Most Bend travel guides cater to weekend getaways or top-ten lists. That didn’t work for us and the month-long stay we planned. Extended trips require a backlog of options to account for must-do hikes, town recovery days, trail closures, smoke pivots, or the days you simply don’t feel like leaving the couch.
We spent months planning what to do, what to see and how to plan out the list of 150 potential adventure activities. This is what we actually ended up doing during our 32-night stay in Bend, OR.
Trip at a Glance
Nature Highlights: We explored 21 hikes, 3 major volcanic summits, 5 cinder cones and crater rims, 8 waterfalls, and 3 caves.
Outdoor Adventure Highlights: We completed 2 e-bike days, 1 backcountry OHV adventure, 2 Deschutes river floats, and 4 rounds of disc golf.
Trail Time: We logged 106 miles of trails, 22,822 ft elevation gain (via AllTrails) and took 581,228 steps over the course of the entire trip.
Energy Days: We had 8 strenuous/high, 8 moderate, 11 low and 6 rest/wildfire days during the trip.
Bend Activities
Here’s a complete list of everything we saw and did during the trip.
Week 1: Days 1-7
| Day | Activities | Energy Level | What we did |
|---|---|---|---|
| 1 | Arrival, Logistics and Town Walk | Low | Check-in, full grocery run, gear staging, and neighborhood walk. |
| 2 | Pilot Butte, Farewell Bend Park and Bend Ale Trail | Low | A quick walk up Pilot Butte for amazing views, exploring Farewell Bend Park and our first Bend Ale Trail at Monkless Ale. |
| 3 | Misery Ridge (Smith Rock State Park) and Coyote Den Disc Golf | High | Completed the loop at Misery Ridge and played the first 9-holes at Coyote Den Disc Golf. |
| 4 | Green Lakes Trail | High | First alpine hike along Cascade Lakes Highway. Permit required, approximately 12 miles. Highly recommend. |
| 5 | Shopping, Drake Park, the Deschutes Brewery | Low | Planned on bike ride in Sunriver but needed reservations, so we did some shopping at the Bend Outlet Mall and walked to Drake Park from the Old Mill District. |
| 6 | 4th of July Events | Low | Downtown pet parade and fireworks celebration. |
| 7 | Three Fingered Jack | Strenuous | Rugged wilderness terrain hike in the Mount Jefferson Wilderness. Permit required. |
Week 2: Days 8-14
| Day | Activities | Energy Level | What we did |
|---|---|---|---|
| 8 | Disc Golf and River Float #1 | Low | 18-holes at the Pine Nursery Disc Golf and floating the Deschutes from Riverbend Park to Drake Park. |
| 9 | Obsidian Trail and Dee Wright Observatory | High | Alpine hike through obsidian, mountain views and waterfalls and a quick stop at the historic Dee Wright Observatory on the way back to Bend. |
| 10 | High Desert Museum and Float #2, and Crux Fermentation | Low | We spent the morning at the famous (and well-worth it) High Desert Museum, enjoyed another river float and experienced more of the Bend Ale Trail. |
| 11 | Mount Bachelor Summit | Strenuous | Relentless cinder and scree conditioning push straight up the ski runs. |
| 12 | Bend Ale Trail, Blockbuster and Sun Mountain Fun Center | Low | Full rest day off trail visiting local spots and the last Blockbuster. Enjoyed The Cellar and McMenamins downtown Bend. |
| 13 | Oregon High Desert Classic Horse Show | Rest | Spent the morning watching a horse jumping competition and afternoon resting. |
| 14 | Newberry Caldera Part 1 – Lava River Cave, Lava Butte and Visitor Center | Moderate | Subterranean hike in a dark lava tube paired with a volcanic cinder crater hike. We skipped the shuttle bus and walked up Lava Butte. |
Week 3: Days 15-21
| Day | Activities | Energy Level | What we did |
|---|---|---|---|
| 15 | Newberry Caldera Part 2 – Paulina Falls, Obsidian Flow Trail and La Pine State Park | Moderate | This was a big day broken into two parts: Morning: Newberry Caldera including Paulina Falls, Paulina Peak, Paulina Lake, and the Obsidian Flow Trail. Afternoon: La Pine State Park including Disc Golf, the Big ‘Red’ Ponderosa Tree Hike and Fall River Falls. |
| 16 | Tumalo Falls Day Hike and Skyline Disc Golf Park | Moderate | Shaded forest waterfall singletrack north of town and a 9-hole round at the Skyline Disc Golf Park. |
| 17 | E-Biking the Sunriver Paths and Benham Falls | Low | Cycling around the Sunriver path system including going up Lava Butte, visiting Benham Falls and enjoying the scenic river trail. |
| 18 | Tam McArthur Rim to No Name Lake | Strenuous | High alpine ridge climb to turquoise glacial water below Broken Top. |
| 19 | Mt. Bachelor’s Disc Golf Course, the Sun Mountain Fun Center and Hayden Homes Amphitheater | Low | High-elevation downhill throwing at Bachelor, mini-golf and evening show at the Hayden Homes Amphitheater. |
| 20 | Rest day including a movie at the local cinema, and Bend Ale Trail | Rest | Rest day with a movie and Upp Liquids in the Old Mill District |
| 21 | Fort Rock State Park, Fort Rock Museum and Hole-in-the-Ground Crater | Low | Day trip to the Fort Rock area with a light hike, museum and viewpoint of the Hole-in-the-Ground Crater. |
Week 4: Days 22-28
| Day | Activities | Energy Level | What we did |
