Felted Christmas Ornaments & Small Stockings
Join us for this playful felting workshop where participants will create stockings and garlands perfect for the holiday season. Participants will be guided in learning the basics of the felting …
Hometown Holidays in Sisters, Oregon
Come Hang Your Stocking in Sisters this Season
We’re going overboard this holiday with 60+ events and counting! From Thanksgiving to New Year’s, there’s always something to do in Sisters. So book a stay, pack your skis and snowshoes, and get ready to make this the best holiday season ever.
Holiday Events
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.
Give a Gift from Sisters
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.
Letters to Santa
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.
Town of Tiny Lights
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.
Stay in Sisters
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.
Tour of Gingerbread Homes
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.
Holiday Events
54 events found.
Events
List of events in Photo View
Wreath Making Workshop
This workshop is offered on two dates, November 11th or 12th. Please choose your preferred session upon registration. Join us for a festive workshop in the Pine Meadow Ranch Center …
Wreath Making Workshop
This workshop is offered on two dates, November 11th or 12th. Please choose your preferred session upon registration. Join us for a festive workshop in the Pine Meadow Ranch Center …
Holiday Market at the Ranch
Find something special for the people on your list. Join us at the ranch for an afternoon of holiday shopping, local farmers and makers, good food, and mead. Explore gifts …
Thanksgiving Dinner
Enjoy a delicious Thanksgiving dinner at Black BUtte Ranch’s main lodge.
4th Friday Holiday Artwalk
On the fourth Friday of each month, downtown Sisters comes alive with the Sisters Arts Association’s 4th Friday Artwalk, a celebration of creativity and community. Local galleries open their doors …
Turkey Trot 5K Fun Run
THE SHORT COURSE is approximately 1.2 miles, is from the Lakeside Activity Center to the Big Meadow Clubhouse, and returns the same way. This route is primarily intended for kids 12 …
Holiday Tree Lighting + Caroling
Tree Lighting with Sisters’ High School Jazz Choir. Sparkling lights, warm drinks, and holiday magic under the pines at Black Butte Ranch. Festive cheer is officially here! Hot Cocoa & …
Kalamazoo’s Old-Fashioned MAGICAL Christmas Extravaganza!
THIS is an Antique, VINTAGE Christmas shoppers’ paradise! Scads of vintage Christmas Items all for sale and gathered for this event! Shiny Bright Ornaments galore, Snow Globes, Blow Molds, Wooden …
Kalamataca Ranch Tree Hunt
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.
Holiday Marketplace at the Vineyard
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, …
Holiday Palooza Parade & Tree Lighting
Enjoy two holiday favorites in one spectacular event! The Holiday Palooza will kick off with the holiday parade down Main Street and culminate with holiday activities, including the tree lighting …
Holiday Mimosa Sundays
Festive Sundays at Makin’ it Local in Downtown Sisters! Who says Sundays can’t have a little sparkle? Join us for Holiday Mimosa Sundays, featuring Seriously Great Art from Oregon artists, …
Holiday Marketplace at the Vineyard
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, …
Kalamataca Ranch Tree Hunt
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.
Camp Sherman Holiday Bazaar
Get ready to enjoy the coziest of cozy winter experiences: The Camp Sherman Holiday Bazaar at the historic Community Hall! Friday, December 4th: 5-8pm Saturday, December 5th: 10am-3pm Shop beautiful …
Ugly Sweater Run or Walk 5K
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 …
Camp Sherman Holiday Bazaar
Get ready to enjoy the coziest of cozy winter experiences: The Camp Sherman Holiday Bazaar at the historic Community Hall! Friday, December 4th: 5-8pm Saturday, December 5th: 10am-3pm Shop beautiful …
Kalamataca Ranch Tree Hunt
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.
Kids’ Entrepreneur Holiday Market
An entirely kid-run, eco-friendly market for ages 7–17 where young entrepreneurs sell handmade artwork, crafts, food, toys, jewelry, and more. A real-world experience that sparks creativity, builds confidence, and teaches …
Wreath Making Party
Christmas Season is almost upon us! Come join us for a fun, rustic wreathing making workshop! Faith Hope & Charity invites you to learn to make & decorate your own …
Friends and Vine Bubbles Tasting
Celebrate the season with our 3rd Annual Bubbles Tasting at Friends and Vine. Sample more than 20 sparkling wines from around the world, including French Champagne, Spanish Cava, Italian Prosecco, …
Holiday Mimosa Sundays
Festive Sundays at Makin’ it Local in Downtown Sisters! Who says Sundays can’t have a little sparkle? Join us for Holiday Mimosa Sundays, featuring Seriously Great Art from Oregon artists, …
Kalamataca Ranch Tree Hunt
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.
Holiday Makers Market
Swing by The Barn in Sisters for a Holiday Makers Market filled with locally crafted gifts for all your special people.
