If You’re Visiting Oregon, Here’s Exactly Where You Should Go

Written By Mimi Albano

Planning a trip to Oregon? Here’s my official Oregon Bucket List plus a few itineraries I recommend using to fit as much in as possible! First let’s go over the 7 regions of Oregon and what to expect.

  • 🏖️ 🌊 🪸 🐚 🐳 🐦 🚤 🏄‍♂️ 🥾 🏝️

    Beachcombing & tidepools
    Scenic drives on Highway 101
    Whale watching & fishing
    Hiking coastal trails & dunes

  • 🍷 🚴‍♀️ 🌾 🥕 🧀 🥂 🛶 🏡 🥗 🌳

    Wine tasting (Pinot Noir country)
    Cycling through vineyards & farms
    Farmers markets & local dining
    Exploring historic small towns

  • 🍜 🍺 📚 🌹 🏙️ 🖼️ 🚲 🎶 🌉 🌲

    Food carts & breweries
    Garden hopping (Japanese, Rose gardens)
    Urban hiking & biking trails
    Riverfront festivals & markets

  • ⛰️ ❄️ 🎿 🥾 🌲 🍎 🍐 🌊 🍷 🚗

    Waterfalls & scenic overlooks
    Skiing & snowboarding on Mount Hood
    Hiking alpine meadows, forests & canyons
    Windsurfing, kiteboarding & fishing on the Columbia
    Fruit orchards & farm stands on the Hood River Fruit Loop
    Wineries, cider houses & breweries

  • 🧗‍♀️ 🚣‍♂️ 🔭 🚵‍♀️ 🌋 🏜️ 🌌 🐟 🥾 🏕️

    Rock climbing or hiking at Smith Rock
    Rafting or kayaking the Deschutes
    Stargazing in the high desert
    Mountain biking & lava field hikes

  • 🌊 🛶 🎭 🍇 🚤 🌲 🥾 ⛺ 🍷 🔥

    Exploring Crater Lake
    River rafting & jet boating
    Wine tasting & farm tours
    Attending theater & outdoor performances

  • 🐎 🤠 🏞️ ✨ 🐏 🛻 🏹 🥾 🛶 ♨️

    Backpacking in Wallowas & Hells Canyon
    Stargazing at dark sky preserves
    Rodeos & cowboy culture
    Hot springs soaking & scenic drives

Next, decide on your priorities.

I’ll give you a few to inspire you: mountains, waterfalls, coast, rivers, lakes, recreation, relaxation, hiking, biking, wildlife… Oregon has it all and unless you have 6+ days you’ll have to make scarifies.

Haystack Rock at Cannon Beach

My Absolute Bucket List Must Sees

There’s a few must see’s if you’re visiting Oregon that you simply cannot skip. Those are:

1. Mount Hood

Not only does this mountain have longest ski season in North America it’s also an active volcano and one of the most gorgeous mountains in the US. Mount Hood National Forest and the nearby area offers tons of accommodations options from dispersed camping, established campgrounds, airbnbs, boutique stays. It’s always a good time to visit, seriously every season is gorgeous. If you’re not a skier, visit in the summer to enjoy stunning views of this beauty across Trillium or Lost Lake or at many of the hiking trails such as High Prairie Trail. If you are a skier, Hood is home to 3 major ski resorts plus free access to 1 uphill route per day since they’re all on national forest land. Timberline offers blues and greens as well as incredible terrain parks and large jumps. This is an amazing place to learn to ski or snowboard or just enjoy winter from the cozy historic Timberline Lodge. If you like winter but not skiing, try a snowmobile ride or cross country ski tour through Mount Hood Outfitters.

Trillium Lake within Mount Hood National Forest

2. Cannon Beach

Probably the most famous stretch of sand in Oregon — and for good reason. Haystack Rock rises dramatically from the shoreline, and at low tide you’ll find tidepools teeming with colorful starfish and anemones. The town itself is full of cozy cafés, local shops, and art galleries that make it perfect for a slow coastal day. Stay for sunset — the golden light against Haystack is unforgettable. Two surreal experiences here feel straight out of a movie: building a bonfire on the sand as the waves crash in the background, and catching sight of the wild elk that roam nearby. Both make Cannon Beach feel more like a film set than real life.

Haystack Rock on Cannon Beach

3. Samuel H. Boardman Scenic Corridor

Down on the southern coast, this 12-mile stretch is Oregon’s coastline at its most dramatic. Rugged cliffs, natural bridges, secret coves, and sea stacks rising out of turquoise water make it feel almost unreal. This is straight out of Pinterest. You can pull off at different viewpoints for quick stops or hike the Oregon Coast Trail to see arches and secluded beaches. It’s the kind of place that reminds you how wild and cinematic Oregon really is.

