If you live in Preston Village, you already know the walk. Out past the entrance circle, along Upchurch Meadow Road, the path slips behind Green Hope Elementary School Park before it lets you out across the street from Cary Tennis Park. It takes maybe fifteen minutes if you're pushing a stroller, less if the dog is setting the pace. You've probably done it a hundred times without ever checking what the trail is officially called.
It's the Preston Village Greenway, and this year the Town of Cary has been talking a lot about greenways, because the system just crossed 100 miles. There's a year-long celebration built around the number, with a full calendar of events and a photo contest running through the fall. If you've seen the signage or caught a mention on Nextdoor, you might assume your own quarter-mile connector is part of that big number. It isn't, exactly, and understanding why tells you more about how to actually use the system this fall than the milestone press release does.
Your Trail Has a Different Job Than the One in the Headlines
The Town's own designation for the path behind Preston Village is a "street-side trail," not a greenway in the sense that Cary usually means it. It runs 0.7 miles, connecting Upchurch Meadow Road to the Louis Stephens Street-Side Trail, tracing the edge of Green Hope Elementary School Park before ending at the crosswalk into Cary Tennis Park. That's the whole route. It was built to get kids to school and residents to the tennis courts, not to move people for miles through wooded corridors.
Cary Tennis Park itself is worth knowing the real numbers on: 32 courts, free to play, set up for both tennis and pickleball. That's a genuine amenity sitting at the end of a five-minute walk from most Preston Village streets, and it doesn't require a country club membership. Prestonwood Country Club anchors the broader Preston community with its own courts and pools, but you don't need to join anything to use the public courts across the street from your own neighborhood trail.
The 100-mile system the Town is celebrating this year is built on different infrastructure entirely. Black Creek Greenway and White Oak Creek Greenway form the backbone, and they're the ones getting the ribbon cuttings. In May, the Town reopened Phase 2 of Black Creek Greenway between Livingstone Drive and Weston Parkway, a project that included a new 285-foot pedestrian bridge rising roughly 50 feet above the creek, the tallest pedestrian structure of its kind in Cary. That's the kind of capital project a 100-mile milestone gets built on. Your street-side connector to the tennis courts was never competing for that budget line, and it doesn't need to.
What the Milestone Actually Changes for You
None of this means the celebration is irrelevant to Preston Village. It means the payoff isn't a renovated trail behind your house. It's an invitation to go a little farther than you normally do.
Fred G. Bond Metro Park sits just south of the neighborhood, close enough that it functions as the on-ramp from your everyday loop into the larger system. Bond Park has its own tree identification trail and a ropes course, and it's also the physical home base for the milestone celebration itself. The Town's 100 Miles of Greenways photo contest exhibition runs at the Bond Park Community Center from October 7 through December 13, and on October 17, the Town is holding Great Trails State Day as part of Harvest Fest, one of the dated events built specifically around this year's mileage milestone.
If you already know the Preston Village Greenway by heart, that stretch of calendar is a reasonable excuse to extend the walk. Instead of turning around at Cary Tennis Park, keep going toward Bond Park and pick up a piece of the system that actually earned this year's headlines. You'll be walking the same general direction you already walk, just further, and you'll land somewhere the Town has put real effort into displaying this year.
A few reference points if you're planning that longer loop:
- Preston Village Greenway connects Upchurch Meadow Road to the Louis Stephens Street-Side Trail (0.7 miles)
- The route skirts Green Hope Elementary School Park before reaching Cary Tennis Park
- Fred G. Bond Metro Park, just south of the neighborhood, is the nearest connection point into the Town's larger celebrated network
- Great Trails State Day at Harvest Fest lands on October 17 at Bond Park
- The 100 Miles of Greenways photo exhibition runs at the Bond Park Community Center from October 7 through December 13
After the Walk
Preston Village's location does most of the work for a second half to the outing. Stone Creek Village, a short drive up the road off Davis Drive and High House Road, has become the neighborhood's go-to for a sit-down meal after a long walk, with Lugano Ristorante and Bella Monica both drawing residents back regularly. It's not a destination anyone drives across town for, which is exactly the point. It's close enough to be a Tuesday-night habit rather than an occasion.
That's really the shape of daily life in this pocket of Cary. The big system, the one getting the anniversary coverage and the new bridge and the photo contest, is a few minutes away by car or a longer walk by foot. The small system, the one that actually runs past your mailbox, was built for a narrower job: getting you to a park, a school, and a set of free tennis courts without needing to get in the car at all. Both are worth knowing, and neither one makes the other less useful.
If you're weighing whether it's worth the extra fifteen minutes to walk your dog as far as Bond Park this October, or you're just curious what your own street-side trail is officially called on a Town map, that's the kind of small local detail that adds up to actually knowing a place rather than just living near it.
If you're a longtime Preston Village neighbor who's started wondering what a home like yours is worth in the current market, or you know someone eyeing a move into this corner of Cary, Karen Coe Realty Group has spent years tracking exactly these kinds of neighborhood details alongside the numbers. Request a home valuation whenever you're ready to talk specifics.
