Two Ways to Explore Oregon: Travel Itineraries for City and Nature Lovers

From the vibrant arts scene and lively nightlife of downtown Portland to the mountain peaks and winding trails of Sunriver, Oregon offers escapes for every type of traveler. Here's how to plan the perfect Oregon getaway, depending on your travel style.

Oregon Itinerary #1: The City Escape

A Weekend in Downtown Portland

Discover cozy coffee shops, lively craft breweries, scenic walking trails, and a thriving arts scene in downtown Portland. With the tagline, "Keep Portland Weird," this city is renowned for its creative energy and laid-back spirit. 

Where to stay: RiverPlace Hotel

Day 1: Check In and Explore the Waterfront

Once you arrive, drop your bags at the tranquil RiverPlace Hotel, a riverfront oasis in the heart of downtown Portland. From there, you're steps from the scenic Willamette River, known for its picturesque walking and biking paths, riverside dining, and public beach access. Finish the evening with a sunset dinner cruise or waterfront cocktails. 

• Wander through Tom McCall Waterfront Park
• Book a sunset dinner cruise down the Willamette River
• Enjoy cocktails with a view at RiverPlace Kitchen + Bar

Day 2: Discover Portland's Creative Side

No Portland travel itinerary is complete without a peek into the city's iconic arts scene. After breakfast at the hotel, make your way to the trendy Pearl District, which blends historic warehouses with unique storefronts. Stoll through artisan markets, local galleries, upscale boutiques, and indie bookstores, where you'll find unique souvenirs that capture the creative side of the city. 

• Discover gems at the Portland Saturday Market
• Stroll through art galleries in the Pearl District
• Explore Powell’s City of Books, the world's largest independent bookstore

Day 3: Get Outdoors in the City

Despite being Oregon's largest city, Portland has plenty of opportunities to enjoy the great outdoors. Experience Pacific Northwest charm in Forest Park, one of America's largest urban forests, or wander through the nearby Washington Park, home to some of the city's most iconic attractions. End the day at a local brewery or coffee shop to experience the the flavors that make Portland a must-visit travel destination. 

• Explore over 8 miles of trails in Forest Park
• Escape to the serene Portland Japanese Garden
• Unwind at Widmer Brothers Brewing or Stumptown Coffee Roasters

Oregon Itinerary #2: The Nature Retreat

A Mountain Escape in Central Oregon

Open skies and alpine air await in Central Oregon, where adventure is always in season. Unplug on winding walking trails, tee off beside flowing rivers, and simply savor the stunning scenery from your private balcony. 

Where to stay: Sunriver Resort

Day 1: Check In and Unwind in Nature

Make nature your destination at Sunriver Resort, a wilderness retreat located 15 minutes from Bend, Oregon. Spread over 3,300 acres of stunning Pacific Northwest landscape, it's your gateway to picturesque hikes, outdoor adventures, and unobstructed mountain views. Start your trip by exploring one of the scenic onsite trails before savoring fireside s'mores and stargazing. 

• Stroll or bike past flowing rivers, towering pine trees, and sunlit horse pastures
• Visit the Oregon Observatory to experience the state's first designated Dark Sky Place
• Enjoy s’mores at the lakeside fire pits 

Day 2: Adventure Through Central Oregon

Fuel up for a day of adventure with breakfast and mountain views at the Lodge Kitchen. From there, head to the marina to explore Central Oregon by water, or book a guided trail ride at the premier Sunriver Stables. Just beyond the resort, discover the natural wonders of the region, from volcanic lava tube caves to natural hot springs. 

• Kayak, paddleboard, or canoe down the tranquil Deschutes River
• Go horseback riding through scenic trails
• Soak in the Paulina Lake Hot Springs with scenic mountain views

Day 3: Slow Down and Savor the Landscape

End your Oregon getaway by embracing the region's slower rhythm. Sunriver offers endless ways to relax in nature, from panoramic pools and lakeside dining to wildlife tours and outdoor sports. For golf lovers, don't miss the resort's four award-winning golf courses, set across 600 acres of scenic woodlands and preserved wetlands. 

• Tee off on championship golf courses
• Take a dip in The Cove's indoor and outdoor pools and jetted spas
• Get competitive with a game of pickleball

• What are the best places to visit in Oregon for a weekend getaway?

  Oregon offers a variety of weekend destinations depending on your travel style. Portland is ideal for travelers seeking vibrant arts, culture, dining, and nightlife, while Central Oregon is perfect for outdoor adventures, mountain views, golfing, hiking, and relaxing in nature.

• What is the best time of year to visit Oregon?

  Oregon is a year-round destination. Spring and summer offer great weather for hiking, biking, kayaking, and enjoying live music and arts festivals, while fall brings colorful foliage and cozy nature escapes. Winter is ideal for alpine adventures like skiing, snowboarding, ice skating, or exploring the cozy coffee shops of downtown Portland. 

• What are the best things to do in Portland, Oregon?

  Some of the best things to do in Portland include exploring the city's scenic riverfront, browsing local shops and galleries in the Pearl District, visiting the iconic Powell's City of Books, and discovering handmade goods at the Portland Saturday Market. Outdoor enthusiasts can hike through Forest Park, one of the nation's largest urban forests, or stroll through the tranquil Portland Japanese Garden. No visit is complete without experiencing Portland's renowned coffee culture, craft breweries, and vibrant food scene.

• What are the best things to do in Central Oregon?

  Popular activities in Central Oregon include kayaking the Deschutes River, exploring miles of walking and biking trails, horseback riding, skiing at Mt. Bachelor, golfing, and enjoying lakeside evenings under the stars.

• Where should I stay in downtown Portland?

  RiverPlace Hotel is an ideal base for exploring downtown Portland, Oregon. Located along the Willamette River, the hotel provides easy access to waterfront trails, local restaurants, the Portland Saturday Market, and the city's most popular neighborhoods and attractions.

• Where should I stay in Central Oregon?

  Sunriver Resort offers unrivaled access to the best of Central Oregon, with onsite hiking, biking, kayaking, golf, and scenic mountain landscapes, all just 15 minutes from Bend.