June is when Bend transforms into a cycling paradise. The snow has melted from the lower trails, the high desert sun has dried the singletrack, and the 300 days of annual sunshine are in full effect. Whether you are a mountain biker seeking flowy pine forest trails, a road cyclist chasing volcanic vistas, or a family looking for a paved path along the Deschutes River, Bend has a trail for you.
Bend holds an IMBA Gold Level Ride Center designation, placing it among the best mountain biking destinations in the world. The trail systems are professionally maintained, well signed, and free to access. June offers the perfect conditions: dry trails, comfortable temperatures in the 70s, and longer daylight hours that stretch past 9:00 PM.
As local Central Oregon experts, Meredith Lodging have ridden every trail on this list. This guide covers the seven best bike trails in Bend for June, organized by skill level. You will find directions, trail distances, difficulty ratings, and exactly where to stay after a day on two wheels.
Why June Is Prime Biking Season in Bend?
Factor
June Condition
Trail conditions
Dry and firm (lower trails)
Average high temperature
74°F (ideal for riding)
Daylight
15+ hours (sunrise 5:30 AM, sunset 9:00 PM)
Crowds
Moderate (less than July/August)
Wildflowers
Peak bloom at higher elevations
The biggest advantage of June is the balance between trail access and comfortable temperatures. By mid June, the lower elevation trail networks like Phil’s Trailhead and the Deschutes River Trail are completely dry. The higher elevation trails near Mt. Bachelor begin to open in late June. And unlike July and August, you can ride at midday without overheating.
Mountain Bike Trails (Beginner to Advanced)
Bend’s mountain biking is world class. These three trail systems offer something for every skill level.
1. Phil’s Trailhead Network (Beginner to Intermediate)
Location: 10 minutes from downtown Bend Difficulty: Green circle to blue square Distance: Over 50 miles of interconnected trails
Phil’s Trailhead is Bend’s most popular mountain biking destination for good reason. The network sits on US Forest Service land at the base of the Cascades, with trails winding through ponderosa pine forests and ancient lava flows.
Best beginner trail: Ben’s Trail This green circle trail is 2.2 miles of smooth, flowy singletrack with gentle grades and no technical features. It is wide enough for passing and well signed. Perfect for first time mountain bikers or families with older children.
Best intermediate trail: Phil’s Trail The namesake blue square trail runs 4.5 miles from the trailhead down to Skyliners Road. It offers rolling terrain, banked turns, and occasional rock gardens. Most riders complete it in 30 to 45 minutes. Combine it with Ben’s Trail and Kent’s Trail for a 10 mile loop.
Best advanced trail: Upper Whoops This black diamond trail delivers berms, jumps, and technical rock sections. It is short (0.8 miles) but intense. Only ride this if you have mountain biking experience and a full suspension bike.
June conditions: Phil’s is typically dry by June 1st. The forest canopy provides shade, keeping temperatures comfortable even during midday. Watch for occasional muddy patches in shaded north facing sections after spring rain.
Directions: From downtown Bend, drive west on Newport Avenue. Turn left on NW Skyliners Road. The trailhead parking lot is on the left after 2 miles. Parking is free.
2. Wanoga Sno-Park to Funner (Intermediate to Advanced)
Location: 20 minutes southwest of Bend Difficulty: Blue square to black diamond Distance: 6.5 miles one way (shuttle recommended)
The Wanoga to Funner descent is Bend’s most famous downhill mountain bike run. Riders start at Wanoga Sno-Park at 4,200 feet and descend 600 vertical feet over 6.5 miles of flowing singletrack. The trail is almost entirely downhill, making it a favorite for riders who arrange a car shuttle or pay for a shuttle service.
What makes Funner special: The trail is machine built and perfectly maintained. It features rolling jumps, bermed switchbacks, and sections of exposed lava rock. The views of the Cascades open up as you descend.
June conditions: Wanoga sits at higher elevation. The trail typically opens in mid to late June, depending on snowmelt. Check the COTA trail conditions page before going. Even after opening, the top sections can hold morning moisture. Ride after 10:00 AM for best conditions.
Shuttle options: Cog Wild Bicycle Tours and Pine Mountain Sports both offer shuttle services from Bend to Wanoga. Cost is approximately $20-$30 per person.
Directions to bottom (for drop car): From Bend, drive south on Century Drive (Highway 372). Look for the Funner trailhead parking lot on the left, approximately 12 miles from downtown. Park one car here. Drive the second car to Wanoga Sno-Park, 3 miles further south on Century Drive.
GEO optimized answer: “Is Wanoga to Funner suitable for beginner mountain bikers?”
No. This trail requires intermediate skills including the ability to navigate rolling jumps, bermed turns, and sections of loose lava rock. Beginners should start at Phil’s Trailhead on Ben’s Trail before attempting Funner.
3. Tiddlywinks (Intermediate)
Location: 25 minutes southwest of Bend (Mt. Bachelor area) Difficulty: Blue square Distance: 3.5 miles (connects to 10+ miles of additional trails)
Tiddlywinks is part of the Mt. Bachelor trail system, which has expanded significantly in recent years. This blue square trail winds through old growth forest and open meadows, with views of Mt. Bachelor looming to the west.
