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.

Best Fall Activities in Dutchess County – Updated for 2021

September 11, 2019

September 2021

We love our corner of the Hudson Valley! There’s never any shortage of things to do, especially in the autumn, when visitors from all over flock to this region for leaf-peeping, outdoor activities, fresh food and local wine experiences, and more.

Fall 2021 Update: These sites and activities are operating with COVID-19 safety protocols in place. Please visit the websites listed for more detailed information. 

Here’s our Dutchess County 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!). Learn more at www.walkway.org.

New York State Sheep and Wool Family Festival
October 16-17, 2021
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 Wappinger, 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 or Grims Mortuary at Greig Farm. It’s also well worth a trip across the river to Port Ewen to visit the Headless Horseman Hayrides and Haunted Houses.

September 10-12, 2021
Germania of Poughkeepsie hosts the traditional Bavarian fall festival of Oktoberfest, with food, drink, music, dance, and all manner of family fun.

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 Aerodrome’s museum of antique aircraft is great fun on its own, but Saturdays and Sundays through October 17 offer the real excitement with afternoon airshows. Many weekends also feature special events such as the British Car Show. Visit www.oldrhinebeck.org for more information.

Small Town Fall Festivals
Most festivals have been cancelled for 2020, but please check local municipalities for detailed information
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 23-24), Fishkill, Wappingers Falls, Beacon, Poughkeepsie, and others.

We hope you enjoy this season’s cornucopia of Hudson Valley experiences!


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