Ashland, Oregon Road Trip from Pocatello, Idaho - 6 Day Itinerary

Day 1: Travel to Boise

Pocatello, Idaho on September 22, 2024

9:00AM

Breakfast at The Smoky Mountain Cafe

Start your journey with a hearty breakfast at The Smoky Mountain Cafe, known for their delicious omelets and pancakes.
Drive from your accommodation to Smoky Mountain Cafe.
USD15, 1.5 hours

10:30AM

Drive to Boise

Hit the road to Boise, enjoying the scenic views along I-15.
Follow I-15 N to Boise.
USD0, 2.5 hours

1:00PM

Lunch at Boise Fry Company

Indulge in award-winning fries and a variety of delicious burgers at this local favorite.
Drive from Boise to Boise Fry Company.
USD12, 1 hour

2:30PM

Visit the Idaho State Capitol Building

Explore the historic Idaho State Capitol, known for its stunning architecture and rich history.
Walk to the Idaho State Capitol, just a few blocks away.
USD0, 1 hour

4:00PM

Check into Hotel 43

Relax and unwind at this upscale hotel located in downtown Boise.
Drive to Hotel 43.
USD150, 1 hour

6:00PM

Dinner at The Basque Market

Enjoy a delightful dinner featuring Basque homeland dishes and local wines.
Drive from Hotel 43 to The Basque Market.
USD30, 1.5 hours
View Hotel Availability

Day 2: Explore Ontario

Ontario, Oregon on September 23, 2024

8:00AM

Breakfast at The Rolling Hills Cafe

Savor a menu filled with American classics like breakfast burritos and fresh coffee.
Walk from the hotel to The Rolling Hills Cafe.
USD12, 1 hour

9:30AM

Drive to Ontario

Journey onward to Ontario, known as the city of two states.
Follow I-84 E to Ontario.
USD0, 2 hours

11:30AM

Visit the Oregon Trail Interpretive Center

Dive into the rich history of the Oregon Trail through engaging exhibits.
Drive from Ontario to the interpretive center.
USD5, 1.5 hours

1:00PM

Lunch at Old Towne Pizza

Relish delicious pizza with fresh ingredients and a cozy atmosphere.
Drive from the center to Old Towne Pizza.
USD15, 1 hour

2:30PM

Explore Nyssa’s Farmer’s Market

If it's a Saturday, wander through local produce and crafts, showcasing the best of Oregon.
Drive to Nyssa’s Farmer’s Market.
USD0, 1.5 hours

4:00PM

Check into Best Western Inn

Unwind at this comfortable hotel with all the amenities for a pleasant stay.
Drive to Best Western Inn.
USD120, 1 hour

6:00PM

Dinner at Mexican Restaurant La Fuente

Enjoy authentic Mexican cuisine to round off your day.
Drive to La Fuente.
USD25, 1.5 hours
View Hotel Availability

Day 3: Scenic Drive to Bend

Bend, Oregon on September 24, 2024

8:00AM

Breakfast at Squeeze In

Start your day with famous omelets and smoothies packed with flavor.
Walk to Squeeze In.
USD15, 1 hour

9:30AM

Drive to Bend

Travel towards Bend with the scenic views of the Cascade Range.
Follow US-20 W to Bend.
USD0, 3 hours

12:30PM

Lunch at Deschutes Brewery

Taste some local brews and tasty pub food at this iconic brewery.
Drive from your hotel to Deschutes Brewery.
USD20, 1 hour

2:00PM

Visit the High Desert Museum

Learn about the natural and cultural history of the high desert region.
Drive to High Desert Museum.
USD15, 2 hours

4:30PM

Check into The Oxford Hotel

Relax at this luxurious hotel offering stunning river views.
Drive to The Oxford Hotel.
USD200, 1 hour

6:30PM

Dinner at 10 Barrel Brewing

Enjoy outdoor seating with stunning views and good food at this lively spot.
Walk to 10 Barrel Brewing.
USD30, 1.5 hours
View Hotel Availability

Day 4: Journey to Medford

Medford, Oregon on September 25, 2024

8:00AM

Breakfast at The Breakfast Club

Enjoy a casual breakfast menu with omelets, pancakes, and hash browns.
Walk to The Breakfast Club.
USD10, 1 hour

9:30AM

Drive to Medford

Take the scenic route southward towards Medford.
Follow OR-97 S and I-5 S.
USD0, 2 hours

11:30AM

Visit Harry & David's headquarters

Tour this famous gourmet food company and sample delicious treats.
Drive to Harry & David's.
USD10, 1 hour

1:00PM

Lunch at The Corner Point

Enjoy a laid-back meal featuring hearty sandwiches and salads.
Drive to The Corner Point.
USD15, 1 hour

2:30PM

Explore Medford's Pear Blossom Park

Stroll through this beautiful park known for its vibrant flowers and peaceful atmosphere.
Drive to Pear Blossom Park.
USD0, 1 hour

4:00PM

Check into Inn at the Commons

Relax at this welcoming hotel with unique touches in each room.
Drive to Inn at the Commons.
USD120, 1 hour

6:00PM

Dinner at the Olive Garden

Enjoy delicious Italian dishes and great service to end your day.
Drive to Olive Garden.
USD25, 1.5 hours
View Hotel Availability

Day 5: Finally, Arrival at Ashland

Ashland, Oregon on September 26, 2024

8:00AM

Breakfast at Dutch Bros Coffee

Grab a quick coffee and enjoy a light breakfast of pastries before hitting the road.
Walk to Dutch Bros Coffee.
USD8, 30 minutes

8:30AM

Drive to Ashland

A short and scenic drive finally takes you to Ashland.
Follow I-5 N to Ashland.
USD0, 30 minutes

9:15AM

Check into Ashland Springs Hotel

Settle in at this charming hotel which is conveniently located in the heart of downtown.
Drive to Ashland Springs Hotel.
USD150, 1 hour

11:00AM

Explore Lithia Park

Stroll through one of Oregon's most treasured parks, featuring botanical gardens and scenic paths.
Walk to Lithia Park.
USD0, 1.5 hours

12:30PM

Lunch at Omar’s Fresh Seafood

Savor fresh seafood dishes with a cozy and inviting ambiance.
Walk to Omar’s Fresh Seafood.
USD20, 1.5 hours

2:00PM

Visit the Oregon Shakespeare Festival

Catch a performance at the prestigious theater which showcases outstanding plays.
Walk to Oregon Shakespeare Festival.
USD50, 2.5 hours

5:00PM

Dinner at Peerless Hotel Bistro

Finish your day on a high note with fine dining at this luxurious bistro.
Walk to Peerless Hotel Bistro.
USD40, 2 hours
View Hotel Availability

Day 6: Departure and Conclusion

Ashland, Oregon on September 27, 2024

8:00AM

Breakfast at Morning Glory Cafe

Enjoy a delightful breakfast featuring locally sourced ingredients and organic options.
Walk to Morning Glory Cafe.
USD15, 1 hour

9:30AM

Free time for last-minute sightseeing

Take a leisurely morning walking through the downtown area or last minute shopping.
Walk around downtown Ashland.
USD0, 2 hours

11:30AM

Lunch at Caldera Tap House

Enjoy a relaxing lunch with a selection of craft beers and locally inspired dishes.
Walk to Caldera Tap House.
USD25, 1.5 hours

1:00PM

Check out of Ashland Springs Hotel

Wrap up your stay and prepare for your journey back or next adventure.
Drive to your next destination.
USD0, 30 minutes
View Hotel Availability