14-Day Oregon Adventure and Foodie Itinerary

Day 1: Explore Portland

Portland, Oregon on July 8, 2025

9:00AM

Breakfast at Blue Star Donuts

Begin your Portland adventure with a delicious treat at Blue Star Donuts, known for their gourmet flavors.
Head to the shop located in the Buckman neighborhood.
USD 10, 1 hour

10:30AM

Visit Washington Park

Stroll through the sprawling grounds of Washington Park, featuring lush gardens and scenic views of downtown Portland.
Drive about 15 minutes to Washington Park.
USD 5 parking, 2 hours

1:00PM

Lunch at Pine State Biscuits

Indulge in hearty Southern-style biscuits and gravy at Pine State Biscuits.
Located around 10 minutes drive from Washington Park.
USD 15, 1 hour

2:30PM

Explore the Portland Art Museum

Discover a fantastic collection of art spanning centuries in Oregon's largest art museum.
Drive 10 minutes to the museum downtown.
USD 20, 2 hours

5:00PM

Dinner at Le Pigeon

Enjoy a unique dining experience at the renowned Le Pigeon, focusing on French-inspired American cuisine.
Located conveniently in the East Burnside area.
USD 50, 2 hours
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Day 2: Portland to Columbia River Gorge

Vancouver, Washington on July 9, 2025

8:00AM

Breakfast at Tasty n Alder

Savor a delicious brunch featuring locally sourced ingredients at Tasty n Alder.
Hop into your car and drive to South Park Blocks, just 10 minutes away.
USD 20, 1 hour

9:30AM

Drive to Columbia River Gorge

Hit the scenic road towards the Columbia River Gorge, known for its remarkable waterfalls.
It's about a 30-minute trip via I-84.
Free, 1 hour

10:30AM

Visit Multnomah Falls

Witness the stunning 620-foot Multnomah Falls, one of Oregon's most iconic sites.
Head to the Multnomah Falls trailhead, just 30 minutes after arriving.
Free, 1 hour

12:30PM

Lunch at Multnomah Falls Lodge

Enjoy a meal at the historic lodge, offering a great view of the waterfall.
Dine in right at the lodge location.
USD 25, 1 hour

2:00PM

Explore the Historic Columbia River Highway

Drive along the scenic highway and take in breathtaking vistas and viewpoints.
Follow I-84 for an easy scenic drive.
Free, 2 hours

4:30PM

Visit Hood River

Take a brief stop to explore the charming town of Hood River, famous for local fruit and craft breweries.
30 minutes east from Multnomah Falls via Highway 35.
Free, 1 hour

6:00PM

Dinner at Full Sail Brewing Co.

Enjoy locally brewed beer paired with pub-style food on the patio.
Located riverside in Hood River.
USD 30, 1.5 hours

8:00PM

Drive to Vancouver

Settle into your comfortable lodging in Vancouver for the night.
It's only a 30-minute drive back to Vancouver.
Free, 30 minutes
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Day 3: Columbia River Gorge Exploration

Columbia River Gorge, Oregon on July 10, 2025

8:00AM

Breakfast at Huckleberry's

Start your day with a robust breakfast featuring local favorites.
Located near your lodging in Vancouver.
USD 15, 1 hour

9:30AM

Visit Bonneville Dam

Explore the Bonneville Dam and learn about hydroelectric power in this fascinating facility.
40-minute drive along the Columbia River.
USD 5, 1.5 hours

11:30AM

Scenic Hike at Dog Mountain

Enjoy a moderately challenging hike with stunning views of the Columbia River below.
30-minute drive to the trailhead.
Free, 3 hours

3:30PM

Lunch at Taco Pedaler

Refuel with fresh, delicious tacos from this local favorite food truck after your hike.
Head back to Portland (30 minutes).
USD 12, 1 hour

5:00PM

Visit East Wind Drive-In

Check out this iconic drive-in for a shake and a nostalgic vibe.
10 minutes drive from Taco Pedaler.
USD 10, 1 hour

6:30PM

Drive back to Vancouver

Relax at your lodging after a fulfilling day of exploration.
Just a 30-minute drive back.
Free, 30 minutes
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Day 4: Multnomah Falls Adventure

Multnomah Falls, Oregon on July 11, 2025

8:00AM

Breakfast at The Overlook Cafe

Enjoy breakfast with a view of the stunning falls from the Overlook Cafe.
It's located right at Multnomah Falls.
USD 18, 1 hour

