Park District of Oak Park

Decorate your own Gingerbread House 2-4P
2025-12-13 14:00 - 16:00 (America/Chicago)
Grab your family and purchase a table at beautiful Pleasant Home to decorate your own Holiday Gingerbread House. We will have a light lunch to help power you through your creative blocks. Once finished, pose for a family selfie in the Great Hall of Pleasant Home. Price is per table per family.
All Ages

The Santa Trolley December 14th 9:15A
2025-12-14 09:15 - 10:45
BACK BY POPULAR DEMAND – Two days and two locations! While you wait to board the trolley, you can enjoy “elvish” games and activities or tour the beautiful showrooms at Oak Park Conservatory. While en route to the “ North Pole”, your Head Elves will help get you in the Holiday spirit with festive songs to sing! Santa and Mrs. Claus await your arrival at the beautiful Cheney Mansion or Pleasant Home along with entertainment, beverages, and cookies!
Registration is required for all riders (1 and up) as space is limited on the Trolley. All Ages!

The Santa Trolley December 14th 9:45A
2025-12-14 09:45 - 11:15

The Santa Trolley December 14th 10:15A
2025-12-14 10:15 - 11:45

The Santa Trolley December 14th 10:45A
2025-12-14 10:45 - 12:15

The Santa Trolley December 14th 11:15A
2025-12-14 11:15 - 12:45

The Santa Trolley December 14th 11:45A
2025-12-14 11:45 - 13:15

The Santa Trolley December 14th 12:15P
2025-12-14 12:15 - 13:45

The Santa Trolley December 14th 12:45P
2025-12-14 12:45 - 14:15

The Santa Trolley December 14th 1:15P
2025-12-14 13:15 - 14:45

The Santa Trolley December 14th 1:45P
2025-12-14 13:45 - 15:15

The Santa Trolley December 14th 2:15P
2025-12-14 14:15 - 15:45

The Santa Trolley December 14th 2:45P
2025-12-14 14:45 - 16:15

Sensory Friendly Cookies with Santa 5pm
2025-12-17 17:00 - 18:00
The Park District of Oak Park and WSSRA welcome families in need of sensory-specific events to visit with Santa! Take a photo with Santa and enjoy appropriate activities, cookies, and beverages while you wait. All Ages

Sensory Friendly Cookies with Santa 6 pm
2025-12-17 18:00 - 19:00

Sensory Friendly Cookies with Santa 7 pm
2025-12-17 19:00 - 20:00
The Park District of Oak Park and WSSRA welcome families with sensory issues to an evening at Cheney Mansion and a visit with Santa! Bring your camera for your photo with Santa in the Cheney Library. Appropriate activities will be available while you wait along with cookies and beverages! All Ages

Little Helpers Workshop
2025-12-19 18:30 - 20:00
Parents, need to finish last minute shopping? Drop off your little helper, where they can enjoy a kid-friendly dinner while also rotating through stations including toy testing, games, crafts and special treats for Santa to pack into his sleigh. Ages 4-7

Brunch with the Grinch First Seating
2025-12-20 09:00 - 22:30
Get ready to Whobilate at Cheney Mansion – The Grinch is coming to town! Step into a whimsical winter wonderland as Whoville takes over Cheney Mansion for a magical holiday brunch! Dress in your Grinchiest green, style your hair Whoville-style, and join us for a festive celebration full of fun, food, and heartwarming cheer. Meet the Grinch, play games, and maybe even learn that Christmas isn’t about the gifts – it’s about something a little bit more. Help the Grinch’s heart grow ten sizes as we share laughter, joy, and a whole lot of holiday spirit. All participants must be registered. Infants one year and younger need not register. All Ages

Brunch with the Grinch Second Seating
2025-12-20 11:30 - 13:00

Father Christmas 11 am
2025-12-21 11:00 - 12:00
Travel back in time and visit Father Christmas at Pleasant Home this holiday season. This Victorian themed event will have something for everyone in your family. From hot chocolate, to stories by the fireplace, to holiday goodies! All attendees must be registered and parents must accompany children. ALL AGES
