Fall at Ashokan, O+ Weekend + Art in the Gunks
Peak fall views, a Joni Mitchell tribute at O+, artists painting Mohonk, The Bobby Lees at Bearsville and three Hudson Valley finds worth the detour.
This is the kind of October weekend we wait for.
The forecast is cooperating, the leaves are turning and there are very good reasons to spend as much time out in the Hudson Valley as possible.
So this week, we’re leaning into fall.
We’re heading to the Ashokan for one of the biggest mountain-and-reservoir views in the region, wandering through a wildly beautiful Victorian estate overlooking the Hudson in Rhinebeck, and spending the weekend in Kingston as O+ fills the city with music, art and murals before closing Sunday night with The Road to Joni: Live!, a celebration of Joni Mitchell’s music.
Saturday brings another good excuse to get outside: artists are setting up their easels across Mohonk Preserve to paint the Shawangunks in real time. Then Saturday night, Woodstock’s own The Bobby Lees take over Bearsville Theater.
Looking ahead, the Village of Catskill becomes one big comedy club and the Woodstock Film Festival brings five days of independent film back to the Hudson Valley.
And On Our Radar: apple picking with a mountain view in Red Hook, a Saugerties bookstore-café that feels like a neighborhood living room and a Kingston diner that has been doing its thing since 1976.
Go somewhere beautiful. We’ll bring the soundtrack.
Explore the Hudson Valley
One huge fall view and one Hudson Valley house that looks like it belongs in another century.
This May Be the Best Fall View in Ulster County Right Now
There are plenty of places to see fall color in the Hudson Valley. The Ashokan puts an entire Catskills panorama in front of you.
The Ashokan Rail Trail follows 11.5 miles of the reservoir’s northern edge, with long stretches where the mountains rise directly beyond the water and the former Ulster & Delaware Railroad corridor cuts through woods turning red, orange and gold.
You do not need to tackle all 11.5 miles. Start at one of the three trailheads, walk or bike as far as you feel like going, and turn around when you’ve had enough.
The wide crushed-stone trail is relatively flat, which means the payoff here is not about conquering a summit. It is about having an enormous Catskills view without having to earn it the hard way.
Why we recommend it: If you want one big Hudson Valley foliage picture this weekend, this is the one we’d chase.
There’s a Five-Story Victorian Tower Hiding Above the Hudson
A few minutes outside the center of Rhinebeck, the road disappears into the woods and suddenly one of the Hudson Valley’s most dramatic Victorian houses appears.
Wilderstein began as an Italianate country house before an 1888 transformation turned it into the elaborate Queen Anne mansion you see today — complete with a five-story circular tower, sweeping verandas, ornate rooms and views toward the Hudson.
The house is only half the reason to go.
Its 40-acre landscape was designed by renowned landscape architect Calvert Vaux, with carriage drives, wooded trails, specimen trees and carefully framed views across the property.
In October, the whole thing gets an extra layer: Victorian architecture rising out of fall woods with the Hudson just beyond the trees.
Why we recommend it: We love finding a Hudson Valley place that makes you wonder how you have driven past it for years without knowing it was there. Wilderstein is one of those places.
This Weekend
O+ takes over Kingston, artists paint the Gunks in real time and The Bobby Lees come home to Woodstock.
O+ Is Closing the Weekend With a Love Letter to Joni Mitchell
For three days, Kingston becomes one giant exchange of music, art, murals, wellness and community.
The O+ Festival returns October 9–11 with performances, artists, public art and wellness programming throughout the city — all built around O+’s unusual model of exchanging healthcare for the art and music artists bring to the community.
But the moment we are circling comes Sunday night.
At 7:30 PM at Old Dutch Church, Carmel Holt’s The Road to Joni: Live! closes the festival with musical direction from Meg Toohey and performances from Amanda Seyfried, Laura Stevenson, Carl Newman, Kalmia Traver, Peter Silberman and more.
It is less a traditional tribute concert than a room full of artists answering the songs of Joni Mitchell in their own voices.
Why we’re circling it: O+ is already one of Kingston’s most distinctly local weekends. Ending it with a live celebration of Joni Mitchell makes this year feel especially Radio Woodstock.
Watch Artists Paint the Gunks in Real Time
There are a lot of ways to look at the Shawangunks in October. This weekend, you can watch nearly 30 artists interpret them one canvas at a time.
On Saturday, Mohonk Preserve and Roost Arts Hudson Valley bring back their fifth Plein Air Art Walk at the Testimonial Gateway Trailhead.
Artists spread out along the landscape from 10 AM to 3 PM, painting outdoors as visitors wander the trail and watch the work take shape against the actual ridge, fields and fall foliage that inspired it.
