June transforms Bend into a cycling paradise with dry singletrack, 74°F highs, and 15+ hours of daylight. From mountain biking at IMBA Gold-level Phil’s Trailhead…

November in Oregon brings a special kind of calm – misty mornings, golden light, and that irresistible pull toward cozy escapes. Here at Meredith Lodging, we love this time of year. On the Oregon Coast, the ocean puts on a spectacular show of waves and weather, perfect for storm watching from the warmth of your beachfront rental. Meanwhile, Central Oregon begins to sparkle with early snow and mountain magic – ideal for those who love crisp hikes, craft brews, and fireside nights.
Dream of peaceful beach mornings or fireside evenings in the mountains – November is the perfect time to slow down, savor the season, and experience the best of Oregon with Meredith Lodging.

A beloved coastal tradition returns as Pacific City’s Dory Fleet transforms into a festive Halloween wonderland on the beach. Families can dress up and visit boat-to-boat for candy, treats, and coastal cheer as the iconic fleet lines up along the shoreline. Enjoy live music, hot cocoa, and a friendly, small-town vibe surrounded by ocean views. Kids and parents alike love this charming event that brings together the heart of the community. Stick around afterward to explore local shops or catch a sunset over Haystack Rock.

The spirit of the Wild West comes alive at the Clash of the Cowboys Roughstock Rodeo, held at the Clatsop County Fair & Expo’s Indoor Arena. Watch top riders and bucking broncos compete in thrilling rodeo events that’ll keep you on the edge of your seat. Between events, enjoy hearty local food, craft beer, and family-friendly fun. This is small-town Oregon at its boldest -full of grit, laughter, and cowboy heart. Pair it with a weekend stay in nearby Seaside or Gearhart for a true Northwest adventure.

Every fall, the King Tides return to the Oregon Coast, revealing the incredible power and beauty of the Pacific Ocean. In Pacific City, these dramatic high tides draw photographers, nature lovers, and curious visitors eager to witness the waves at their most impressive. It’s a breathtaking reminder of the ocean’s strength and ever-changing rhythm — best enjoyed from safe viewing spots or the comfort of a cozy coastal stay.

For nearly four decades, Cannon Beach has welcomed artists and art lovers to celebrate creativity during the Stormy Weather Arts Festival. This three-day event features gallery showcases, live music, artist demonstrations, and hands-on workshops. Watch painters at work, meet sculptors, and explore one of America’s top 100 art towns. Even when the skies are gray, the energy in Cannon Beach shines bright. End your day with a fireside dinner and a cozy stay in one of our ocean-view homes.

Sip, stroll, and savor the flavors of Oregon wine at the Seaside Downtown Fall Wine Walk. More than a dozen local wineries set up tasting stations inside participating businesses, creating a festive, walkable experience through the heart of town. Pair your pours with small bites and browse unique boutiques along the way. This event is a favorite among locals and visitors who love to unwind by the sea with a good glass of Pinot. End the evening with a sunset walk on the promenade or dinner at one of Seaside’s cozy eateries.

One of Oregon’s most dazzling traditions, the Holiday Lights at Shore Acres State Park transform the gardens into a glowing wonderland. Over 300,000 lights illuminate the coastal landscape, from twinkling sculptures to themed displays reflected in the pond. Sip cider and listen to carolers as you wander the trails beneath towering evergreens. This event captures the magic of the season and is a must-see for families and couples alike. Bundle up and make an evening of it with a stay in nearby Charleston or Coos Bay.

Brookings’ Azalea Park sparkles each winter with one of the coast’s best holiday light displays -Nature’s Coastal Holiday. Thousands of shimmering lights, glowing tunnels, and festive scenes create a storybook atmosphere beneath the coastal evergreens. Enjoy cocoa, cookies, and a visit from Santa as you explore the illuminated pathways. Locals and visitors alike return year after year to celebrate this heartwarming tradition. It’s the perfect way to end a day of beachcombing or hiking along the Samuel H. Boardman Scenic Corridor.

All aboard the Holiday Express for a nostalgic train ride along the Willamette River! Departing from the Oregon Rail Heritage Center, this festive journey features vintage steam locomotives decked out in lights and garlands. Passengers enjoy hot cocoa, holiday tunes, and visits from Santa while gliding through Portland’s scenic riverside. It’s a magical kickoff to the holiday season that delights train enthusiasts and families alike. Make it a weekend getaway and explore Portland’s markets, lights, and cozy dining spots.

