The Pacific Northwest's 8 Most Festive Downtowns For The Holidays
The Pacific Northwest undergoes a transformation under the snow cover. Its mosaic of charming small towns exudes warmth under the twinkling lights, with historic districts and special events during the holiday season. The snow-dusted rooftops, costumed characters, and decorated windows create a magical atmosphere for holiday shopping, spa indulgence, and even nature walks.
From Leavenworth wrapped in the Cascades to Mount Hood Railroad rides in Hood River, the PNW's best holiday towns thrive on local charm and family-centered experiences. The season accentuates Oregon's artsy towns, like Ashland, while in Washington, you can watch whales migrating out of the Salish Sea along the San Juan Islands.
Ashland, Oregon
Ashland's historic downtown is an inviting blend of boutique hotels, local food haunts, and artisan treasures, where you can up your holiday shopping game, escape into nature, and soak up old-time charm. The tree lighting, or Grand Illumination, is set for November 28 at 5pm, featuring Santa’s Parade, carolers, and photos with Santa. On November 29, walk through thousands of colorful poinsettias during the Poinsettia Festival at the Greenhouse, plus a staged area to take a snap.
In conjunction with Ashland's Festival of Lights, Thanksgiving weekend welcomes the Lithia Artisans Christmas Faire. This event showcases over 50 local artists, setting the stage with live music to browse one-of-a-kind handcrafted goods through 4 pm on Sunday. In addition, the iconic Lithia Park transforms around the Ashland Rotary Centennial Ice Rink through February, with rentals for just $3. Ashland's extensive theater scene warrants a warm evening over a performance.
Hood River, Oregon
Hood River, the "Windsurfing Capital," morphs into a winter wonderland with a festive downtown along the Columbia River. The annual Tree Lighting and Street Festival will feature music, food, and photos with Santa on December 5, a magical evening under the twinkling lights and snowcapped mountain vistas, for shopping and holiday events. Don't miss Ruins Winter Market to stock up on goodies and unique gifts from local artisans and craftsmen on the evening of Dec. 5th and 6th.
The Polar Express Train Ride is a real crowd-pleaser on select days now through early January along the Mount Hood Railroad, bringing the story of a child's journey to the North Pole alive with costumed interpreters and interactive storytelling. This 90-minute train trip to the North Pole is complete with Christmas music, a visit from Santa, and complimentary treats aboard with snowy scenery from the windows. Snow bunnies enjoy sled rides and guided snowshoeing tours through nearby forests.
Cannon Beach, Oregon
Cannon Beach celebrates Haystack Holidays. Festivities begin with the traditional Lamp Lighting Ceremony on December 6 in Sandpiper Square and spread along the lit downtown, from shopping promotions and adult beverages to Holiday Tea at the Cannon Beach Public Library, which also hosts kids' Holiday Story Time by the fireplace. Many descend for the Tolovana Arts Colony Holiday Bazaar on the first two weekends of December, featuring locally made arts, crafts, and gifts.
A Frosted Holiday Celebration at the Cannon Beach History Center & Museum on December 20 featured a hot cocoa bar, cookie decorating, face painting, and more. Enjoy holiday concerts in the week leading up to New Year's, which you can ring in with authentic Northwest wines. Travelers enjoy genuine hospitality and a walkable downtown, wrapped in coastal beauty.
Friday Harbor, Washington
A winter island paradise lures travelers from Seattle and beyond to this bustling town, aglow with holiday lights on the western flank of the largest of the San Juans. The Winterfest festivities include the 6pm tree lighting ceremony and Santa's Workshop on December 5th, on the corner of Argyle and Spring Street, with caroling, hot cocoa, and cookies waiting for Santa to show. It is a perfect winter retreat with unique shopping, spas, and long evenings over fireside dining and local wines.
The Winter Flea & Craft Market will be at the San Juan County Fairgrounds December 6-7, selling handmade gifts and second-hand items, while Brickworks, a converted industrial space, is the site of the Old-Fashioned Christmas Market. This holiday craft market is ideal to mingle with food, local farm products, and libations, Dec 10-11, plus live music and kids' crafts. Whale sightings, including transient orcas and humpbacks, are nothing short of a Christmas miracle from the isle's shores.
