Dutchess County Fall Festivals 2026

Dutchess County fall festivals in 2026 begin with orchard weekends in late September and run through Halloween weekend, and the busiest two days of the season are October 17 and 18, when the NYS Sheep and Wool Festival, Big Apples Fest, the Pumpkin Bombing air show and the Beacon pumpkin festival all land at once. Every date and hour below comes from the organizer's or venue's own page, read the week this was written, and each entry names the closer Farmers Choice and the drive.

The county splits neatly. Everything from Poughkeepsie south is a short run from Farmers Choice Fishkill at 18 Westage Drive, where Route 9 meets I-84. Rhinebeck and Red Hook are a shorter drive from Farmers Choice New Paltz across the river at Thruway Exit 18. Distances to a town come from our own town pages; the rest are OpenStreetMap and OSRM driving estimates, rounded to five minutes.

Which Dutchess County fall festivals run every weekend?

Fishkill Farms Fall Harvest Festival weekends. 9 Fishkill Farm Road, Hopewell Junction. Every Saturday and Sunday through November 1, plus Monday, October 12. The weekend program is pick-your-own apples and pumpkins, wagon rides through the orchard, a one-acre corn maze and live bands on the courtyard stage from 12PM to 4PM. The farm's own visitor guidance says to expect longer donut lines on weekend afternoons through peak season in late September and October, and recommends visiting earlier in the day or on a weekday to skip the wait. Picking needs a reservation, made online; it covers the wagon rides, and you need one to reach the maze, which sells its own ticket at the entrance. Hopewell Junction is about 5 miles and 11 minutes from the Fishkill store.

Barton Orchards festival weekends. 63 Apple Tree Lane, Poughquag. Barton's October festival weekends take in the Hudson Valley Apple Festival, October 3 and 4, and then the Harvest Festival across October 10, 11 and 12. A festival pass starts at 10AM and covers hayrides until 5:30PM, the corn maze until 6PM and live music all day; apple picking costs extra. Use the Apple Tree Lane entrance, because some map apps route you to a back road with no public gate. Barton is about 25 minutes east of the Fishkill store.

Early October: the first weekend of the month

The Country Living Fair. Dutchess County Fairgrounds, Rhinebeck (GPS address 6636 Springbrook Avenue, off Route 9). Friday, October 2 to Sunday, October 4. General admission runs 10AM to 5PM on Friday and Saturday and 10AM to 4PM on Sunday, and the fair says dealers restock every day. More than 200 antiques dealers, makers and small brands, plus workshops, main stage speakers and a folk music stage run with The Bluegrass Situation. Rain or shine, mostly under cover, parking included, no pets. The fairgrounds are about 40 minutes from Farmers Choice New Paltz and about 45 from Fishkill.

Greig Farm ApplePalooza. 227 Pitcher Lane, Red Hook. Sunday, October 4, 11AM to 5PM. A one-day harvest celebration with scenic hayrides, apple, pumpkin and raspberry picking, and food from the farm cafe and food truck. Red Hook is the far corner of the county: about 50 minutes from the New Paltz store and an hour from Fishkill.

Columbus Day weekend: October 10 to 12

Market Day Craft Fair at the Van Wyck Homestead. 504 Route 9, Fishkill, entered from Snook Road. Saturday, October 10, 11AM to 4PM, rain date October 11, free. More than 25 local artisans, a homemade lunch, made-to-order apple fritters, live music, tours of the 1732 house the Continental Army used as officers' headquarters, and a Revolutionary War cannon firing. It sits about a mile and a half up Route 9 from the Fishkill store, a five-minute drive.

Barton's Harvest Festival covers all three days of the long weekend, and Fishkill Farms adds the Monday.

October 17 and 18: the busiest weekend of the season

NYS Sheep and Wool Festival. Dutchess County Fairgrounds, Rhinebeck. Saturday, October 17 and Sunday, October 18. The fairgrounds list show hours of 9AM to 5PM Saturday and 9AM to 4PM Sunday. Hundreds of fiber and wool vendors, sheep and goat shows, a fleece show and sale, author talks and demonstrations, and the festival's own FAQ says to arrive early. One ticket per day, no pets, rain or shine. About 40 minutes from New Paltz, 45 from Fishkill.

