My Great Big Bend, Oregon Mountain Biking Adventure


Last week (July 2016) I finished a mountain biking trip in Bend, Oregon. The trip included seven days of riding, camping in a hammock, and exploring the town of Bend.

It was a spectacular trip!

I biked 277 miles, rode 18 of the trails in the Bend area (just a small fraction of the mountain biking trails in the Bend area).

The trip was filled with spectacular mountain trails, high desert landscape, challenging climbs, and thrilling descents. The entire week was a refreshing break.

Here is what I learned…

  • Bend, Oregon is one of the best places to ride in the USA. Hundreds of miles of well-marked trails and a large number of rainless days allow for a wonderful mountain biking ecosystem. In my seven days of riding, I only rode a small fraction of the vast number of trails available in the Bend area.
  • People in Oregon are kind and helpful to visitors. I always received a kind greeting and a helping hand wherever I went.
  • God gave me good health and allowed me to the encounter another small slice of the vast universe he created. I am thankful to God and acknowledge his wonder, power, and creativity. It is his world, and he allows me to live in it.

Below are my daily experiences, filled with photos, maps, and descriptions of my rides. I hope that you use my experiences to gain a perspective about Bend and that you benefit from my experience …

Day Before the Bend Mountain Biking Trip

Day One – Eugene to Bend

Day Two – Into The Wild

Day Three – Mountain Biking is Art

Day Four – Moving Day

Day Five – Dirt Paths of Life

Day Six – Marianne and Houdini

Day Seven – Easy Day

Day Eight – Last Day (Perfect Day)

Day Eight – Last Day (Perfect Day)

Woke at 7:00 am and packed up to check out of Motel 6. I am moving to a hotel that is close to the bus stop where I pick up a bus that goes from Bend to Portland. Checked out of Motel 6 at 8 am and biked through the town of Bend. It was cool (about 55 degrees) and sunny. Stopped at a local restaurant to fuel up with a bean, egg, and cheese breakfast burrito.


Climbing fuel – breakfast burrito.

I am completely excited about my last day in Bend. I planned to ride TiddlyWinks trail (the 7.2 mile trail on which I fell two days ago), and Storm King trail (4 miles). They are both super fun trails and I begin the day with unbridled anticipation. Rode out of Bend up the Cascade Lakes Highway, 13.5 miles, to Wanoga Snow Park. The trailhead for Tiddlywinks is there. Arrived at the Tiddlywinks trailhead (about 5,500 feet in elevation) at 10:40 am.


Rode to the most challenging section of the trail and stopped to rest and get a drink. The challenging section had danger warning signs, but riding this section of the trail is mountain biking at its best.


Danger ahead – thumbs up!

Loved descending the challenging section of Tiddlywinks trail. The big-time downhill curves and switchbacks were super fun, leaning into the banked berms while riding the disc brakes to keep a safe speed. Zig-zagging through pine trees, flying through the jumps, and nailing the landings was super fun. I rode with a heightened sense of awareness – using all my skills, balancing efforts, quickness, and agility to negotiate the downhill course.


Downhill section of Tiddlywinks trail near Bend, Oregon. Bumps, jumps, banked berms, and fun!


Rock section of Tiddlywinks trail – near Bend, Oregon.

Stopped at the bottom of Tiddlywinks trail for lunch (granola, trail mix, and water). While eating lunch, I noticed a bike about 20 feet up in a tree and took a photo. I wandered, “Did the rider get some big air on a jump and met the tree mid-air? Or was this a rider who met a tree when the snow was so deep that 20 feet up was ground level (snow melted in the spring)?”


Lunch spot at bottom of Tiddlywinks trail.


Bike in tree at bottom of Tiddlywinks trail – near Bend, Oregon.

Saddled back up after lunch and rode the flowy and fast Storm King trail. The ride was mostly downhill and was invigorating.

After riding Storm King trail, I connected up with the Deschutes River trail and rode it downriver towards its end near Bend.

Rode into Bend and checked into my new hotel. Then I returned my bike to the bike shop – loved the sign outside the bike shop. It was late afternoon and was sunny and 80 degrees F.


Walked to dinner and then walked about 2.5 miles to the hotel. Cleaned up and packed up to leave Bend via bus early the following morning.

It was a superb day – a perfect day – the best way to end my mountain biking adventure in Bend.

I rode 38 miles today and topped out at 5,500 feet in elevation.

Back to My Great Big Bend Oregon Mountain Biking Adventure.

