12-Day Relaxation and Cultural Immersion Itinerary in Beautiful Oregon, USA

Day 1: Explore Portland

Portland, Oregon

9:00AM

Breakfast at Blue Star Donuts

Start your day with delicious artisanal donuts, perfect for sharing with your furry friend.
Located in the heart of Portland.
USD12, 1 hour

10:30AM

Visit Washington Park

Wander through lush gardens and beautiful open spaces, allowing your dog to enjoy the freedom to run.
A short drive (15 minutes) from the breakfast spot.
Free, 2 hours

12:30PM

Lunch at Tin Shed Garden Cafe

Enjoy a pet-friendly outdoor patio while savoring locally sourced dishes.
Located in the Alberta Arts District.
USD25, 1.5 hours

2:00PM

Explore Portland's Pearl District

Stroll through art galleries and boutique stores while your dog enjoys the sights.
A short drive (10 minutes) from lunch.
Free, 2 hours

4:30PM

Relax at Forest Park

Witness breathtaking trails with various dog-friendly paths to enjoy the natural beauty.
15-minute drive from the Pearl District.
Free, 2 hours

7:00PM

Dinner at The Farm Cafe

Dine on farm-fresh ingredients while your dog enjoys the outdoor seating.
Drive back towards the city center.
USD30, 1.5 hours
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Day 2: Columbia River Adventure

Columbia River Gorge, Oregon

8:00AM

Breakfast at The Cafe at the Visitor Center

Enjoy baked goods and coffee while taking in views of the Columbia River.
10-minute drive from Portland.
USD15, 1 hour

9:30AM

Visit Multnomah Falls

Hike to the iconic falls and make memories with your pup at this stunning landmark.
Just 30 minutes drive from the café.
Free, 2 hours

12:00PM

Lunch at Hood River Waterfront Park

Enjoy a picnic-style lunch on the waterfront with your dog at the picturesque park.
20-minute drive from Multnomah Falls.
USD20, 1.5 hours

1:30PM

Explore Historic Hood River

Walk through charming shops and local markets with your dog at your side.
5-minute drive from the park.
Free, 2 hours

4:00PM

Visit Hood River Dog Park

Allow your dog to play with fellow pups at this fenced area while you relax.
10-minute drive from the town center.
Free, 1 hour

6:00PM

Dinner at Solstice Wood Fire Pizza

Savor delicious wood-fired pizza on the outdoor patio with your furry friend.
Just 5 minutes away.
USD30, 2 hours
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Day 3: Scenic Journey to Hood River

Hood River, Oregon

9:00AM

Breakfast at Pine Street Bakery

Enjoy tasty pastries and coffee in a cozy atmosphere before heading out.
A 5-minute walk from your accommodation.
USD10, 1 hour

10:30AM

Visit Mt. Adams Viewpoint

Take in sweeping views of Mount Adams and explore the area with your dog.
About 30 minutes drive from the bakery.
Free, 1 hour

12:00PM

Lunch at Full Sail Brewing Co.

Enjoy a beer and hearty meal while sitting on the dog-friendly patio.
20-minute drive back into Hood River.
USD25, 1.5 hours

1:30PM

Visit the Columbia River Gorge Scenic Highway

Experience stunning viewpoints and natural beauty on this iconic drive.
Start along the highway right by the brewery.
Free, 2 hours

4:00PM

Hike the Angel's Rest Trail

Enjoy a rewarding hike with beautiful views at the summit suitable for dogs.
Less than 30 minutes from the scenic highway.
Free, 3 hours

7:00PM

Dinner at Big Horse Brew Pub

End the day with casual dining in a friendly, outdoor setting.
Drive back to Hood River (20 minutes).
USD28, 1.5 hours
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Day 4: Adventure in Bend

Bend, Oregon

8:00AM

Breakfast at The Breakfast Club

Indulge in traditional breakfast fare made unique with local ingredients.
Take a drive to Bend (1 hour 30 minutes).
USD20, 1 hour

9:30AM

Visit Drake Park

Take a leisurely stroll around the park next to the Deschutes River with your dog.
A short drive (5 minutes) from breakfast.
Free, 1 hour

11:00AM

Take a Scenic Drive on Cascade Lakes Highway

Enjoy breathtaking views of lakes and mountains along this picturesque highway.
Start directly from Drake Park.
Free, 2 hours

1:00PM

Lunch at The Dog House

Treat your dog to a delicious meal while you enjoy hot dogs and cold beers.
Just a quick stop along the highway.
USD22, 1 hour

2:00PM

Hike at Smith Rock State Park

Experience amazing rock formations and scenic views on this moderate hike.
Drive to the park (30-minute drive).
Free, 3 hours