Secret Beach in the Samuel H Boardman Scenic Corridor

Hikes

If hiking isn’t usually your thing, trust me give it a try these trails are different — they’re experiences you’ll remember forever. Here are the bucket list hikes I’d add if you’ve got the time.

Wahclella Falls — 1.9 miles easy

Abiqua Falls Trail — 0.7 miles easy

Misery Ridge at Smith Rock State Park — 2.6 miles medium difficulty

At this point you’re probably wondering how on earth to fit all of this into one trip. Don’t worry — I’ve mapped out sample itineraries so you can balance mountains, waterfalls, hot springs, and coastlines without burning out. Whether you’ve got a long weekend or nearly two weeks, here’s how I’d plan it.

  • Day 1 — Portland

    • Start in Portland

    • Walk/hike at Forest Park (year-round)

    • Cool off cliff-jumping at High Rocks Park (summer).

    • Two other quick walk/hike urban parks include Mount Tabor and Rocky Butte.

    • Dinner at Hapa PDX (ramen + whiskey) or Lovely’s Fifty Fifty (wood-fired pizza). Explore more Portland food.

    • Overnight in Portland.

    Day 2 — Mount Hood

    • Head east into the Columbia River Gorge — hike Dry Creek Falls (spring–fall best).

    • Drive up to Mount Hood to Mirror Lake Trail (seasonal) or Umbrella Falls (late spring–early fall), and High Prairie Trail (summer wildflowers, fall colors).

    • Grab a post-hike beer or bite at Charlie’s Mountain View in Government Camp.

    • Overnight in Portland or at Mount Hood.

    Day 3 — Coast

    • Drive out to the coast — start at Cannon Beach and head towards Cape Kiwanda/McPhillips Beach (you can drive onto the sand here, summer/fall best).

    • Dinner at Pelican Brewing.

    • Overnight in in Pacific City or Portland.

  • Day 1 — Portland

    • Arrive/begin in Portland

    • Walk/hike at Forest Park or Mount Tabor for city views

    • Dinner at Lechon (South American) or Bamboo Sushi. Explore more Portland food.

    • Overnight Portland.

    Day 2 — Columbia River Gorge + Mount Hood

    • Morning Gorge hike(s): Visit Multnomah Falls (no hike need to see the falls, hike to the bridge 1.1 miles), other falls include Latourell Falls (short + dramatic) or Wahclella Falls (lush 2-mile loop).

    • Drive to Mount Hood through Hood River.

    • Hikes at Hood for Tamanawas Falls (summer–fall), Mirror Lake Trail, or Timberline Lodge (summer hiking, lodge yearound).

    • Dinner in Government Camp at Charlie’s Mountain View or Ram’s Head.

    • Overnight at Mount Hood or Bend.

    Day 3 — Bend + Cascade Lakes Scenic Byway

    • Start the day by driving to or waking up in Bend.

    • Head west on the Cascade Lakes Scenic Byway to Devil’s Lake + Elk Lake perfect for paddle boarding in summer or fall, or skiing at Mount Bachelor in winter. Hike Tumalo Falls(spring–fall).

    • Dinner in Bend at Bos Taurus (steak) or Ariana (upscale). Explore Bend food.

    • Overnight Bend.

    Day 4 — Crater Lake

    • Full day at Crater Lake National Park → hike Garfield Peak or the Rim Trail (summer–fall).

    • Overnight accommodations or camping near Crater Lake or drive back to Bend.

    Day 5 — Terwilliger Hot Springs + Return North

    • On your way north to Portland plan for a soak at Terwilliger Hot Springs (paid, year-round).

    • Optional stop in Willamette Valley for wine tasting.

    • Back in Portland, dinner at Afuri Izakaya (ramen) or cocktails at Scotch Lodge. Explore Portland food.

    • Depart or overnight in Portland.

  • Day 1 — Portland

    • Urban hikes: Mount Tabor + Forest Park (year-round).

    • Summer: fruit picking on Sauvie Island or sunbathing at the beach.

    • Sunset views at Rocky Butte Park.

    • Dinner: Eem (Thai BBQ), Lovely’s Fifty Fifty (wood-fired pizza), or Bamboo Sushi.

    • Overnight: Portland.

    Day 2 — Columbia River Gorge

    • Breakfast in Portland at Jam.

    • Hike: Multnomah Falls + Wahkeena Falls Loop or Latourell Falls.

    • Dinner in Hood River: pFriem Family Brewers or Celilo Restaurant & Bar.

    • Overnight: Hood River.

    Day 3 — Mount Hood

    • Breakfast at Timberline Lodge or in Government Camp

    • Trails: Tamanawas Falls, Mirror Lake, or sections of the Timberline Trail

    • Dinner at Charlie’s Mountain View in Government Camp

    • Overnight: Mount Hood

    Day 4 — Drive to Bend

    • Breakfast at Sisters Coffee Company.

