Fall Fun for Families in Westchester, Fairfield & Putnam Counties: Activities for Littles and Bigs


Fall is the season for family fun, and there’s no better time to enjoy the crisp air, pumpkin patches, and all the seasonal activities the area has to offer! Whether you're looking for a farm adventure, a fun sporting event, or a spooky Halloween outing, I’ve rounded up some of our family’s favorite fall spots and think you're family will also love them too!


Sometimes the choices can be very overwhelming with weekend options and hidden gems are often overlooked with all the bustle of fall planning. I’ve compiled a list of our go-to fall activities that are sure to make your weekends memorable!


Fall Festivals at the Farm



Outhouse Orchard, North Salem, NY

A family favorite of ours since we were little - most of my siblings even worked here in high school. Amazing donuts, very cute shot, delicious fresh produce. Over the past few year's Outhouse Orchard has strived to be a kid centric place. Parents can go enjoy some beverages, good food, beautiful scenery all while kids are completely content. Make sure you make a reservation ahead of time as fall weekends book up fast.



Harvest Moon, North Salem, NY

Right across the street is another favorite of ours. We enjoy this spot all year round because of the cozy greenhouse dining space. We enjoy grabbing a tasty farm fresh meal and hard cider There are some animals for the kids to visit with and a really nice space. This place transforms for the Holiday Season with an illuminated forest, be sure to watch for when tickets go on sale.


Silverman Farm - Easton, CT

A little crowded for my liking but the best part is the farm animals. If you are able to visit during the week, I would highly recommend! They have a large hayrides, apple picking, and a large pumpkin patch- if you guess your pumpkin's weight you get it for free (my kids thought this was great)!


Muscoot Farm Farmers Market - Katonah, NY

For a more low-key Sunday, head to the Muscoot Farm Farmers Market. With live music, fresh produce, and tons of friendly farm animals, this is a perfect outing for families with young kids. The farm is also very stroller-friendly, making it an easy stop for families with little ones in tow.


Sporting Events


West Point Army Football Game - West Point, NY

If you're looking for a sporting event that’s both exciting and scenic, the Army football games at West Point are a must! The backdrop of the Hudson River and rolling hills makes these games something special. Arrive early to enjoy the pre-game parade and kid-friendly fun at Black Knights Alley. And, trust me, your kids will be in awe when they see the Army cadets jump out of a helicopter to deliver the game ball to center field!


Halloween Fun

Forest of Fear - St. Gregory - Danbury, CT

This one is on our fall bucket list for this year! We’ve heard amazing things about it from other families. During the day, there’s a kid-friendly version of the event, which is just spooky enough to be exciting without being too scary. If you're feeling brave, the evening version is full-on spooky with haunted houses and all the thrills.


Tips for a Smooth Fall Outing with the Family


  • Plan Ahead: Fall weekends are busy, so it's always best to check hours of operation and make reservations where needed.
  • Dress for the Weather: The fall chill can sneak up on you, so layers are key.
  • Pack Snacks & Water: Having a few snacks on hand is always a lifesaver, especially when you’ve got little ones in tow.


I hope this list gives you some inspiration for your next family weekend adventure. There’s no shortage of fun fall activities to enjoy near Westchester, Fairfield, and Putnam Counties, so get out there and make the most of this beautiful season!