Portland Staycation Guide

Portland, OR — Staycation Inspiration

10 Things To Do In Town

1. Washington Park + International Rose Test Garden
   • Vibe: Bloomy and romantic
   • Description: Wander rose-lined terraces, hike forested trails, and pop into the nearby Japanese Garden.
   • Special Events: Portland Rose Festival (May–June)
   • Best Time: Late spring to early summer
2. Powell’s City of Books
   • Vibe: Nerdy and iconic
   • Description: Get lost in the largest independent bookstore in the world — it takes up an entire city block.
   • Special Events: Author events, local zine fairs
   • Best Time: Year-round, especially rainy days
3. Alberta Arts District + Street Art Walk
   • Vibe: Creative and vibrant
   • Description: Browse galleries, boutique shops, and murals — plus unbeatable brunch and coffee.
   • Special Events: Last Thursday Art Walk
   • Best Time: Summer evenings
4. Portland Saturday Market + Waterfront Park
   • Vibe: Local and lively
   • Description: Shop from local artists and food vendors right on the riverfront.
   • Special Events: Holiday Market (Dec)
   • Best Time: March through December weekends
5. Forest Park Hike
   • Vibe: Urban wilderness
   • Description: One of the largest urban forests in the U.S. with over 80 miles of trails — right in the city.
   • Special Events: Trail cleanups and guided hikes
   • Best Time: Spring through fall
6. Lan Su Chinese Garden
   • Vibe: Tranquil and tucked-away
   • Description: A walled oasis downtown with tea tastings, koi ponds, and poetic paths.
   • Special Events: Chinese New Year Celebration
   • Best Time: Spring or fall
7. Ride the Aerial Tram + City Views
   • Vibe: Unique and scenic
   • Description: Catch sweeping views of the city, river, and mountains in just four minutes.
   • Special Events: None
   • Best Time: Clear afternoons
8. Food Cart Pod Crawl
   • Vibe: Tasty and low-key
   • Description: Try everything from Thai to Ethiopian to gluten-free doughnuts — no reservations required.
   • Special Events: Cart Blocks events, summer DJ nights
   • Best Time: Year-round
9. Oregon Museum of Science and Industry (OMSI)
   • Vibe: Interactive and STEM-y
   • Description: Touch science exhibits, tour a submarine, or see a planetarium show.
   • Special Events: OMSI After Dark (21+ nights)
   • Best Time: Winter or rainy weekends
10. Catch a Show at Revolution Hall or Crystal Ballroom
    • Vibe: Indie and iconic
    • Description: See local bands, touring acts, or drag bingo in historic, vibey venues.
    • Special Events: PDX Jazz Fest, MusicFestNW
    • Best Time: Year-round

