Trip Planners

1859’s Trip Planners are your source for exploring the great state of Oregon. Whether you are a local looking for a weekend family getaway or just visiting, each article is an insider’s guide to the best trips in Oregon.

Mother’s Day begins in Central Oregon at the Old Mill District and shopping at upscale shops.

Mother’s Day in the High Desert

The luxury resorts of Central Oregon are a mom’s best friend written by James Sinks Remember when mom used to take you to the playground? This Mother’s Day—or any day, really—you can return the favor. And when it comes to choosing the right playground, few places on the planet tout more satisfying options than Central Oregon, where a seemingly endless menu of recreation, restaurant, and relaxation options await moms of every age, interest and mobility. Here, happy trails are everywhere, from ski trails to bike trails to river trails to hiking trails, and you can even hop onto the Bend Ale Trail and sample a smorgasbord of breweries. If mom likes clubs as much as diamonds, the area boasts two golf courses ranked highly as girls’ trip destinations by Golf Digest. And if she needs to relax, unroll a yoga mat or unwind at any of dozens of upscale spas…

Named after Bandon, Ireland, this coastal gem is known for world-class golf at Bandon Dunes Resort, a picturesque, wild beach and fresh seafood at casual and upscale restaurants.

Southern Oregon Coast

The better season for the hauntingly beautiful Oregon Coast? written by Isabella Golasi The Oregon Coast’s other season is the dead of winter. Yes, it may rain a bit here in the late winter months, but with a little planning for weather, you’ll find mild maritime temperatures in the midst of the most hauntingly beautiful scenery Oregon has to offer. All without the summer crowds. The Southern Oregon Coast from Coos Bay south to the California border is home to the towns of Coos Bay, Bandon, Port Orford and Gold Beach among others. They all have three things in common—a direct connection with the Pacific Ocean, remarkable beauty and unexpectedly exceptional restaurants that enhance your coastal experience. Over the next three days, you’ll walk through these places as if in a misty dreamscape. Day 1 Coos Bay Working your way down the Southern Oregon Coast, Coos Bay was Oregon’s largest…

Milton-Freewater’s cobblestone soil, naturally enhanced by Walla Walla River deposits, yields distinctive wines.

A Destination AVA—Served on the Rocks

Savor, hike and explore Milton-Freewater’s valleys in wine-tastings Written by Angela Ashberry For most wine aficionados, Eastern Oregon’s Milton-Freewater doesn’t register as a wine tasting destination. Its location puts it far from anywhere convenient and 300 miles from the Willamette Valley. Its climate seems more suited to peppers and corn than wine grapes. Its hyphenated name sounds like a corporate law firm. Yet this small town with a population of 7,050 that’s 5 miles south of the Washington state line and 10 miles south of Walla Walla is emerging as a destination for those who are as adventurous with their travel as they are curious about a wine’s terroir. Welcome to The Rocks! Day 1 HEARTY HIKING • WINE TASTING Start your day with an ambitious hike about 37 miles east of Milton Freewater. Head to the South Fork Walla Walla Trailhead 15 miles southeast of town. The Table Springs/Bear…

Battle Rock Beach

Trip Planner: Port Orford Coastal Nirvana

The Pacific beckons: extreme cliffs, ocean paddling, scenic pedaling and rewarding comforts Named in 1792 after George, Earl of Orford, Port Orford had been a quiet Pacific coastal area that was home to the Tututni tribe of the Lower Rogue Athabascan tribes in what would become southwestern Oregon.  As part of a well-known series of events, European explorers encountered the tribe in the eighteenth century and wiped out the majority of Native American populations with small pox and measles. Not long after, white settlers came to town on the Oregon Trail and made land claims under the premise of Manifest Destiny.  Another claim to new statehood came in 1941 from Port Orford mayor Gilbert Gable, a tireless attention seeker who complained of the lack and quality of roads and threatened to secede from Oregon to join California, founding the elusive State of Jefferson movement. The small fishing town with the…

