As the leaves begin to change and temperatures start to drop, it's the perfect time to explore all the fall fun that southern Dutchess County has to offer. From pumpkin picking and corn mazes to apple picking and cozy hayrides, there's something for everyone to enjoy this autumn season. Whether you're looking for family-friendly activities or a fun evening at a local Oktoberfest, this fall fun guide will help you make the most of the beautiful season in southern Dutchess County.
From picking pumpkins to searching for the best cider donut, our guides, online event calendars, and printables create unforgettable adventures this fall. What are you most looking forward to?
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Please note: We are working hard to keep our Macaroni KID Guides updated with the latest events. If you know about a family-friendly event not yet listed, please submit it here and we'll add it to our list!
We will continue to update with events as they are posted, so check back often AND SHARE!
Featured Fall Events & Activities
Want your event featured right here front and center?
Email me about FEATURED GUIDE LISTINGS!
Email Pamelao@macaronikid.com for more information.
Download your FREE Apple & Pumpkin Picking Checklist!
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🍎Apple Picking Farms🍎
- Barton Orchards
63 Apple Tree Ln, Poughquag - Dykeman Farm
31 Dykeman Ln, Pawling - Fishkill Farms
9 Fishkill Farm Rd, Hopewell Junction - Meadowbrook Farm
29 Old Myers Corners Rd, Wappingers Falls
🫶Community Events🫶
- Sept 19 Movies in the Park - Mufasa-PG
- Sept 20 East Fishkill Community Day
- Sept 20 25th Annual Arlington Street Fair
- Sept 20 Slaterpalooza
- Sept 26 Movies in the Park - Sonic 3-PG
- Sept 27 Family Fun Day
- Sept 27 Big Truck Day
- Oct 3 Movies in the Park - Minecraft-PG
- Oct 3 Hudson Valley Regional Portfolio Day
🍁Fall Festivals & Fairs🍁
- Fall Harvest Festivals
- 11th Annual Harvest Festival
- Sept 18-21 Carni"fall"
- Oct 5 Fall Festival & Maker’s Market
- Oct 11 Fishkill Fall Festival & Costume Contest
- Oct 18&19 New York State Sheep & Wool Festival
- Oct 25 Poughkeepsie Farm Project Harvest Fest
- Oct 27 Pawling Rotary’s Fall Fest 2025
- Oct 26&27 Harvest Fest
- Oct 18 New York State Sheep & Wool Festival
- Oct 19 Beekman Fall Festival
- Oct 19 Fishkill Fall Festival
- Oct 19 The Beacon Sloop Club’s Annual Pumpkin Festival
🍻Food, Drinks & Oktoberfest🍻
(some events may be 21+)
- Sept 5-7 Oktoberfest 2025!
- Sept 13-14 Hudson Valley Food and Wine Festival
- Sept 14 Farm Fest’25!
- Sept 21 Catoberfest 2025
CLICK HERE FOR THE HUDSON VALLEY CIDER DONUT TASTING TRAIL
👻Halloween Events & Attractions👻
- Kevin McCurdy's Haunted Mansion
- 38 Sheafe Rd, Wappingers Falls
- Sept 23- Oct 2 DRACULA: THE JOURNAL OF JONATHAN HARKER BY JIM HELSINGER
💃Hispanic Heritage Month Events💃
🎃Pumpkin Picking🎃
- Barton Orchards
63 Apple Tree Ln, Poughquag - Dykeman Farm
31 Dykeman Ln, Pawling - Fishkill Farms
9 Fishkill Farm Rd, Hopewell Junction - Meadowbrook Farm
29 Old Myers Corners Rd, Wappingers Falls
🌽Corn Mazes🌽
- Barton Orchards
63 Apple Tree Ln, Poughquag - Fishkill Farms
9 Fishkill Farm Rd, Hopewell Junction - Hahn Farm*
1697 Salt Point Tpk, Salt Point (*outside region) - Kesicke Farm*
229 Middle Rd, Rhinebeck (*outside region) - Check out the fall orchard printable for more corn mazes nearby!
🎭Shows & Performances🎭
- The Falls Theater
- Bannerman Island
⚾Sports⚾
- Heritage Financial Park
✂️Craft Fairs🖌️