    • Summer: float the river

    • Attend a show at Hayden Homes Amphitheater (by ticket or by paddleboard)

    • Afternoon walk along the riverfront

    • Dinner at Bos Taurus

    • Overnight: Bend

    Day 5 — Bend Nature + Cascade Lakes Scenic Byway

    • Paddle at Elk Lake or Devil’s Lake (summer/ fall)

    • Other hikes: Tumalo Falls

    • For a longer alpine hike, try No Name Lake or Broken Top Crater Trailhead — or just enjoy the scenic drive

    • Dinner at Ariana

    • Overnight: camping along the Byway or back in Bend

    Day 6 — Painted Hills + Smith Rock State Park

    • Optional early morning at the Painted Hills (1 hr 50 min from Bend)

    • On the way back, stop at Smith Rock State Park (30 min from Bend) for the Misery Ridge Trail

    • Overnight in Bend or head toward Crater Lake

    Day 7 — Crater Lake

    • Drive to or wake up at Crater Lake

    • Options: Rim Drive (summer), Garfield Peak Hike, or the Wizard Island Boat Tour (summer)

    • Overnight near Crater Lake or toward Umpqua National Forest

    Day 8 — Hot Springs + Head to Coast

    • Visit Umpqua Hot Springs early in the morning to beat the crowds and stay on schedule

    • Drive to Brookings

    • Sunset hike at Natural Bridges

    • Overnight: Brookings

    Day 9 — Brookings → Coos Bay

    • Wake up in Brookings

    • Hike the Secret Beach Trail or Arch Rock State Park

    • Drive north, have lunch, and explore Bandon Beach

    • Overnight near Coos Bay

    Day 10 — Drive on Sand + Central Coast

    • Rent single, double, or quad dune buggies to explore the Oregon Dunes National Recreation Area

    • Drive north optional stops: Sea Lion Caves, Tokatee Klootchman State Natural Site, Yaquina Head Lighthouse, Cape Perpetua, and Devils Punch Bowl

    • If you want to drive your own car on the sand → head to Cape Kiwanda State Natural Area/McPhillips Beach.

    • Dinner at Pelican Brewing

    • Overnight: Pacific City.

    • Lodging recommendation: Headlands Coastal Lodge & Spa

    Day 11 — Oregon Coast

    • Morning: Tunnel Beach

    • Drive to Cannon Beach → tidepools + Haystack Rock

    • Dinner at The Schooner Restaurant & Lounge

    • Sunset at Ecola State Park

    • Overnight: north of Cannon Beach

    Day 12 — Beach + Astoria

    • Morning: drive on the beach in Gearhart

    • Visit Del Rey Beach

    • Dinner at Fort George Brewery

    • Overnight: Astoria or Portland

🌟The Ultimate Oregon Bucket List🌟

Portland + Surrounds

  • Mount Tabor

    • tabor dance every wednesday at 6 PM during summer

  • Forest Park

  • Sauvie Island

    • Columbia Farms U-Pick (berry picking summer)

    • Topaz Farms (fall, kids family fun)

    • Collins Beach (nude)

  • Rocky Butte Park (sunset)

  • High Rocks Park (summer)

  • Portland Dining

    • Friendship Kitchen

    • Kate’s Ice Cream

    • Canard

    • Bamboo Sushi

    • Albina Press

    • Coava Coffee

    • Keeper Coffee

  • Abiqua Falls

Columbia River Gorge

  • Multnomah Falls

  • Oneonta Trailhead

  • Horsetail Falls Trailhead

  • Munra Falls

  • Elowah Falls

  • Wahkeena Falls Loop

  • Latourell Falls

  • Dry Creek Falls

  • Eagle Creek Trailhead (summer swimming at Punch Bowl Falls)

  • Wahclella Falls Trail

  • Dog Mountain Trail (wa side, summer wildflowers)

Mount Hood

Willamette National Forest

  • Terwilliger Hot Springs

  • Belknap Hot Springs, Lodge and Gardens

  • Bigelow Hot Springs (depending on river level)

  • Tamolitch Falls (Blue Pool)

  • Sahalie Falls

  • Proxy Falls

Central Oregon / Bend

Crater Lake + Umpqua

  • Crater Lake

    • Rim Drive (summer)

    • Garfield Peak Trail

    • Wizard Island Boat Tour (summer)

  • Umpqua Hot Springs

Southern Coast

  • Samuel H Boardman Scenic Corridor

  • Arch Rock State Park

Central Coast

Northern Coast

  • Tunnel Beach

  • Cannon Beach (tidepools + Haystack Rock)

  • Ecola State Park (sunset)

  • Gearhart Beach (drive on sand)

  • Del Rey Beach

  • Astoria

    • Fort George Brewery

Mimi Albano https://mimithecoolcat.com
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Boutique Farm Stay at Mount Hood: Highland Farms