This weekend kicks off October, a month filled with cooler weather, pumpkin picking, and halloween. So dress up and parade through the zoo at opening weekend of Boo at the Zoo, begin your family’s search for the perfect pumpkin at Pumpkin Day and the Pumpkin Patch, or venture to Randall’s Island to visit with the chickens at to the Harvest Festival. Your family won’t even miss summer by the time you’re through with this weekend!

Photo: Bronx Zoo Boo at the Zoo via Flickr 


Loops and Hoops Festival
Celebrate the importance of play with children around the world on World Hoop Day. Hoop and dance to live music as you enjoy the benefits of a hoop as a universal toy and fitness tool. Bring your hoop and share in the fun, games and laughter. Sat. 1-5 p.m. Upper West Side. Free. All ages. Event details.

Autumn Crafts Festival
Your little ones will enjoy walking around, people watching and taking in the ongoing entertainment and you’ll get to do a little shopping! Spend the afternoon roaming over 250 vendors, ranging from jewelry to clothing to one of kind pieces. If your little ones are on their best behavior, you can pop into the candy store, It’s Sugar, for a sweet treat. Sat. 11 a.m.-8:30 p.m. & Sun. 10 a.m.-6:30 p.m. Upper West Side. Free. all ages. Event details.

Medieval Festival
Travel back in time to the Middle Ages when Fort Tryon Park is transformed into a medieval market town decorated with bright banners and processional flags. Performers, guests and festival goers dress in medieval costume and visitors are greeted by authentic medieval music, dance, magic, jugglers and jesters. The afternoon is concluded with a thrilling joust between four knights on horseback. Costumed vendors will be on hand to demonstrate and sell a wide variety of medieval crafts as well as food and drink. Sun. 11:30 a.m.-6 p.m. Washington Heights. Free. All ages. Event details


Monsters in the Making
Bring your little monsters to create some monsters of their own. They can use water colors and straws to create their own unique monster, all while practicing math skills, learning about colors, counting and more. Swing by before and catch a screening of Sesame Street: Arts and Crafts Playdate at 11 a.m. Pre-registration is require for both events, RSVPSat. Noon-1 p.m. Midtown East. Pre-k to kindergarten learning level. Free. Event details


Sea Monster Shadow Puppet Theater
During Medieval and Renaissance times, cartographers and mapmakers would indicate unexplored or little known areas with mythical sea monsters on the maps they created. Bring your little artists to this workshop where they will create sea monsters as shadow puppets and then let their imagination soar as they build their own adventure on the shadow puppet screen. Fri. 2:30-5:45 p.m. Soho. Ages 5 and up. Free with museum admission. Event details

Who doesn’t love a pickle? Check out 20+ picklers, 30+ local food and fashion vendors, activities, DJs, live music, and a home pickling contest at this annual pickle celebration. Your kiddos can taste pickle on a stick, pickled brittle, pickled truffles, pickle slices, and much more. Sun. Noon-5 p.m. Lower East Side. Free. All ages. Event details


Pumpkin Day
Kick of the fall season with the Town Square’s Pumpkin Day. Spend the day in the park listening to live music, enjoying arts & crafts, face painting, and of course snacking on delicious food. The fair is free, but if you buy a ticket your little ones can also enjoy the pick-your-own pumpkin patch where they can roam freely in search of the perfect pumpkin. The ticket will also send your kiddos home with a special trick-or-treat bag filled fun things to decorate their newely acquired jack-o-lantern. Sat. Noon-3 p.m. Greenpoint/Williamsburg. Free ($10/child to enter pumpkin patch purchased in advance; $15/child to enter pumpkin patch purchased at gate). All ages. Event details

This parade is all about the kiddies. Put on your best costume and march along side other kids in creative get ups. Everyone gets a free gift and the grand prize winners for the “most creative costume” win a bike! So use your imagination and strut your stuff. Sat. Registration begins at 11 a.m.; Parade begins at 1 p.m. Free. All ages. Event details

Sugar Sweets Festival
Ok, so you’re going to have to say yes to a little chocolate if you hit up this festival, but hey it’s the weekend. Snack on delicious treats at the bake sale and watch a Blue Ribbon Baking Competition. Then let your little ones burn off their sugar high dancing to live music, playing dress up, hanging with the Lego Lady and much more. Sun. 10:30 a.m.-4 p.m. Williamsburg. Free. All ages. Event details.  


Pumpkin Picking on the Farm
Skip the pumpkins at your local corner store and head to the farm, don’t worry it’s just in Queens. Your kiddos can wander through a field of orange to find their perfect pumpkin to take home and carve. Wrap up the day with some delicious apple cider and pick up some apples, or for a real treat, apple pie, to take home. Sat. & Sun. 11 a.m.-4:30 p.m. Floral Park. Free. All ages. Event details


Boo at the Zoo
It’s opening weekend! Get some extra use out of that Halloween costume and dress to impress. Join in a parade, get lost in the Hay Maze, make creepy masks, catch a magic show and so much more. Your kiddos can even trick-or-treat around the zoo, so be prepared to come home with some loot. Not to mention, you’re at the zoo, so visit with the animals! Sat. & Sun. 10 a.m.-5 p.m. Pelham Parkway. Free with admission. All ages. Event details

Randall’s Island

Harvest Festival
Celebrate Fall at this annual festival. Your kiddos can fly kites, go on a pumpkin hunt, get their face painted and even meet the chickens at the Urban Farm. Bask in the cooler fall weather with a picnic lunch (BYO or grab something to eat at the festival) while enjoying live music. Sat. Noon-4 p.m. Randall’s Island. Free. All ages. Event details

How will your family rock the the first weekend in October? Share with us in the comment section below.

—Caitlin Dowling