The State Line Runs Through the Best Saturday in Hillsdale and Copake

Ask someone who has hiked to Bash Bish Falls a dozen times which state they were standing in when they took their photo at the top of the gorge, and most people pause. The honest answer is that they don't know, and they've never needed to. That small hesitation is the whole story of a Saturday in this stretch of Columbia County. The best version of the day treats the New York-Massachusetts line as a technicality, something that matters to a park ranger's paperwork but not to anyone actually walking the trail, riding the chairlift, or picking up a loaf of bread.

That's worth sitting with, because it changes how you think about what "local" even means out here. Taghkanic, Hillsdale, and Copake don't function as a self-contained pocket of New York. They function as the New York half of a loop that keeps crossing into Massachusetts and back, often without anyone noticing they've left the state.

The Falls Are in Massachusetts. The Trailhead Isn't.

Bash Bish Falls is the most photographed waterfall within a half hour of Hillsdale, and it sits inside Massachusetts, inside Bash Bish Falls State Park, fed by the Green River. But the easier, more forgiving way to see it starts in New York, at the Taconic State Park trailhead off Route 344 in Copake Falls.

The two approaches aren't close to equivalent. The New York side is a gradual, mostly flat walk along Bash Bish Brook, about 1.5 miles round trip, and it's the route the Massachusetts Department of Conservation and Recreation itself describes as the moderate option, suited to families. The Massachusetts side, reached from a small 24-car lot on Falls Road in Mount Washington, is shorter on paper but steeper and more rugged, closer to 0.6 miles round trip and rated difficult.

So the practical move, the one locals make without thinking about it, is to park in New York and walk into Massachusetts to see the water. You start the hike in one state and end it in another, and the only real evidence of that is a sign near the border where hikers stop for a photo. The falls themselves, split by a boulder into twin cascades dropping roughly 60 feet, don't care which side of the line they're on. Neither does anyone standing there in October, with the gorge walls going orange and red above the water.

The Chairlift Straddles the Border on Purpose

Keep driving north from Copake Falls and you land at Catamount, a four-season resort that sits literally on the New York-Massachusetts border in Hillsdale. In fall, Catamount runs its Ridge Quad chairlift on weekends and holidays purely for the view, no skis required, for around $15 a rider. It's a five-minute ride up and the same back down, and depending on where the lift line happens to fall that day, part of the ascent takes place in a different state than the one you bought your ticket in.

That's not a quirk anyone advertises. It's just geography. The mountain doesn't reorganize itself around a survey line, and neither does the foliage. What changes is the framing: a free 1.5-mile walk to a waterfall in the morning, a paid five-minute lift ride to a ridge view in the afternoon, both crossing the same invisible boundary, both counted by the people who live here as simply "going up to Catamount" or "going to the falls," full stop, no asterisk about which state actually holds the ground under your feet.

Saturday Morning Still Belongs to New York

Not everything in the loop blurs the line. The Copake Hillsdale Farmers Market runs Saturdays from 9 a.m. to 1 p.m., Memorial Day through Halloween, in the Harvest Barn at Roeliff Jansen Park on Route 22 in Hillsdale, and it is entirely, unambiguously a New York institution. Heirloom vegetables, grass-fed meat, pressed cider, and a rotating cast of local musicians, all inside a state that, for once, isn't sharing credit with its neighbor.

That contrast matters more than it looks like it should. The market is the one anchor in the day that stays put administratively, which is exactly why it works as a baseline. If the falls and the mountain are proof that residents treat the state line as scenery, the market is proof they still know exactly where home is. You don't drive to Massachusetts for produce. You drive to Roeliff Jansen Park, every Saturday, for five months, because that's where the market has always been.

The Bookstore That Chose the Other Side

The newest piece of this loop makes the same point from a different direction. Books & Cake opened at 8 Anthony Street in Hillsdale in October 2025, run by two longtime friends and children's book authors, Eve Yohalem and Julie Sternberg. Sternberg's family had been part-time residents of Copake for twenty years before the store opened. Yohalem's family has been in the Berkshires for decades. Neither of them lived in Hillsdale. They chose it anyway, because it was the hamlet with no new-book seller within 20 miles and, as Yohalem has said publicly, an unusually welcoming community for a bookstore to land in.

A business built by two people rooted in Copake and the Berkshires, opened in Hillsdale, tied by events to Roe Jan Brewing's beer garden a few blocks over. That's not a coincidence. That's just how the geography works here.

The store's ties reach further into the loop than its address suggests. Earlier this year it hosted a Battle of the Books event in the beer garden at Roe Jan Brewing Company, panelists making the case for their favorite title over pints. It also runs a recurring Tiny Bookstore Concert series, small live sessions inside the shop that have run on and off since spring. None of that required Books & Cake to be in Copake, or Roe Jan Brewing to be in Hillsdale. The businesses simply operate as if the space between the two hamlets doesn't function as a real divider, because for the people running them, it never has.

What the Loop Actually Tells You

Put the four stops in order and the pattern holds all the way through:

• Morning: Copake Hillsdale Farmers Market, Roeliff Jansen Park, Hillsdale, NY. Squarely local.
• Midday: Bash Bish Falls, trailhead in New York, waterfall in Massachusetts.
• Afternoon: Catamount's Ridge Quad, chairlift straddling the state border in Hillsdale.
• Evening: Books & Cake, a Hillsdale storefront built by Copake and Berkshires residents, tied by programming to a Hillsdale brewery.

Only one of those four stops is unambiguously, only, New York. The other three either cross the line, sit on it, or were built by people who live on the other side of it. That's the claim worth holding onto if you've lived here long enough to stop noticing it yourself: this isn't really a New York neighborhood with a scenic Massachusetts border nearby. It's one continuous stretch of the Taconics that happens to have a state line running through the middle of its best Saturday, and the people who live here have simply stopped treating that line as a boundary worth respecting when they're deciding where to hike, where to ride a chairlift, or where to open a bookstore.

If you've ever tried to explain to an out-of-town friend why "just up the road" sometimes means driving into another state, now you have the short version.

If a friend ever asks you what it's actually like to live in this corner of the county, on both sides of that line, Paula Redmond has spent more than four decades tracking exactly how neighborhoods like this one work, in Columbia County and across the border into Litchfield County, Connecticut. When the conversation turns from a Saturday hike to a real decision, her Request a Confidential Home Valuation is a good place to start.