Day Seven – Easy Day

Woke up at 6:30 am and got on the bike at 8:30am. I planned on making this an “easy day”, spending some of the afternoon exploring the town of Bend.

Rode out of Bend ascending up Skyliner road. It was 57 degrees F when I began riding. Took Skyliner road until it turned into a dirt road that leads to Tumalo Falls. Rode the dirt road to Tumalo Falls and climbed to the top of the falls.

Tumalo Falls – near Bend, Oregon.

Rode the Tumalo Creek trail (2.9 miles) to Skyliner trail (3.2 miles). Stopped to eat lunch (granola bar and trail mix). Cruised on to what has become one of my favorite trails in the Bend area – Lower Whoops trail (1.8 miles).

Blew down Lower Whoops, taking the air and cruising the banked curves. Lower Whoops is super fun! I am very thankful for the health and the coordination with which God has blessed me in order to ride trails like Lower Whoops.

Flew down Phil’s trail (6.1 miles) loving its fast, flowing curves and easy-to-negotiate hazards.

Stopped at the bottom of Phil’s trailhead and played on the Slalom Loop trail. Rode the most difficult (black diamond) part of the trail. It had lots of jumps and curves.

Slalom Loop trail at Phil’s trailhead – near Bend, Oregon)

Rode back to Bend and cruised downtown. Downtown Bend had colorful hanging flower planters on each street corner. Bend is beautiful in the summer.

Hung out in Drake Park on the Deschutes River, near downtown Bend. People are floating the river in groups. The park is filled with walkers, bikers, river floater, families, and others outside on this beautiful summer day. It is a warm 87 degrees F.

Then ate dinner at Bend Burger Company in downtown Bend.

Rode back to the hotel and cleaned up.

I rode 35 miles today.

Day Eight – Last Day (Perfect Day)

Day Six – Marianne and Houdini

My bike is named Marianne. The bike shop from which I rented names their bikes so that renters in groups may easily identify their bike when many bikes are parked together. Marianne is a Specialized  Rockhopper 29’er. She is a hard tail (meaning front shock/suspension, but no rear shock/suspension),  29 inch wheels, 24 speeds, and hydraulic disk brakes.Marianne has been a good bike – handling the stress of up and downhill riding, clattering over rocks and roots, carving S-turns through banked berms, braking my speed with disc brakes, flying off earth mounds through jumps into the air, complete with bone-jarring landings.

Marianne – the Specialized Rock Hopper hardtail 29’er mountain bike.

Woke up at 7:30 am, temperature was about 55 degrees F when I left the hotel and will go to 82 degrees F today. It is a beautiful, sunny day. Began riding at 9 am.

Rode out of Bend on the Cascade Lakes Highway towards Mt. Bachelor. Took about 3 hours to climb 18 miles to the Swampy Lakes trailhead at 5,800 feet altitude. I was exhausted by the time I arrived at the Swampy Lakes trailhead (the altitude gets me every time). It was noon, so I ate lunch (granola bar, trail mix, and water), laid down in some mountain grass, and took a nap in the sun.

After a brief nap, I mounted up and ascended Swampy Lakes trail (2.1 miles) and hit 6,000 feet altitude. Took several wrong turns, backtracked several times, and finally found South Swede trail (3 miles of up and down). Then i connected with Sector 16 trail (3.3 miles). Then i rode down Upper Whoops trail (2.1 miles), followed by the super-fun downhill Lower Whoops trail (1.8 miles). The last trail for the day was downhill on fast and flowy Phil’s trail (6.1 miles). I was beat from all the riding and was dehydrated, even though I had been drinking all day.

Ate dinner at Taco Salsa on the route between my trail’s end and my hotel. Drank four huge glasses of a cold soft drink – hit the spot as I was feeling dehydrated.

Rode to the town park (Drake Park) and laid down in the cool, green fescue grass and enjoyed the evening sun.

Lots of teenagers and young adults were walking thru the park looking intently on at their phones. They would walk a certain direction, then look at their phone and change direction. I asked if they were geo-caching. One girl answered, “Kind of – we are finding Pokemon characters all over the park – geocaching for 90’s kids”.

A brown rabbit hopped up to me while I was at the park. He hung close to me for about 30 minutes. His owner came by and told me the rabbit’s name was Houdini. Drake Park in Bend is a happening place!

At dusk I rode back to Motel 6, showered, and cleaned up, and fell asleep. It was another good day and I fell asleep feeling blessed.