|---|---|---|---|
| 22 | OHV Rental | Moderate | Wilderness exploration with OHV rental exploring the Skylight Cave, Black Sand Dunes and Cache Mountain. |
| 23 | Wildfire Smoke Day #1 | Rest | Wildfire AQI kept us indoors all day. |
| 24 | Wildfire Smoke Day #2 and Hayden Homes Amphitheater | Rest | Wildfire AQI kept us indoors most of the day until our evening show at Hayden Homes Amphitheater. |
| 25 | Wildfire Smoke Day #3 and Guided Skull Cave Tour | Moderate | Escaping surface wildfire smoke via an underground lava tube tour. |
| 26 | Crater Lake including hikes and nearby waterfalls | High | Day trip to Crater Lake to escape the smoke. Dual rim summits (Watchman & Garfield) paired with nearby Toketee Falls and Watson Falls. |
| 27 | Hot Air Balloons, Donuts and exploring the Deschutes River Trail | Low | Pre-dawn balloon launch photography followed by delicious donuts, a morning hike around the Deschutes River Trail and libations back at Upp Liquids. |
| 28 | Vista Butte and the Mt. Bachelor Disc Golf Green Course | Moderate | Quick morning hike with Sister views and a round of disc golf back at Bachelor. We were still escaping the lingering smoke and closures throughout the area. |
Week 5: Days 29-33
| Day | Activities | Energy Level | What we did |
|---|---|---|---|
| 29 | Tamolitch Falls (Blue Pool) and Clear Lake Kayak Rental | Moderate | Old-growth forest hike to a blue pool and flatwater paddling over sunken forests. |
| 30 | South Sister Summit | Strenuous | The endurance climax: 12 miles and nearly 5,000 ft of vertical grind. |
| 31 | Summit Recovery Day | Rest | Rest day with a movie at the local cinema and ice cream. |
| 32 | Canyon E-Bike Loop | Moderate | E-Bike day to Archie Briggs canyon and 7th Mountain Resort before a last night in downtown Bend at our favorite restaurant of the trip, J-Dub. |
| 33 | Checkout & Transition | Rest | Packing gear, rental turnover, and hitting the road home. |
Lessons Learned From a Month in Bend
1. Be prepared for a lot of walking
We stayed in the Old Mill District overlooking the shopping plaza near REI, and from a location standpoint, it was perfect. We could walk to almost everything in town including ale houses, coffee shops, the local cinema, restaurants, Drake Park, and evening shows at Hayden Homes Amphitheater. The flip side? Because we were staying in the busiest part of Bend, driving wasn’t really an option as parking was limited and we ended up taking about 18,000 steps every day with the extra walking.
2. Driving in Bend was worse than we expected.
Bend traffic is far worse than expected. The town seemingly outgrew itself overnight when it became overly popular with new residents. While town river floats, amphitheater concerts, and the Deschutes River Trail were easily accessible from the Old Mill District, nearly every other adventure required driving out of town. Luckily, Mount Bachelor and Green Lakes are an easy 25-minute cruise up Cascade Lakes Highway, but expect a minimum 45- to 60-minute drive in each direction for almost every other cave system, crater, secondary trail, or regional day trip.
Read more about Driving in Bend.
3. The Central Cascades permit system controls your schedule.
Day-use permits govern the wilderness trails across the Three Sisters, Mount Washington, and Mount Jefferson wilderness areas. If bad weather rolls in or wildfire smoke settles over the basin on the day of your reservation, you cannot simply postpone until tomorrow. You are forced back into the rolling 7:00 AM reservation lottery alongside everyone else competing for limited cancellations. On the positive side of things, once you do get a permit, you’ll get to enjoy a fairly crowd-free day in the mountains.
4. Weather and wildfire smoke will likely ruin at least a few of your days.
Bend summers are a bit of a wildcard. You may end up with higher than average snowpack, lightning storms that blow in two hours before an outdoor amphitheater show (yes, that happened), or wildfire smoke that ruins your hiking days. You’ll want to have a decent list of backups including lava tube tours, indoor rest days, or day trips out of the area.
5. Book popular adventures well in advance.
Do not expect to walk up and rent gear on a whim in July. High-traffic summer tourism means guided cave excursions, boat rentals, and even standard paved cruiser bike rentals in Sunriver routinely book out days or weeks ahead. We were shut out of an e-bike rental in Sunriver because we did not call ahead. Call around for reservations early so you aren’t forced to pivot on the fly.
6. The activity list will remain unfinished.
We had 32 nights on the ground and still only completed a fraction of what we researched. Central Oregon has a staggering volume of world-class terrain, and we found ourselves cutting out amazing looking hikes because we simply didn’t have enough time. You will end up skipping trails, viewpoints, and lakes that would be considered top-tier highlights anywhere else in the country to see something that is just a bit better. The good news? This means you can come back and explore more.