50 Hikes 50 States–Massachusetts

Thanks to Southwest Air‘s companion pass, we made our way from Chicago Midway (and our Illinois and Indiana hikes) to Boston Logan’s airport in just a few hours. Landing at 3:30, we grabbed a car and headed as far west as we could go in Massachusetts before arriving in New York.

Sunset loomed.

Thus, our plans for a longer hike got dashed and we snuck in at the last sunset minute to Bash Bish Falls in Massachusetts. But first, we had to resolve our confusion on where to start our hike, New York or Massachusetts.

Two States, Two Entries, One Falls

Bash Bill Falls falls right on the New York-Massachusetts border. You can approach it from two ways, and if you plan it right, you can knock out two states in one hike by starting in New York and hiking up to the Falls in Massachusetts. We didn’t want to “cheat” though on our 50 Hikes 50 States project, so we stuck to the Massachusetts approach instead.

But if you start in New York, you’re in for a treat. Park in the Taconic State Park parking lot and walk the pleasant 2/3 mile flat, wide trail along the creek bed to the Falls. I’d recommend this approach in order to pick up some distance. Arrive at the Falls, then hike up the steep incline in Massachusetts to the overlook for another 1/2 mile. Then, for a full 3 1/2 miles round-trip, you’ll have a great hike across two borders that’s both fun and challenging.

We didn’t do that.

Down We Go

With the sun quickly looking to end its day, we started at the parking lot in the Bash Bish State Park on the Massachusetts side of the trail. My teen and husband joined me. I quickly learned from our hike in Illinois that my teen needs inspiration to hike. A waterfall was all it took. She was off like a bat at dusk looking for dinner.

Straight down the trail she flew. My husband and I were a bit slower. Steep, rocky, and without rails, this trail, named as one of the Most Dangerous Tourist Attractions in the US, kept our wits about us. I had taken time to slip my boots on, thanksully, but I was wishing for my poles. I seriously underestimated that a “little hike the to Falls” would be so challenging. I started to rethink my decision to approach the Falls from the Mass side rather than from New York.

None the less, we persisted.

Through a forest of sugar maple, yellow birch, American beech, and white ash, we balanced, jumped, slid, and stepped along a rocky trail of roots, rocks, and steps for a vertical drop of 328 feet in less than a 1/2 mile. The sky’s colors started to burst with sunset brilliance as the horizon popped between the trees. In a quick 15 minutes, we arrived at the Falls.

The biggest Falls in Massachusetts.

Bash Bills Falls cascade nearly 200 feet total, splitting into twins falls over rocks for another 80 feet to the final pool of inviting water. But don’t go swimming. None allowed. Although no one seemed to pay attention to the No Swimming and Danger signs.

My teen lit up. She pulled out her new Instax camera and got to snapping. While her instaphotos popped out from the top of her camera, I sat back and enjoyed the sounds of the waterfall and the giggles of everyone enjoying them. But our time was short. The sun began its sink below the horizon; we had limited time to get back up through the darkening forest.

Back Up, Oh God

Up. Up. Up. Count the steps, it goes faster. Up. Up. Up.

We made it up in 21 minutes (I think our Colorado altitude training had helped!) with enough daylight left to continue the climb to the Overlook.

And then a scrabble

Get your scrabble and scramble on. To finish off our dash up Bash, we went straight up a rock face aided by a metal chain for about 100 feet to the Overlook.

It was worth the climb to watch the sun disappear over the woods of the Taconic Mountains and its Berkshires valley. A quick pic was all the time we had.

Perhaps we should have had head lamps. None the less, the metal chain guided us down the rock face to our car. Granted, we had only hiked maybe a total of 1 1/2 miles (next time we’ll do the longer New York-Mass-New York out-n-back), but it was really fun to squeeze in a great hike at the end of the day. And to appreciate what fires up my teen. That was cool.

For dinner, we grabbed some grub from a grocery and ate it on the back patio of our funky AirBnB near East Chatham where the vibes vibrated and the essence ascended. A bit trippy but fun.

Next up, we’ll hike Connecticut. Stay tuned.

What You Need to Know about this Hike (click for interactive map)


  1. Les

    Awesome waterfall!



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handsome hiking couple

Chris and Steve, the empty-nesting nomads, travel the world, one month at a time, housesitting and Airbnbing along the way. We uncover urban walks, great hikes, and vegan/vegetarian eats that other guide books miss. And we throw in a bit about Forex trading along the way.

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