I rode 42 miles today, ascending from 3,500 feet to 6,000 feet in altitude (and back down again).

Day Seven – Easy Day

Day Five – Dirt Paths of Life

Woke up at 7:30 am in the Motel 6 – what a luxury (compared to camping in a hammock)!

Did not eat breakfast – just geared up and got ready to ride. It was 54 degrees F outside when I began riding.

I saddled up and hit the trail for another day, cranking up the mountain towards Mt. Bachelor. I’ll use all my 24 gears on today’s ride – another day of adventure!


“Of all the paths you take in life, make sure a few of them are dirt.” ― John Muir

I wonder what John Muir was like many years ago – perhaps he would be a mountain biker if he lived in this day and time! I am privileged to take his advice on this day, following some wonderful dirt trails on my mountain biking adventure.

It is another great day. I am thankful for the exquisite beauty that God made in his creation. The way the sun rises to warm my skin, the way a tree grows and extends its shade, the grace of a bird in flight on the mountain updraft, the symmetry of a bright flower’s bloom, the thundering rush of a stream over a waterfall falling at its base and running downstream. God’s hand is everywhere I see, hear, and feel – and in everything I experience.

And I am grateful for the health with which God has granted me. Due to health issues, many are not able to ride mountain trails as I ride them. And my health is not taken as granted – I consider health a gift from God each and every day.

So I started the day thankful and amazed at what God had in store. I rode out of Bend towards Mt. Bachelor, on the Cascade Lakes Highway, headed for an epic advanced/difficult trail called “Tiddlywinks” (7.2 miles long).


Sign on Cascade Lakes Highway – near Bend, Oregon

The climb was gradual for the first few miles out of Bend. But the elevation grade kicked up soon. I geared down and kept cranking. Many vehicles headed out of Bend on the highway carried mountain bikes, road bikes,  kayaks, paddle boards, and other recreational equipment. Many bikers passed me as we cranked uphill. Most of the bikers  going up and down that highway were road bikers. Each had an encouraging  word as we passed. I saw a cross country skier with poles and roller blades going up and down the highway – he was training seriously in the off season (summertime).

With stops to rest and to check navigation, it took me about 3 hours of ascending 13.5 miles to get to the Tiddlywinks trailhead. I stopped and ate lunch (granola bar, trail mix, and water) near the trailhead.

Tiddlywinks trailhead, near Bend, Oregon.

Don’t let the trail name Tiddlywinks confuse you. This is one epic mountain biking trail, not some fru-fru trail. The trail begins with a mile, or so, of relatively flat downhill. Then some climbing to a ridge. After this things get interesting – multiple danger warning signs on the trail – see the “skull and crossbones” on the pink sign below.

Some serious. steep downhill trail after the signs. I rode down multiple switchback curves through the trees – the trail was similar to a motorcycle motocross track with MONSTER banked earth berms and deep ruts.

Switchback curve and banked earth berm on Tiddlywinks trail – near Bend, Oregon.

Switchback after challenging switchback took me downhill. It was a big drop. I thought the curves would never end. It was mountain biking heaven! I was riding the brakes most of the way down, using both front and rear brakes to check my speed. In between the curves were earth mounds and rocks for launching jumps into the alpine air.

I took multiple jumps and had my only fall of the entire trip. I saw another earth mound, let go of the brakes to gain speed, and launched into the jump, only to discover a rock outcropping out of sight, but visible as I launched past the mound. Mountain rock embedded in the landing zone (LZ) is not what you wish for. My front tire hit one of the rocks in the LZ, and my front wheel slowed. The rear-end of the bike kept moving forward with my momentum, and my speed forward launched me over the handlebars. This move is called an “endo” (short for end-over-end). My bike and I tumbled to a stop just off the trail. I was still clipped in to the pedals. When all the tumbling stopped, I was located upside down (and sideways) in some low bushes, with the bike on top of me. I think my backpack took some of the impact of my falling body when it hit the ground. And my helmet did its job protecting my head. I lay there for a minute, letting the adrenaline and the shock of the crash subside. During that time I was doing a self-assessment – was anything broken or bleeding? No visible injuries. Then it took a few minutes to get the bike off of me, to untangle myself and the bike from the bushes, and to right myself.

