When does a trail stop being under construction? On Smuggler Mountain, the people who built the two newest lines expect riders to finish the job. The Roaring Fork Mountain Biking Association said as much when it announced Ramble On and Midnight Rambler on August 31, 2026. It called Ramble On a "fast and raw" downhill-only trail and asked riders to help "ride them into shape."
That makes this fall the first season of shaping for both trails, and the season is short. Trailforks shows riders on both trails as late as October 31, 2026. The day after that, Aspen Snowmass started requiring uphill straps on all four mountains. For people in East Aspen, Smuggler and the uphill routes are close to home, and right now the two seasons overlap.
A Line Item in the County's Plan
The trails started on paper. In December 2024, Pitkin County Open Space & Trails adopted an updated management plan for Smuggler Mountain after two public comment periods. According to RFMBA, many of its members took part in those comment periods. One of the plan's Recreation Management Actions, Action #3, read: "Explore feasibility of constructing an advanced mountain biking trail on the north-facing slope connecting Smuggler Mountain Road to Smuggler trails." The City of Aspen posts the Smuggler Mountain Open Space Management Plan as a download for anyone who wants the full document.
The plan asked for one advanced trail. The mountain got two. Joey Giampolo of Pitkin County Open Space & Trails and Derek Thomson of Apex Trails cut Ramble On. RFMBA also thanked the crew behind Midnight Rambler without naming them. New signage went in over the summer. RFMBA's announcement was timed to that signage, after riders had already started finding the trails on their own.
Two Trails, Two Very Different Grades
Both trails are short. What sets them apart is how much vertical each one fits into that distance. Here are the Trailforks listings side by side:
| Ramble On | Midnight Rambler | |
|---|---|---|
| Difficulty | Black Diamond | Double Black Diamond |
| Length | 1,545 ft | 1,145 ft |
| Descent | 178 ft | 367 ft |
| Average grade, derived | About 11.5% | About 32% |
| Direction | Downhill only | Downhill only |
| E-bikes | Not allowed | Not allowed |
The grade row is simple division of descent by length. Midnight Rambler is about three-quarters as long as Ramble On but drops roughly twice as far. That works out to almost a third of a foot of drop for every foot of trail. RFMBA called Midnight Rambler a "rare double diamond." The numbers support that.
Ramble On spends its vertical differently. It opens with a steep drop into a wide draw, then runs over bumpy ground and embedded log features. A short climb follows, then a crossing of the Tenth Mountain Trail. After that it picks up speed through dark timber, with more logs and uneven terrain on the way down. The lower average grade comes from that short climb and the long run through the trees. Its difficulty comes from the terrain underfoot more than from the pitch.
Finding the Drop-Ins
Both trails start from routes that people who ride Smuggler already know, and both end up at Lollipop.
- Midnight Rambler. Climb Smuggler Mountain Road. About three-tenths of a mile past the top of Tootsie Roll Trail, the trail drops off the road. Riders choose between an A line and a B line. Both descend steeply to Lollipop Trail and have a few catch berms to help control speed.
- Ramble On. Climb toward the top of Lollipop Trail. Just past the boardwalk feature, the trail starts on your left.
The City of Aspen describes Smuggler Mountain Road as a 1.5-mile moderate dirt and gravel road that climbs the mountain and connects to the Hunter Creek Valley. For Midnight Rambler, you only need part of that climb. You turn off at three-tenths of a mile above Tootsie Roll and the trail takes you down to Lollipop.
What "Raw" Means in Late Fall
RFMBA's description of Ramble On makes a plain prediction about how the trail will change:
"This raw trail can be expected to change each season as the faster lines get ridden into shape."
A raw trail is one where the line isn't settled yet. Each pass helps decide where the tread wears in, which entries hold up and which logs end up being the obvious features. That shaping depends on what the ground is like when people ride it. Trailforks lists both trails as open year-round and advises against riding them when muddy or wet. On a trail this new, tire ruts cut into soft dirt can harden into the line the next season starts with.
The most recent report on either trail is a good one. On October 27, 2026, a mountain biker filed a Trailforks report on Midnight Rambler rating it "Variable," marked the trail All Clear / Green, and wrote that it was "holding onto the moisture nicely... Wet but not problematic." Ramble On had no written trail reports on Trailforks as of late October, though its last logged ride was October 31, 2026. Trail users submit these reports, and conditions on a north-facing slope in November can change from one day to the next. Treat late October's "wet but not problematic" as a starting point, and check the Midnight Rambler and Ramble On pages before heading up.
The Mountain's Other Users
The road to the new trails carries a lot more than bikes, and the City's rules reflect that. Under Aspen's guidance on enjoying the trails with your dog, dogs may play off leash on Smuggler Mountain Road while their owners watch them. Leashes are required on all trails. The City's trail use regulations require cyclists to slow down and announce themselves when passing. City trails are multi-use unless posted otherwise. The new downhill-only trails are posted otherwise, which is why their signage matters.
Riders headed for Midnight Rambler will share the road with walkers and off-leash dogs before dropping in. On the descent there's no uphill traffic, because both new trails run one way.
The Uphill Season Has Already Started
The new trails are on the side of the valley across from Aspen Mountain. As November goes on, people who climb for exercise will spend more of that effort on the ski area's uphill routes, and those come with their own rules. Aspen Snowmass requires uphill straps on all four mountains from November 1, 2026 through April 18, 2027. The main points from its uphill pass page:
- Cost. The uphill pass is $74, and $10 of that goes to Mountain Rescue Aspen. It's included at no charge with a Premier Pass. One pass covers both a single day and the full season.
- Who needs it. Anyone uphilling, whether skiing, walking or snowshoeing, needs the pass. That includes Full Moon Dinners and Social Breakfasts.
- Hours. Uphilling is allowed daily from 5 a.m. to 10:30 p.m., on designated routes only.
- Aspen Mountain cutoff. Uphillers must reach the top by 9 a.m.
- Dogs. Dogs aren't allowed on any of the mountains during ski area operating hours, 7:45 a.m. to 4:45 p.m.
- Early-season closures. Snowmaking and mountain preparation can close specific routes or all uphill access. Aspen Snowmass posts closures in the Aspen Snowmass App.
A strap also requires a current season sticker and a sleeve for the pass. Both are available at a ticket office. Season passholders also need a signed waiver on file.
The dog rules change as you cross the valley. On Smuggler Mountain Road, the City allows dogs off leash under watch. On Aspen Mountain during operating hours, dogs aren't allowed at all, and Aspen Snowmass has said it could end the after-hours allowance if incidents continue.
Where the Trails Go From Here
RFMBA expects Ramble On to look different every season. Whatever lines riders establish on it before snow covers the north-facing slope will be what the trail starts from next spring. The December 2024 plan that led to these trails is available in full, with the City linking it on its management plans page. RFMBA also had a suggestion for riders heading up: put some Rolling Stones or Led Zeppelin on the playlist.
At Aspen Lodge Properties, we follow the details that shape daily life in East Aspen, from the plans behind a new trail on Smuggler to the season's first uphill on Aspen Mountain. If you'd like to talk about what the trails and open space close to home mean for a property you own or are considering, we invite you to Schedule a Confidential Consultation.
