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Highland Farm/ Caballos

4.7 ★★★★★ 12 Google reviews · Running trail in Darien, Connecticut · Dawn to dusk

Runner's snapshot

Surface
Not reported
Distance
Not reported
Shape
Not reported
Shade
Not reported
Access
Dawn to dusk

Confirmed from Highland Farm/ Caballos' own listing, the park or land manager's website, and runner reviews. Blank cells mean we could not verify that fact — we would rather say "not reported" than invent one. There is no Easy / Moderate / Hard rating on this page on purpose: a one-word difficulty score tells you nothing about whether a trail suits your run. Surface, distance, shade and hours do.

Highland Farm/ Caballos — running trail in Darien, CT, photo 1

What runners say about Highland Farm/ Caballos

Pulled from public reviews of this trail (12 of them) — the things people bring up again and again, in their own words. Nothing here is written by us.

Nice place to walk around during day, take the dogs 🐶 for a stroll, or watch the stars at night. 🌌

★★★★★ — Saskia , Oct 2021

Excerpts from public Google reviews. Read all 12 reviews →

Plan your run at Highland Farm/ Caballos

The practical stuff

  • AccessDawn to dusk — the gates close, so do not plan a run that finishes after dark
  • DistanceNot reported. Trail systems often quote total path mileage rather than a single loop, so measure the route you actually want before you drive out.
  • ShadeNot reported. Assume some of it is exposed and carry water in summer.
  • Websitedarienct.gov
  • Phone(203) 656-7325
  • Social Instagram · Facebook

Hours

Monday 5 AM–10 PM
Tuesday 5 AM–10 PM
Wednesday 5 AM–10 PM
Thursday 5 AM–10 PM
Friday 5 AM–10 PM
Saturday 5 AM–10 PM
Sunday 5 AM–10 PM

Posted hours for the park or trailhead. Gates and parking lots often close earlier than the trail itself, and seasonal hours change — worth a check before a pre-dawn or after-dark run.

Where to find Highland Farm/ Caballos

560 Middlesex Rd, Darien, CT 06820

Get directions

Running trails near Darien

Other trails within easy driving distance — useful when this one is flooded, gated, or just not the run you had in mind today.

Cherry Lawn Park

4.7 ★★★★★ 257 reviews

Darien, CT

ScenicDog-friendly

A 27.5-acre park with a community garden, nature center, playground, sports fields & tennis courts.

1.1 miles away

Darien Nature Center

4.8 ★★★★★ 31 reviews

Darien, CT

Lit

1.1 miles away

Tilley Pond Park

4.7 ★★★★★ 151 reviews

Darien, CT

ScenicDog-friendly

Peaceful and charming park with fountains featuring ducks and Canada geese.

1.5 miles away

Piacentini Nature Preserve

3.3 ★★★☆☆ 3 reviews

Darien, CT

1.6 miles away

Waveny Park

4.8 ★★★★★ 1,041 reviews

New Canaan, CT

ScenicDog-friendly

250-acre city park featuring indoor & outdoor sports courts, a pool, plus a performing arts center.

1.7 miles away

Dunlap Woods (Darien Land Trust)

3.7 ★★★★☆ 7 reviews

Darien, CT

Dog-friendly

1.8 miles away

All running trails in Darien, CT →

Nearby towns

Listing verified July 2026 from public records, the trail's own website and runner reviews. Trail conditions change — paths flood, gates close at dusk, and shaded woods stay muddy for days after rain. Something out of date? Report a correction. Manage this trail? Send us the details — it is free.