Wreath Making Party
Christmas Season is almost upon us! Come join us for a fun, rustic wreathing making workshop! Faith Hope & Charity invites you to learn to make & decorate your own …
Black Butte School Holiday Program
Join Black Butte School for this annual tradition as students take to the stage in “Winter Gifts,” led by performing arts teacher Jennie Sharp.
Motel Kalifornia Christmas Concert
Get ready for a magical night of holiday cheer and classic rock as Motel Kalifornia brings their signature sound to all your favorite Christmas classics. A Holiday Concert Like No …
Let’s Watch! Holiday Movie Bingo
A charming small town, decked out for the holidays. A busy big-city professional, short on holiday spirit. An attractive stranger, struggling to keep the family business afloat. A Christmas deadline. …
Winter Choir Concert
Get yourself in a festive mood with a winter choir concert at Sisters Community Church.
Photos with Santa & Ornament Making
Snag a photo op with Santa and share your holiday wish, then make a holiday ornament of your own.
Santa Claus is coming to Spoons
Santa Claus will be at Spoons on Saturday December 12 from 9:00 AM – 2:00 PM. Every kid will be able to pick a free ornament from our Christmas Tree.
Golf Holiday Open House
Make holiday shopping effortless at the Big Meadow Golf Shop Holiday Open House! This festive event combines a golf-themed holiday celebration with an exclusive sale, offering 20% off on accessories, …
Annual Christmas Party @ Cold Spring Resort
There’s nothing quite like Christmas in the mountains. Crisp winter air, cozy cabins, twinkling lights, and the joy of gathering with family and friends—it all comes together during our favorite …
Winter Dance Recital
Enjoy performances from Sisters Dance Academy at their winter dance recital.
Winter Dance Recital
Enjoy performances from Sisters Dance Academy at their winter dance recital.
Holiday Mimosa Sundays
Festive Sundays at Makin’ it Local in Downtown Sisters! Who says Sundays can’t have a little sparkle? Join us for Holiday Mimosa Sundays, featuring Seriously Great Art from Oregon artists, …
Breakfast with Santa
FivePine Catering is proud to host a magical visitor Sunday, December 7, 2025! Enjoy a wonderful breakfast, deluxe hot chocolate station, and very special visit with our friend from the …
Ladies Ornament Exchange
You’re invited to our 3rd Annual Ornament Exchange! Bring a wrapped ornament and get ready for a fun-filled exchange. We’ll draw numbers, pick ornaments, and if tradition holds, a little …
Winter Choir Concert
Get yourself in a festive mood with a winter choir concert at Sisters Community Church.
Return of the Light: A Pre-Solstice Gathering at Daybreak
Celebrate the return of the light in the longest nights of the year. Join Dr. Siobhan Gray and the PeakMD/Daybreak community for a free pre-solstice evening: a short lantern walk …
Solstice Celebration: Never Come Down w/ Skillethead (Seated)
Formed in 2017, Never Come Down was born from the vibrant if not occasionally overlooked music scene of Portland, Oregon. Much like the city that inspired them, they’re a smart, …
Solstice Celebration: Never Come Down w/ Skillethead (Standing)
Formed in 2017, Never Come Down was born from the vibrant if not occasionally overlooked music scene of Portland, Oregon. Much like the city that inspired them, they’re a smart, …
Breakfast With Santa
Enjoy a buffet breakfast followed by photos with Santa and cookie decorating! Reservations Required.
Holiday Mimosa Sundays
Festive Sundays at Makin’ it Local in Downtown Sisters! Who says Sundays can’t have a little sparkle? Join us for Holiday Mimosa Sundays, featuring Seriously Great Art from Oregon artists, …
Winter Solstice Celebration
Enjoy a fire & a contemplative walk, marking the shortest day of the year and the beginning of winter season. Hang out afterward for a cup of cocoa or tea. …
Carriage Rides @ Black Butte Ranch
Enjoy festive carriage rides at Black Butte Ranch. Rides are approximately 30 mins long. Advance reservations are available.
Solstice Book Flood Celebration
We’re big fans of the Icelandic tradition of Jolabokaflod, or the “Christmas Book Flood.” We love putting on our own version – the PSB Solstice Book Flood – and we’re …
Christmas Eve Service
Christmas Dinner at The Lodge
Enjoy a delicious Christmas dinner at Black Butte Ranch’s main lodge.
Community Christmas Dinner
The Sisters-Camp Sherman Fire District is hosting a free community Christmas Dinner at the Fire Hall.
New Year’s Eve Bash
Ranchowner + Guest New Year’s Eve Bash. Get your dancing shoes ready! They’re ringing in the New Year with a celebration you won’t want to miss. This is an age …
New Years New York Style!
Why wait until midnight? Join us as we celebrate the famous ball drop on New York time with great company, festive decorations, and a celebratory toast. Your admission includes a …
New Year’s Eve With Kota Dosa
Celebrate New Years Eve with Kota Dosa and Jeshua Marshall and The Flood! Kota Dosa is a creative collective with roots in New York, New Orleans, and Oregon. Known for their eclectic sound …