There’s nothing like spending the holidays in a small mountain town — walking past festive shop windows, hot cocoa in hand and hopefully fresh snow on the streets. Add Old West-style storefronts and the snowcapped Cascade mountains as a backdrop, and you’ve got Sisters, Oregon.
This is the time to start new holiday traditions, and Sisters is just the place for it. From Thanksgiving through New Year’s, Sisters Hometown Holidays packs the calendar with events for the whole family. Make an annual date with the Christmas tree lighting, vote for your favorite gingerbread house or break out your most ridiculous holiday attire at the Ugly Sweater 5K Run/Walk. And leave plenty of time for shopping, great food and a cozy night by the fireplace. Here’s some inspiration to help plan your trip.
Parades, Lights and Holiday Fun
The Saturday after Thanksgiving kicks off the celebrations with Holiday Palooza. In the afternoon, downtown Sisters serves up holiday cheer with a Main Street parade featuring horses, holiday characters, fire trucks and maybe even a corgi or two. There’s music, crafts, free hot cocoa and photos with the big man in red himself, Santa. And as the sun sets, the holiday season feels official with the grand tree-lighting ceremony.
For a sweet display, check out the Gingerbread Trail the three weeks leading up to Christmas, when local businesses show off their elaborate gingerbread-house creations. Pick your favorites and let the family vote. When evening falls throughout the month, drive or stroll along decorated storefronts and streets aglow with the Town of Tiny Lights. Wander and window-shop while crossing a few names off your gift list.
Test your holiday-movie knowledge at The Belfry, an historic church event space, on December 11, 2026, for Holiday Movie Bingo. Grab a bingo card and watch classic movie moments with a little friendly competition, complete with prizes. The event is free, but it’s a good idea to sign up ahead of time.
Ready to hit the slopes or race down the tubing hill? Wrap up the year at Hoodoo Ski Area, just 20 miles west of Sisters on Santiam Pass. Spend New Year’s Eve making a few nighttime laps under the lights until 10 p.m. Party with live music and ring in the new year with midnight fireworks on the mountain.
Gifts, Good Food and Local Finds
Trade those crowded mall parking lots for the boutiques, galleries and specialty shops in Sisters. Stroll beneath the holiday lights, popping into locally owned shops filled with clothing, home decor, handmade gifts and outdoor gear, and enjoy some small-town hospitality along the way.
Browse clothing and accessories at Bedouin, where you might even find something for yourself. For home decor and gifts with a vintage flair, stop in Rescued Living and check out its beautifully decorated holiday displays for a little inspiration of your own. Find loads of seasonal gifts and fun finds at the family-owned The Hen’s Tooth. For festive holiday markets, check out Lazy Z Ranch Wines’ Holiday Market at the Ranch on November 21 and the Three Sisters Lions Club Holiday Faire, November 27–December 19, 2026, for handmade crafts and goods from local makers.
When it’s time for something besides candy canes and marshmallows, grab a smoked tri-tip sandwich with provolone and barbecue sauce at Sisters Meat and Smokehouse. When dinnertime calls, head to The Open Door for classic lasagna with Italian sausage and ricotta. Or exchange gifts and laughs at Frankie’s with a hot seasonal cocktail or a Sisters Sour, a twist on the classic New York Sour.
Make a Weekend of It Around the Fireplace
Stay the night or, better yet, stay the whole weekend. At FivePine Lodge & Spa, sink into a plush chair beside the lobby’s massive stone fireplace for the nightly wine-and-beer reception. Then head to your private cabin tucked among the ponderosa pines, complete with a fireplace and a soaking tub. It’s a great place to unwind after a lot of family fun. For extra pampering, book a treatment at the on-site Shibui Spa.
Right in downtown Sisters, the Ski Inn Tap House Hotel offers boutique rooms above its tap house. Grab the Eddy burger with bacon, grilled onions and house-made sauce and a local brew or two downstairs, knowing your cozy room is just a flight of stairs away. Also in downtown is the Sisters Bunkhouse with four cozy guest rooms and the Corral, a shared space for morning coffee or a family card game after dinner.
One winter weekend just isn’t enough, and luckily, Sisters gives you plenty of reasons to come back. From Fourth of July festivities in summer to Halloween’s Trunk-or-Treat in fall, this small Central Oregon town knows how to celebrate year-round.
