I Let an Algorithm Plan My Art Weekend. Here's Where It's Taking Me.
A preview of Upstate Art Weekend 2026, routed by machine, experienced by two.
There’s something fitting about trusting a planning algorithm to send you into the landscape to look at art.
This year, Upstate Art Weekend launched an Adventure Builder — a new interactive itinerary tool that lets you filter by day, region, interest, and drive time, then generates a sequenced route across the weekend’s 670+ program listings in 69 towns. It’s practical and, frankly, overdue. UAW has always been one of those events that rewards the obsessive planner and quietly punishes everyone else. The Hudson Valley is gorgeous and sprawling, and without a system, you’ll spend your weekend driving in the wrong direction between things you’ve already missed.
So I used it. I filtered for what I care about — contemporary art, fiber and textile, immersive installation, outdoor work, free admission — and let it build my three-day route. It came back with 18 suggested stops across Kingston and Ulster County, 408 estimated drive minutes, and a very clear opinion about where I should be and when.
I’m going to follow it. Mostly.
I should also mention: I’ll have my five-year-old with me.
Why This Matters Beyond the Itinerary
I’ve been thinking a lot this year about presence as a scarce resource — it’s the conceptual thread running through my Working Creative editorial calendar. We talk constantly about attention economy, about digital overwhelm, about reclaiming focus. And yet the answer is rarely to go analog for the sake of it. It’s to make choices about where and how we show up.
Upstate Art Weekend, for me, is one of those choices. It’s one of the few events that still asks you to actually go places — to drive up a county road, find parking in a field, walk into a barn, and stand in front of something someone made. The Adventure Builder makes that easier. Bloomberg Connects, the official digital guide partner for UAW, is part of why experiences like this can build the infrastructure to meet audiences where they are.
But the tool is only as good as what you bring to it. I’m bringing fifteen years of brand and cultural strategy, an active painting practice, a deeply particular set of interests, and an almost kindergartner who will absolutely ask me to explain every single thing.
That, honestly, sounds like the right conditions for paying attention.
The Route
The planner built my weekend around Kingston and Ulster County, working south to north across three days.
Friday, June 26 opens at Nervous System in Palenville — a fitting start, honestly, given that Nervous System (Jessica Rosenkrantz and Jesse Louis-Rosenburg) works at the intersection of computation, biology, and form. From there the route moves into Kingston proper: Artport Kingston’s open-air car installation exhibition, the UAW HQ’s curated Earthen Plot show, Front Room Gallery’s Expanded Field, and UTOPIA’s Iron and Indigo, which brings together artists using natural pigments and land-based media. The day closes at Villa Isis in Highland — an immersive Nordic-New York environment with sculpture, sound, lace demonstrations, and outdoor film.
Saturday, June 27 — the day of The Gallery ATX’s own ART IN ATX: Pride Market back in Austin, which I’ll be tracking from upstate — takes us to Whimsy Flowers Farm in Kerhonkson for Echoes of Nature, through two Ellenville stops, up to RAVENWOOD’s The Shape of Color in a 1850s barn, down to Army of Frogs Studio in High Falls, and ending at Alpana Bawa’s Held in Thread, a three-artist fiber show.
Sunday, June 28 begins at Hudson Valley Seed Company in Accord for Fleeting Bloom, Fixed Form, moves through Thicker Dust at Station Kingston and Hey, Friend at Stony Kill Studios, then to Glasshouse Project’s 24-hour durational performance in New Paltz, and closes at Woodstock School of Art’s outdoor art fair and Available Items x Amin Tadj Studio’s Sense of Place in Glenford.
Three days. One county. A lot of fiber, natural materials, outdoor work, and land-rooted practice. The algorithm, it turns out, knows my taste.
What I’ll Be Looking For
I make paintings. Mostly landscape — imagined environments where natural forms and industrial structures share the same picture plane. I’m interested in the tension between systems that promise order and the unruly humanness that persists anyway. Looking at art about land, place, and material feels continuous with that.
What interests me most in this lineup is the consistent thread of land-based and ecologically rooted practice. Earthen Plot, Iron and Indigo, Fleeting Bloom Fixed Form, Echoes of Nature, Sense of Place — the titles alone suggest a field (no pun intended) preoccupied with where we come from and what the ground means. That’s not a trend, it’s a reckoning, and I want to look at it carefully.
I’m also genuinely interested in the immersive and durational work. The 24-hour performance at Glasshouse Project and the Villa Isis experience both ask something of the visitor beyond passive viewing. With a five-year-old, I’ll find out quickly whether “immersive” is a promise or a sales pitch.
Follow Along
I’ll be posting from the road on Instagram throughout the weekend. A Substack piece on the full experience — what landed, what surprised me, what I’ll carry back into my own practice — will follow the week after.
I’m also considering making this a vlog. We’ll see. The algorithm can plan the route but it can’t tell me whether I’m brave enough to put a camera in my face on a country road while explaining fiber installation to a five-year-old.
Stay tuned.
Working Creative is a newsletter about brand strategy, cultural intelligence, and the business of creative work. If this resonated, subscribe and share.
++++++++++++++++++++++++++++++++++++++++++
Reb Carlson is a brand and digital marketing strategist specializing in cultural relevance for luxury, travel, and lifestyle brands. She has led brand marketing for HUGO BOSS, Evian, Marriott, Master & Dynamic, and others — and currently serves as President of The Gallery ATX, an Austin-based nonprofit amplifying underrepresented artists through community programming and exhibitions.
If something here sparked an idea for your brand, she’d love to talk → https://www.linkedin.com/in/rebcarlson/