Right now, the pool at The Highlands is on a diet. Not closed, not full-tilt summer either. Somewhere in between, and if you've lived in the neighborhood a few years you already know the rhythm: daily swims all summer, then one Monday the gate sign changes to weekends only, and everyone quietly recalibrates their calendar.
That shift already happened. The pool opened daily on Saturday, May 23, and ran that way through Sunday, August 23. As of this week, it's down to Saturdays and Sundays only, now that Chesterfield County Public Schools is back in session. Three weekends remain. Labor Day falls on Monday, September 7 this year, which means the traditional final splash lands the following weekend, September 12 and 13, before the gates close for the season.
Here's the part most residents miss while they're mourning the pool: the golf course doesn't slow down when the pool does. It speeds up. And for one Thursday in the same stretch, it stops being a members' course at all.
The Slow Fade Isn't A Cliff
It helps to see the taper laid out, because "pool season ends in September" undersells how gradual the wind-down actually is.
| Phase | Dates | What Changes |
|---|---|---|
| Full summer schedule | May 23 – Aug 23 | Open daily |
| Post-school-year taper | Late Aug – early Sept | Weekends only |
| Final weekend | Sept 12 – 13 | Last splash, then closed for the season |
Three weekends is a short runway. If you've been meaning to use a guest pass, host the last cookout, or just get one more lap in before the cover goes on, the window is smaller than it feels from the outside.
But treating that final weekend as the end of anything happening at The Highlands would be a mistake. The golf course runs on a different calendar entirely, and it's about to have its busiest week of the fall.
The Course Doesn't Follow The Pool's Calendar
The Golf Club at the Highlands hosts its own full slate of member events year-round, from scramble tournaments to member-member weekends. Most of that is business as usual for the golfers in the neighborhood and invisible to everyone else.
One event breaks that pattern. It's called the Highlands-Massey Classic, and it's a charity tournament that's run on this course every September for at least the last five years, benefiting VCU Massey Cancer Center.
That's not a small-stakes cause. Massey is among the top 4 percent of cancer centers in the country and one of only two centers in Virginia designated by the National Cancer Institute to help shape the country's cancer research agenda. The tournament exists to funnel local dollars toward that work, and it happens on the same course residents drive past every day.
Five Septembers, Five Thursdays
If you track the tournament across recent years, a pattern emerges:
- 2021: Thursday, September 23
- 2023: Thursday, September 14
- 2024: Thursday, September 19
- 2025: Thursday, September 18
Every single one landed on a Thursday, and every single one fell inside the same three-week window in mid-to-late September, the exact stretch when the pool is finishing its taper. The format holds steady too: registration and lunch at noon, shotgun start at 1 p.m., all at 8136 Highland Glen Drive.
The same three weeks that close the pool are the three weeks that turn the golf course into something bigger than a Tuesday round.
For this year, the HOA's own event calendar is the most reliable place to confirm the exact date once it's posted, since the tournament has moved by as much as nine days between years.
What The Day Actually Looks Like
Registration and lunch open the day, giving golfers and sponsors time to mingle before the shotgun start sends every group out at once. It's a format built for volume and for visibility, not a quiet weekday nine holes. For a course that's semi-private the rest of the year, that one Thursday means more cars in the lot, more unfamiliar faces at the clubhouse, and a course that's briefly serving a purpose bigger than recreation.
You don't have to golf to notice the difference. If you drive past the club that afternoon and see a fuller lot than usual, that's the reason.
The Handoff Keeps Going
Once the pool closes and the tournament wraps, the neighborhood's fall pattern typically continues rather than pausing. Past years have included a Fall Festival with its own local charity component, collecting canned and boxed goods for the Chesterfield Food Bank and winter items like scarves and coats for the VFW. Coffee & Cars meetups have run through the fall months in past seasons, and the Nifty Fifties...Plus social group keeps its own calendar going for residents 50 and up, independent of what the pool or golf course are doing.
None of this is guaranteed to repeat on identical dates this year, and the HOA's site is the place to check as the season firms up. But the shape of it has held for years: pool closes, golf course has its one big outward-facing week, and then the social calendar picks the slack back up before the weather turns.
Why This Matters If You Live Here
The easy read on Labor Day weekend is that it marks the end of something. The more accurate read, at least at The Highlands, is that it marks a handoff. The pool's gate closes on one predictable Sunday. The golf course's biggest week of the year opens up right alongside it, on a course that spends the other 51 weeks being a members-only amenity most residents only see from the road.
If you've lived in the neighborhood a while and never paid attention to what happens on the course in September, this is the year to notice. Watch for the date on the HOA calendar, and know that the Thursday it lands on will look different from every other Thursday on that course all year.
Team Hensley keeps a close eye on what's actually happening in neighborhoods across Midlothian and Chesterfield, not just what's listed for sale in them. If you're curious about life in The Highlands or any of the communities we cover, reach out anytime.