Relieved that I had no injuries, I rested. Then I got back in the saddle after a few minutes and rode the rest of Tiddlywinks trail downward to a trail called Storm King (4.1 miles). Storm King was a fun, downhill, flowing trail. Then I hooked into Catch and Release trail (2.5 miles). Then I rode the Deschutes River trail (4 miles) back to Bend, following the Deschutes River. Stopped next to a place upriver of Bend called “Lava Island” and ate a snack. It was sunny and 82 degrees F.

Lava Island, Deschutes River, Oregon.

Then I rode streets of Bend to get a snack at Taco Salsa. I thought it would be a snack – I ordered a bean and cheese burrito – and they delivered a monster burrito that became my dinner. It was delicious and hit the spot at the end of a full day of biking.


Eating outdoors at Taco Salsa.

It was early evening, so I biked to Bend’s town park (Drake Park) on the Deschutes River and enjoyed the green grass and relatively cool temperature.

I biked 39 miles today and hit 5,500 feet in atitude.

I took several dirt paths today – like John Muir suggested. It was a good day and I was grateful for the blessing of this adventure.

“Of all the paths you take in life, make sure a few of them are dirt.” ― John Muir

Day Six – Marianne and Houdini

Day Four – Moving Day

Woke up at 6 am. It was 39 degrees for a low last night (brrrrrrr). I stayed warm all bundled up in my hammock.

Ate breakfast – granola, nuts, and hot tea. Used a MSR Pocket Rocket backpacking stove to heat water for oatmeal and for tea/cocoa. It was good to eat something warm after a cold night.

Today is moving day. I had planned  to stay seven days at Tumalo State Park. But when I checked in, the ranger told me I could only stay three days – this was a complete surprise to me as I had called ahead and mentioned that I was planning on staying a week, and asked how bikers can camp there. At no time during the phone call did the ranger mention that there was a three day limit for hiker/biker campers. I checked the state park website for rules/restrictions. The state park’s website had no mention of a three day camping limit for hikers/bikers. Neither was the unpublished rule posted on the park’s signage. The state park website allows car campers to book reservations more than seven sequential days. But hiker/biker campers can only stay three days.

There were many extra camping spots at the hiker/biker area of the camp. I explained all this to the park rangers and I requested special dispensation from the rangers.  But the park rangers seemed to be more bureaucrat types, less customer service oriented types (a typical government operation), fond of stating the unpublished rule (a rule found nowhere on their website, not on the park’s signage, and not mentioned on the phone when I called ahead to plan the trip), and apparently the park rangers seemed unmoved by reasonable logic.

Having such an unpublished rule, and then refusing to extend grace to a camper who asks for an exception to the unpublished rule is not a particularly helpful way to treat guests. I asked the rangers to update their website to inform hiker/biker campers of the unpublished three day limit.

So I broke camp. I was the only person in the hiker biker camp and had to leave, according to the ranger bureaucracy, leaving zero hiker/biker campers at the campsite. I packed up, loaded all the gear on my back, and rode my bike the six miles into Bend, loaded down with gear. There are no other campsites around Bend, so I checked into a Motel 6.

Next, I rode west out of Bend. Bend is a “bike-friendly” town. Well-marked bike lanes are everywhere, with signs informing vehicle drivers of bike lanes. People ride everywhere in and around Bend. And Bend drivers are careful with riders and pedestrians, stopping if a rider or pedestrian is at a crosswalk, always looking for them. Bend drivers made a very positive impression on me. This is a far cry from Plano, Texas (near Dallas) where drivers seem to have a distinct dislike for bike riders – a biker takes his life into his own hands when he rides the roads around Dallas. Plano and Dallas are some of the least bike-friendly cities in the world.

I rode out of Bend, up Skyliner Road to Phil’s trailhead. There, I hung out in the whoop-de-do section at the trailhead (here I am in the short video below).

Trail marker at the top of Lower Whoops trail, part of the Phil’s trail complex.

Climbed up Ben’s trail (5.5 miles) to Lower Whoops trail (1.8 miles). Took Lower Whoops trail down (1.8 miles), kicking up dust to Phil’s trail and took Phil’ trail down (6.1 miles).  Stopped to take a photo of the chicken, in mid-trail.

The “Flaming Chicken” on Phil’s trail near Bend, Oregon.


Today is the first clear day – you can see Mt. Bachelor and Sisters Peaks.

Sisters peaks in the distance.

I biked back down to Bend and ate a burger at a local restaurant. Rode 32 miles today. It was also Free Slurpee Day (July 11 – 7/11), so I got a cold slurpee (thanks 7-Eleven, it hot the spot).

