If you could design the perfect outdoor town from scratch, you'd probably end up with something a lot like Bend, Oregon. It's got 300 days of sunshine, a river running right through downtown, world-class mountain biking out the back door, a volcano you can summit before lunch, and more breweries per capita than almost anywhere in the country. Oh, and the entire Cascade Range is your backyard.
Bend is the kind of town that rewards repeat visits — there's always another trail, another lake, another patio. Here's our guide to making the most of it.
Mountain Biking
Phil's Trail Complex
This is why mountain bikers move to Bend. Phil's Trail is a sprawling network of singletrack just minutes from downtown. The trails wind through ponderosa pine forest on volcanic soil that drains fast and stays buff. There's something for everyone—flowy beginner loops, punchy intermediate climbs, and technical descents that'll keep expert riders honest. Start with the Phil's Trail to Ben's Trail loop if it's your first time.
Pro tip: Go early in the morning during July and August. By 2 PM the dust can get thick. Bring a buff for your face.
Mount Bachelor Bike Park
If you want lift-served downhill, Mount Bachelor opens their bike park every summer. It's got everything from smooth green runs to gnarly black diamond rock gardens. Rent a full-suspension rig at the base if you didn't bring your own.
Gear up at: Trek Bikes, Competitive Cyclist
Fly Fishing
The Deschutes River
The Deschutes is one of the best trout rivers in the West. The stretch through Bend is loaded with rainbow trout and brown trout, and you can literally walk from downtown restaurants to prime fishing water. The river runs cold and clear year-round thanks to volcanic spring feeds.
For the best action, head to the upper Deschutes between Wickiup Reservoir and Bend, or drive north to the lower Deschutes canyon for steelhead in the fall. A drift boat trip with a local guide is worth every penny.
What to bring: 5-weight rod, dry flies in summer (pale morning duns and caddis are money), nymphs and streamers in spring. Simms waders are the go-to out here.
Crooked River
About 30 minutes north of Bend, the Crooked River at Smith Rock is a year-round tailwater fishery. It's stocked with redband trout and fishes well even in winter. Plus, you get to cast with Smith Rock's incredible spires towering above you.
Hiking
South Sister
Distance: 12 miles | Elevation Gain: 4,900 ft
South Sister is the third-highest peak in Oregon, and it's a non-technical walk-up—no ropes or scrambling required. That doesn't mean it's easy. It's a long, steady grind through forest, lava fields, and volcanic scree before you reach the summit crater with its tiny glacier lake. The views from the top are absolutely massive—you can see Mount Hood, Mount Jefferson, Broken Top, and the entire Cascade chain stretching north.
When to go: Late July through September, once the snow melts off the upper mountain. Start by 5 AM to beat the afternoon thunderstorms.
Broken Top Crater
If you want something a bit shorter but equally dramatic, hike to the Broken Top crater. The trail takes you to a glacial lake surrounded by crumbling volcanic walls. It feels like you're on another planet. About 8 miles round trip.
Smith Rock State Park
Oregon's rock climbing mecca also has excellent hiking. The Misery Ridge loop (3.8 miles) gives you incredible views of the Crooked River canyon and the rock spires. It's steep but short, and the views are worth every step.
On the Water
Bend is a paddling town. The Deschutes River Paddle Trail runs 10 miles through town, and on any summer afternoon you'll see hundreds of people floating it on SUPs, kayaks, and inner tubes. Rent gear from the shops along the river or bring your own.
For something more remote, paddle Sparks Lake or Hosmer Lake in the Cascade Lakes region. Hosmer is fly-fishing-only and crystal clear—you can see the brook trout swimming below your kayak.
Gear up at: NRS for kayaks and PFDs
The Après Scene
Let's be honest—part of the Bend experience is the beer. Deschutes Brewery, Boneyard, 10 Barrel, Crux Fermentation—they're all within a few miles of each other. The classic move is to finish a ride at Phil's and head straight to Crux, which has a killer patio with views of Broken Top.
Getting There & Getting Around
Bend has a regional airport (RDM) with direct flights from several West Coast cities. If you're driving, it's about 3 hours from Portland over Mount Hood. A car is essential—you'll want it to access trailheads and the Cascade Lakes.
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