If there was just one perfect state for a 4-day road trip, then Oregon would be in the lead. With diverse terrain that includes mountains, lakes, and endless waterfalls, it promises the adventure of a lifetime.
Last updated: July 29, 2025
4-Day Oregon Road Trip from Medford to Portland and Back
Slightly larger than the United Kingdom, Oregon suits perfectly for a short road trip. You can literally cross the entire state from south to north within a matter of a few days. If that was the only case, then a 2-day road trip would be more than enough to see Oregon.
But don’t let the size of the state mislead you. Despite being the second smallest state on the West Coast of the U.S., Oregon offers more natural wonders than one can ask for.
The Oregon road trip was never our ultimate plan. Initially, we planned to visit Portland and its surroundings. But since airfares were extremely high, we decided to fly into Medford (Southern Oregon) and explore the state on our way to the largest city in the north.
Along the way, we had to adjust our Oregon road trip itinerary due to the weather conditions. But this one is pretty close to the one we had planned initially.
OUR ULTIMATE 4-DAY OREGON ROAD TRIP FROM MEDFORD TO PORTLAND
DAY 1: MEDFORD TO EUGENE
If traveling on a budget is one of your goals, I’d recommend starting your Oregon road trip in Medford. Airline fares to Medford are almost half of what you’d pay to fly directly into Portland.
Stop 1: Samuel H. Boardman State Scenic Corridor
Direction: Head west from Medford along I-199 South and I-101 North towards Brookings. From there follow I-101 North for about 6 minute to Samuel H. Boardman State Scenic Corridor. The whole trip takes approximately 2.5 hours.
The dramatic Samuel H. Boardman State Scenic Corridor is a must-see destination on the Oregon Coast. This thickly forested, rugged coastline extends for 12 miles and offers some of the most gorgeous views. Thanks to its raw beauty, the Samuel H. Boardman State Scenic Corridor can easily be the highlight of your Oregon road trip.
Here are some of the best stops along the Samuel H. Boardman State Scenic Corridor stops
- House Rock
- Whaleshead Overlook
- Thomas Creek Bridge
- Natural Bridges (one of the places I fell in love with on our Oregon road trip)
- Thunder Rock Cove
- Secret Beach
- Arch Rock
Stop 2: Bandon
Continue for about 1.5 hours on I-101 North along the coast to Bandon. Named after a small town in Ireland, the city is famous for its beaches and rock formations, including Face Rock State Scenic Viewpoint.
Stop 3: Coos Bay
You can add Coos Bay as an additional or alternative stop to your Oregon road trip adventure. Located about 20 miles away from Bandon, it continues to impress with panoramic views of the Oregon Coast.
Stop 4: Eugene
Direction: From Coos Bay head back onto I-101 North for about 27 miles, then turn right onto OR-38 East and continue on for another 50 miles. Near Cottage Grove merge onto I-5 North. Stay on it for 30 miles till you get to Eugene. If you plan your Oregon road trip during summer and spring when the days are longer, you can add a visit to Terwilliger Hot Springs to your itinerary.
We spent a night at Econo Lodge, Eugene. Within a 7-minutes walk from the hotel, we found an Indian restaurant, Evergreen Indian Cuisine. The place was pretty packed, but it offered a dinner buffet even late in the evening.
Our second favorite restaurant in Eugene is Mucho Gusto Mexican Kitchen. With the focus on locally grown produce, the restaurant serves hearty and affordable burritos, burrito bowls, tostadas, and taco plates.
DAY 2: EUGENE TO THE DALLES VIA PORTLAND
The second day of the Oregon road trip includes a decent amount of stops and may appear as an overwhelming journey. The majority of these destinations, however, are located within a short drive from each other, leaving you with enough time to explore them through and through.
Stop 1: Portland
Direction: Head north on I-5 for approximately 2 hours. Your next road trip destination is Portland, the largest city in Oregon. Spend a few hours exploring the city before heading east toward the Columbia River Gorge.
What to Do in Portland, Oregon
- Visit a zoo, forestry museum, rose garden, and the Japanese garden in Washington Park
- Hike in Forest Park
- Grab a bite at Pine Street Market
- Shop at Union Way
- Get new books at Powell’s City of Books
Stop 2: Bridal Veil Falls
Direction: Continue heading to the east along I-84. Drive for approximately 25 minutes, then take exit 28. From there turn right onto the Historic Columbia River Highway and travel for about 2 minutes until you reach Bridal Veil parking lot.
