December 6th, 2025
10am - till the cows come home
Get ready to rustle up some holiday cheer at Bailey’s Cowboy Christmas!
This here’s a Christmas celebration with a true Western twist—now sprinkled with a little North Pole magic! Mosey on down for toe-tappin’ live music, hearty grub from the Glen Isle Chuck Wagon, and unique, handmade gifts in our Holiday Market heated tent, filled with talented local artisans. This year’s theme, Santa's Workshop transforms our cowboy Christmas into a whimsical wonderland where the rugged spirit of the West meets the joy and sparkle of the holidays. From the jingle of spurs to the jingle of sleigh bells, it’s a celebration the whole family will love!
Let the kiddos enjoy free photos with Cowboy Santa and holiday activities just for them.
As dusk settles, gather ‘round for the magical tree lighting ceremony, then stick around for the grand nighttime parade lighting up Main Street. Cowboy Christmas is where Bailey shines brightest—y’all won’t want to miss it!
EVENT SCHEULE
Shop The Holiday Market
Get ready to find unique, handcrafted gifts and festive treasures at the Cowboy Christmas Santa's Workshop Holiday Market! With local artisans and vendors offering everything from one-of-a-kind crafts to delicious treats, it’s the perfect place to check off your holiday shopping list. Come support small businesses, discover amazing finds, and soak in the holiday spirit!
Show off your holiday spirit!
REGISTER A PARADE ENTRY
DEADLINE TO REGISTER: December 1
Saddle up and join the festivities by creating your own parade entry for Bailey’s Cowboy Christmas! The theme of this year's event is Santa's Workshop. So go wiled! Whether it’s decked out with holiday lights, themed costumes, or a creative float, your entry will add sparkle to the grand nighttime parade.
There will be three award categories for 2025:
- Best of Show
- Best Santa's Workshop Theme
- Best Kids Entry
Show off your holiday spirit and be part of a cherished community tradition—register your entry today and help make this year’s parade unforgettable!
Show off your festive flair!
COSTUME CONTEST
Y'all are invited to keep the Cowboy Christmas spirit going at the After Party Costume Contest at Craft Mountain Brewing! Show off your festive flair and compete in fun categories: Best Ugly Sweater, Best Holiday Beard, Best Holiday Cowgirl, Best Holiday Cowboy, and Best Dressed Holiday Pet! Whether you’re rockin' a beard full of tinsel, a sparkling cowgirl hat, or a pup in reindeer antlers, there’s a category for everyone. Join us for good laughs, great prizes, and some holiday cheer with friends—don’t miss out on the fun!
LIGHT It UP!
BUSINESS DECORATING CONTEST
All Bailey businesses with storefronts are invited to join in the Business Decorating Contest and help light up our town with holiday cheer! Deck out your spaces, inside and out, and bring the spirit of Cowboy Christmas to life with a festive, Western twist by December 1, Whether it’s stringing up extra lights, adding a touch of rustic charm, or creating a full holiday display, let’s make Bailey shine! The more lights, the merrier, so get creative and help make this season unforgettable for our community and visitors alike. Plus, there will be trophies awarded for the best decorations, so don’t miss your chance to claim bragging rights and show off your holiday spirit!
We need your help!
VOLUNTEER
Join in the holiday spirit by volunteering for Bailey’s Cowboy Christmas! We’re looking for enthusiastic volunteers to help make this festive celebration a success. Whether you’re setting up decorations, assisting with activities, or helping out during events, your support will make a big difference in our community’s holiday experience. It’s a great way to meet new friends, spread cheer, and enjoy the magic of the season. Sign up today and be part of the fun as we bring Cowboy Christmas to life!
We will be posting a link soon to sign up as a volunteer!