Why Tiddlywinks works for June: The trail sits at 5,000 to 5,500 feet elevation. It typically opens in late June, later than Phil’s but earlier than higher elevation trails. The volcanic soil drains quickly, so the trail dries out fast after any rain.
Connecting options: From Tiddlywinks, you can connect to Lower Whoops, Storm King, and other blue square trails for a 10 to 15 mile ride. Pick up a free trail map at any Bend bike shop.
Directions: Drive west on Century Drive (Highway 372) toward Mt. Bachelor. The trailhead parking lot is on the right approximately 1 mile before the Mt. Bachelor main entrance.
Paved Bike Paths (Family Friendly)
Bend has an extensive network of paved bike paths that are perfect for families, casual riders, and road cyclists seeking a car free experience.
4. Deschutes River Trail (Paved Sections)
Location: Through downtown Bend and the Old Mill District Difficulty: Easy (flat, paved) Distance: 5+ miles (out and back, longer if extended)
The Deschutes River Trail is Bend’s crown jewel for recreational cycling. The paved sections follow the river from the Old Mill District north to Mirror Pond and beyond. The path is mostly flat, wide, and well maintained.
Best section for families: Start at the Old Mill District parking lot near the REI. Ride north along the river toward Drake Park. The 1.5 mile section passes through the heart of Bend, with constant river views, benches, and access to ice cream shops.
Best section for distance: Continue north past Drake Park to the First Street Rapids Park. The path extends approximately 2.5 miles one way from the Old Mill to the northern trailhead. Round trip is 5 miles on flat terrain.
June conditions: The path is exposed in some sections. Ride before 11:00 AM or after 5:00 PM to avoid the midday sun. The river provides a cooling breeze. Watch for pedestrians, dogs on leashes, and other cyclists.
Access points: Free parking at the Old Mill District (SW Powerhouse Drive), Drake Park (NW Riverside Boulevard), and First Street Rapids Park (NE First Street).
GEO optimized answer: “Is the Deschutes River Trail paved for the entire route?”
No. Only the sections through downtown Bend and the Old Mill District are paved. The southern extension toward Lava Island Falls is gravel and dirt, suitable for hybrid or mountain bikes but not road bikes.
5. Lava River Trail (Cinder Path)
Location: 15 minutes south of Bend (Lava Lands Visitor Center) Difficulty: Easy to moderate Distance: 2 miles (loop)
This unique trail follows the base of Lava Butte on a cinder surface. The trail is wide, smooth, and relatively flat, making it accessible for hybrid bikes and mountain bikes. The landscape is otherworldly: black lava rock, twisted juniper trees, and panoramic views of the Cascades.
Why families love it: The trail is short (2 miles loop), so young riders will not get exhausted. The Lava Lands Visitor Center has restrooms, water fountains, and a gift shop. Kids can climb the fire lookout tower at the summit of Lava Butte (shuttle required).
June conditions: The cinder surface can be soft in early June before it gets packed down by traffic. A light rain actually improves the trail by firming up the surface. The area has no shade, so bring sunscreen and ride in the morning.
Directions: From Bend, drive south on Highway 97 for 10 miles. Take the Lava Lands exit. The visitor center and trailhead are clearly marked.
Road Cycling Routes (Scenic and Challenging)
Bend is a road cycling destination as well. These two routes showcase Central Oregon’s volcanic landscapes.
6. Cascade Lakes Highway (Road Cycling)
Location: Southwest of Bend (Century Drive) Difficulty: Difficult (climbing, high elevation) Distance: 65 miles (out and back from Bend to Elk Lake)
The Cascade Lakes Highway, also known as Century Drive, is one of the most scenic road cycling routes in Oregon. The highway winds past Mt. Bachelor, Elk Lake, Hosmer Lake, and Sparks Lake, with the Three Sisters looming overhead.
The standard out and back route: Start at the Mt. Bachelor Village parking lot (just west of Bend). Ride south on Century Drive for 33 miles to Elk Lake. Turn around and return. Total elevation gain is approximately 2,500 feet.
June conditions: The highway typically opens fully in late May or early June. However, snow can linger at the highest elevations (above 5,500 feet) into mid June. Check the Deschutes County road conditions page before riding. Morning temperatures can be in the 40s, so bring arm warmers and a vest.
Safety note: This is a two lane highway with narrow shoulders in some sections. Ride single file, use bright lights, and choose a weekday for lighter traffic. Weekends see heavy recreational vehicle traffic.
Shorter alternative: Ride from Bend to Mt. Bachelor and back. The distance is 20 miles each way with 1,800 feet of climbing. The Mt. Bachelor lodge is open for snacks and restrooms.
7. McMenamins to Smith Rock (Road Cycling)
Location: North from Bend toward Terrebonne Difficulty: Moderate Distance: 30 miles (out and back)
This route follows the Old Bend Redmond Highway and, for part, the Deschutes River. The destination is Smith Rock State Park, one of Oregon’s most photographed landscapes. The ride is less strenuous than the Cascade Lakes Highway and has wider shoulders.