10 Things To Do Within 30 Miles

1. Multnomah Falls (Edge of range but worth it!)
   • Vibe: Majestic and photogenic
   • Description: Visit Oregon’s most famous waterfall and hike to the top for panoramic gorge views.
   • Special Events: None
   • Best Time: Spring and early summer
2. Sauvie Island Beach + U-pick Farms
   • Vibe: Rural and relaxing
   • Description: Swim, sunbathe, or pick berries and pumpkins on this quiet island escape.
   • Special Events: Pumpkin Patch + Maze (Oct)
   • Best Time: Summer and fall
3. Mt. Tabor Sunset or Morning Hike
   • Vibe: Woodsy and local
   • Description: Hike an extinct volcano inside the city and catch sunrise or sunset views.
   • Special Events: Free yoga and music events
   • Best Time: Spring and fall
4. Tryon Creek State Natural Area
   • Vibe: Peaceful and quiet
   • Description: A lesser-known forest park with mossy trails, ferns, and bridges — a great solo walk spot.
   • Special Events: Wildflower walks
   • Best Time: Spring
5. Edgefield (McMenamins)
   • Vibe: Quirky and relaxed
   • Description: Explore gardens, pubs, a movie theater, and a soaking pool at this funky hotel/brewery resort.
   • Special Events: Summer concert series
   • Best Time: Summer and fall
6. Lake Oswego Farmers Market + Park
   • Vibe: Charming and clean
   • Description: Stroll this pretty suburb’s lakeside market with fresh flowers, baked goods, and local music.
   • Special Events: Summer concerts
   • Best Time: Summer weekends
7. Willamette River Kayaking or SUP
   • Vibe: Water-loving and active
   • Description: Paddle through the heart of the city or down a more peaceful nearby stretch.
   • Special Events: Paddle races and cleanups
   • Best Time: Summer
8. Milwaukie Bay Park + Food Truck Night
   • Vibe: Underrated and cute
   • Description: Chill by the water, grab bites from local vendors, and enjoy family-friendly events.
   • Special Events: Summer concerts
   • Best Time: Summer
9. Tualatin Hills Nature Park
   • Vibe: Birdwatch-y and mellow
   • Description: Explore wetlands and woodlands in the suburbs — perfect for a quiet nature break.
   • Special Events: Guided bird walks
   • Best Time: Spring and fall
10. Oaks Amusement Park + Skating Rink
    • Vibe: Retro and fun
    • Description: Ride classic carnival rides or roller skate under a disco ball.
    • Special Events: Oktoberfest, holiday skate nights
    • Best Time: Summer and holidays

10 Things To Do Within 60 Miles

1. Columbia River Gorge Scenic Drive
   • Vibe: Jaw-dropping and wild
   • Description: Waterfalls, hikes, and epic views await just east of the city — bring your camera.
   • Special Events: Wildflower season
   • Best Time: Spring through early fall
2. Hood River Wine + Kiteboarding Day Trip
   • Vibe: Windy and wonderful
   • Description: Taste wine with river views or watch kiteboarders fly across the Columbia.
   • Special Events: Harvest Fest (October)
   • Best Time: Summer and early fall
3. Willamette Valley Wine Country
   • Vibe: Cozy and classy
   • Description: Sip Pinot Noir among rolling hills and wildflowers — solo tasting rooms welcome!
   • Special Events: Memorial Day and Thanksgiving wine weekends
   • Best Time: Late spring through fall
4. Silver Falls State Park
   • Vibe: Waterfall wonderland
   • Description: Hike the Trail of Ten Falls for a waterfall-packed loop near Salem.
   • Special Events: None
   • Best Time: Spring and early summer
5. Mount Hood Adventure (Timberline or Trillium Lake)
   • Vibe: Alpine and refreshing
   • Description: Go for snow sports in winter or hikes and lake lounging in summer.
   • Special Events: Summer ski season
   • Best Time: Summer and winter
6. Astoria or Cannon Beach (edge of 60–90 mi but worth a mention!)
   • Vibe: Coastal and cinematic
   • Description: Day trip to Oregon’s iconic coastline with tide pools, dramatic views, and Goonies nostalgia.
   • Special Events: Storm Watching Season (winter), Sandcastle Contest
   • Best Time: Summer or early fall
7. Sauvie Island Wildlife Refuge
   • Vibe: Quiet and meditative
   • Description: Spot herons, deer, and wildflowers on peaceful walking loops.
   • Special Events: Birdwatching festivals
   • Best Time: Fall and spring
8. Molalla River Recreation Area
   • Vibe: Woodsy and wild
   • Description: Hike, swim, or picnic by emerald-green riverbanks with mountain views.
   • Special Events: None
   • Best Time: Summer
9. Enchanted Forest (Salem)
   • Vibe: Campy and fun
   • Description: Retro fairy tale theme park that’s weird, wonderful, and very Oregon.
   • Special Events: Seasonal fests
   • Best Time: Summer
10. Brewery Loop to Hood River or Tillamook
    • Vibe: Hoppy and road trip-ready
    • Description: Make a day of brewery stops and stunning drives — perfect for chill weekend wandering.
    • Special Events: Oregon Beer Week (June)
    • Best Time: Fall or summer