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.
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Don't forget to print out your monthly calendar and fill it with all the exciting events, and things to do right here 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 21 Shop Cycle - Shopping Spree for Free!
- Sept 21 Community Day
- Sept 21 24th Annual Arlington Street Fair
- Sept 21 Slaterpalooza
- Sept 22 Adoption Day and Fundraiser
- Sept 27 Movies in the Park
- Sept 28 Big Truck Day
- Sept 29 Touch a Truck
- Oct 4 Hudson Valley Regional Portfolio Day
- Oct 5 Deepen Family Bonds Through Reading: A Special Meet & Greet Event with Author Sandy Bastien!
🍁Fall Festivals & Fairs🍁
- 6th Annual Sunflower Festival
- Fall Harvest Festival
- Oct 28 Pawling Rotary Fall Fest!
- Oct 5 10th Annual Harvest Festival
- Oct 5 Poughkeepsie Farm Project Harvest Fest
- Oct 11,12&13 Carni"fall"
- Oct 12 Fall Festival
- Oct 19&20 New York State Sheep & Wool Festival
- Oct 26&27 Harvest Fest
- Oct 19 Beekman Fall Festival
- Oct 19 Fishkill Fall Festival
- Oct 20 Beacon Sloop Club’s Annual Pumpkin Festival
- Oct 20 LaGrange Fall Festival and Makers Market
- Oct 26&27 Locust Grove Harvest Fest
- Oct 26 Fall Fest 2024
🍻Food, Drinks & Oktoberfest🍻
(some events may be 21+)
👻Halloween Events & Attractions👻
- Kevin McCurdy's Haunted Mansion
- 38 Sheafe Rd, Wappingers Falls
- Dracula
- Haunted House and Corn Maze
- Oct 5 Halloween Reptile Program
- Oct 12&13 A Very Fluffy Halloween
- Halloween Paint Night
- Oct 18 Howlin' Halloween Trunk or Treat
- Oct 19 Wicked Wappingers - Halloween Festival+Parade
- Oct 25 Fright at the Farm
- Oct 25 Something Strange in the Neighborhood
- Oct 27 Halloween Parade
💃Hispanic Heritage Month Events💃
- Hudson Valley Renegades, Copa de la Diversión: Hispanic Heritage Month Kickoff
- 10.5 Hispanic Heritage Festival
- Hispanic Heritage Month: Community Art
- Hispanic Heritage Festival
🎃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
- Hudson Valley Renegades Murder Mystery Night
- Hudson Valley Renegades, Copa de la Diversión: Hispanic Heritage Month Kickoff
- Hudson Valley Renegades: Fan Appreciation
- Sunday Family Funday
✂️Craft Fairs🖌️