Beginning October 11, the finished pieces will be displayed at the Mohonk Preserve Visitor Center Gallery through November 1 and offered in an online auction benefiting the artists, Mohonk Preserve and Roost Arts.
Why we’re circling it: Fall foliage is already worth looking at. Getting to watch artists turn it into something else while you are standing there makes this one considerably more interesting.
The Bobby Lees Come Home to Bearsville Saturday Night
This one feels especially close to home.
Woodstock-born The Bobby Lees return to Bearsville Theater Saturday night with the kind of loud, jagged garage-punk that has earned them fans including Iggy Pop, Debbie Harry and Henry Rollins.
The band’s fourth album and Epitaph Records debut, New Self, pushes their sound even further — produced by Dave Sardy and Alex Pasco and built around the raw energy that has always made their live shows the real point.
They’re joined by Scattrbrain.
Why we’re circling it: A Woodstock band, an independent streak and a Saturday night at Bearsville. This one did not require much debate.
Plan Ahead
An entire village turns into a comedy club and five days of independent film take over the Hudson Valley.
For One Weekend, Catskill Becomes One Big Comedy Club
Next weekend, comedy spills out of a single theater and into an entire village.
The Catskills Comedy Festival returns October 16–18 with three days of stand-up, improv, alternative comedy, film, panels and free programming spread across seven walkable venues in Catskill.
Friday night brings Ophira Eisenberg, Jocelyn Chia and Raanan Hershberg to the Community Theatre. Saturday’s programming includes the festival’s Main Stage headliner show plus performances, conversations and shows throughout the village.
There is also an important reason behind the laughs: proceeds support the festival’s free comedy workshops, classes and programming for young people.
Why we’re circling it: We like any festival that makes you walk through town to find the next thing — especially when the next thing is funny.
Five Days of Independent Film Take Over the Hudson Valley
The Woodstock Film Festival returns next week with five days of independent cinema, filmmaker Q&As, panels, special events and screenings spread across Woodstock, Kingston, Rosendale and Saugerties.
The festival has spent more than two decades building the kind of environment where filmmakers actually stick around after the credits — which means the conversations can be as memorable as the movies.
Why we’re circling it: It is one of those weeks when the Hudson Valley briefly feels like the center of the independent film world.
On Our Radar
Apple picking with a Catskills view, a Saugerties bookstore-café built for lingering and a Kingston classic worth another look.
There are plenty of places to pick apples in the Hudson Valley, but Greig Farm gives you a little more reason to stay awhile.
The family-run farm has been here since 1942, and right now the orchards are open for apple picking alongside pumpkins and other fall farm finds. On weekends, you can add a hayride, visit the goats, walk the farm trails or stop into the market and café before heading home with a bag of apples.
Why it’s on our radar: Because October should probably involve at least one afternoon that smells like apples, leaves and a farm.
227 Pitcher Lane · Red Hook · Apple picking + pumpkins · Seasonal · Weekend hayrides available · Check current picking conditions & plan your visit
Part bookstore, part café, part neighborhood living room, Inquiring Minds is one of those places that makes you want to browse without a plan.
Along with shelves of books, the shop regularly hosts author talks, poetry nights and writing events — the kind of programming that makes it feel like more than a store.
Why it’s on our radar: Because every town needs a place where you can buy a book, get a coffee and accidentally stay for two hours.
200 Main Street · Saugerties · Visit Inquiring Minds
Not everything on our radar has to be new. Broadway Lights Diner has been feeding Kingston since 1976, and in a Hudson Valley dining scene where something new seems to open every week, there is something especially good about a place that has simply kept showing up.
This is the real diner deal: big breakfasts, burgers, Reubens, Greek specialties, homemade soups, pies and pastries, plus egg creams and milkshakes. The menu is enormous, the portions are generous and breakfast can turn into lunch without anybody rushing you out the door.
Why it’s on our radar: Because sometimes the place worth circling is the one that has been there all along.
713 Broadway · Kingston · Family-owned since 1976 · See the menu
Curated each week by the Radio Woodstock team.
This weekend: catch the fall color along the Ashokan, wander a Victorian estate in Rhinebeck, spend the weekend with O+ in Kingston, watch artists paint the Gunks or head to Bearsville when The Bobby Lees come home.
And looking ahead: put the Catskills Comedy Festival and Woodstock Film Festival on the calendar.
If you find yourself somewhere in the Hudson Valley thinking How did I not know about this?, send it our way at promotions@radiowoodstock.com.
Those are exactly the places we’re looking for.
We’ll see you next Thursday.