8-Day Family Road Trip: Portland to Bend, Oregon Wine Country, and Oregon Coast Adventure

Day 1: Portland to Bend

Portland to Bend, Oregon on June 29, 2025

8:00am

Departure from Portland

Start the trip early from Portland heading east towards Mount Hood to enjoy scenic views.
USD0, 0h30m

9:00am

Mount Hood viewpoint stop

Stop at the designated viewpoint near Mount Hood for photos and a light walk. The iconic snow-capped peak is breathtaking and perfect for family pictures.
USD0, 1h0m

10:30am

Drive to Bend

Continue the scenic drive southeast to Bend, Oregon’s outdoor recreation hub known for its rugged beauty.
USD0, 2h0m

12:30pm

Lunch at Zydeco Kitchen & Cocktails, Bend

Enjoy a family-friendly lunch with Cajun-inspired flavors in a fun atmosphere. Open 11am to 9pm.
USD50, 1h0m

2:00pm

Explore downtown Bend & Pilot Butte hike

Walk around Bend's charming downtown with shops and galleries, then take a moderate 1.5-mile hike up Pilot Butte for panoramic town and mountain views.
USD0, 3h0m

6:00pm

Dinner at Bend Brewing Company

Casual dining with local brews and American classics, great for families and teens.
USD60, 1h30m

8:00pm

Check-in at Riverhouse on the Deschutes

Comfortable hotel along the river, approx $190 per night, family friendly with easy access to downtown.
USD190, overnight
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Day 2: Bend Exploration

Bend, Oregon on June 30, 2025

8:00am

Breakfast at The Victorian Cafe

Well-loved breakfast spot serving hearty plates and good coffee, opens at 7am.
USD40, 1h0m

9:30am

Smith Rock State Park hiking

Drive 30 minutes to Smith Rock for hiking and rock climbing views. Try the Misery Ridge Trail for stunning vistas, about 3 hours hike.
USD5 park fee, 3h0m

1:00pm

Lunch at Riverside Retreat

Relax waterside with classic American lunch, open until 3pm.
USD50, 1h0m

3:00pm

Deschutes Brewery Tour

Join a guided tour (family-friendly) of one of Oregon's most famous breweries, sampling for teens and adults alike with non-alcoholic options.
USD25, 1h30m

5:00pm

Downtown Bend exploration and souvenir shopping

Pick up mementos and enjoy the lively streets before dinner.
USD variable, 1h30m

7:00pm

Dinner at Jackson's Corner

Cozy dining featuring Pacific Northwest cuisine, family friendly, closes at 9pm.
USD60, 1h30m

9:00pm

Relax at hotel

Return to Riverhouse on the Deschutes for rest.
USD0, overnight
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Day 3: Wine Country Day

Bend to McMinnville, Oregon on July 1, 2025

7:30am

Early breakfast at hotel

Start the day with a hotel breakfast or grab coffee and pastries to go.
USD30, 0h30m

8:00am

Drive to Willamette Valley wine region

Travel west to one of Oregon’s renowned wine regions, focusing on visiting WillaKenzie Estate or similar wineries for tastings and tours (check opening hours 10am-5pm).
USD50 tasting fees, 3h0m

12:00pm

Lunch at The Painted Lady in Newberg

Upscale dining in a historic home with farm-to-table cuisine, reservation recommended.
USD80, 1h30m

2:00pm

Drive to McMinnville, check-in

Charming small town with historic downtown, stay at Hotel Oregon or similar, approx $200 per night.
USD200, overnight

3:30pm

McMinnville Downtown and Evergreen Aviation Museum

Explore quaint shops downtown and visit the nearby Evergreen Aviation & Space Museum, open until 5pm, fascinating for teens interested in planes and space.
USD30, 1h30m

6:00pm

Dinner at Community Plate

Casual and family-friendly spot offering American favorites, closes at 8:30pm.
USD50, 1h0m
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Day 4: Coastal Drive

McMinnville to Manzanita, Oregon Coast on July 2, 2025

8:00am

Breakfast at Cozmic Cafe, McMinnville

Popular local spot with creative breakfast dishes and strong coffee, opens at 7am.
USD40, 1h0m

9:30am

Drive to Manzanita, Oregon Coast

Head west towards the scenic Oregon Coast, approx 1.5-hour drive.
USD0, 1h30m

11:00am

Check-in to The Stephanie Inn, Manzanita

Charming oceanfront hotel with comfortable family rooms, rates around $200/night. Perfect for relaxation.
USD200, overnight

12:00pm

Lunch at Manzanita Sea Level Bakery & Cafe

Delicious sandwiches and fresh bakery items in a cozy setting.
USD45, 1h0m

1:30pm

Relax and beach time at Manzanita Beach

Enjoy the expansive sandy beach; family can relax or explore tide pools.
USD0, 2h0m