9:30AM

Hike to the Top of Multnomah Falls

Hike up to the top of the iconic falls for an unparalleled view.
Trail starts right from the cafe.
Free, 2 hours

12:00PM

Lunch at the Falls

Pack a picnic lunch to enjoy while admiring the falls’ grandeur.
Prepare at the cafe prior to departing for the hike.
USD 10, 1 hour

1:30PM

Visit Latourell Falls

Experience another breathtaking waterfall without the crowds.
15-minute drive from Multnomah.
Free, 1 hour

3:00PM

Explore the Gorge Waterfalls Loop

Complete your day by enjoying this scenic loop that encompasses several waterfalls.
It's a lovely drive along the historic highway.
Free, 3 hours

6:30PM

Dinner at The Farm Cafe

Enjoy a farm-to-table experience at The Farm Cafe, emphasizing local ingredients.
Head back to Portland for the meal.
USD 25, 1.5 hours
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Day 5: Silver Falls Adventure

Silver Falls State Park, Oregon on July 12, 2025

8:00AM

Breakfast at The Original Breakfast

Fill up on hearty breakfast classics before hitting the trails.
Located in downtown Portland.
USD 15, 1 hour

9:30AM

Drive to Silver Falls State Park

Head out towards Silver Falls State Park, known for its gorgeous hiking trails.
About a 1-hour drive from Portland.
USD 5 parking, 1 hour

10:30AM

Hike the Trail of Ten Falls

Embark on this renowned hiking trail that winds past spectacular waterfalls.
Park entry point is at the south end.
Free, 3 hours

2:00PM

Lunch at Silver Falls Lodge

Take a break at the lodge, offering homemade meals and snacks.
Located conveniently within the park.
USD 20, 1 hour

3:30PM

Continue Exploring Silver Falls

Take more time to enjoy the park's serene and beautiful environment.
Explore more of the trails.
Free, 2 hours

6:00PM

Drive back to Portland

Return to Portland for a cozy evening.
Same route back.
Free, 1 hour

7:30PM

Dinner at Pok Pok

Savor some of the best Thai food outside of Thailand at Pok Pok.
Downtown Portland, a short drive away.
USD 30, 1.5 hours
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Day 6: Willamette Valley Wine Tasting

Willamette Valley, Oregon on July 13, 2025

8:00AM

Breakfast at The Bakery Bar

Try a breakfast pastry and coffee at this delightful spot renowned for fresh baked goods.
Downtown Portland, a quick drive.
USD 10, 1 hour

9:30AM

Drive to Willamette Valley

Make your way to the picturesque Willamette Valley, famous for its Pinot Noir.
It's a 1-hour drive south from Portland.
Free, 1 hour

10:30AM

Wine Tasting at Domaine Serene

Enjoy a guided tasting of world-class wines in a stunning vineyard setting.
Located just off the main road in the valley.
USD 25, 1.5 hours

12:30PM

Lunch at Red Hills Market

Savor artisanal sandwiches and fresh salads in this rustic eatery.
A short 10 minutes drive from Domaine Serene.
USD 20, 1 hour

2:00PM

Visit Another Vineyard

Stop by another vineyard for additional wine tasting experiences.
Choose from many options in the area.
USD 20, 2 hours

5:00PM

Drive back to Portland

Head back to Portland to enjoy the evening.
The same scenic route back will do.
Free, 1 hour

6:30PM

Dinner at A Cena

Indulge in exquisite Italian cuisine made from local seasonal ingredients.
A cozy drive away from downtown.
USD 40, 1.5 hours
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Day 7: Portland Day

Portland, Oregon on July 14, 2025

8:00AM

Breakfast at Biscuit Bar

Dig into mouthwatering biscuit sandwiches in a cozy atmosphere.
A short drive in the heart of Portland.
USD 15, 1 hour

9:30AM

Explore the Portland Japanese Garden

Wander through carefully crafted landscapes in one of the most authentic Japanese gardens outside of Japan.
10-minute drive to Washington Park.
USD 15, 2 hours

12:00PM

Lunch at Lardo

Indulge in innovative sandwiches and hearty fare at this popular food stop.
Just a short drive from the garden.
USD 20, 1 hour

1:30PM

Visit Powell's City of Books

Explore the world’s largest independent bookstore and maybe pick up a souvenir.
Located downtown, 10 minutes away.
Free, 2 hours

4:00PM

Coffee at Stumptown Coffee Roasters

Savor some of the best coffee in the city to recharge.
Near Powell's, a quick walk.
USD 5, 30 minutes

