The Hudson Valley’s Secret Season: 12 Things to Do Between Summer and Fall

There is a brief stretch in the Hudson Valley when you can leave the house in shorts, come home wanting a sweatshirt, eat a tomato that actually tastes like a tomato, and somehow also justify buying a cider donut.

This is the Hudson Valley's secret season.

Late August and September don't quite belong to summer or fall. The pools are still open. Farm stands are overflowing. The mountains are mostly green. But orchards are opening, nights are getting cooler and the first hints of autumn are starting to show up.

And frankly, this may be one of the best times of the entire year to roam.

Before October brings peak foliage, packed trailheads and Route 9 traffic that suddenly moves at the speed of a hay wagon, here are 12 ways to make the most of the Hudson Valley's transition into fall.

1. Get One Last Big Summer Day In

Don't surrender summer prematurely.

Late August still gives us plenty of warm days for swimming, paddling, picnicking and eating outside. Instead of spending the weekend mourning the unofficial end of summer, pick one thing that feels unmistakably July.

Spend an afternoon beside a lake. Rent a kayak. Find an outdoor table for dinner. Take the kids for ice cream after dark.

The beauty of late summer in the Hudson Valley is that you can have your summer day and still wake up the next morning ready for apples.

2. Go to the Dutchess County Fair

If you're looking for a proper sendoff to summer, it's difficult to beat the Dutchess County Fair in Rhinebeck.

The 180th Dutchess County Fair runs August 25–30, 2026, bringing carnival rides, concerts, livestock, exhibits and an impressive amount of fair food back to the Dutchess County Fairgrounds.

It is one of those Hudson Valley traditions that works whether you're bringing kids, meeting friends or simply looking for an excuse to consume something deep-fried before September arrives.

Roam tip: Go hungry. This is not the day to pack a sensible lunch.

3. Start Apple Picking Before Everyone Else Does

Yes, apple picking is a fall cliché.

It is also a very good cliché.

Apple season begins ramping up around the Hudson Valley from late August into September, and going early has a major advantage: you can get the orchard experience without necessarily getting the peak-October orchard crowds.

Wilkens Fruit & Fir Farm in Yorktown Heights notes that September is the best time for apple picking, while Hopedale Farm near Hudson plans to open for its 2026 U-pick season over Labor Day weekend.

Other longtime favorites throughout the region include orchards around Warwick, New Paltz, Clintondale, Red Hook and the greater Hudson area.

Pick apples. Buy cider. Get the donut.

You knew you were going to anyway.

4. Watch the Sky Fill With Hot-Air Balloons

One of September's most photogenic weekends returns September 4–6.

The 35th Hudson Valley Hot-Air Balloon Festival is scheduled for Tymor Park in LaGrangeville, with hot-air balloons and family activities planned throughout the weekend.

There is something wonderfully surreal about standing in a Hudson Valley field while enormous balloons slowly rise above the landscape.

Even if you've lived here for years, this is the sort of event that makes the region feel like a vacation destination again.

5. Spend Labor Day Weekend in New Paltz

If your ideal weekend involves art, handmade goods, food and wandering around without much of an agenda, point the car toward New Paltz.

The Woodstock-New Paltz Art & Crafts Fair returns Labor Day weekend, September 5–7, bringing hundreds of makers and artists together for one of the region's longstanding creative traditions.

Make a day of it.

Visit the fair, grab lunch in New Paltz, wander through town and then head toward the ridge for an evening drive.

That's a pretty solid Hudson Valley Saturday.

6. Take a Hike Without Chasing Peak Foliage

Here is a potentially controversial Hudson Valley opinion:

You do not need red leaves to enjoy a mountain.

September hiking gives you cooler temperatures, long stretches of daylight and landscapes that haven't yet attracted every leaf-peeper within a three-state radius.

Try a familiar trail before it transforms for autumn, or explore somewhere you've been meaning to visit.

Minnewaska State Park Preserve, Mohonk Preserve, Black Creek Preserve, Ferncliff Forest, Franny Reese State Park and sections of the Shawangunk Ridge all offer dramatically different versions of the Hudson Valley landscape.

