We’re going overboard this holiday with 60+ events and counting! So book a stay, pack your skis and snowshoes, and get ready to make this the best holiday season ever.
We’re crazy about the holidays here in Sisters. We have over 60 events for you to enjoy between Thanksgiving and New Year’s. Parades, tree lightings, meet and greets with Santa, craft markets, and plenty more to inspire your festive side.
Explore local businesses where cozy boutiques, galleries and vintage marketplaces teem with curated treasures. Discover artisan homewares, locally-crafted treats, and one-of-a-kind gifts brimming with holiday spirit.
Have a holiday wish? Drop a line to Santa. Deliver a letter to The Nugget Newspaper between November 29th – December 15th, 2025 to receive a reply from Old Saint Nick himself.
During this most wonderful time of the year downtown Sisters is adorned with thousands of tiny lights. Take a drive-through tour or stroll the streets after dark and be whisked away in our winter wonderland.
Enjoy a seasonal retreat in Sisters. From cozy cottages to boutique hotels, and places for the whole family to gather, you’ll find it right here. Book your stay today and share in this most magical time of the year.
The holiday season is about to get a little sweeter. From December 5–23, participating businesses will showcase their creative gingerbread displays. Follow the Gingerbread Trail, enjoy the creativity, and vote for your favorites.
Featuring local vendors with high quality unique handmade items. Free admission, daily from November 28, 2025 to December 20, 2025 at Sisters Art Station. Monday-Friday 10:00am-8:00pm Saturday 10:00am-6:00pm Sunday 10:00am-4:00pm.
Explore the Kalamataca Ranch and find your perfect tree for the holidays. Kalamataca is not a tree farm. It is, however, an 80-acre spread full of natural Christmas trees.
Explore the holiday marketplace at Faith, Hope & Charity Vineyards. Faith, Hope & Charity Vineyards is filled with iconic experiences for our visitors, including concerts, wine release parties, winemaker dinners, …
Swing by The Barn in Sisters for a Holiday Makers Market filled with locally crafted gifts for all your special people.
Stop by Luckey’s Woodsman Trailside Kitchen for a festive tree lighting. Delicious food and beverages available for purchase.
Join Faith Hope and Charity Vineyard for a wreath making party to create a beautiful rustic Christmas Wreath or centerpiece!
Holiday crafts made by kids, sold by kids. Join Commonplace Homeschool Co-op for a kids holiday craft market at The Hub. Santa will be stopping by the market for photos …
Shop First Friday in downtown Sisters featuring street buskers playing some of your favorite holiday tunes. Search participating local shops for unique holiday gifts among the glowing lights of downtown …
Get ready to enjoy the coziest of cozy winter experiences: The Camp Sherman Holiday Bazaar. After a 15 year hiatus, this beloved tradition was revived in 2019 and is well …
Snag a photo op with Santa and share your holiday wish, then make a holiday ornament of your own.
Santa Claus is coming to town and he’s making a stop at Spoons restaurant. Get your photo taken and share your holiday wish.
It’s time for the 4th Annual UGLY SWEATER 5K RUN OR WALK!! Bring the whole family, come dressed in your favorite Ugly Christmas Sweater and kick off the Holiday Season …