Oregon Trails Fly Drive

Those looking to get off the beaten track and explore the real west need look no further than this journey through Oregon.

Incredible Oregon offers a fly drive experience like nowhere else.  Scenic byways abound, remote forested mountains recall the days of frontiersmen and a rugged coast provides breath taking views at every turn. Fun and friendly towns and cities serve the freshest produce, procured from this verdant state’s farmlands, rivers, vineyards, coastal waters and microbreweries. 

Tour highlights

    • Discover Oregon’s rugged coast
    • Explore independent shops and restaurants in lively Portland
    • Stunning Crater Lake National Park
    • Discover the Applegate Valley, a true hidden gem


Days 1-2

UK to Portland

Arrive into Oregon’s largest city and discover a hip urban hotspot known for its fantastic cuisine, vibrant arts scene and array of wonderful shops.  Portland brews its own beer, roasts its own coffee and embraces the fresh produce found on its doorstep from the Columbia River to the Pacific Ocean.

Day 3

Portland to Newport

Collect your car and travel north west out of Portland toward the Pacific Coast. Taking the longer route to today’s destination allows you to see even more of this spectacular coastline, starting at the mouth of the Columbia River and the picturesque town of Astoria. Journey south along Highway 101, passing bays and fishing towns, before reaching Newport.

Day 4


Having notched up some miles yesterday enjoy a day exploring Newport and its surrounds. The Oregon Coast Aquarium is a must visit, snap a picture of the Yaquina Head Lighthouse, stroll through Newport’s historic bay front and spend an evening at nostalgic Nye Beach where boutique shops, cafés and restaurants occupy an enviable position on the seafront.

Day 5

Newport to Coos Bay

Today’s drive is not huge so take the time to make the most of your journey. Opportunities for photo stops abound as you continue south on the Pacific Coast Scenic Byway, with forested hills to your left and the lapping waves of the Pacific to your right. Perhaps stop at Oregon Dunes National Recreation Area for a dune buggy ride en route. Coos Bay, with its history as a logging town, is a convenient place to break the journey before tomorrow’s trip in land.

Day 6

Coos Bay to Grants Pass

Just south of Coos Bay is the town of Bandon, marking the end of your coastal journey. Turn inland along scenic Highway 42 and gradually vineyards begin to cover the hillsides. Stop for some wine tasting or to pick up a souvenir bottle before arriving into the town of Grants Pass.

Day 7

Grants Pass

Spend today driving the scenic Applegate Valley in southern Oregon, where streams from the surrounding mountains feed the patchwork of small-scale vineyards which are interspersed with meadows and quaint towns. Make a stop in the former mining town of Jacksonville where every building is on the National Historic Register before returning to Grants Pass. In the evening book onto a magical dinner cruise on the Rogue River or for those in search of adrenaline, try an exhilarating jet boat ride.

Day 8

Grants Pass to Bend

Travel on the Volcanic Legacy Scenic Byway to its northern end and the spectacular Crater Lake National Park. Crater Lake is open year round although access is restricted as winter sets in. There are a variety of walking routes depending on your time and fitness but each turn yields incredible views of this wonder – the deepest lake in the USA. The azure blue waters that have collected in an extinct volcano’s crater are punctuated by a couple of dramatic islands and surrounded by 2,000ft sheer cliffs.

Day 9


Bend is famed for its enviable location in the wilderness, making it a great hub for adventures in the great outdoors. For a leisurely afternoon drive the loop of the Cascade Lakes Scenic Byway, which winds its way through the Deschutes National Forest. Walkers, photographers and nature lovers can ride the chairlift to the summit of Mount Bachelor while the more adventurous can jump on a mountain bike or join a river rafting trip.

Day 10

Bend to Baker City

Today’s drive eastward brings you onto the Journey Through Time Scenic Byway. This stretch of road has achieved such an evocative name because of the array of historic points along the route. Take time to stop at the amazing Painted Hills where the scenery is daubed in lines of yellow, red, black and gold rocks.

Day 11

Baker City to Pendleton

A gentle drive north brings you to the Umatilla Indian Reservation and the remarkable museum at the Tamastslikt Cultural Institute. This fantastic facility tells the story of westward expansion from a Native American point-of-view and demonstrates the heritage of tribes who have lived in Oregon for 10,000 years. Finish the day in the fun town of Pendleton with its wild west, country feel.

Day 12

Pendleton to Hood River

Join the Columbia River and enjoy the stunning drive along the banks of this meandering waterway.

Day 13

Hood River to Portland

It is an easy 1 hour drive back to Portland but we recommend booking a late flight out so you can take some time to explore on your last day. Stop at the Cascade Locks for a vanilla ice cream cone at Eastwine Drive Inn, or maybe the passengers will want to try the beers at Thunder Island Brewing with views of the mighty Bridge of the Gods. Take the old highway back to Portland and drop off your car before boarding your flight home. 

Your vehicle

Full Size 4 Door

Dodge Charger, Ford Fusion or similar

Capacity:Up to 4 adults & 1 child
Luggage:Up to 3 suitcases & 1 medium sized bag

Your car hire includes:
  • Unlimited mileage
  • Zero excess
  • Loss damage waiver
  • Theft waiver
  • Third party liability
  • Supplementary liability insurance (up to $1million).
  • Rentals starting in California include free additional drivers.

Min Rental age: 21. Drivers under 25 will be charged a supplement locally.

Additional Info

Best at Travel works with a number of car hire companies to bring you a huge selection of routes, depots and car types.  Precise conditions and inclusions vary between companies so ask your Best at Travel consultant for details of what is the best hire for you.


This fly drive itinerary runs all year round

Let us plan your perfect trip to Portland, call 0203 811 7785 to speak to one of our experts

Enquire now

Why choose us?

Best at Travel

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We constantly negotiate exceptional hotel deals and exclusives for our customers.


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