And then come back in October.

Same trail. Completely different experience.

7. Explore the Hudson River Valley Ramble

September is also Hudson River Valley Ramble season.

Throughout the month, communities, historic sites, parks and organizations host walks, tours, hikes, paddles and special programs celebrating the landscape and history of the Hudson River Valley.

More than 150 events are traditionally held throughout September, making the Ramble particularly useful for discovering places you might otherwise drive past without realizing what's there.

For 2026, scheduled activities already include historic tours, nature programs, sunrise walks and hands-on experiences such as apple cider making.

This is one of the best ways to roam the Hudson Valley in the most literal sense.

8. Have a Farm Day That Isn't Just About Apples

Fall farms have evolved.

You can certainly walk into an orchard, pick six pounds of apples and leave.

But farms throughout the Hudson Valley now turn autumn weekends into full-day experiences with corn mazes, hayrides, animals, food, live music, cider, pumpkins and activities for kids.

Hurds Family Farm in Clintondale, for example, has its Falling in Love with Fall Weekend September 11–14, with its regular farm activities continuing through the season.

Barton Orchards in Poughquag also stretches its Sunflower Festival into Labor Day weekend.

For families especially, September is a sweet spot. You get the farm experience while temperatures can still be warm enough to spend most of the day outside comfortably.

9. Follow the Harvest Instead of the Calendar

One of the easiest ways to experience the Hudson Valley seasonally is also one of the simplest:

Go to a farm stand and buy whatever looks best.

Late summer and early fall overlap beautifully here. Tomatoes, corn, peppers and other summer produce can still be abundant while apples, squash and other autumn staples begin arriving.

Build dinner around what you find rather than arriving with a shopping list.

Better yet, turn it into a mini road trip. Pick a stretch of road through Ulster, Dutchess, Columbia or Orange County and stop at farm stands along the way.

No reservations. No tickets.

Just roam.

10. Eat an Unreasonable Amount of Garlic

We would be remiss if we discussed September in the Hudson Valley without mentioning garlic.

The Hudson Valley Garlic Festival returns to Saugerties September 26–27, 2026, with garlic growers, food, artisans, entertainment and cooking demonstrations.

Garlic lovers already understand why this is exciting.

Everyone else should know that the festival is about considerably more than buying bulbs of garlic. It has become one of the region's signature fall events and a great excuse to spend a day in Saugerties.

Just perhaps don't schedule a first date immediately afterward.

11. Head Into the Catskills for Oktoberfest

By the final weekend of September, fall starts getting serious.

Oktoberfest at Hunter Mountain Resort begins September 26 and continues into October, combining live music, food, vendors and mountain scenery.

Even before foliage reaches its absolute peak, the drive into the Catskills becomes part of the experience.

Take your time getting there.

Stop somewhere you haven't stopped before.

This is Roam Hudson Valley, after all. The destination is only half the point.

12. Take a Drive With Absolutely No Plan

This may be our most important recommendation.

Pick a direction.

Not a destination.

Drive through Accord and Stone Ridge. Follow back roads toward High Falls. Wander through Columbia County farm country. Cross the Hudson and explore Dutchess County. Head toward Warwick. Drive north into Greene County.

Stop when you see a farm stand.

Turn around when a road looks interesting.

Get coffee somewhere you've never been.

Pull over at the scenic overlook.

The Hudson Valley has become a major tourism destination, and there are countless itineraries telling us precisely where we're supposed to go.

Sometimes the best way to experience it is to ignore them.

Don't Rush Fall

October will come.

Soon enough, the Hudson Valley will explode into reds, oranges and yellows. The pumpkins will appear on every porch. Scenic overlooks will fill with visitors. Every bakery will smell like cinnamon.

But we're not there yet.

Right now we have warm afternoons and cool nights. Tomatoes and apples. Sunflowers and cider donuts. Green mountains beginning their slow transformation.

So don't rush through this part.

There are still a few weeks when you can have summer and fall on the very same day.

And around here, that's a pretty good reason to get out and roam.