Cheshire, CT

Roaring Brook Falls

The tallest single-drop waterfall in Connecticut, sitting at the top of a steep, barely-marked climb in Cheshire. I hiked it solo to scout it first. Big payoff, but this one's for older kids, not the stroller crew.

Drive time

About 35 min

Difficulty

Moderate to strenuous. Steep, and with almost no trail markings.

Distance

About 1.5 mi round trip

Admission

Free β€” town of Cheshire open space

Parking

Minimal lot plus street parking on Roaring Brook Road (827 Roaring Brook Rd). Free, no fee or sticker. GPS gets you right there.

Bathrooms

None at the trailhead β€” go before you come

Picnic

No tables; it's a hike-in falls, not a picnic park

Dogs

Yes, on leash

The trip

I went up to scout this one solo before dragging the whole family out, and I'm glad I did. It's the tallest single-drop waterfall in Connecticut, eighty feet in one clean shot, and that part lives up to the hype. Getting to it is a different story than I expected.

GPS drops you right at the end of Roaring Brook Road. Parking is minimal, basically a small lot plus whatever street parking you can grab, but it's free, no fee or sticker, and cell signal is solid at the trailhead. That last part matters more than it should, because the trail markings are almost nonexistent. I actually took a wrong turn once and had to double back. Do yourself a favor and pull up a trail app with the route downloaded before you start.

80 feet of water in one clean drop. You just have to earn the climb, and actually find it.

The first stretch is flat and easy, running right past Lily Pond, and that part you could genuinely do with a stroller. Then it turns. From there it's all dirt and rock, and it climbs, steep enough that I'd call it not for the faint of heart. About a mile and a half round trip. This is the honest part I got wrong before I went: this is not a hike for a three or five year old. I'd wait until the kids are preteen and up before bringing them on the climb.

The falls at the top are worth the work. Standing under eighty feet of water dropping in a single line is exactly the payoff you want. So this one's staying on the family list, just a few years out. When the girls are big enough for the climb, we'll go back and I'll write the real trip with their ratings.

The plan

Stop by stop

  1. 1

    Trailhead and the Lily Pond flat

    Morning Β· 5-10 min
    Trailhead

    Park at the end of Roaring Brook Road and start along the flat path by Lily Pond. This opening stretch is easy and even stroller-doable. Enjoy it, because it doesn't last.

  2. 2

    The steep, unmarked climb

    Morning Β· The bulk of the hike
    Hike

    Past the pond it's all dirt and rock, and it climbs hard. The markings are almost nonexistent, so keep your trail app open. I went the wrong way once. Take it slow and watch your footing on the loose rock.

    Rainy swap: The rocks get genuinely slick when wet, and the footing is already loose. Save this for a dry day, or at least the day after the rain rather than during it.

  3. 3

    The falls

    At the top Β· As long as you want to sit with it
    Waterfall

    Eighty feet of water in a single clean drop. This is the whole reason you climbed. Take it in, get your photos, and keep well back from the slick rocks near the edge.

Checking this weekend's weather…

Dad tips

  • β–ΈBring a trail app with the route downloaded. The markings are almost nonexistent and I took a wrong turn once. Good news: cell signal at the trailhead is strong.
  • β–ΈThis is not a little-kid hike. The climb is steep and rocky. I'd save it for a preteen and up, not a three-to-five year old.
  • β–ΈThe only stroller-friendly part is the flat start by Lily Pond. Once it climbs, it's dirt and rock the rest of the way.
  • β–ΈReal shoes with grip. The footing is loose and steep, and it gets slick near the water. Sneakers are fine, sandals are not.
  • β–ΈNo bathroom at the trailhead, so everyone goes before you leave.
  • β–ΈParking is a small lot plus street parking, and it's free. Go earlier on a nice weekend to be safe.

What to bring

  • βœ“Your phone with a trail app and the route downloaded
  • βœ“Sturdy sneakers or hiking shoes with grip
  • βœ“Water for everyone (short trail, but it's a real climb)
  • βœ“A small backpack so your hands are free for the steep parts
  • βœ“Bug spray in summer
  • βœ“Cash or a card for ice cream on the way home

Best time to visit

Spring snowmelt or a day or two after heavy rain. In a dry summer it can slow to a trickle, so check the weather before you drive out.

While you're out there

Nearby stops

Ice cream

  • Sweet Claude's Ice Cream

    Homemade, 30-plus years in Cheshire, porch seating. The classic post-hike stop.

  • Micro Creamery of Connecticut

    80-some ice creams from CT creameries under one roof, family games upstairs, dog-friendly.

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