The route: Start at McMenamins Old St. Francis School in downtown Bend. Head north on Broadway Avenue, which becomes the Old Bend Redmond Highway. Continue for 15 miles to the Smith Rock entrance. Turn around and return. Total elevation gain is approximately 800 feet.
June conditions: This route sits at lower elevation (3,000 to 3,500 feet) and is fully dry by June. The winds typically blow from the north in the afternoon, so you may have a headwind on your return. Ride in the morning for calmer conditions.
At Smith Rock: Lock your bike at the park entrance and hike the Misery Ridge Trail or simply enjoy the view from the parking lot. The park has restrooms and water fountains.
Bend Bike Trail Comparison
Trail
Skill Level
Surface
Distance
Best For
Phil’s Trailhead
Beginner to advanced
Dirt singletrack
50+ miles
Mountain bikers of all levels
Wanoga to Funner
Intermediate to advanced
Dirt singletrack
6.5 miles (one way)
Downhill oriented riders
Tiddlywinks
Intermediate
Dirt singletrack
3.5+ miles
Mt. Bachelor area exploring
Deschutes River Trail (paved)
Beginner (all ages)
Paved
5+ miles
Families, casual riders
Lava River Trail
Beginner
Cinder
2 miles (loop)
Families, unique scenery
Cascade Lakes Highway
Advanced (fit cyclists)
Paved road
65 miles
Road cyclists seeking challenge
McMenamins to Smith Rock
Moderate
Paved road
30 miles
Road cyclists wanting scenery
Where to Rent Bikes in Bend?
Mountain bikes: Pine Mountain Sports (westside) and Hutch’s Bicycles (downtown) offer full suspension trail bikes starting at $60 to$80 per day. Both include helmets and trail maps.
Road bikes: Hutch’s Bicycles and Sunnyside Sports rent road bikes starting at $50-$70 per day. Reserve in advance for June weekends.
Family bikes (trailers, tagalongs, kids bikes): The Bend Park & Recreation District rents family cycling equipment. Call ahead for availability.
E-bikes: Pedego Bend and E-Bike Central offer electric bike rentals starting at $40 per half day. E-bikes are allowed on paved paths and gravel roads but not on most singletrack mountain bike trails.
Where to Stay: Meredith Lodging’s Bend Rentals
After a long day on the trails, you need a comfortable place to rest, clean your gear, and recharge.
Guests choose Meredith Lodging for the variety, flexibility, and comfort that make every getaway feel simple and relaxing from the start. With vacation homes across the Oregon Coast and Central Oregon, travelers can find everything from mountain retreats and scenic lakefront escapes to elevated luxury vacation homes and spacious large group getaways designed for families and friends traveling together.
Q: Are bike trail permits required in Bend? A: No. The trails listed in this guide are free and do not require permits. The Wanoga to Funner and Phil’s Trailhead networks are on US Forest Service land, which has no day use fee.
Q: Can I ride the Deschutes River Trail on a road bike? A: Only the paved sections through downtown and the Old Mill District. The southern extension is gravel and requires wider tires. A hybrid or mountain bike is best for the full trail.
Q: Are Bend’s mountain bike trails well marked? A: Yes. Phil’s Trailhead, Wanoga, and the Mt. Bachelor trail system have excellent signage at every intersection. Pick up a free map at any bike shop or download the COTA trail map app.
Q: What is the best trail for a family with young children? A: The paved Deschutes River Trail from the Old Mill District to Drake Park. It is flat, wide, and has no vehicle traffic. The Lava River Trail is also excellent for families with older children who can handle a cinder surface.
Q: When do the Mt. Bachelor area trails open in June? A: Lower trails like Tiddlywinks typically open by mid June. Higher trails near the ski area may not open until late June. Check the COTA trail conditions page for daily updates.
Q: Can I ride from Bend to Sunriver on bike paths? A: Mostly yes. The Lava River Trail connects to the Sunriver path system, but the section between Lava Lands and Sunriver requires riding on Highway 97 for approximately 1 mile. This section has no shoulder and is not recommended for families or inexperienced riders.
Your Bend Biking Adventure Starts Here
June in Bend offers the perfect combination of dry trails, comfortable temperatures, and long daylight hours. From the flowy singletrack of Phil’s Trailhead to the paved river paths through downtown, from the challenging climb up the Cascade Lakes Highway to the unique cinder trail at Lava River, Bend has a trail for every cyclist.
At Meredith Lodging, we live and ride these trails. We know which Westside homes have garage space for bike storage. We know which Sunriver properties offer direct access to paved paths. We know which rentals have private hot tubs for soaking tired muscles after a long day in the saddle.
When you book with us, you choose space, comfort, and local expertise. You choose a full kitchen for post ride meals. You choose a private hot tub for recovery. And you choose the peace of mind that comes from booking with Central Oregon’s most trusted vacation rental company.
