Circle This · A Radio Woodstock Guide
Week of October 1, 2026

500 Acres of Art, Trails and Fall Views at Storm King

Sarah Sze, Fallen Sky, 2021. Image courtesy of Storm King Art Center.

Storm King in fall, vintage planes at Old Rhinebeck Aerodrome, Country Living Fair, Arrowood Harvest Fest, Margaret Glaspy and a few Hudson Valley finds worth the detour.

After two weekends of weather getting in the way, we finally have a reason to make plans outside.

This week, we’re walking among monumental sculpture at Storm King, watching century-old airplanes take off at Old Rhinebeck Aerodrome, shopping 200+ vendors at the Country Living Fair, heading to Arrowood for an all-day harvest celebration and spending Saturday night with Margaret Glaspy in Kingston.

Looking ahead: witches on paddleboards in Sleepy Hollow, Ani DiFranco at Bearsville, and a new record store in New Paltz.

The weather is finally giving us a window. Take advantage of it.

Explore the Hudson Valley

Two places made for a weekend when the best room in the Hudson Valley is outside.

Sarah Sze's Fallen Sky at Storm King Art Center
Sarah Sze, Fallen Sky, 2021. Image courtesy of Storm King Art Center.
New Windsor · Storm King Art Center

500 Acres of Art, Trails and Fall Views at Storm King

After two weekends when the forecast kept interfering with everybody’s plans, this feels like the weekend to go big.

Very big.

Storm King Art Center stretches across 500 acres of fields, woods and rolling hills, where monumental sculpture becomes part of the landscape rather than something you look at from across a gallery.

You can spend hours walking between works by some of the most important modern and contemporary artists, following paths through open meadows and wooded sections with the Hudson Highlands rising around you.

And fall is exactly when the scale of the place really makes sense: sculpture against changing leaves, long views across the property and enough room to wander without feeling like you are checking items off a museum list.

Why we recommend it: If the weather finally gives you a beautiful fall day after two washed-out weekends, spending it walking through 500 acres of art seems like a pretty good response.

1 Museum Road, New Windsor · October weekends · 9 AM–6 PM · Plan your visit
Vintage aircraft at Old Rhinebeck Aerodrome
Photo courtesy of Old Rhinebeck Aerodrome
Red Hook · Weekends through October 18

There’s a Living Museum in Rhinebeck Where the Airplanes Still Fly

A lot of museums ask you not to touch anything.

At Old Rhinebeck Aerodrome, some of the museum pieces start their engines and take off.

The flying museum is devoted to the earliest decades of aviation, with antique aircraft, period automobiles and hangars full of aviation history stretching from the pioneer era through World War I and the Golden Age of flight.

On Saturdays, the History of Flight show moves from the earliest airplanes into the 1920s and ’30s.

Sundays turn into the theatrical World War I Dogfight Spectacular, complete with antique aircraft, vehicles, heroes and villains.

And if watching from the ground isn’t enough, open-cockpit biplane rides are available before and after weekend shows, weather permitting.

Why we recommend it: This isn’t history sitting behind glass. It flies directly over your head — and a good-weather weekend is exactly when you want to see it happen.

9 Norton Road, Red Hook · Saturday & Sunday air shows through October 18 · Gates open 10 AM · Show begins approximately 2:15 PM · Flying and biplane rides are weather dependent · Plan your visit

This Weekend

Antiques and Americana in Rhinebeck, a harvest celebration in Accord and Margaret Glaspy in Kingston.

Country Living Fair
Photo courtesy of Country Living Fair
Rhinebeck · October 2–4

200+ Vendors, Antiques and Americana Take Over Rhinebeck

If the nice weather has you looking for somewhere to wander for a few hours, Rhinebeck is giving you plenty of reasons.

The Country Living Fair returns to the Dutchess County Fairgrounds for three days of antiques, craftsmanship, food, music and full-on fall-in-the-Hudson-Valley energy.

More than 200 antiques dealers, artisans and small boutique brands fill the fairgrounds alongside hands-on workshops, demonstrations and a Main Stage packed with designers, makers and familiar faces.

This year also adds an Americana Music Stage curated with The Bluegrass Situation, which gives us one more reason to work it into the weekend.

Saturday’s speaker lineup includes Mike Wolfe of American Pickers, plus designers, authors and tastemakers talking vintage finds, collecting and country living.

Why we recommend it: This is more than a shopping fair. It is 200+ reasons to wander the fairgrounds on a good fall weekend — with antiques, makers, food and live Americana all in one place.

Friday–Sunday, October 2–4 · Dutchess County Fairgrounds, Rhinebeck · Country Living Fair details
Harvest Fest at Arrowood Farms
Photo courtesy of Arrowood Farms
Accord · Saturday, October 3

Harvest Season Takes Over Arrowood Farms

If the weather is finally going to cooperate, spending Saturday on a 48-acre farm feels like the right move.

Arrowood Farms is turning its Accord grounds into a full-day celebration of the Hudson Valley harvest, with local food, artisan vendors, family activities, farm-brewed beer and spirits and live music running throughout the day.

The music builds toward a 6:30 PM headline set from The Big Takeover, bringing their reggae and ska-rooted sound to Arrowood’s outdoor stage.

And there’s a community piece too: 20 percent of festival proceeds will benefit the Rochester Food Pantry.

Why we recommend it: Sunshine, live music, local food and drinks, a farm in Accord and nine hours to enjoy all of it. This is exactly the kind of weekend the last two rainy ones owed us.