Big Apples Fest. Heritage Financial Park, 1500 Route 9D, Wappingers Falls. Saturday, October 17, 10AM to 4PM. The Hudson Valley Renegades' free fall festival at the ballpark: live music, games, crafts and apples. Admission is free, and parking is paid, sold in advance on the team's site or on the day. Wappingers Falls is about 6 miles and 12 minutes from the Fishkill store.

Pumpkin Bombing at the Old Rhinebeck Aerodrome. 9 Norton Road, Red Hook. Saturday, October 17 and Sunday, October 18, the last air show weekend of the 2026 season. Gates open at 10AM, with pre-show activities at 2PM and the air show itself starting around 2:30PM, and Destination Dutchess lists the weekend as the Pumpkin Bombing finale, with the vintage planes dropping pumpkins. About 50 minutes from New Paltz.

Beacon Sloop Club Pumpkin Festival. Pete and Toshi Seeger Riverfront Park, 4 Red Flynn Drive, Beacon, next to the train station. Sunday, October 18, free; Destination Dutchess lists 12PM to 5PM. Pumpkin pie with whipped cream, hot pumpkin soup and apple cider, craft vendors and two solar-powered music stages on the riverfront. Beacon is about 5 miles and 10 minutes from the Fishkill store.

Late October: the Walkway Market and the last orchard weekends

Walkway Market: A Taste NY Experience. Dutchess Welcome Center, 61 Parker Avenue, Poughkeepsie, at the foot of the Walkway Over the Hudson. Saturday, October 24, 10AM to 4PM, with a rain date of October 25, free. Thirty New York State makers, plus a walk on the bridge, which is a non-smoking park. Poughkeepsie is about 18 minutes north of the Fishkill store, and the Walkway's Highland side is about 13 minutes from Farmers Choice New Paltz.

Fishkill Farms closes the season. The orchard's last two weekends are October 24 and 25 and October 31 and November 1, with live music on the courtyard stage from 12PM to 4PM as it runs every weekend of the season. The farm's own visitor guidance points to the donut line easing outside its late-September-to-October peak, so the closing weekends are the calmer pick.

Which Farmers Choice is closest to each festival?

From Farmers Choice Fishkill, 18 Westage Drive: Van Wyck Homestead about 5 minutes, Beacon riverfront about 10, Hopewell Junction about 11, Wappingers Falls about 12, Poughkeepsie about 18, Barton Orchards about 25. The store has its own lot, and Thursday to Saturday it stays open until 11PM, which covers a late drive back from the fairgrounds.

From Farmers Choice New Paltz, 1 Old Route 299 at Thruway Exit 18: the Walkway's Highland side about 13 minutes, the Dutchess County Fairgrounds about 40, the Old Rhinebeck Aerodrome and Greig Farm about 50. The Kingston-Rhinecliff Bridge is the crossing from the fairgrounds to Route 9W and Exit 18.

Flower, pre-rolls, edibles and infused beverages, all lab tested and all from licensed New York producers, are on the menu at both stores. The county hub for the Dutchess County stores and towns lists every town page with directions.

Keep a purchase sealed

A vehicle is not a place New York allows cannabis to be consumed, so whatever comes home from the farm stand comes home sealed. Farms, fairgrounds and parks write their own rules for their grounds, and the Walkway is a non-smoking park, so nothing on this list is a place to open the bag. For the full map of where consumption is allowed and where it is not, read our guide to New York cannabis laws.

Festival first, farm stand second is the easy order of the day. Order Now from the Fishkill menu once the last stop is done, and most orders are ready inside an hour. The door check is a valid government-issued photo ID, and it has to show you are 21 or older; at the counter, a Farm Hand will help with any label you cannot make sense of.