Fly into Redmond Airport, just 30 minutes from Bend, a small, green city of 100,000 inhabitants, passionate about two things: the great outdoors, and great food and drink. These two things about sum up Oregon. So while you can also fly into Portland and rent a car there to start the journey, I find Bend a more localized introduction to the state.

Stay

• The Oxford: Only boutique hotel in town. Let me arrange the King Room with a terrace for you—it’s the best in the building. The ground-floor restaurant is also worth a stop.

• Bunk & Brew: Clean and cozy budget accommodation with private rooms, dorms, and even hammocks for rent outside on the warmer nights. Food trucks in the backyard. Free beer upon check-in. Chill vibes.

Do

• Float the river: The classic Bend activity. Kayaks, tubes, and paddleboard rentals are readily available. Just be careful of the rapids.

• Walk: Up to Pilot Butte Viewpoint for panoramic views of the area and Cascade Mountains, or the Deschutes River Trail for something flatter and greener.

• Munch & Music: Summer Thursday nights in Drake Park. Free event, local vendors, local bands, local vibes.

Eat & drink

• Farmer’s Deli: Food truck using hyper-local ingredients only. I had a breakfast sandwich and knew where my eggs, cheese, and bread came from.

• D&D Bar: Bend’s proper dive. Pub food had no business being that good.

• River Pig Saloon: Some of the best curly fries ever?

• UPP Liquids Pub: $4 pours on Thursdays. Yuzu ginger beer was delicious.

• Monkless Belgian Ales: Crazy selection of Belgian beer.

• Bend Brewing: Large outdoor space on the river. Great for long afternoons, card games, family gatherings.

This selection of stops covers the southern half of Oregon State. It can be done in one day, but I’d recommend two nights on the 101 to give yourself that proper, laidback road trip feel.

• Cape Perpetua Overlook & Thor’s Well: Easy walk through Oregon's coastal pines. Be mindful of misty morning weather. It can obstruct views, but I found the mist in the trees equally as beautiful.

• Haceta Head Lighthouse: One of many historic lighthouses, overlooking a beautiful bay. There's also a small museum/visitor's center with a bit of history.

• Sea Lion Caves: Massive colony of the silliest creatures. $18 adult admission. Alternatively, further south, find Simpson Reef Overlook for a free option. You won't get as close, but you can still smell them.

• Oregon Dunes Recreation Area: Frank Herbert's inspiration for "Dune." Pull off at Oregon Dunes Day Use area for easy views of this sandy stretch of otherwise rocky coast.

• Bandon: Tony’s Crab Shack or Bandon Bait for fish and chips. Bandon Rain for local craft ciders.

• Langlois Market: Didn’t make it here before they closed for the day, but apparently they have killer hot dogs.

• Sunset: Cape Sebastian for an easy 10-minute walk to an elevated, uncrowded, endless coastal viewpoint. Myers Creek Beach for the seaside.

• Natural Bridges: Probably the most picturesque 101 pulloff. Pictured at top of guide.

• Brookings: Final town before the state line. Good place to grab groceries and gas before heading towards your next stop.

Welcome to the most spectacular trees in the world. Nothing can prepare you. Give yourself two days. (I could have stayed forever.)

Stay

• Smith River, California: Rustic accommodations in nature, close to park entry road. I did a glamping sort of thing through AirBnb.

• Crescent City: Nearest city with a few larger motels, a variety of dining options. By the water.

Jedediah Smith Redwoods State Park

Before your hike, first get breakfast at the Historic Hiouchi Cafe. Try to arrive early or expect a bit of a wait.

There are a handful of trails in Jedediah. Here are the two I took.

• Grove of Titans: Shorter option. ~1.5 miles round trip. Quite accessible as there is a raised walkway to protect roots. Beautiful payoff for almost no effort.

• Boy Scout Trail: Longer option. ~5 miles round trip. Otherworldly old-growth forest trail. I couldn’t walk more than five minutes without stopping in my tracks, in awe. Home to the namesake Boy Scout Tree, 238 feet (72 meter) tall and over 2,000 years old. There were hardly any people on this trail, as this area is less-touristed than the other Redwood parks further south.

If you needed another a reason to visit, here's a bonus. Park entry is free.

Pretty little town in southern Oregon. Cute main street. Home to the well-known Oregon Shakespeare Festival, an expensive but delicious ice cream shop, and a banging beer bar. A perfectly nice stop to break up your drive back north.

• Three Penny Mercantile: Fun vintage stop.

• Skout Taphouse & Provisions: Huge selection of local brews and beyond.

• Mix Bakeshop: Delicious ice cream. A bit expensive, but you can taste the quality.

• Lithia Park: Large green space with an almost laughably picturesque babbling brook.

The glory of Central Oregon. Formed by a massive volcanic eruption thousands of years ago, this is the deepest lake in the U.S. (1,943 feet, 592 meters), and among the top ten deepest lakes in the world. $30 entry for vehicles.

I recommend the Garfield Peak Trail: a 2–3 hour out-and-back with views all the way up. It’s a steady incline to the top, requiring a decent level of fitness, but also doable in sneakers.

Opt for the Discovery Point trail for something flatter. Still beautiful.

My friend from Ashland also suggested I visit the nearby Jackson F. Kimball State Recreation Site, a bit south of the park. Unfortunately, I didn’t have the time, but it looks like a gorgeous place for swimming, kayaking, etc.

Drop your rental car in Portland (city center location ideally, to avoid an Uber from the airport). Then, drop your bags and hit the pavement.

Stays

• The Nines: Luxury choice, heart of downtown. (Book with me and get $100 food/bev credit, breakfast daily, upgrade and extended check-in/out whenever possible.)

• KEX: Boutique/budget option on the East Side.

My 36 hours in Portland involved almost nothing besides eating and drinking and thrifting. What a crazy good food city. Also… big daytime happy hour culture here—food included. Very easy to eat/drink on a budget.

Food & drink

• Meta Pizza: Super solid za. Owner is a good dude.

• Jake’s Famous Crawfish: An old-school classic. Go for happy hour starting at 3 p.m. for the deals.

• Mucca Osteria: Regarded as the best Italian restaurant in town. I have no means of comparison, but I did have the duck and candied fennel linguine, and it was divine. Reservations recommended.

• Screen Door: Louisiana-style comfort cooking. Chicken and waffles are up there with the best I’ve ever had. Biscuits and gravy, too. Make a res or expect a wait.

• Teardrop Lounge: Portland institution. Cocktail people, don’t miss.

• Loyal Legion: Crazy beer bar. Must have had 50+ taps. My cocktail friend also approves.

Vintage stops

• Telephone Vintage: Big space, requires a bit of digging. Rotating coat rack. Found my friend a mint condition collector’s item Trailblazers hat.

• Tip Top Vintage: Awesome assortment of clothes, knick-knacks, furniture. Lots of rugs.

• Banshee: Higher-end women’s pieces. Well-curated and super cute.

• Yellowstone Vintage: Two locations. Variety of clothing in top condition.