Saturday, October 3 · Arrowood Farms · 236 Lower Whitfield Road, Accord · Tickets & Harvest Fest details
Margaret Glaspy
Photo courtesy of Margaret Glaspy / Assembly
Kingston · Saturday, October 3

Margaret Glaspy Takes Over Assembly Saturday Night

Saturday night belongs to the guitars.

Singer-songwriter and guitarist Margaret Glaspy comes to Assembly in Uptown Kingston with Julia Zivic.

Glaspy’s music can move from stripped-down songwriting into jagged guitar lines and full-band intensity without losing the feeling that the song itself is still driving.

Put that inside Assembly’s intimate Wall Street room and this becomes the weekend’s live-music pick.

Why we’re circling it: Spend the afternoon outside. Come inside when the guitars start.

Saturday, October 3 · Assembly · 236 Wall Street, Kingston · Tickets & information

Plan Ahead

Witches on paddleboards in Sleepy Hollow and Ani DiFranco coming to one of Woodstock’s most intimate rooms.

Witches and warlocks paddle on the Hudson River during SUP Witches Festival
Photo courtesy of SUP Witches Festival / Rivertowns SUP & Yoga
Sleepy Hollow · Saturday, October 10

A Coven of Witches Is Paddling Down the Hudson

Sleepy Hollow has figured out how to make stand-up paddleboarding considerably more seasonal.

On October 10, witches and warlocks in full costume take to the Hudson off Kingsland Point Park for the annual SUP Witches Festival.

The festival runs from noon to 5 PM with live music, vendors, food and drinks onshore. The actual witch paddle happens at 2 PM.

Spectators are strongly encouraged to dress accordingly.

Why we’re circling it: Witches. Paddleboards. Hudson River. Sleepy Hollow. Some events require a lot of explaining. This isn’t one of them.

Saturday, October 10 · Kingsland Point Park, Sleepy Hollow · Rain date Sunday, October 11 · SUP Witches Festival
Ani DiFranco performing live
Photo courtesy of Righteous Babe Records
Woodstock · Thursday, November 12

Ani DiFranco Is Coming to Bearsville This November

November just gave us a very good reason to stay close to home.

Ani DiFranco comes to Bearsville Theater on November 12, bringing more than three decades of fiercely independent songwriting to one of Woodstock’s most intimate rooms.

The Grammy-winning singer, songwriter and guitarist built her career outside the traditional record-industry system, founding Righteous Babe Records in 1990 and moving freely through folk, punk, soul, hip-hop and electronic music.

Her recent releases include Unprecedented Sh!t and the 30th-anniversary edition of Not a Pretty Girl.

Sweet Petunia opens the night.

Why we’re circling it: Ani DiFranco in Bearsville is one of those artist-and-room pairings that makes immediate sense.

Thursday, November 12 · Bearsville Theater · 291 Tinker Street, Woodstock · Tickets & information

On Our Radar

New openings, local collaborations and places with enough personality to make us curious.

💿 A Record Label Gets a Store
Bad Time Records · New Paltz

New Paltz just got a record store with a very specific point of view. Bad Time Records opened its brick-and-mortar headquarters and shop on Church Street in September, bringing the independent label’s world of punk, ska, reggae and jazz into an actual storefront.

Inside you’ll find new and used vinyl, CDs and tapes alongside label releases, merch, rarities, collectibles and a few things you probably were not expecting to find next to the record bins.

Why it’s on our radar: This feels less like somebody opened another record shop and more like an actual music scene finally got a clubhouse.

11 Church Street, Suite 3 · New Paltz · Visit Bad Time Records

🌾 Farm-to-Sushi Rice
Medo Woodstock + Ever-Growing Family Farm

Woodstock’s Japanese restaurant Medo has taken local sourcing somewhere we did not expect: the rice bowl.

Medo is now using rice grown by Ever-Growing Family Farm in Kerhonkson, bringing one of the most fundamental ingredients in Japanese cooking surprisingly close to home.

Rice is not the crop most people picture when they think of the Hudson Valley, which is exactly what makes this collaboration so interesting. Instead of treating rice as the anonymous base underneath the meal, Medo is connecting it directly to a local farm and the landscape around us.

Why it’s on our radar: We talk a lot about farm-to-table in the Hudson Valley. Farm-to-sushi-rice — grown in Kerhonkson and served in Woodstock — is a local food story we did not see coming.

Medo Woodstock · Woodstock · Ever-Growing Family Farm · Kerhonkson · Visit Medo Woodstock · Follow Ever-Growing Family Farm

🥃 Find the Bookcase
The Baldwin Speakeasy · Pine Bush

Pine Bush now has a cocktail bar you have to find behind a bookcase. The Baldwin opened this summer inside the former Baldwin Vineyards tasting room as the new home base for Liquid Mercantile Distillery and Speakeasy Motors Whiskey Co.

The space leans hard into the story: vintage furnishings, handmade copper-and-brass details, old film gear, a player piano, Victrola, live music and a hidden entrance that apparently has some first-time visitors wondering whether they have accidentally wandered into an escape room. Outside, there’s also a large yard and stage for performances and events.

Why it’s on our radar: Somebody built a hidden-door whiskey bar inside an old Hudson Valley vineyard. We’re listening.

174 Hardenburgh Road · Pine Bush · Visit The Baldwin

Curated each week by the Radio Woodstock team.

This weekend: walk through 500 acres of art, watch vintage airplanes take to the sky, hunt for antiques in Rhinebeck, spend Saturday on a farm in Accord or head inside when Margaret Glaspy plugs in at Assembly.

And looking ahead: put witches on paddleboards in Sleepy Hollow and Ani DiFranco at Bearsville 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.