"Highland Farm is not a park, and therefore is not managed by the Parks and Recreation Department."
That line ran in a Town of Darien newsletter in September 2024. The same paragraph said events at the property fall under the Selectman's Office and must follow Planning and Zoning special permit conditions, which the town called "relatively strict and lengthy."
Two years later, Darien Parks & Recreation is hosting its First Annual Fall for Darien on that same field at 560 Middlesex Road. It runs Saturday, October 10, from 11 a.m. to 2 p.m. Admission is free and all ages are welcome. Gunsmoke will play live, and there will be family activities and local vendors. The town's listing says it hopes the event becomes "a favorite annual Darien tradition." Patch's September 22 preview adds a petting zoo, face painting, local artisan vendors, and $20 caricature drawings.
On paper it's a three-hour community afternoon. It's also a clear look at what the town can do with a field it has owned for nearly a decade under rules it agreed to when it bought the land.
What the town bought, and what came with it
Highland Farm is the former northern field of the Ox Ridge Hunt Club, whose wider property sits at 512 Middlesex Road. In November 2016 the Board of Selectmen unanimously approved a $6.25 million purchase of the field. In February 2017 the Representative Town Meeting approved it at $6.34 million, a figure that includes bonding costs. Town records put the parcel at about 16 acres. The Selectmen's account says 16.3 and the RTM approval says roughly 16.6.
The land came with conditions already attached. Darienite reported that a 2012 tax settlement had given Darien a right of first refusal on any club property sold through 2052. The settlement also placed 22.7 acres, including this field, under an open-space deed restriction running through June 2042. Jayme Stevenson, then a selectman, said the town had been weighing the purchase since April 2016.
At the time of purchase, officials described the field's possible future in modest terms. Darienite reported that officials mentioned up to four non-permanent recreation fields for sports such as soccer and lacrosse. Artificial turf and field lighting were ruled out, and football was possible only if the goalposts could be removed. Under the 2016 terms the club could keep using the field for its annual charity horse show one week a year. The town could add parking, walkways, and one single-story building of up to 1,000 square feet for storage, restrooms, and possibly a concession stand.
A decade of small, careful upgrades
What followed was a series of small upgrades rather than one big build-out. Each step added a little access, and none added anything permanent on the field itself.
| When | What happened |
|---|---|
| July 2018 | Planning & Zoning approved site improvements, including parking and a jogging and walking path. A special permit allowed programming once fencing and parking were in place. |
| December 2018 | First Selectman Jayme Stevenson said the field was available to the whole community, with temporary parking and a permanent fence going in. |
| June 2019 | The RTM approved $609,000 for two parking areas with 92 spaces in total, a 12-by-20-foot mower shed, walking path work, and light grading. It removed permanent bathrooms from the plan in favor of portable toilets. |
| FY2021 | The town's financial report listed the $609,000 improvement phase as complete. |
| 2021–2022 | A $92,000 grant paid for a Highland Farm pollinator pathway. The project plan is dated July 21, 2021, and the gardens were photographed in bloom in July 2022. |
The pollinator gardens and the walking path are the parts of Highland Farm that see the most regular use. Dogs are allowed on the property if they stay on a leash or lead at all times, according to the town's dog rules updated in July 2025. That same document groups Highland Farm with the town's parks while marking it as a separate case. The town's own wording about who runs the field has changed over the years. The 2024 newsletter named the Selectman's Office, and the 2026 festival is a Parks & Recreation event.
The rules decide what kind of event fits
This spring the field's limits came up in a different debate. At a May 6, 2026 meeting, the RTM Parks & Recreation Committee discussed a proposed $75,000 study of traffic circulation and accessible routes at Cherry Lawn Park. One member asked to pull it from the vote because the town hadn't fully discussed using other fields, Highland Farm among them, to ease programming pressure on Cherry Lawn. Committee Chair Adele Conniff answered that Highland Farm has limited usage because of "contractual restrictions that prohibit permanent structures and require set intervals between scheduled usage to accommodate parking." The study failed 4–5, with one abstention.
The 2016 terms allowed a small building. The restriction Conniff described rules out permanent structures. Whatever the reason for the difference, the 2026 version is the one now in effect.
Set Fall for Darien against those limits and the format makes sense. The festival runs three hours and ends at 2 p.m. Every attraction on the bill can come and go in a day: a band, a petting zoo, face painting, artisan tables, a caricature artist. Nothing stays on the grass afterward. Parking comes from the 92 spaces the RTM paid for in 2019. A one-time Saturday also avoids the problem that comes with weekly league play, which needs gaps between scheduled uses so the lots can clear.
So the field that couldn't take pressure off Cherry Lawn's soccer schedule is getting its first Parks & Recreation festival this fall.
The long weekend, in order
Columbus Day falls on Monday, October 12 this year, so the festival opens a three-day weekend. Two town dates bookend it.
- Saturday, October 10, 11 a.m. to 2 p.m. Fall for Darien at Highland Farm, 560 Middlesex Road. Admission is free, and vendors will have items for sale. Caricature drawings are $20. Leashed dogs are allowed on the property under the July 2025 rules. If you plan to bring one, consider how crowded the petting zoo area will be.
- Monday, October 12. The Weed Beach paddle tennis courts open for the 2026–2027 season. Seasonal reservation applications closed September 10, and a lottery was scheduled for September 15 if demand called for one. From October through March, the Weed Beach Paddle Hut is reserved for paddle parties only.
For details beyond the town's calendar listing, check the Darien Parks & Recreation page. The town points visitors there for festival updates.
Around town that weekend
If you're looking for a stop on the way to or from Middlesex Road, a few places are open and others are still on the way.
Open now. DoChéri, the European chocolate shop Maryna Steadman founded, soft-opened on the Post Road in May. CTBites reported its autumn flavors as pumpkin chai, apple caramel, and cranberry. Steadman described the town's response to the shop as welcoming.
Coming this fall, no date yet. Romanacci is set to open at Heights Crossing, 346 Heights Road, in Noroton Heights. Patch reported on September 30 that it's due "this fall," with no specific day announced.
Downtown, still under construction. The Corbin District's most recent posted construction update is dated June 1. Developer David Genovese wrote that Tatte had started its work a couple of weeks earlier and that more tenants would begin work that month. He said exact opening dates would be shared once they were firm. Tatte's own site still lists its Darien location as "Opening 2026." MiniLuxe, which announced a Corbin District lease on September 11, is targeting early 2027. No published source confirms whether the new traffic signal at the Boston Post Road and Corbin Drive intersection is working yet, so allow extra time if your route goes through downtown.
That leaves Highland Farm as the newest public event in town this long weekend. It runs on 16 acres the town bought in 2016 and has improved in careful, temporary steps ever since. If the "first annual" label holds, a second Fall for Darien in 2027 will follow the same rules.
Want to know how town-owned open space like Highland Farm affects the streets around it, or what Darien's open-space commitments mean for a particular property? Konstantine G Wells follows these town decisions closely and can go through them with you. Request a free home valuation or schedule a consultation.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
