Carnival season has officially rolled into Dutchess County—aka the time of year when kids start plotting their ride strategy while parents start calculating how many wristbands they can afford without refinancing the house. 😅
Let’s be real: those unlimited ride wristbands? Not exactly “pocket change.” And once you add in the fried Oreos, funnel cakes, giant lemonades, and maybe a stuffed animal you did not win on the first try, you’re looking at a solid chunk of change in the name of family fun.
But here’s the thing—we do it anyway. Because the smiles, the sticky fingers, the neon lights after sunset… they’re kind of worth it. And this year? We’ve got you covered with the ultimate roundup of Dutchess County carnivals and fairs so you can pre-plan like a pro, know where the best fair food is hiding, and even enter to win FREE wristbands to kick the season off.
I put this guide together to help fellow parents find some of the best carnivals popping up around Dutchess County. I'll be keeping it updated as more events get announced, so be sure to check back often—because we all know how fast those weekends fill up! Know of a carnival or fair I missed? Let me know!
🎟️ Enter now HERE to win a Family 4-Pack of Unlimited Ride Wristbands to the Hudson Valley Fair at Heritage Financial Park, Wappingers Falls — happening May 7–11. That's four wristbands (aka unlimited rides = happy kids), totally on us. |
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Hudson Valley Fair Carnival
📍 Location: Heritage Financial Park, Wappingers Falls
📅 When: May 7 – May 11, 2025
🕐 Hours: Wed–Thurs: 5–10 PM, Friday: 5–11 PM, Saturday: 12–11 PM, Sunday: 12–10 PM
🚗 Admission & Parking: FREE!
🎟️ Wristband Info:
Unlimited Ride Wristbands (for riders 36" & taller): $37 on site (or $35 cash!) 💻 Pre-sale online before Wed., May 7 at 5 PM: $29 each, 2 for $55, or 4 for $99 🎟️ Ride tickets also available online and at the event Pre-sale special: $45 for 50 tickets + 1 FREE ride (rides take 2+ tickets each)
Cash or Credit: All major credit cards & debit cards are accepted at the ticket boxes at the carnival. Most food vendors accept them as well. There is an ATM also available.
Publisher Note: Enter to win a family 4-pack of unlimited ride wristbands! Three winners will be chosen on May 1, 2025.
The Sons of Italy Italian Festival
📍 Location: Hopewell Recreation Park, 392 Route 376
📅 When: Memorial Day Weekend, May 22-25
🕐 Hours: Unknown
🎟️ Ticket Info: Unknown
Publisher Note: Updated info for 2025 can not yet been posted. The carnival typically occurs annually on Memorial Day Weekend and offers options for ride tickets and wristbands. As I find more info on this Carnival, I will update this listing. If you or someone you know knows the details, please email me.
LaGrange Community Day
📍 Location: Freedom Park, 212 Skidmore Rd, Lagrangeville, NY
📅 When: June 14, 2025
🕐 Hours: Noon-10pm
🎟️ Ticket Info: Free
Publisher Note: While not exactly a carnival or fair, Lagrange Community Day offers residents an affordable way to enjoy many of the same sights, sounds, and fun you get at the carnival including: food trucks, music, fireworks, petting zoo, bounce houses, games, face painting, entertainment, and more.
LaGrange Knights of Columbus Family Carnival
📍 Location: 126 Stringham Rd, Lagrangeville
📅 When: Usually the last weekend of June (probably will be June 25-28)!
🎟️ Ticket Info: Unknown
Cash or Credit: Unknown
Publisher Note: The link here currently has 2024 information. As I find more info on this Carnival, I will update this listing. If you or someone you know knows the details, please email me.
Pleasant Valley Firemen’s Carnival
📍 Location: Cady's Field
📅 When: Usually in mid-July
🎟️ Ticket Info: Unknown
Cash or Credit: Unknown
As I find more info on this Carnival, I will update this listing. If you or someone you know knows the details, please email me.
Pawling Fireman's Carnival
📍 Location: Freedom Park, 212 Skidmore Rd, Lagrangeville, NY
📅 When: August 13-16, 2025, with the parade on Friday and fireworks on Saturday.
🕐 Hours: Unknown
🎟️ Ticket Info: Unknown
Publisher Note: Official information for 2025 has not been posted yet. The carnival, parade, and fireworks are scheduled for August 13-16, 2025. Organized by the Pawling Fire Department, the carnival serves as a fundraiser and community gathering, featuring:
- Amusement rides and games
- Live music and entertainment
- A diverse selection of food vendors
- A parade showcasing the local fire department and community groups
- A fireworks display to cap off the festivities
Dutchess County Fair
📍 Location: Dutchess County Fairgrounds, Rhinebeck
📅 When: August 19-24
🕐 Hours: Daily Fair Hours: Tues-Sat 10:00 AM–10:00 PM | Sun 10:00AM–8:00PM;
All Rides Run Daily: Tues-Sat 11:00 AM til Closing | Sun 11:00AM–8:00PM
🎟️ Ticket Info: Children 11 and under are admitted FREE. Ride tickets or wristbands ($30 in advance or $40 at the gate) can be purchased separately and are required for any guest who wishes to ride midway rides. Parking is FREE. General Admission ticket is single-use and good for any ONE DAY during the Fair. $15 in advance (ends 8/19) or $20 at the gate.
General Admission ticket does not include the Ride All Day Wristband; must be purchased separately.
There are multiple ATMs located throughout the fairgrounds. If you'd like to avoid the carnival cost there is a number of free entertainment options at the fair, including the popular Dock Dogs, Racing Pigs, Stilt Circus, Petting Zoo, Stunt Show, Frisbee Dogs, and MUCH more! Also don't miss Livestock Hill and the AgriVenture Kids Activity Area, horticulture buildings, historic train station, on-site museums, horse shows, and arts and crafts!
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