5-Day Scenic Road Trip from Issaquah to Northern California Highlights

Day 1: Issaquah to Portland

Issaquah, WA to Portland, OR on June 2, 2025

8:00am

Departure from Issaquah

Start your road trip early to maximize sightseeing. The drive to Portland is about 3 hours, so plan for stops en route.
USD0, 0h30m

10:00am

Breakfast break in Olympia

Stop in Olympia at Broders Café & Bookstore (open 7am-3pm) for a delightful brunch with local baked goods and coffee to fuel the trip.
USD15, 1h

11:00am

Drive to Portland

Continue south to Portland with scenic views of the Columbia River Gorge along the way.
USD0, 2h

1:00pm

Lunch at Pine Street Market

Explore the vibrant Pine Street Market, featuring diverse food vendors. Try Marukin Ramen or other local specialties.
USD20, 1h

2:30pm

Visit Portland Japanese Garden

Experience tranquil beauty at the Portland Japanese Garden (open 10am-6pm), a top-rated serene spot for nature and culture lovers.
USD20, 1h30m

4:30pm

Check-in and rest at hotel

Relax at a downtown Portland hotel before dinner.
USD0, 1h30m

6:00pm

Dinner at Le Pigeon

Savor modern French-inspired cuisine at Le Pigeon, known for its creative dishes and cozy atmosphere (open until 9:30pm).
USD50, 1h30m
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Day 2: Portland to Ashland

Portland, OR to Ashland, OR on June 3, 2025

8:00am

Breakfast at Blue Star Donuts

Grab artisan donuts and coffee at Blue Star Donuts (open 7am-5pm) before an extended drive south.
USD12, 0h45m

9:00am

Drive to Ashland with stop at Eugene

Drive 3.5 hours to Ashland with a route break in Eugene for a short walk at Alton Baker Park for fresh air and stretch.
USD0, 4h

1:00pm

Lunch at King Estates Winery

Enjoy wines and lunch at King Estates Winery near Eugene, offering picturesque vineyard views and quality food options (open 11am-5pm).
USD35, 1h30m

3:00pm

Continue drive to Ashland

Drive the final 2 hours to Ashland, known for the Oregon Shakespeare Festival and lovely town vibe.
USD0, 2h

5:15pm

Check-in and relax at Ashland hotel

Settle in and rest before evening activities.
USD0, 1h

6:30pm

Dinner at Larks Home Kitchen

Enjoy farm-to-table dining at Larks Home Kitchen, featuring regional Oregon cuisine (open until 9pm).
USD45, 1h30m
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Day 3: Ashland to Mount Shasta

Ashland, OR to Mount Shasta, CA on June 4, 2025

8:00am

Breakfast at Morning Glory

Start the day with hearty breakfast at Morning Glory, renowned for their cinnamon rolls and omelets.
USD18, 1h

9:30am

Drive to Mount Shasta

Enjoy a scenic 1.5-hour drive south to Mount Shasta, passing through beautiful forested landscapes.
USD0, 1h30m

11:00am

Visit Mount Shasta Trailhead

Take a leisurely hike or short walk around the base of Mount Shasta to soak in breathtaking views and fresh mountain air.
USD0, 2h

1:00pm

Lunch at Lilly's Restaurant

Enjoy homestyle meals and sandwiches at Lilly's Restaurant, perfect for a relaxed meal after hiking (open 11am-3pm).
USD20, 1h

2:30pm

Drive to Redding

Head 1.5 hours south to Redding, gateway to natural spots like Turtle Bay Exploration Park.
USD0, 1h30m

4:00pm

Visit Turtle Bay Exploration Park

Explore the botanical gardens, aquarium, and museum at Turtle Bay (open until 5pm), a lovely stop for nature and science enthusiasts.
USD20, 1h30m

5:30pm

Check-in and rest at hotel in Redding

Relax before dinner.
USD0, 1h

7:00pm

Dinner at Moonstone Bistro

Dine at Moonstone Bistro offering creative American fare with local ingredients (open until 9pm).
USD40, 1h30m
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Day 4: Redding to Oregon Coast

Redding, CA to Newport, OR on June 5, 2025

7:30am

Breakfast at Black Bear Diner

Begin early with a classic American breakfast at Black Bear Diner (open from 6am).
USD15, 1h

8:30am

Drive to Newport via Interstate 5 North and US-20 West

Enjoy a long scenic drive (approx 4.5 hours) through northern California and Oregon, with an optional stretch break near Eugene.
USD0, 5h

1:30pm

Lunch at Mo's Seafood & Chowder in Newport

Taste the famous clam chowder and seafood in this iconic Oregon coastal eatery (open 11am-9pm).
USD25, 1h

2:30pm

Visit Yaquina Head Outstanding Natural Area

Explore lighthouse views, tide pools, and sea wildlife at Yaquina Head (open daylight hours).
USD7 parking, 1h30m

4:00pm

Check in at Newport hotel

Relax and enjoy coastal sunset views.
USD0, 1h

6:00pm

Dinner at Local Ocean Seafoods

Dine on fresh, locally-sourced seafood with ocean views (open until 9pm).
USD45, 1h30m
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Day 5: Oregon Coast to Issaquah

Newport, OR to Issaquah, WA on June 6, 2025

7:30am

Breakfast at Tiny House Coffee

Grab artisanal coffee and a light breakfast from this popular Newport spot (open 7am-2pm).
USD12, 0h45m

8:15am

Drive back north to Issaquah

Embark on the 5-hour drive back up through Oregon and Washington with a planned rest/stretch break halfway near Portland.
USD0, 5h

11:30am

Lunch break at Portland's Laurelhurst Park area

Stop for a relaxing lunch at one of the cafes near Laurelhurst Park, such as Sizzle Pie for pizza (open 11am-10pm).
USD20, 1h

12:30pm

Final leg drive to Issaquah

Finish the final 3-hour drive back to Issaquah, concluding your scenic road trip.
USD0, 3h
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