5:30PM

Dinner at Deschutes Brewery

Enjoy local craft beers and a casual menu in a vibrant atmosphere.
Drive back to Bend (30 minutes).
USD35, 1.5 hours
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Day 5: Serenity in Sisters

Sisters, Oregon

8:00AM

Breakfast at Sisters Coffee Company

Experience locally roasted coffee and baked goods in a charming setting.
Drive 30 minutes from Bend.
USD15, 1 hour

9:30AM

Explore Sisters Downtown

Wander through unique shops and art galleries in this quaint town’s center.
Walk to the downtown area, a few steps away.
Free, 2 hours

11:30AM

Hike at Indian Ford Meadow Preserve

Enjoy scenic trails while surrounded by open fields and wildflowers.
Short drive (15 minutes) from Sisters.
Free, 2 hours

2:00PM

Lunch at The Stitchin’ Post

Savor delicious meals rich in local flavor in a friendly atmosphere.
Drive back to town (15 minutes).
USD18, 1.5 hours

3:30PM

Visit Black Butte Ranch

Spend leisurely time walking through beautifully maintained landscapes with your dog.
20-minute drive from lunch.
Free, 2 hours

6:00PM

Dinner at The Village Green

Relax with a great dinner on a pet-friendly patio and catch up on your day.
Return to Sisters town center (20 minutes).
USD30, 1.5 hours
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Day 6: Majestic Crater Lake

Crater Lake National Park, Oregon

8:00AM

Breakfast at Crater Lake Lodge

Start your day with breakfast while overlooking the stunning blue waters of Crater Lake.
Drive to Crater Lake National Park (1 hour 30 minutes).
USD25, 1.5 hours

9:30AM

Explore Rim Drive

Drive around the crater's rim, stopping at viewpoints to soak in the beauty.
Direct access from the lodge.
Free, 2 hours

12:00PM

Lunch at Mazama Village Restaurant

Enjoy a hearty meal after exploring the park.
Just a short drive from Rim Drive.
USD20, 1 hour

1:00PM

Scenic Hike at Garfield Peak

Hike to enjoy more breathtaking views and dappled shade throughout the trek.
Drive back towards the trailhead (30 minutes).
Free, 3 hours

5:00PM

Return to Crater Lake Lodge

Relax and take some time in the lodge after your adventures.
Drive back to the lodge (30 minutes).
Free, 1 hour

6:30PM

Dinner at Crater Lake Lodge

Enjoy a relaxing dinner at the lodge surrounded by stunning natural beauty.
Right within the lodge.
USD40, 1.5 hours
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Day 7: Adventures in Grant's Pass

Grant's Pass, Oregon

8:00AM

Breakfast at Riverside Grill

Enjoy a riverside breakfast with views of the Rogue River.
Drive to Grant's Pass (1 hour).
USD20, 1 hour

9:30AM

Explore Rogue River Trail

Hike along the Rogue River to enjoy wildlife and scenic riverside views.
Start at a trailhead nearby.
Free, 2 hours

12:00PM

Lunch at The Twisted Cork

Visit this dog-friendly restaurant for a casual lunch with local wines.
5-minute drive from the trail.
USD25, 1.5 hours

1:30PM

Visit the Grants Pass Caveman Statue

Take fun photos with this iconic landmark.
Drive to the downtown area (10 minutes).
Free, 1 hour

3:00PM

Relax at Riverside Park

Enjoy some downtime at this beautiful park with your dog and local wildlife.
Just a short drive from the statue.
Free, 1.5 hours

5:00PM

Dinner at The China Garden

Have delicious Chinese food with outdoor seating for your dog.
Drive into town (5 minutes).
USD30, 1.5 hours
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Day 8: Cozy Coastal Retreat

Gold Beach, Oregon

8:00AM

Breakfast at The Grumpy Crab

Start your coastal adventure with hearty breakfast options overlooking the ocean.
Drive to Gold Beach (1 hour 15 minutes).
USD15, 1 hour

9:30AM

Explore the Oregon Coast Trail

Hike along the breathtaking coastline with stunning views of the Pacific.
Begin at the nearby trailhead.
Free, 3 hours

12:30PM

Lunch at Spinners Seafood, Steak & Chop House

Indulge in a seafood feast with lovely outdoor seating for pups.
Drive 10 minutes from the trailhead.
USD30, 1.5 hours

2:00PM

Visit the Gold Beach Bookstore

Discover a treasure trove of books in this quaint bookstore that welcomes dogs.
Less than 5-minute drive from lunch.
Free, 1 hour

3:30PM

Relax at the Beach

Take some time to relax on the beach while your dog enjoys the sand and surf.
Just a short walk from the bookstore.
Free, 2 hours