Mountain biking is a rush – one must stay constantly alert, assessing the terrain ahead while negotiating obstacles. Leaning into banked curves, negotiating rock gardens, and landing jumps takes skill, coordination, and snap judgement. Trees do NOT move. Wise mountain bikers choose their line carefully…

In addition, mountain biking is great way to stay fit. Biking up the mountains around Bend, Oregon is challenging for this flatlander who lives at 600 feet altitude in Plano, Texas. The higher altitude makes for less oxygen – climbing is a challenge, especially with less oxygen. Bend is at 3,500 feet altitude, and the Bend area trails go upwards from there.

Much challenging riding out there. But hey, If it doesn’t challenge you, it doesn’t change you!


Day Five – Dirt Paths of Life

Day Three – Mountain Biking is Art

Woke up at 5 am, but laid in my hammock until 6 am. It was 47 degrees F for a low last night. Wore wool socks, gloves, hat, and fleece pullover while sleeping. My shelter included a sleeping bag placed on top of a thermal pad inside a hammock covered with a rainfly.

Hammock with rainfly.

Ate breakfast – oatmeal, nuts, dried fruit, and hot cocoa.

I made an animal-proof canister to store food and to store other items that contained a scent (soap, shampoo, etc). Had a problem on last year’s bikepacking trip with chipmunks chewing  through my storage bags to get to my food. Not this year – I built an animal-proof canister out of heavy duty PVC pipe. Cut the PVC pipe to desired length. Put an endcap on one end of the pipe and placed a threaded endcap on the other end of the pipe. Chipmunks and other animals (bears, raccoons, and cougars) can’t unscrew the threaded endcap. Take that, you little rascals!!!


Animal proof food container.

Geared up and got biking by 8 am. Biking weather was cool (overcast and 55 degrees F with no sun to warm me up). High temperature for the day was 61 degrees F. Started off biking without a jacket, thinking I might warm up once I got cranking. It was cool enough that I put on a jacket after 30 minutes in the saddle.

Skyliner trailhead sign.

I biked from Tumalo State Park into the town of Bend, then upward in elevation to Skyliner Road, heading up to the massive number of mountain biking trails west of Bend. Biked Skyliner trail (3.2 miles) from the trailhead to Lower Whoops trail (1.8 miles), to Phil’s trail (6.1 miles), to Kent’s trail (4.2 miles). Then back to Bend and to camp. Rode 40 miles, beginning at 3,500 feet elevation, up to 4,900 feet, and back down again.

Lower Whoops trail – earth berms create banked turns for maximum traction and speed.

Riding a challenging trail like Lower Whoops trail is a work of art for me – similar to a musician playing a composition. Each rider rides the trail differently, with his own style. Riding Lower Whoops trail is a rush for all senses. My eyes constantly scanning for obstacles, my brain determining the best line to ride, wind whistling in my ears with the sound of sand, rocks, and earth crunching under the knobby tires, the smell of fresh pine in the air, the feel of the shake, rattle, and roll in my feet and hands as they respond rapidly to changes in pressure.

My body leans from side to side as I lean into the banked turns that provide maximum traction. I take the high line on the left-banked earth berm, swoop down into the trough of the trail, shift your weight and lean right hitting the right-banked earth berm on the high line, scream down the earth berm to the next obstacle. My body feels the shake and rattle as I feel the knobby tires seeking purchase on the hard packed trail turns.

Skyliner trail – typical rock obstacles.

I look ahead and see a earth mound. My being prepares for the jump as the mound launches me into the air. Move the body weight towards the rear tire, positioning for the launch. Hit the mound and explode into the air, balancing as I fly. Prepare for impact, and take the shock as I land, rolling on to the next obstacle. This is one part of the art of mountain biking.

Skyliner trail – bike parked for lunch break.

Sunset on the Deschutes River near Bend, Oregon.

There is definitely an art to getting into a hammock and situating your bed for a cold night. The low for tonight is 39 degrees F. So I got in the hammock, leaving my shoes on the ground directly below me so I can get out in the morning without getting my feet dirty. I am dressed for warmth with wool socks, tights, shirt, fleece jacket, gloves, hat, sleeping bag liner, sleeping bag, Thermarest insulating pad, and an extra blanket. Getting all that gear situated in a normal bed is not hard, but takes some effort in a hammock. Lots of wriggling and turning side-to-side to manipulate all the insulating items.

Here is a summary of my week of mountain biking in Bend, Oregon…

Day 4 – Moving Day