Fall foliage at Dover Stone Church hiking trail in Dutchess County NY

Community Meets Luxury

Sleight Farm’s blog about building a custom home and living in Dutchess County, NY.

Things to Do in Dutchess County This Fall – 2023

September 17, 2023

It’s that time! Sweaters, apples, and pumpkin spice lattes. Mother Nature starts turning the leaves into colorful fireworks. Most of the bugs (and humidity) go away and let us enjoy the outdoors in a whole new way. How do you make the most of this spectacular season? The Poughkeepsie area is the right place to start.

Here’s our local fall activities bucket list:

Walkway Over the Hudson - Poughkeepsie NY
Walkway Over The Hudson
This pedestrian bridge connecting Poughkeepsie and Highland is the world’s longest, at a mile and a quarter long, and 212 feet above the Hudson River. Walk, bike, rollerblade, take your dog, and bring a picnic to eat on either side (or even right in the middle!). Park on the Poughkeepsie or Highland side, or take the elevator (when open) from Water Street. The Walkway offers frequent special events such as Sunrise Walks and Walkway at Night. Our favorite is Walktoberfest, a farmers and makers market happening on October 21 and 22, 2023. Learn more at www.walkway.org.


New York State Sheep and Wool Family Festival
October 21-22 2023
You don’t have to be a knitter or fiber artist to enjoy this annual event at the Dutchess County Fairgrounds in Rhinebeck. There are craft vendors, livestock to meet, great food and drink, live music, kids’ activities, educational demonstrations, workshops, and more. Always the third weekend in October. Learn more at www.sheepandwool.com.
Pick Your Own orchard - Dutchess County NY
Pick Your Own and “Day On The Farm” Fun
It’s a win-win: Support local growers and enjoy Dutchess County’s bounty. Just a few of our favorite farms and orchards offering pick-your-own activities include: Brittany Hollow Farm, Fishkill Farms, Greig Farm, and Mead Orchards. We especially love Barton Orchards in Poughquag, where in addition to picking apples, produce, and pumpkins, visitors can enjoy the corn maze, dog park, “fun park,” farm market and bakery, tap room, and a new TreeTop Adventures Park.
Dutchess Rail Trail
The Dutchess Rail Trail is a 13-mile rail trail for walking and biking that stretches from the former Hopewell Junction train depot, north to the Poughkeepsie entrance of the Walkway Over the Hudson. Along the way, it runs through the towns of Wappingers Falls, LaGrange, and Poughkeepsie. Trail heads in each of these towns provide easy access to the trail with parking. The Dutchess Rail Trail will soon be part of the Empire State Trail, a continuous 750-mile route spanning the state from New York City to Canada and Buffalo to Albany, creating the longest multi-use state trail in the nation.
Historic Estates
Whether you’re into history, design, art, or exploring beautiful riverfront grounds and fall scenery, visiting one of Dutchess County’s famed historic estates are a great way to spend the day. There’s the FDR Presidential Library and Museum, the Staatsburg State Historic Site (Mills Mansion), Vanderbilt Mansion National Historic Site, Mount Gulian Historic Site, and Wilderstein – to name just a few.
Haunted Houses
It’s not fall without Halloween, and vice versa! If you’re looking for some frightful fun, check out Kevin McCurdy’s Haunted Mansion. It’s also well worth a trip across the river to Port Ewen to visit the Headless Horseman Hayrides and Haunted Houses.
Stormville Airport Antiques Show and Flea Market
Take off into the fun, electric, family-friendly vibe at the Stormville Airport every month, with literally acres of vendors (over 600 from more than eight states) for browsing or discovering bargains, treasures, and one-of-a-kind finds. Check their website at www.stormvilleairportfleamarket.com for exact monthly dates.
One of the big draws of living in or visiting Dutchess County is its incredible natural beauty, and there’s no better way to fully immerse yourself in that than getting outside for a hike. You’ll find trails for all levels, time frames, and types of scenery at sites like Mount Beacon, Peach Hill Park, Dover Stone Church, Poet’s Walk, and more. We recommend Dutchess Tourism’s Hiking listings as a great one-stop resource for planning your next adventure.
Dutchess Wine Trail
Well, yes – we do have our own “wine country” right here in the Hudson Valley! The Dutchess Wine Trail  connects Clinton Vineyards and Millbrook Vineyards & Winery. The fifteen-minute drive between the two takes you past other local vineyards, orchards, farms, horse farms, dairies, and woodlands. Both Millbrook Vineyards and Clinton Vineyards offer tours, tastings, and other delights.
Old Rhinebeck Aerodrome
The Old Rhinebeck Aerodrome’s museum of antique aircraft is great fun on its own, but Saturdays and Sundays through October 31 offer the real excitement with afternoon airshows. Many weekends also feature special events such as the British Car Show. Visit the Aerodrome’s Facebook page for more information.
Innisfree Garden
Did you know that one of “the world’s ten best gardens” is located right here in the Hudson Valley? Innisfree Garden in Millbrook combines outdoor art with gorgeously designed landscape. perfect for enjoying an autumn amble. Open Wednesdays through Sundays, then weekends only after October 9.
Small Town Fall Festivals
The fall festival is a classic tradition across the U.S., and our local Dutchess County communities embrace that. Whether you live in town, hail from nearby, or are visiting from afar, these local celebrations of everything that’s timeless about fall – and community – are great fun for everyone. (And if you’re thinking of relocating to Dutchess County, they’re a wonderful way to get a feel for what it’s like to live here.) Look for fall festivals in LaGrange (October 15 from 12pm -4pm at Freedom Park), Fishkill (October 14 at 4pm in Geering Park), Beacon, Poughkeepsie, and others.
We hope you enjoy this season’s cornucopia of Hudson Valley experiences!


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