4:00pm

Short hike at Neahkahnie Mountain Trail

Moderate 3-mile round trip hike offering panoramic ocean views, great for teenagers who enjoy nature.
USD0, 2h0m

7:00pm

Dinner at Big Wave Cafe

Family-friendly casual eatery with burgers and seafood, open till 9pm.
USD60, 1h30m
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Day 5: Cannon Beach day

Manzanita to Cannon Beach, Oregon Coast on July 3, 2025

8:00am

Breakfast at hotel

Start with a healthy breakfast onsite to fuel up for the day.
USD40, 1h0m

9:30am

Drive to Cannon Beach

Short 20-minute drive to one of Oregon Coast’s iconic beaches with Haystack Rock.
USD0, 0h30m

10:00am

Explore Cannon Beach and Haystack Rock tide pools

Walk along the beach, see the famous Haystack Rock, and explore local tide pools with abundant marine life.
USD0, 2h0m

12:30pm

Lunch at Driftwood Restaurant & Lounge

Coastal dining in a rustic setting with fresh seafood and kid-friendly options.
USD70, 1h30m

2:00pm

Ecola State Park hiking

Take a moderate 2-mile roundtrip hike on the Clatsop Loop Trail for stunning coastline views, easily accessible and great for teens.
USD5 park fee, 2h0m

4:30pm

Visit Cannon Beach shops and art galleries

Enjoy browsing local artisan shops and galleries, great for souvenirs and casual strolling.
USD variable, 1h30m

7:00pm

Dinner at Pelican Brewing Company

Relaxed environment with tasty meals and local brews, kid-friendly with non-alcoholic options.
USD60, 1h30m

9:00pm

Return to Manzanita hotel

Drive back and relax for the night.
USD0, overnight
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Day 6: Manzanita Relax & Explore

Manzanita, Oregon Coast on July 4, 2025

8:00am

Breakfast at Bread and Ocean Bakery & Cafe

Freshly baked pastries and coffee to start the day, opens at 7am.
USD35, 1h0m

9:30am

Relaxing beach morning or optional kayaking

Spend the morning relaxing on beach or rent kayaks for a light adventure with family.
USD0-80 depending on activity, 3h0m

12:30pm

Lunch at Manzanita Commons Restaurant

Casual and locally sourced meal in the heart of Manzanita.
USD50, 1h0m

2:00pm

Visit Nehalem Bay State Park

Enjoy easy hiking trails and birdwatching at this beautiful state park nearby, kid-friendly and peaceful.
USD5 park fee, 2h0m

5:00pm

Return to hotel for rest

Relax and refresh for dinner.
USD0, 1h0m

7:00pm

Dinner at The Owl Point Cafe

Family-friendly cozy cafe featuring comfort food and local ingredients, closes at 9pm.
USD60, 1h30m
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Day 7: Final Coast day

Manzanita and nearby on July 5, 2025

8:30am

Breakfast at hotel

Enjoy a leisurely breakfast at The Stephanie Inn to start the final day on the coast.
USD40, 1h0m

10:00am

Visit Oswald West State Park and Short Sand Beach

Explore a beautiful stretch of coastline with an easy hiking trail to Short Sand Beach, perfect for nature lovers and families.
USD5 park fee, 3h0m

1:30pm

Lunch at The Angry Elk Cafe

Lunch in Manzanita with locally sourced ingredients and a family-friendly atmosphere.
USD50, 1h0m

3:00pm

Pack and prepare for drive back

Relax and get ready for departure the next day.
USD0, 2h0m

7:00pm

Dinner at Bread and Ocean Bakery & Cafe

Finish with a casual dinner and bakery treats.
USD50, 1h0m
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Day 8: Return to Portland

Manzanita to Portland, Oregon on July 6, 2025

8:00am

Breakfast and check-out

Have breakfast and check out from The Stephanie Inn.
USD40, 1h0m

9:00am

Drive back to Portland

About a 90-minute drive back to Portland with scenic views along the way.
USD0, 1h30m

11:00am

Visit Washington Park (Portland)

Explore the expansive park including the Portland Japanese Garden and the International Rose Test Garden, open 10am-5pm.
USD30 (Japanese Garden entry), 3h0m

2:00pm

Lunch at Screen Door

Famous for Southern comfort food, great for an afternoon meal, opens 11am.
USD60, 1h30m

4:00pm

Check-in at Hotel Lucia, Portland

Trendy boutique hotel near downtown, approx $200 per night, comfortable for family stay.
USD200, overnight

6:00pm

Early dinner at Deschutes Brewery Portland Public House

Friendly atmosphere with a menu accommodating teens and adults alike.
USD70, 1h30m

8:00pm

Evening stroll along the waterfront

Relax with a peaceful walk along the Willamette River before ending the trip.
USD0, 1h0m
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