View of Mt. Shasta on I-5 S

 

From snow-capped peaks of the Shasta to tax-free shopping, to guilt free wining and dining, here is how a standard drive to Portland and back turned into a curated Pacific Northwest experience, writes Vansh Gupta.

Living in the Bay Area, we are often guilty of thinking the world revolves around the tech bubble. We are spoiled with beaches, mountains, and downtowns, but sometimes, you just need to hit the road and go somewhere where the wallet feels at ease.

Recently, I traded the 880 and 101 for the I-5 to see if it’s as boring as people make it out to be. The verdict? If you know where to stop, the drive is the destination.

Glimpses our Insta-worthy meals throughout the trip.
Glimpses our Insta-worthy meals throughout the trip.

The Ascent. Our first major pitstop was Redding. Craving stomach fuel, we struck gold at The Brunch House. Since we traveled on Thanksgiving to beat traffic, options were scarce, but this spot delivered a hearty Californian brunch that powered us up for the first main character: Mt. Shasta. Even without snow at the base, the volcanic peak stood in all its white-coated glory.

We made our base in Beaverton at the Tru Hotel by Hilton Aloha. Just 15 minutes outside Portland, it’s a welcoming suburb with plenty to do. Famished from the cold, we found Lanna Thai nearby. A no-frills spot, it served one of the best Thai meals I’ve had. Back at the hotel, we almost didn’t make it to bed, distracted by the lobby filled with coffee, a pool table, and games.

Pioneer Place, Portland, Or.

The “War Zone” (That Wasn’t). The next morning, we headed for the “War Ravaged” Portland. Clutching our water bottles and protecting our wallets, we stepped out at Pioneer Place near the Apple Store and Louis Vuitton. We didn’t know what to expect in this supposed «anarchy hellscape.» Sorry Trump. Clearly you haven’t visited Portland recently.

Protestors at Apple Store – Pioneer Place, Portland, Or.

Amidst the rain and clouds, the city gleamed with Christmas spirit. We saw locals holding mountains of shopping bags and a tree lighting ceremony at the town square. It felt like Downtown San Jose, but cleaner and more affordable. The only sign of “anarchy” were protests situated amidst the luxury stores.

Shopping done, we grabbed sandwiches at Potbelly (the PNW equivalent of Mr. Pickles). Fresh ingredients and delicious dressings made this spot an instant hit. The Toasted Smores Bar for dessert is a must visit, as well. Next stop? More shopping. Oops.

A creative ad at the Woodburn Outlets.

Tax-Free Therapy. A trip to Oregon isn’t complete without a pilgrimage to the Woodburn Premium Outlets. It’s massive and, best of all: NO SALES TAX. For a Bay Area resident accustomed to seeing over 10% tacked onto every bill, this feels like an automatic discount. The place was buzzing like a fair during Black Friday, and I celebrated the savings with croissants from Le Macaron. I was also beaming at the gas prices throughout Oregon.

Lobby of The Lodge at Riverside in Grants Pass, Or.

The Detox. After the urban rush and shopping spree, we headed south to Grants Pass for «the detox.» We checked into The Lodge at Riverside late, welcomed by freshly baked cookies. The next morning revealed the surprise: a serene landscape right on the Rogue River. The air felt cleaner. Even I—usually the laziest person—went for a morning walk.

Glimpses of our Insta-worthy meals throughout the trip.

After a breakfast of fresh waffles, potatoes, toast, and coffee, we crossed the bridge next to our stay into Applegate Valley, Oregon’s answer to Napa. We spent the afternoon at Schmidt Family Vineyards. Between the wood-fired pizza and manicured gardens, it rivals any California vineyard experience—just with a refreshing chill in the air. We even squeezed in a drive through historic Jacksonville, a town that feels like a Gold Rush movie set.

Glimpses our Insta-worthy meals throughout the trip.
Views of the Schmidt Family Winery in Applegate Valley, Or.
Views of the Schmidt Family Winery in Applegate Valley, Or.

The Home Stretch. The drive home gave us one last clear view of Shasta before a burger stop at Drizzle and a walk across Redding’s festively illuminated Sundial Bridge.

Views of Sundial Bridge in Redding.

So, is the I-5 boring? Only if you don’t venture around. We returned to the Bay Area with a full trunk and clarity in our heads. In a world of volatile markets, a tax-free, stress-free road trip is a guaranteed return I’ll take any day. Oregon, I hope to see you again, soon!

Best part? Oregon’s low gas prices with higher octane.

 

All images: Vansh A. Gupta/Siliconeer