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Fall festivals and fairs

Bring your family out for a day of fun

Hudson Valley Fall festivals and fairs

Fall in the Hudson Valley is chock full of family fun festivals and fairs. Check out our list by county here.

Dutchess County

September 1-3, 32nd Annual Hudson Valley Hot-Air Balloon Festival. Tickets sold online only. Lagrangeville 5am. 

September 1-4, 5th Annual Sunflower Festival. Poughquag. 4pm.

September 2-3 & October 7-8, Stormville Airport Antique Show and Flea Market. Stormville. 8am.

September 9 & 10, 21st Annual Hudson Valley Wine & Food Fest. Rhinebeck. 11am.

September 9 & 10, Oktoberfest. Poughquag. 11am. 

Weekends, September 9 – October 22, Fishkill Farms Fall Harvest Festivals. Hopewell Junction. 9am.

September 16, Arlington Street Fair. Poughkeepsie. 12pm.

September 16-17, Mid-Hudson Comic Con. Poughkeepsie. 10am.

September 16, Pawling 24Hour Trail Running Festival. Pawling. 11am.

Weekends, September 23 – October 29, Kesicke Fall Festival. Rhinebeck. 10am.

September 23, Hardscrabble Music Festival. Red Hook. 10am.

September 23, East Fishkill Community Day. Hopewell Junction. 12pm.

September 29, Bountiful Harvest Celebration 2023. Millbrook. 5pm. 

September 30, Harvest Fest at Stony Kill Farm Environmental Education Center. Wappingers Falls. 11am.

September 30, Dutchess County Irish Festival. Lagrangeville. 12pm.

September 30 – October 1, Handcrafted Octoberfest at Rhinebeck. Rhinebeck. 10am.

October 1Spirit of Beacon. Beacon. 11am.

October 6, Generational Crossings. Annandale-on-Hudson. 7pm. 

October 6 - 9, Third Annual Town of Wappinger Carni"fall". Wappingers Falls. 3pm. 

October 14, 11th Annual Cider Tasting. Poughkeepsie. 11am.

October 14, The Hudson Valley Spirit Festival. Poughkeepsie. 6pm. 

October 15, The Beacon Sloop Club Annual Pumpkin Festival. Beacon. 12pm.

October 27, Movies from the Balcony. Poughkeepsie. 7:30pm

Orange County

September 2, 4th Annual Sweet Corn Festival on the Wright Farm, Hosted by Uncle Shoehorn.  Warwick. 12pm.

September 9, General Montgomery Day. Montgomery. 10am.

Weekends, September 9 – October 15, Grape Stomp. Washingtonville. 1pm. 

September 10, Monroe Cheese Festival 2023. Monroe. 11am.

September 16, Hamptonburgh Country Festival. Campbell Hall. 11am. 

September 21-24, Fall Wrap-up Carnival. Pine Island. 5pm/Thur. & Fri., 1pm/Sat. & Sun.

September 22-24, Fall GreekFest 2023. Newburgh. 4pm/Fri., 11am Sat. & Sun.

September 23, Weekend of Wallkill. Wallkill. 10am.

September 23 & 24, Sugar Loaf Film Festival. Chester. 11am.

September 23 & 24, Tri-State Seafood + Music Festival. Warwick. 12pm.

September 23, 24, 30, October 1, 7, 8, New York Renaissance Faire. Tuxedo Park. 10am.

September 30, Harvest Fest 2023. Walden. 11am.

September 30 - October 22, weekends, Bear Mountain Oktoberfest. Bear Mountain. 12pm.

October 1, Warwick Applefest. Warwick. 9am.

October 1, Devitt's Anniversary Car Show & Fall Festival. New Windsor. 10am.

October 7, Empanada and Latin Festival. Newburgh. 1pm.

October 8, 51st Annual Fall Festival 2023. Cornwall. 10am.

October 15, 30th Annual Fall Foliage Festival. Port Jervis. 10am. 

October 21, Newburgh Free Library’s Mini-Comic Con the NFLXpo. Newburgh. 12pm. 

Ulster County

September 2, Fall craft and vendor fair. Kingston. 11am.


September 2-4, Woodstock-New Paltz Art & CraftsFair. New Paltz. 10am.


September 3, Bearsville Jazz & Art Festival2023. Woodstock. 2pm.


September 3, Catskills Celebration: Family Fun at the Catskills Visitor Center. Mount Tremper. 10am.


September 6, 13, 20, 27 & October 4, 11, Woodstock Farm Festival. Woodstock. 3pm.

September 22-24, Love fest Parade. Kingston. 6pm/Fri., 12pm Sat. & Sun.


September 23, 3rd Annual Hispanic Heritage Festival. Kingston. 11am.

September 23, 52nd Annual Apple Festival at the Port Ewen Methodist Church. Port Ewen. 8am. 

September 23, Weekend of WallkillWallkill. 10am.

September 23 - October 21, Kelder's Fall Harvest Celebration. Kerhonkson. 10am.

September 30, 1st Annual Town of Wallkill Community Day. Middletown. 12pm.


September 30- October 1, Hudson Valley Garlic Festival™. Saugerties. 10am.

September 30- October 1, Grape Stomping Festival. New Paltz. 11am.

September 30- October 1, Apples & Wine Festival. Marlboro. 11am.

October 1, 18th Century Autumnfest. Kingston. 11am. 

October 6-8, 13th Annual O Positive Kingston Festival. Kingston. 6pm.

October 7, Heart of the Hudson Valley Bounty Festival. Kingston. 10am.

October 7, Fallnicia Festival. Phoenicia. 11am.

October 7, Ellenville and Wawarsing Harvest FestivalEllenville. 9am.

October 7, Indigenous Peoples Day Celebration. Kingston. 10am.

October 8, 16th Annual Italian American Festival. Kingston. 12pm.

October 8, 58th Annual Saugerties Mum Festival. Saugerties. 12pm.

October 13, Saugerties Food Truck FestivalSaugerties. 4pm.

October 14, Elting Memorial Library's 66th Annual Library Fair. New Paltz. 9am. 

October 15, The 26th Annual Rosendale International Pickle Festival. New Paltz. 10am.

October 15, Fall Family Fun Fest. Olivebridge. 10am.

October 21, Walktoberfest Farmers & Makers Market. Highland. 12pm.

Sullivan County

September 10, Artisan Fair & Farmers Market. Wurtsboro. 11am.

September 23, Nineteenth Century Base Ball Showcase. Grahamsville. 12pm.

September 23, Annual Liberty Museum Poetry Festival. Ferndale. 1pm

Other Counties

September 9-10, ONETWOHEARTU's Summer Shakedown Festival. Peekskill, 1pm.

September 16, OZland Festival. Peekskill.

September 30, Chappaqua Children's Book Festival. Chappaqua. 10am.

September 30, Oktoberfest. Sleepy Hollow. 1pm.

October 7, Brewster Rotary Fall 5K Run/Walk. Brewster. 9am.

October 21-22, Walktoberfest Farmers and Makers Market. Highland. 12pm.

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