Ashland, Oregon

Ashland Wine Tasting: Shakespeare and chardonnay, a fine pairing in Southern Oregon

written by Kevin Max vines • wine • tapas There is no better place in America to combine bold wines and the boisterous Bard than in Ashland. So far south in Oregon, Ashland feels as much northern California as it does Southern Oregon. Climate doesn’t strictly respect state borders, but the climate for wine growing in Southern Oregon does have its boundaries. There are warmer Spanish tempranillos and cooler pinots, with syrahs and chardonnays in between. The stages of the Oregon Shakespeare Festival bud and bloom with wit, sarcasm, churl and charm. Spring and summer in the Southern Oregon tasting rooms and vineyards bring a full-bodied intensity with a note of drama and an air of openness. For visitors who have never been to Ashland, the first thing you’ll notice is the beautiful hills and rolling terrain surrounding it to the west, south and east. It’s on the faces of…

Trip Planner—The Dalles

Trip Planner—The Dalles. Nestled at the eastern end of the Columbia River Gorge National Scenic Area, The Dalles sits in a region rich in history, affords breathtaking scenery and is the perfect place for epic outdoor adventures.

Union County Oregon

Trip Planner — Union County

Union County is a mix of rugged beauty, farmland hospitality and a few surprises written by Catie Joyce-Bulay Of Oregon’s thirty-six counties, Union may not be the sexiest—you won’t find any sweeping beaches, hipsters or third-wave coffee, and the only haystacks are made of actual hay. What you will find is a nature lover’s playground spanning a diverse landscape, from high desert shrub steppe to rugged mountains, where three national forests converge over three mountain ranges, lush farmlands sprawl across valley floors and genuine local hospitality echoes the pioneering spirit of the Oregon Trail. DAY 1 MOUNTAINS • BREWS • BOUTIQUE HOTEL Oregonians are probably most familiar with I-84 along the Columbia River Gorge, but it’s no less scenic once it parts ways with the river. The stretch crossing into Union County is one of my favorite drives and a perfect example of how incredibly beautiful overlooked Eastern Oregon can…

Union County, Oregon

Trip Planner: Union County

Union County is a mix of rugged beauty, farmland hospitality and a few surprises written by Catie Joyce-Bulay OF OREGON’S THIRTY-SIX COUNTIES, Union may not be the sexiest—you won’t find any sweeping beaches, hipsters or third-wave coffee, and the only haystacks are made of actual hay. What you will find is a nature lover’s playground spanning a diverse landscape, from high desert shrub steppe to rugged mountains, where three national forests converge over three mountain ranges, lush farmlands sprawl across valley floors and genuine local hospitality echoes the pioneering spirit of the Oregon Trail. DAY 1 MOUNTAINS • BREWS • BOUTIQUE HOTEL Oregonians are probably most familiar with I-84 along the Columbia River Gorge, but it’s no less scenic once it parts ways with the river. The stretch crossing into Union County is one of my favorite drives and a perfect example of how incredibly beautiful overlooked Eastern Oregon can…

Trip Planner — Wine Country of Newberg and Chehalem

written by Sheila Miller Seems like these days, the world has discovered Oregon’s Willamette Valley and its wine, but the epicenter always seems to be McMinnville. There are so many other little outposts around the region. We decided to focus our tour in Newberg and Chehalem and see what the rest of the world might be missing. DAY 1 COFFEE • DOWNTOWN • WINE TASTING Most tasting rooms open at 11 a.m., so that’s when it’s apparently OK to start drinking wine. Get acquainted with the town of Newberg by enjoying wine right in the downtown core—you can get to the views tomorrow. Start in an industrial district a few minutes from downtown Newberg, and since it’s early, you can grab a coffee from Caravan Coffee’s roastery. The shop is a longtime favorite in Newberg, ethically sourcing its beans and making a great cup of coffee. You can tour the…