Road Trip from San Jose to Seattle via Ashland, Oregon State University, and Portland

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Day 1: Travel to Ashland

San Jose, CA to Ashland, OR on July 28, 2025

7:30am

Breakfast at The Original Pancake House

Start your day with a hearty breakfast at this popular San Jose spot known for its classic pancakes and omelets, open from 7am.
USD20, 1h

8:30am

Drive from San Jose to Ashland

Embark on a scenic 5.5-hour drive (approx. 340 miles) northbound through California and into Oregon. Plan for a few short breaks to stretch and refuel.
USD50 (gas), 5h30m

2:00pm

Lunch at Larks Home Kitchen Cuisine

Enjoy farm-to-table cuisine highlighting Pacific Northwest flavors in Ashland’s charming downtown, open 11:30am - 2:30pm on weekdays and weekends.
USD35, 1h

3:30pm

Explore downtown Ashland

Walk around the vibrant downtown filled with boutique shops, galleries, and the famous Oregon Shakespeare Festival venues.
Free, 2h

6:00pm

Dinner at Standing Stone Brewing Company

Relax over locally brewed craft beers and delicious pub fare in this cozy brewpub, open until 9pm.
USD30, 1h
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Day 2: Oregon State University Visit

Ashland to Corvallis, OR on July 29, 2025

7:00am

Breakfast at Morning Glory Cafe

Enjoy a wholesome breakfast emphasizing fresh ingredients in Ashland before heading out, open from 7am.
USD15, 1h

8:00am

Drive to Oregon State University

Drive approx. 3 hours (about 170 miles) to Corvallis, Oregon. Ideal to start early to maximize university visit time.
USD30 (gas), 3h

11:30am

Lunch at The Broken Yolk Cafe

Stop for a hearty lunch offering classic American breakfast and lunch dishes, located near campus and open 7am-3pm.
USD20, 1h

12:30pm

Oregon State University Campus Tour

Explore the main campus, including the Memorial Union, library, and botanical gardens. Guided tours available but self-guided possible too.
Free, 2h

3:00pm

Walk through downtown Corvallis

Stroll through Corvallis’s quaint downtown to enjoy shops, cafes, and the Willamette River waterfront.
Free, 1.5h

5:00pm

Drive to Portland

Depart for Portland, approximately a 1.5-hour drive (about 75 miles).
USD20 (gas), 1h30m

6:30pm

Dinner at Deschutes Brewery Portland Public House

Enjoy Pacific Northwest inspired pub fare and craft beers in downtown Portland. Open until 10pm.
USD30, 1h
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Day 3: Explore Portland

Portland, OR on July 30, 2025

8:00am

Breakfast at Blue Star Donuts

Try gourmet donuts with unique flavors, a Portland specialty, open from 7am.
USD10, 0h30m

9:00am

Visit Portland Japanese Garden

Discover beautiful landscapes and authentic Japanese architecture. Open 10am-5pm, best to arrive at opening to avoid crowds.
USD20, 1h30m

11:00am

Walk through Washington Park

Explore the wider park area including Rose Garden and trails near the Japanese Garden.
Free, 1h

12:30pm

Lunch at Pine Street Market

Casual food hall with diverse local vendors and cuisines in downtown Portland.
USD20, 1h

2:00pm

Explore Pearl District

Shop boutiques, galleries, and enjoy Portland’s vibrant arts scene in this trendy neighborhood.
Free, 2h

5:00pm

Relax at Tom McCall Waterfront Park

Stroll along the Willamette River and enjoy the sunset views in this scenic urban park.
Free, 1h

6:30pm

Dinner at Andina Restaurant

Experience award-winning Peruvian cuisine in a welcoming ambiance, open until 9pm.
USD40, 1h
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Day 4: Travel to Seattle

Portland, OR to Seattle, WA on July 31, 2025

7:30am

Breakfast at Mother’s Bistro & Bar

Start your day with hearty farm-to-table breakfast fare in Portland, open from 7am.
USD20, 1h

8:30am

Drive from Portland to Seattle

Drive approximately 3 hours north on I-5 (about 175 miles) to Seattle. Consider stopping at scenic viewpoints or small towns en route.
USD30 (gas), 3h

12:00pm

Lunch at Pike Place Market

Explore the iconic market and enjoy fresh seafood or local bites at numerous stalls and eateries open around noon.
USD25, 1h

1:30pm

Visit Space Needle

Take in panoramic views from the landmark tower, open daily 10am-8pm.
USD35, 1h

3:00pm

Explore Chihuly Garden and Glass

Marvel at stunning glass art displays adjacent to the Space Needle, open 10am-6pm.
USD35, 1.5h

5:00pm

Check into hotel and rest

Take some downtime before dinner at your hotel or nearby.
Varies, 1h

6:30pm

Dinner at The Pink Door

Enjoy Italian-American dining in an intimate setting near Pike Place Market. Reservations recommended, open until 10pm.
USD50, 1.5h
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Itinerary created by AI-assisted, human-reviewed