Park District of Oak Park

The Santa Trolley December 7th 11:45A
2025-12-07 11:45 - 13:15 (America/Chicago)
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 7th 12:15P
2025-12-07 12:15 - 13:45

The Santa Trolley December 7th 12:45P
2025-12-07 12:45 - 14:15

The Santa Trolley December 7th 1:15P
2025-12-07 13:15 - 14:45

The Santa Trolley December 7th 1:45P
2025-12-07 13:45 - 15:15

The Santa Trolley December 7th 2:15P
2025-12-07 14:15 - 15:45

The Santa Trolley December 7th 2:45P
2025-12-07 14:45 - 16:15

Cookies with Santa 4pm
2025-12-10 16:00 - 17:00
Join the Holiday countdown at Cheney Mansion and have some cookies with Santa before he embarks on his annual journey around the world. Bring your wish list and your camera and snap a selfie with jolly Old St. Nick! Our 6:00P and 7:00 P time slot will feature a Santa with a darker complexion, celebrating the joy and diversity of the season. All ages

Cookies with Santa 5pm
2025-12-10 17:00 - 18:00

Cookies with Santa 6pm
2025-12-10 18:00 - 19:00
Join the Holiday countdown at Cheney Mansion and have some cookies with Santa before he embarks on his annual journey around the world. Bring your wish list and your camera and snap a selfie with jolly Old St. Nick! Our 6:00P and 7:00 P time slot will feature a Santa with a darker complexion, celebrating the joy and diversity of the season. All ages.

Cookies with Santa 7pm
2025-12-10 19:00 - 20:00
Join the Holiday countdown at Cheney Mansion and have some cookies with Santa before he embarks on his annual journey around the world. Bring your wish list and your camera and snap a selfie with jolly Old St. Nick! Our 6:00P and 7:00P time slot will feature a Santa with a darker complexion, celebrating the joy and diversity of the season. All ages.

Holidays Around the World - Pair Registration
2025-12-12 18:30 - 20:00
All "aboard" Flight 1225 on Holiday Airlines for your chance to experience Holiday traditions in different countries and cultures. Let the first floor rooms of Pleasant Home be your "globe" as you make your way to each "country" for crafts, traditions and treats Have your "passport" stamped at each stop and at the end of your journey receive a special keepsake treat to help you remember your "journey." Each person must be registered and parents needs to accompany children. Ages 5+ with adult

Holidays Around the World - Additional Guest Registration
2025-12-12 18:30 - 20:00
Use this tile to register additional family members for Holidays Around the World.

Pet Photos with Santa 9:15A
2025-12-13 09:15 - 09:30
Santa will be waiting for you and your four-legged family member in the Greenhouse on the grounds of Cheney Mansion to capture your holiday photo for the whole family! Registration is per family–just 1 person needs to be registered. Digital photos from our professional photographer are included in your registration. All ages

Pet Photos with Santa 9:30A
2025-12-13 09:30 - 09:45
Santa will be waiting for you and your four-legged family member in the Greenhouse on the grounds of Cheney Mansion to capture your holiday photo for the whole family! Registration is per family–just 1 person needs to be registered. Digital photo images from our professional photographer are included in your registration. All ages

Pet Photos with Santa 9:45A
2025-12-13 09:45 - 10:00
Santa will be waiting for you and your four-legged family member in the Greenhouse on the grounds of Cheney Mansion to capture your holiday photo for the whole family! Registration is per family–just 1 person needs to be registered. Digital photos from our professional photographer are included with your registration. All ages

Pet Photos with Santa 10:15A
2025-12-13 10:15 - 10:30
Santa will be waiting for you and your four-legged family member in the Greenhouse on the grounds of Cheney Mansion to capture your holiday photo for the whole family! Registration is per family–just 1 person needs to be registered. Digital photos from our professional photographer are included. All ages

Pet Photos with Santa 10:30A
2025-12-13 10:30 - 10:45

Pet Photos with Santa 10:45A
2025-12-13 10:45 - 11:00
Santa will be waiting for you and your four-legged family member in the Greenhouse on the grounds of Cheney Mansion to capture your holiday photo for the whole family! Registration is per family–just 1 person needs to be registered. Digital photos are included from our professional photographer are included. All ages

Decorate your own Gingerbread House 11A-1P
2025-12-13 11:00 - 13:00
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

Pet Photos with Santa 11:15A
2025-12-13 11:15 - 11:30

Pet Photos with Santa 11:30A
2025-12-13 11:30 - 11:45

Pet Photos with Santa 11:45A
2025-12-13 11:45 - 12:00

Pet Photos with Santa 12:15P
2025-12-13 12:15 - 12:30

Pet Photos with Santa 12:30P
2025-12-13 12:30 - 12:45

Pet Photos with Santa 12:45P
2025-12-13 12:45 - 13:00

Decorate your own Gingerbread House 2-4P
2025-12-13 14:00 - 16:00

The Santa Trolley December 14th 9:15A
2025-12-14 09:15 - 10:45

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
