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
- 2Hike
The steep, unmarked climb
Morning Β· The bulk of the hikePast 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.
- 3Waterfall
The falls
At the top Β· As long as you want to sit with itEighty 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 weatherβ¦
Dad tips
- βΈBring 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.
- βΈThis 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.
- βΈThe only stroller-friendly part is the flat start by Lily Pond. Once it climbs, it's dirt and rock the rest of the way.
- βΈReal shoes with grip. The footing is loose and steep, and it gets slick near the water. Sneakers are fine, sandals are not.
- βΈNo bathroom at the trailhead, so everyone goes before you leave.
- βΈParking is a small lot plus street parking, and it's free. Go earlier on a nice weekend to be safe.
What to bring
- βYour phone with a trail app and the route downloaded
- βSturdy sneakers or hiking shoes with grip
- βWater for everyone (short trail, but it's a real climb)
- βA small backpack so your hands are free for the steep parts
- βBug spray in summer
- βCash 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.
Keep exploring
Related adventures
Berlin, CT
Ragged Mountain
The biggest challenge on my list. A rugged traprock loop with real rock scrambles and bare-cliff views down onto Wassel Reservoir and Hart Ponds, in Berlin. About 35 minutes away. Next up.
Bethany, CT
Beacon Cap
A quiet, all-woods loop to a striking glacial boulder in the Naugatuck State Forest. Good exercise and total solitude, but no views the whole way except the one you climb the rock for. Honestly, not my favorite.
Hamden, CT
West Rock Ridge
My favorite hike, just ahead of Mount Higby, and it's the closest real ridge to home. A busy family pond at the bottom with fishing and a bathroom, then you climb and the ridge is all yours, quiet enough to hear the chickadees. About 20 minutes away.