Portland’s Annual Tree Lighting Ceremony marks the official start of the city’s holiday season, drawing locals and visitors alike to downtown’s Pioneer Courthouse Square. Led by Thomas Lauderdale of Pink Martini, the event features live performances from Portland’s finest musicians, choirs, and community singers in a heartwarming sing-along. At dusk, Santa Claus “flips the switch,” illuminating nearly 10,000 twinkling lights that sparkle across the city’s grand holiday tree. Bundle up, sip on hot cocoa, and join the crowd as Portland lights up the night in true holiday spirit.

Step into the chilling world of “The Haunting of Hill House,” a psychological thriller brought to life on stage by the talented team at Cascades Theatrical Company. This gripping production explores fear, memory, and the human mind in a hauntingly beautiful way. The intimate theater setting amplifies every eerie sound and flicker of shadow. Perfect for those who crave one last brush with spooky season before winter sets in. Pair your evening with a pre-show dinner in downtown Bend for a complete night out.

It’s time to do the “Time Warp” again! The Rocky Horror Show returns to Bend’s historic Tower Theatre for a night of outrageous fun, music, and audience participation. This cult classic brings together locals and visitors in costumes, laughter, and endless energy. Expect dazzling performances, rock ’n’ roll anthems, and a festive crowd ready to celebrate. Make it a full Bend weekend by exploring craft breweries and staying warm in one of our cozy vacation homes nearby.

Honor the heroes who’ve served at Bend’s beloved Veterans Day Parade, a Central Oregon tradition. The streets fill with marching bands, vintage vehicles, and proud community members waving flags in support. It’s a family-friendly, heartfelt event that captures Bend’s strong community spirit. After the parade, explore local cafés or take a crisp walk along the Deschutes River Trail. A meaningful day to celebrate service and unity in the heart of Oregon.

Get your holiday shopping started early at the Redmond Holiday Food & Gift Festival! Browse hundreds of booths filled with handmade crafts, gourmet treats, and festive décor. Sample local wines, chocolates, and sauces while chatting with artisans and small business owners. With live music, giveaways, and plenty of holiday cheer, it’s the perfect weekend outing. Make it even merrier by staying nearby in a cozy Redmond or Sisters rental.

The holiday season officially begins with Sunriver’s Grand Illumination – a magical evening of lights, music, and fireworks. Families gather for the tree lighting ceremony, Santa’s arrival, and festive fun across the resort. Enjoy hot cocoa, carriage rides, local food vendors, and live entertainment beneath the starry Central Oregon sky. It’s a memory-making event that captures the wonder of winter in the mountains. Don’t miss the fireworks finale that lights up the night.

The Bend Pops Orchestra brings seasonal magic to life with its annual Fall Concert. Enjoy a mix of holiday classics, upbeat favorites, and surprises performed by talented local musicians. Families can indulge in home-baked treats during intermission while soaking in the festive spirit. It’s the perfect way to ease from autumn into winter with music and community connection. A warm, joyful evening that reflects Bend’s artistic heart.

Kick off the holiday season at Redmond’s Holiday Village Market, where local artisans and food vendors fill the park with color and cheer. Browse handmade gifts, enjoy seasonal snacks, and sip cider as carolers spread joy throughout the day. Each weekend features new vendors and flavors, so every visit feels fresh and festive. It’s a perfect way to shop local and experience Redmond’s holiday magic. Pair your visit with a cozy stay nearby to keep the spirit going all weekend long.

Grab your skis and snowboards – winter adventure returns to Mt. Bachelor! Depending on conditions, the mountain opens for the 2025–26 season with fresh powder and excitement in the air. Locals and visitors gather to celebrate the first runs, hot cocoa in hand, surrounded by snow-dusted peaks. Whether you’re carving the slopes or enjoying the mountain views, it’s an unforgettable kickoff to the snowy season. Stay close by in Bend or Sunriver for easy mountain access and cozy après-ski relaxation.
From oceanfront homes in Newport and Cannon Beach to riverside cabins in Sisters and Sunriver, Meredith Lodging has your perfect November escape. Enjoy long beach walks followed by clam chowder by the fire, or crisp hikes among golden larches and early snow flurries in the Cascades. Plan your Thanksgiving getaway early – many of our homes feature gourmet kitchens, fireplaces, and hot tubs ideal for Thanksgiving feasts and family movie nights.
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