Every autumn, this picturesque region offers a plethora of enchanting experiences from scenic autumn hikes to charming harvest festivals. Make sure to make the most of this colorful season in Dutchess County!
1. Take a scenic hike at one of the many breathtaking trails across the county.
- Dutchess Rail Trail
- Norrie Point Trail in Staatsburg
- Poet’s Walk Romantic Landscape Park Trail in Red Hook
- Stissing Mountain Trail in in Pine Plains
- Thompson Pond Trail in Pine Plains
- Tivoli Bays Trail
2. Try to find your way out of a Corn Maze.
- Barton Orchards in Poughquag
- Manza Family Farm in Montgomery
- Fishkill Farms in Hopewell Junction
3. Attend a Farmers Market year-round!
- Rhinebeck (May to December)
- Millbrook (May to October)
- Millterton (May to December)
4. Go apple picking!
- Cedar Heights Orchards in Rhinebeck
- Mead Orchards in Tivoli
- Rose Hill Farm in Red Hook
- Greig Farm in Red Hook
- Fishkill Farms in Hopewell Junction
- Barton Orchards in Poughquag
5. Go to a Pumpkin Patch!
- Dykeman Farm in Pawling
- Kesicke Farm in Rhinebeck
- Fishkill Farms in Hopewell Junction
6. Take a stroll on Walkway over the Hudson: a pedestrian bridge that connects Poughkeepsie and Highland. Spanning over a mile long and 212 feet above the Hudson River, it is the perfect place to admire the Fall colors.
7. Go to the New York State Sheep and Wool Festival! Even if you do not participate in the craft, there is plenty of wonderful food, drinks, activities, and workshops to take part in!
9. Visit a Historic Estate.
- Franklin D. Roosevelt Presidential Library and Museum in Hyde Park
- Montgomery Place in Red Hook
- Mills Mansion in Staatsburg
- Vanderbilt Mansion National Historic Site in Hyde Park
10. Go to the Old Rhinebeck Aerodrome! The Aerodrome is a museum in Red Hook, showcasing aircraft from the Pioneer Era, World War l, and the Golden Age of Aviation between the World Wars. Adding to this already magnificent showcase, they also contain a number of antique automobiles!
11. Have a picnic at Innisfree Garden in Millbrook. Enjoy the beautiful, Chinese-influenced garden while you look at the beautiful fall colors!
12. Enjoy your fill of cider donuts at the Montgomery Place Orchard Farm Stand in Red Hook!
13. Go wine-tasting at Millbrook’s very own Millbrook Vineyard’s and Winery! Enjoy wonderful food from their vendors, as well as the incredible scenery!
14. Get in on a Farm Tour at Clover Brooke Llama and Alpaca Farm in Hyde Park! Learn about the history of the animals at the farm, as well as discover new and fun facts! This is a perfect family outing for the fall.
15. Enjoy a very fluffy fall at Lilymoore Alpaca Farm with your friends and family!
16. Visit Plan Bee Farm Brewery and sip your way through an exquisite vintage bottle tasting set within the restored 1830s barn and brewery. Experience the rich tapestry of flavors as you savor samples from both the tap selection and the cherished vintage bottles sourced from Plan Bee’s exclusive private cellar.
17. Cozy up under the stars for an outdoor double feature movie showing at the Four Brothers Drive-In. Get takeout from the Four Brothers Restaurant and desserts from the Grand Shack.
18. Stroll through the Hessell Museum of Art and adjoining CCS Bard Galleries for free!
19. Pop out to the Beacon Sloop Club Pumpkin Festival for a day of eating and music! Not only are there hundreds of pumpkins to choose from, but there will also be live music and fresh fall food. Sunday, October 18.
20. Stop by the Stormville Airport Antique Show and Flea Market for an afternoon of hunting for treasures and eating food! The market offers a range of items from jewelry to furniture to artwork. October 10 & 11, November 7.
21. Watch the Poughkeepsie Regatta from the waterfront in Waryas Park! This 3-mile rowing race on the Hudson River will not be one to miss.
22. Visit Boutique Wines & Spirits for the opportunity to taste the largest selection of craft cider in New York! Bigger and better than last year, with some new ciders from your favorite producers.
23. Have Tea Time at Clover Brooke Farm while being surrounded by llamas and alpacas!
24. Go fly fishing at Orvis Sandanona! Take a lesson with an instructor, watch one of their online videos, or just head right in for an afternoon of fun.
Tenmile Distillery, image by Rana Faure.
25. Visit the town of Wappinger’s Carnifall 2026! Enjoy a fall themed carnival with rides, food trucks, vendors, live music, and more.