Leavenworth, Washington
From Thanksgiving through February, Leavenworth transforms into the "Village of Lights" under over half a million twinkling lights from 6am to 11pm daily. You can hear Leavenworth’s original Christmas song, performed by local musicians, on November 29 at 7pm and expect daily Santa visits through December 23. On weekends, kids enjoy photos and mingling with special characters like Rudolph, Frosty, and Friends at the Gazebo at Front Street Park, the heart of the festive downtown.
Don't miss the warming station with kids’ crafts, free gift wrapping, and a gingerbread house exhibition. The nearby Festhalle offers story time, whimsical photo stations, and official Christmastown merchandise for gifts and souvenirs. Other unique accents include Santa costumes from around the world, holiday-themed parodies, and sledding in town, plus a local reindeer farm. Together with its Bavarian motif, this festive town makes for a family-fun, enriching retreat.
Newport, Oregon
This small town with sea fever lures the like-minded boaters, maritime fans, and those after unique holiday displays. Whether you're a storm catcher, a seafood lover, or a holiday shopper, the annual Yaquina Bay Lighted Boat Parade is a free, family-friendly tradition in early evening on December 5, followed by the winners' award party for the most decorated vessel. You can watch from Abbey Street Pier, the elevated Yaquina Bay Bridge, or waterfront restaurants like Local Ocean.
Enjoy hot cocoa and cookies, then the tree lighting along the historic bayfront across from Ripley's Believe It or Not! With its deep maritime history and commercial fishing, no trip to the Dungeness Crab Capital of the World goes without seafood and wine, lighthouse sightings, and storm watching. The palpable change of season along the humid ocean coast is all the more rewarding when you venture through the lit downtown to warm up at local cafes and stock up on artisanal crafts.
Port Townsend, Washington
This Victorian city brings holiday traditions alive on the northeastern tip of the Olympic Peninsula, luring travelers with nostalgia and glamour to stock up on gifts amid historic architecture. From the First Saturday Art Walk in November, the port town is aglow along the Main under the twinkling lights, with its strong small business scene and warm sentiments like window- and gingerbread-decorating contests, kids' ornament-making, and caroling.
Santa will arrive on the Kiwanis Choo Choo at Pope Marine Park on December 6, the day of the tree lighting with Santa by Haller Fountain at 4pm under the ceremonial Fire Bell Tower ringing, and the concluding parade with Santa to the American Legion. The 19th-century-inspired holiday events, like the Salish Sea Makers Market at the Cotton Building, make for a heartwarming season. Mix it up on a stroll around Kah Tai Pond downtown with walking trails.
Rupert, Idaho
Don't fret about venturing deep into the heart of the PNW for the holidays, particularly Rupert. This peaceful summer retreat along the Snake River has the holiday game on point, featuring a traditional theme and the Rupert Christmas Festival, a recurring multi-day celebration at its gorgeous Rupert City Square. The classic town square is worth slowing down to soak up the charm with welcoming shops, historic buildings, and the jewel Wilson Theatre, featuring events through the snowy months.
Santa's Square Lighting takes place the day after Thanksgiving, with evening fireworks and festivities for the next two weekends, including a Christmas Market and visits with Santa. Travelers of all ages enjoy a chili feed, caroling, and ice skating, making memories to outlast the season. The "Beet Drop" on the square marks the arrival of the New Year, featuring a giant, illuminated sugar beet named "Crystal," a tribute to Idaho's sugar beet industry, lowered from a crane at midnight, then fireworks.
Where Holiday Charm Shines
Book now and pack appropriately to soak up the spirit in the crisp air, watching vessels during Newport’s Yaquina Bay Lighted Boat Parade or treading tidepools on a guided Haystack Rock walk in Oregon. Each is a real crowd-pleaser, so you can expect a lively atmosphere but also catered experiences and secret nooks for a more intimate feel.
There are no better places to find unique handicrafts and gifts than local shops, curated boutiques, and holiday markets. Downtowns continue to glow through winter months, with fewer crowds for after-holiday sales in the same warm ambience. Save the dates for main events, best taken with a side of sled rides, snowshoeing trails, or a local reindeer farm.