5:00PM

Dinner at Ken's Artisan Pizza

Finish your day with delicious gourmet pizzas made with local ingredients.
Head to the restaurant located nearby.
USD 25, 1.5 hours
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Day 8: Travel to Cannon Beach

Cannon Beach, Oregon on July 15, 2025

8:00AM

Breakfast at Sweet Basil Cafe

Enjoy a scenic breakfast featuring farm-to-table ingredients.
Head back to Cannon Beach (1.5 hours).
USD 20, 1 hour

9:30AM

Drive to Cannon Beach

Scenic drive along Route 101 brings you to the lovely coastal town of Cannon Beach.
Relax and enjoy the coastal views along the way.
Free, 1.5 hours

11:00AM

Explore Ecola State Park

Wander through miles of hiking trails boasting stunning views of the Pacific Ocean and Haystack Rock.
Just a short drive into Ecola State Park.
USD 5 parking, 2 hours

1:00PM

Lunch at Cannon Beach Cafe

Feast on fresh seafood and local cuisine overlooking the ocean.
Cannon Beach Cafe is close to the beach.
USD 25, 1.5 hours

2:30PM

Beach Time in Cannon Beach

Stroll along the picturesque beach and take in the stunning coastal vistas.
Just walk from the cafe to the beach.
Free, 2 hours

5:00PM

Dinner at The Irish Table

Indulge in hearty Irish fare in a cozy setting.
Located in the heart of Cannon Beach.
USD 30, 1.5 hours
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Day 9: Explore Bend

Bend, Oregon on July 16, 2025

8:00AM

Breakfast at The Breakfast Club

Start your day at this local favorite spot known for its inventive breakfast dishes.
Drive approximately 3 hours to Bend from Cannon Beach.
USD 20, 1 hour

9:30AM

Drive to Bend

Make your way to the charming town of Bend, known for outdoor recreation.
Enjoy scenic views along Highway 20.
Free, 3 hours

12:30PM

Lunch at Deschutes Brewery

Savor delicious pub food paired with local craft beers.
Located in the heart of downtown Bend.
USD 25, 1.5 hours

2:00PM

Visit Smith Rock State Park

Explore the stunning rock formations and hiking trails at this iconic park.
Short drive northeast of Bend.
USD 5 parking, 2 hours

5:00PM

Dinner at Zydeco Kitchen & Cocktails

Enjoy delectable Southern-inspired dishes at this popular eatery.
Back to downtown Bend, a quick drive.
USD 30, 1.5 hours
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Day 10: Explore the Oregon Redwood Trail

Oregon Redwood Trail, Oregon on July 17, 2025

8:00AM

Breakfast at The Sparrow Bakery

Enjoy the famed Ocean Rolls and coffee from this bakery before heading out.
Drive about 30 minutes from Bend.
USD 10, 1 hour

9:30AM

Drive to Oregon Redwood Trail

Head towards this remarkable trail showcasing the towering redwoods.
Around a 90-minute drive from Bend.
Free, 1.5 hours

11:30AM

Hike the Oregon Redwood Trail

Experience the awe of these ancient giants while walking the shaded trails.
Start the hike at the trailhead.
Free, 2 hours

2:00PM

Lunch at a Picnic Spot

Enjoy a packed lunch amid the serene redwoods for a truly serene dining experience.
Prepare your own picnic before the hike.
USD 15, 1 hour

3:30PM

Explore more of the Redwood Area

Take additional time to hike other trails and soak in the beauty.
Explore other paths beyond the main trail.
Free, 2 hours

6:00PM

Drive back to Bend

Return to Bend for a relaxing evening.
Head back the same way.
Free, 1.5 hours

7:30PM

Dinner at RamenMatsu

End your day with satisfying noodle dishes at this local ramen spot.
Return to downtown Bend.
USD 20, 1.5 hours
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Day 11: Adventure near Toketee Falls

Toketee Falls, Oregon on July 18, 2025

8:00AM

Breakfast at The Midtown Bakery & Cafe

Grab a quick coffee and pastry to fuel your journey.
One last drive through Bend.
USD 10, 1 hour

9:30AM

Drive to Toketee Falls

Travel towards Toketee Falls, which is a stunning waterfall surrounded by lush wilderness.
Follow Route 138 East for about an hour.
Free, 1 hour

10:30AM

Hike to Toketee Falls

Embark on a short hike to see the waterfalls and enjoy the tranquil surroundings.
Trailhead easily accessible from the parking lot.
Free, 2 hours