Hike: To see the waterfall you need to hike. There are two hiking rails. The upper, shorter trail gives you a good overlook of the surrounding area. And the lower, short and easy 0.6-mile round-trip trail takes you directly to Bridal Veil Falls.
Stop 3: Latourell Falls
Jump back in the car and drive for another 6 minutes to Latourell Falls. You can see the waterfall right from the parking lot. There are also two short trails. The first one leads to a small observation platform. The second trail goes down to the plunge pool, so close to the stream that you can even touch the water as it cascades down.
Stop 4: Wahkeena Falls
After admiring the beautiful Latourell Falls, drive 12 minutes back down the Historic Columbia River Highway. Similar to Latourell Falls, Wahkeena Falls can be seen from the parking lot. The waterfall starts as a fan that rushes down a cliff and eventually turns into a creek. This small stream continues to carry water farther away from the base of the waterfall.
When visiting Wahkeena Falls in Oregon, make sure to stretch your legs and add a short 0.2-mile hike to your road trip itinerary. The trail takes you to a stone arch bridge with the best views of Wahkeena Falls.
Stop 5: Multnomah Falls
Multnomah Falls is located just 2 minutes away from Wahkeena Falls. With its powerful streams and the historic Benson Bridge, it’s one of the biggest and busiest waterfalls in Oregon. Therefore, finding a parking spot here can be an issue even on a rainy day.
Stop 6: Horsetail Falls
Continue your road trip to the east via the Historic Columbia River Highway in Oregon for another 5 minutes until you reach Horsetail Fall. This waterfall is located by the road and is entirely visible from the parking lot.
As you get back onto I-84 and drive east to The Dallas, check out the Bridge of the Gods, Cascade Locks, and Hood River. You can spend a night in or near Hood River. Accommodations is The Dallas, however, are cheaper than in Hood River. We stayed at Oregon Motor Motel in The Dallas. When it comes to dinner options, we’d recommend stopping at Kobe Hibachi Sushi.
DAY 3: THE DALLES TO BEND
Stop 1: Trillium Lake
Direction: From The Dalles head back to the Hood River, located about 20 miles away. Then drive southwest on OR-35 for approximately 50 minutes before turning left onto Trillium Lake Road. In about 5 minutes you’ll get to your first destination of day 3 of the Oregon road trip.
TIP: Make sure to check weather conditions and get snow chains if you travel to Trillium Lake in winter. On top of the deep snow, the road to the lake can be closed during this time of the year.
While driving to Trillium Lake, keep checking the view on your right. The snow-capped summit of Mount Hood towering over endless vineyards will accompany for a while.
Stop 2: Smith Rock State Park
A few hours is enough time to explore Trillium Lake. The next destination on our Oregon road trip is Smith Rock State Park, located about 1 hour 40 minutes away. The park is notable for its deep river canyon, sheer cliffs of tuff and basalt, and scenic views. There are plenty of hiking trails to see different sides of the place. One of the easiest and shortest paths is the Rim Rock Trail followed by the 2.5-mile River Trail.
The town of Bend is located about 35 minutes south. And if you want to stretch your budget further, Dunes Motel offers some of the most affordable rooms in the town.
DAY 4: BEND TO MEDFORD
Stop 1: Pilot Butte
Before you leave Bend and continue your road-trip adventures exploring Oregon, head over to Pilot Butte. This scenic lookout is set on the eastern part of the town and offers splendid views of Bend and the Cascade Range. The road to the Pilot Butte is normally open from mid-April until late fall. But a 1-mile hiking trail allows you to reach the place all year round.
Stop 2: Crater Lake National Park
Once you say goodbye to Bend, drive southwest for about 1 hour 40 minutes to Create Lake National Park. The park is known for its namesake Crater Lake with deep blue water. The creation of the famous lake is attributed to the now-collapsed volcano, Mount Mazama.
TIP: Some sections of Crater Lake National Park are accessible all year long. Others may be closed during the colder seasons. So, make sure to check the park’s website for all possible road closures.
When in the park, check out the Rim Drive, a scenic drive surrounding the lake, and the Sun Notch Trail. The latter astounds with the stunning views of Crater Lake and a tiny island called Phantom Ship.
After stretching your legs in Greater Lake National Park, hit the road once again and drive back to Medford. The last leg of this Oregon road trip takes approximately 1 hour 30 minutes. Upon arrival, make sure to stop at El Arriero Mexican Restaurant for the best Mexican food in town.