6:00PM

Dinner at the Port Hole Cafe

Experience a great seafood dinner while enjoying views of the harbor.
Only a few minutes drive.
USD35, 1.5 hours
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Day 9: Relaxed Coastal Vibes

Brookings, Oregon

8:00AM

Breakfast at The Landing Restaurant

Enjoy a breakfast with beautiful ocean views before heading out for the day.
Short drive to Brookings (30 minutes).
USD20, 1 hour

9:30AM

Visit Harris Beach State Park

Explore the sandy beach trails and natural rock formations at this state park.
Quick drive (10 minutes) from the restaurant.
Free, 2 hours

12:00PM

Lunch at The Hungry Clam

Indulge in clam chowder or fresh seafood while seated outside.
5-minute drive from the park.
USD22, 1.5 hours

1:30PM

Explore Brookings Harbor

Wander the scenic harbor area and relax by the water with your pup.
Just a short drive or walk from lunch.
Free, 1 hour

3:00PM

Visit Azalea Park

Enjoy the beautifully landscaped park with trails and spaces for picnics.
Take a short drive (5 minutes) from the harbor.
Free, 1.5 hours

5:00PM

Dinner at Chetco Brewing Company

Enjoy on-site brewed craft beer and outdoor dining with your pup.
Back towards downtown (10-minute drive).
USD30, 1.5 hours
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Day 10: Wine Country Exploration

Medford, Oregon

8:00AM

Breakfast at The Buttered Biscuit

Savor delightful breakfast biscuits in a charming setting.
Drive to Medford (1 hour).
USD15, 1 hour

9:30AM

Visit Roxy Ann Peak

Hike to this local mountain for stunning views of the Rogue Valley.
Close by (15-minute drive).
Free, 2 hours

12:00PM

Lunch at The Redwood Grill

Enjoy a farm-to-table experience with seasonal ingredients.
Drive back to Medford (15 minutes).
USD28, 1.5 hours

1:30PM

Wine Tasting at RoxyAnn Winery

Relax and sip wine in this dog-friendly atmosphere.
A short drive from lunch (30 minutes).
USD15, 2 hours

4:00PM

Take a Stroll at Medford's Riverside Park

Relax in this lovely park with wide open spaces and paths.
Drive to the park (15 minutes).
Free, 1.5 hours

6:30PM

Dinner at Harry & David’s

Enjoy a delightful meal and sample local products in the heart of Medford.
A quick drive from the park (10 minutes).
USD35, 1.5 hours
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Day 11: Cultural Delight in Ashland

Ashland, Oregon

8:00AM

Breakfast at TLc Bakery

Indulge in fresh pastries and coffee at this local bakery.
Drive to Ashland (30 minutes).
USD12, 1 hour

9:30AM

Visit Lithia Park

Wander through beautiful gardens and enjoy the tranquility of this park.
Short drive to the park (10 minutes).
Free, 2 hours

12:00PM

Lunch at Caldera Brewery

Taste local craft beers and enjoy a great meal on the outdoor patio.
Drive back into Ashland (10 minutes).
USD20, 1.5 hours

1:30PM

Explore Downtown Ashland

Discover local shops, galleries and enjoy a relaxed pace of life.
Stroll through downtown; it’s very walkable.
Free, 2 hours

4:00PM

Visit Oregon Shakespeare Festival

Explore the cultural heart of Ashland at this renowned festival's theater.
A walk from downtown (5 minutes).
USD40, 2 hours

6:30PM

Dinner at The Brown Room

End your day at this fine dining location with delicious offerings.
Short walk from the festival (5 minutes).
USD45, 1.5 hours
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Day 12: Return to Portland

Portland, Oregon

8:00AM

Breakfast at Mother’s Bistro & Bar

Relish a homestyle breakfast in the cozy atmosphere before finishing your journey.
Drive back to Portland (4 hours).
USD18, 1.5 hours

10:00AM

Visit the Portland Japanese Garden

Take a serene walk in this beautiful garden to reflect on your adventure.
Drive to the gardens (15 minutes).
USD20, 1.5 hours

12:00PM

Lunch at Pok Pok

Savor authentic Thai street food in an outdoor setting with your dog.
Only a 10-minute drive from the gardens.
USD25, 1.5 hours

1:30PM

Explore Portland's famous food carts

Sample the city's unique offerings from various food trucks in one area.
A quick drive (10 minutes) to the food cart pod.
Free to peruse; food costs vary., 2 hours

4:00PM

Relax at a Local Dog Park

Enjoy the afternoon at a local park allowing your dog to play freely.
Drive to the park (15 minutes).
Free, 1.5 hours

6:00PM

Farewell Dinner at Le Pigeon

End your journey with a fine dining experience featuring French cuisine.
A short drive from the dog park.
USD70, 2 hours
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