Westchester County acquired Blue Mountain Reservation in 1926, which makes 2026 the park's centennial. If you live in Cortlandt Manor, you already know the entrance off Welcher Avenue, the pond by the playground, the parking lot that fills up on Saturdays. That's not the story. The story is that the county turned the anniversary into a scoreboard.
From Sunday, June 7 through Wednesday, September 16, the parks department is running a 100-miles-in-100-days challenge across the reservation. Registration is free. There is no entry fee, no leaderboard prize worth chasing, no medal ceremony to plan around. What there is, for anyone within a fifteen-minute drive of the trailhead, is a reason to stop treating a 1,538-acre park like a special-occasion destination and start treating it like a standing appointment.
The math nobody does out loud
One hundred miles across one hundred and one days works out to just under a mile a day. Split into a normal adult schedule, that's three miles three times a week with a rest day, or a five-mile Saturday plus a couple of Wednesday-evening loops. It is genuinely doable on foot. On a bike, it is a rounding error. The challenge counts hiking, running, and riding, which means the family that walks the yellow trail once a weekend is halfway there without adjusting anything.
The interesting part isn't whether you finish. It's that once you register, the park stops being a place you visit and becomes a place you're keeping a ledger on. Every walk with the dog counts. Every after-work loop counts. The mental accounting changes what you do on a Tuesday at 6:15 p.m., which is the entire point of a challenge like this.
Where the miles actually come from
Blue Mountain isn't one trail. It's roughly thirty miles of interconnected singletrack and carriage road across 1,538 acres, with a difficulty mix that skews harder than most people expect. The Westchester Mountain Bike Association, which helps maintain the trails, describes the system as roughly 20% beginner, 20% intermediate, and 60% expert. That last number is the one to sit with before you clip in.
Here's how the mileage tends to add up for people who live nearby:
- Dickey Brook carriage road. The forgiving warm-up. Gentle climb, wide surface, useful for logging quick two-mile loops when you don't want to think about line choice.
- Ned's Left Lung. A serious climb off the Dickey Brook approach that puts you near the highest bike-accessible point in the park. This is where the 60%-expert figure starts to feel accurate.
- Mt. Spitzenberg. One of the two named summits. Short hike, real payoff, occasional Hudson River sightlines through the canopy.
- Blue Mountain summit. The bigger of the two peaks. A legitimate hike that earns its distance on the ledger.
- The Briarcliff-Peekskill Trailway. A twelve-mile unpaved corridor that connects into the Blue Mountain system. If you're chasing miles rather than technical challenge, this is the fastest way to bank them.
The Sportsman Center sits inside the park boundary as well, which is worth knowing mostly so you don't accidentally wander your dog into an area where dogs aren't allowed. Everywhere else in the park, leashed dogs are fine.
What the difficulty split means for your first ride
The 60%-expert figure gets underplayed in most write-ups because it sounds discouraging. It isn't. It just means the trail system was designed for people who wanted to be challenged rather than for people who wanted a nature stroll, and knowing that in advance changes how you plan the first outing.
If you have never ridden Blue Mountain before, start on the carriage roads and treat the singletrack as a graduation. If you're hiking the challenge, the yellow trails will absorb most of your miles without asking your knees for much. If you brought guests from the city expecting Central Park terrain, the honest move is to steer them toward Croton Gorge or Teatown for the first afternoon and save Blue Mountain for the second visit. Nobody's proud of a first ride that ends with a walk-out.
One hundred miles is not the goal. The goal is the ninety-eight days between the first mile and the last one, when the park stops being scenery and starts being routine.
Where the ride ends, dinner starts
The reason this is a Cortlandt Manor post and not a general Westchester post is that the food geography around the park has quietly gotten more interesting in the last twelve months, and the timing lines up with the challenge in a way that rewards locals specifically.
Hemlock Hill Farm at 500 Croton Ave has been a working farm since 1939, and it is roughly six minutes from the Welcher Avenue entrance. If you're finishing a Saturday morning ride and thinking about dinner, this is the pantry stop. One detail matters for July and August: the farm pauses its Saturday walking tours during peak summer heat because the animals move to cooler areas and become hard to spot. Tours resume in September and October at 10:30 a.m. and noon on Saturdays. The store stays open through the summer regardless, so the ride-plus-butcher combination works all challenge long. The tours are a fall bonus.
The Goodmark, at 276 Watch Hill Road, opened quietly on November 7, 2025, and had a Hudson Valley Chamber of Commerce ribbon cutting in December. Mark and Gina Goodenow moved to Cortlandt Manor in June 2009, and Mark's path from culinary school through a decade in aerospace before opening his first restaurant was profiled in Westchester Magazine in February. The reason to care in July: they opened the patio for the warm season, which is the reward-meal version of a post-ride destination that didn't exist last summer. Rated 4.7 on 49 OpenTable reviews as of April, with a menu that leans elevated American, sunchoke puree, pistachio-crusted salmon, that kind of range.
A week that actually closes the loop
Assume you're logging the challenge on foot with occasional bike days. A workable Cortlandt Manor summer week, entirely inside a five-mile radius of home:
- Monday. Rest, or a two-mile evening walk on the yellow trail before dinner. Logs two miles.
- Wednesday. Three-mile after-work loop on Dickey Brook. Logs three miles.
- Friday. A short summit push up Mt. Spitzenberg. Logs two miles with a real elevation payoff.
- Saturday. Longer morning outing, five to six miles depending on route. Stop at Hemlock Hill on the way home for the week's meat and produce. Logs five to six miles.
That's twelve to thirteen miles a week, which puts you at ninety-plus across a ten-week stretch. Add a couple of guest-weekend hikes and the ninety-eight-day window covers you comfortably. Skip a week for vacation and the math still holds. This is the meaningful thing the challenge does: it converts a big number into a small number of decisions, most of them Wednesday-shaped.
What August is quietly doing to the schedule
There's a real seasonal wrinkle. July and August at Blue Mountain get humid enough that morning and evening riding becomes noticeably more pleasant than midday. Hemlock Hill has already told you the animals feel the same way, which is why the farm tours pause in those two months. Plan the harder trail days for early June and September if you have the flexibility. The middle stretch is for maintenance miles on the flatter routes, the walks the dog would have gotten anyway, the Wednesday evening loops after the sun drops below the ridge.
September 16, when the challenge ends, is the same week Hemlock Hill's Saturday tours restart. That's not a marketing coincidence, it's just how the calendar shakes out, and it gives the post-challenge weekend an obvious shape: finish your last miles Saturday morning, walk the tour at 10:30 a.m., pick up something for the grill, book a Saturday-night patio table at The Goodmark. That's a Cortlandt Manor day that didn't exist in this configuration a year ago.
The centennial reframe
The version of this story that's easy to write is a list of things happening at the park. The version worth writing is that a centennial challenge is the parks department's way of reminding people who already live here that a park you drive past every day is different from a park you use every week. Blue Mountain has been open the whole time. The scoreboard is what's new, and the scoreboard is the whole point.
If you live in Cortlandt Manor and you're thinking about your next move, upsizing for a bigger yard, downsizing after the kids leave, or just curious about what your equity looks like right now, the outdoor life around your address is a real line item in the value of the property. It's worth having someone in your corner who can talk about the trails as knowingly as the comps.
Ready to talk through what your next chapter in Cortlandt looks like? Nicole Biello is booking free strategy calls this summer, and she'd rather meet you at the trailhead than the office.
