on it. For the table cover, we used a simple kraft roll so that they could draw and color while they sat down. For the table settings, we used a Halloween night-time theme (144 Pieces Full Moon Night Sky Halloween Party Supplies) along with a Headless Horseman Tin Can Craft to hold the crayons.
THE TWEEN/TEEN TABLE
For our tween/teen table, we went with a Halloween night-time theme (144 Pieces Full Moon Night Sky Halloween Party Supplies) and added a few items with nods to the book: 11” Standing Wooden Headless Horseman Scene Silhouette in the center.
For each table setting, we also added a horse from the Action War Horse Animals Building Blocks Set and a pumpkin from the Cropland Set Farm Field Accessories Building Blocks Brick Playset (though you can also get pumpkins separately as well). We didn’t have any revolutionary war minifigures but we at the activity table, they could sift through our minifigures pile to see if they could create one on their own 🙂
THE ADULT TABLE
For the adult table, we went with a more autumn theme with browns and fall colors. We also added a lucky horseshoe as a nod to the horse from the Headless Horseman.
PARTY FOOD
No party is complete without some party food! You can always serve some typical (or fancier) party food, but you can also keep in theme with a few clever labels or snacks 🙂
Food is featured prominently in the Legend of Sleepy Hollow as its main character loves to eat. This makes it much easier for anyone hosting a Legend of Sleepy Hollow party (or dinner party). While you can go all out with some homemade yummies, you can always opt for some store-bought versions to save some time 🙂
We like to add some quotes or references to the books / party theme on our food table, so we also added some nods to the book by a few of the dishes 🙂
- Snacks
- Apples – “On all sides he beheld vast store of apples; some hanging in oppressive opulence on the trees; some gathered into baskets and barrels for the market; others heaped up in rich piles for the cider-press”
- Main Courses
- Ham – “besides slices of ham and smoked beef;”
- Chicken – “not to mention broiled shad and roasted chickens”
- Pot pie – “the pigeons were snugly put to bed in a comfortable pie, and tucked in with a coverlet of crust;”
- Sides
- Corn – “Farther on he beheld great fields of Indian corn, with its golden ears peeping from their leafy coverts”
- Desserts:
- Donuts – “There was the doughty doughnut, the tender oly koek, and the crisp and crumbling cruller;”
- Pies (apple, peach, pumpkin) – “And then there were apple pies, and peach pies, and pumpkin pies”
These sites have some great posts on Sleepy Hollow Dinner Parties if you want to go all out – How to Plan a Menu for Your Sleepy Hollow Party by InLiterature and The Legend of Sleepy Hollow: The Feast by Rhubarb and Lavender
ACTIVITY TABLE(S)
We typically set up an activity table for kids to keep entertained while everyone arrives AND after all the games are done. These activities are simple and easy and typically don’t require too much supervision.
- Coloring Pages – There are quite a few sites that share some printable coloring pages for the Headless Horseman! Print out a few and let the kiddos get creative with their coloring skills. We picked a few from getcoloringpages.com (Headless Horseman Coloring Pages)
- Lego Horseman & Soldiers – If your guests are fans of Legos, some basic blocks can get them started on a fantastic scene from the book (or movie).
- 1000 Piece Jigsaw Puzzle Headless Horseman – Set out a table dedicated to a puzzle and have everyone wander over and solve a few pieces 🙂 By the end of the party, you might be done (or maybe mostly? :):):) )
GAMES
What’s a party without some fun and memorable games??? Kids will definitely have fun just running around and coming up with their own games, BUT adding in a few themed games will definitely be a hit with your guests! Here were a few of ours.
- Headless Horseman Board Game – This one is self explanatory 🙂 It’s based of the Disney version and is a good game for the family
- Dodge the Pumpkins (or Cannonballs) – If you have a large space or yard, you can play “dodge the cannon balls’ or ‘dodge the pumpkins’. In the story, Ichabod is a soldier who supposedly lost his head because of a cannon ball in battle. He also gets a pumpkin tossed at him by the Headless Horseman at the end. Using black or orange foam balls, balloons, or water balloons, you can ‘dodge these objects’ too!
- Ghost Stories – If you’re a fan of the Legend of the Sleepy Hollow, you may love a good ghost story! Turn off the lights or head into the yard and night with flashlights and go around telling some spooky stories!
THANK YOU!!!
Thank you so much for checking out our party planning article. Hopefully it gave you some great ideas for your next celebration!
If you did enjoy this, please let us know below or follow us on Pinterest. Also, If you haven’t already and are still looking for that perfect party theme, feel free to check out some of our other Party Guides or Halloween Ideas!
Happy Party Planning & Happy Halloween!
