Sentinel

Winter at Sentinel 

Celebrate the most wonderful time of the year. 

When the giant tree in Pioneer Courthouse Square flicks on its 10,000 lights and the air smells faintly of rain and roasted chestnuts, Portland shifts into holiday mode. The city feels cozy but charged—perfect for a winter stay where great wine, glowing streets, and a historic hotel all meet in one place.

Sentinel sits in Portland’s West End, a historic property designed for forward-thinking travelers, with Jake’s Grill, Fortune, and the Domaine Serene Wine Lounge all under one roof. It’s an ideal launchpad for holidays in the city: close to tree-lighting ceremonies and markets, yet just a short drive from Willamette Valley’s world-class vineyards.

Holidays in the City: A Wine-Lover’s Guide to Portland with Sentinel

Portland in December has a charm all its own—twinkling lights, crisp air, and a pace that invites you to slow down just enough to savor the moment. For wine lovers, it’s also one of the most rewarding times to experience the region’s world-class pours.

This is your guide to celebrating the holidays through the lens of Oregon wine—whether you’re staying close to your guest room or venturing into the Willamette Valley.

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LOCAL WINTER EVENTS

DOWNTOWN & BEYOND

  • Durant at Red Ridge Farms

    Holiday Wreath Workshop

    Guests are guided by Durant’s experienced staff to build a handcrafted wreath using estate-harvested greenery — olive branches, cedar, fir, bay, plus cones, moss, twigs, berries.

    Dec 6, 2025

    Winter Table Centerpiece Workshop

    A relaxed, creative workshop where participants craft a winter-themed centerpiece using fresh winter greens and natural materials from the farm.

    Dec 7, 2025

    Watercolor Workshop

    A casual, artsy afternoon amid vineyard setting: participants paint under guidance of a Portland-area artist (in past years) while surrounded by the farm’s natural charm.

    Dec 6, 2025
  • Domaine Serene Wine Lounge

    Live Music

    Intimate live music with high-end wines in a refined lounge setting — very on-brand for Sentinel guests looking for an “evening in the city” pairing.

    December evenings

    Blind Tasting

    Guests taste three wines “blind” and test their palate — a fun, cozy mid-week ritual that feels smart and slightly elevated.

    Every Wednesday in December 2025
  • Christmas Festival of Lights at The Grotto

    A serene walk among thousands of lights with choir performances — a quiet, evocative holiday outing.

    Nov 28 – Dec 30, 2025
  • Winter Wonderland at Portland International Raceway

    Drive-through (or walk/bike) light show — convenient, cozy, and good for a low-effort evening.

    Nov 28 – Dec 31, 2025
  • Peacock Lane Christmas Lights

    A classic, neighborhood-scale holiday tradition — ideal for a relaxed stroll with a cup of something warm.

    Dec 15 – Dec 31, 2025 (pedestrian nights Dec 19–20)
  • Christmas Ships Parade

    A romantic, waterside holiday tradition — especially memorable if arriving from or near a hotel stay.

    November–December 2025 (various nights)
  • Portland Night Market

    Local-maker gifts and artisanal finds — great for guests looking for unique Portland-style souvenirs

    Dec 4–7, 2025
  • Crafty Wonderland Holiday Market

    A highlight of Portland’s creative community — aligns with city-style charm and boutique hotel guests’ sensibilities.

    Dec 12–14, 2025
  • Magic at the Mill

    Holiday lights, local market, Santa visits, and community charm — a low-key, cultural outing not far from the city.

    Nov 28 – Dec 1, 2025
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Winter Wonderland Wedding

When the city slows into its quieter, cozier rhythm, winter becomes an unexpectedly beautiful moment to say I do. At Sentinel, the season’s soft glow, timeless architecture, and intimate gathering spaces create a setting that feels naturally romantic—perfect for couples looking for something a little more personal, a little more magical.

Season of Celebration

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Park, Shop and Stay with Ease

Give yourself a little more room to move through the city with ease. This limited package pairs effortless valet parking with a $100 Nordstrom gift card—perfect for seasonal wardrobe updates, thoughtful gifts, or a little self-treating between meetings.

Book holiday magic