1:00PM

Lunch at Diamond Lake Lodge

Enjoy a peaceful meal overlooking Diamond Lake's stunning beauty.
Drive about 30 minutes to the lodge.
USD 25, 1.5 hours

2:30PM

Visit Crater Lake National Park

Drive to the majestic Crater Lake National Park and soak in the spectacular views.
It's just a short drive from there.
USD 10 entry fee, 1.5 hours

4:00PM

Explore Crater Lake

Spend time admiring the deep blue water and breathtaking vistas at Crater Lake.
Take advantage of the scenic viewpoints.
Free, 2 hours

6:00PM

Check-In at Crater Lake Lodge

Settle into your lodge, taking in the natural beauty surrounding you.
Located inside the park and easy to find.
USD 200, 1 hour

7:30PM

Dinner at Crater Lake Lodge Dining Room

Enjoy a cozy meal overlooking the beauty of Crater Lake at the lodge dining room.
Dine right at the lodge.
USD 40, 1.5 hours
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Day 12: Day at Crater Lake

Crater Lake National Park, Oregon on July 19, 2025

8:00AM

Breakfast at Crater Lake Lodge Dining Room

Start your day with breakfast while enjoying the breathtaking views.
Served at the lodge.
USD 20, 1 hour

9:30AM

Hike the Rim Trail

Take in panoramic views by hiking around the rim of Crater Lake.
Access the trail from the lodge.
Free, 3 hours

1:00PM

Lunch at Crater Lake Lodge Dining Room

Fuel up after your hike with a delicious meal at the lodge dining room.
Return to the lodge for lunch.
USD 25, 1 hour

2:30PM

Explore Rim Drive

Drive along Rim Drive, stopping at various viewpoints for stunning photography.
Start the drive from the lodge.
Free, 2 hours

5:00PM

Return to Crater Lake Lodge

Head back to the lodge to relax and enjoy the serene atmosphere.
Drive back to the lodge.
Free, 30 minutes

6:00PM

Dinner at Crater Lake Lodge Dining Room

Enjoy your final dinner at this iconic lodge overlooking tranquil lake waters.
Dinner at the lodge dining room.
USD 40, 1.5 hours
View Hotel Availability

Day 13: Return to Portland

Portland, Oregon on July 20, 2025

8:00AM

Breakfast at Crater Lake Lodge Dining Room

Enjoy your last breakfast with a view in the dining room.
Served at the lodge.
USD 20, 1 hour

9:30AM

Drive back to Portland

Make your way back to the vibrant city of Portland, reflecting on your trip.
About a 2.5-hour drive.
Free, 2.5 hours

12:30PM

Lunch at The Griswold

Enjoy flavor-packed dishes with a local twist at The Griswold.
Located in downtown Portland.
USD 20, 1 hour

2:00PM

Visit the Oregon Museum of Science and Industry

Engage with the interactive exhibits and learning experiences at this popular museum.
Short drive from the restaurant downtown.
USD 15, 3 hours

5:00PM

Coffee at Cat Six Coffee Roasters

Wind down with coffee at this local roastery known for its artisanal brews.
Just a quick drive from OMSI.
USD 5, 1 hour

6:30PM

Dinner at Andina

Treat yourself to a delightful Peruvian-inspired meal in a warm atmosphere.
Situated in the Pearl District.
USD 40, 1.5 hours
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Day 14: Wrap Up in Portland

Portland, Oregon on July 21, 2025

8:00AM

Breakfast at Voodoo Doughnut

Indulge in the iconic and quirky donuts of Voodoo Doughnut to cap your journey.
Head to the famous downtown location.
USD 10, 1 hour

9:30AM

Last-Minute Shopping at Portland Saturday Market

Explore local crafts and snacks at this vibrant arts and crafts market.
A quick drive or walk from your hotel.
Free, 2 hours

12:00PM

Lunch at Pine Street Market

Sample various dishes from eclectic vendors at this popular food hall.
Downtown Portland, just a short drive.
USD 20, 1.5 hours

1:30PM

Final Walk along the Willamette River

Finish your trip by taking a peaceful walk along the scenic river.
Head to the riverfront park nearby.
Free, 2 hours

4:00PM

Coffee atesser act Coffee

Reflect on your Oregon adventure over a final cup of local coffee.
Just a short drive away.
USD 5, 1 hour

5:30PM

Departure

Say goodbye to Portland filled with wonderful memories from your trip.
Return your rental car and head to the airport.
Free, 1 hour
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