Oliver Hudson's family is heading into a new chapter.
The Happy Gilmore 2 actor and wife Erinn Bartlett moved their eldest son Wilder Hudson into his dorm as he kicked off his freshman year of college and it stirred up a boatload of feelings for the couple.
"This little guy turned 19 yesterday and we moved him into college last week," Erinn captioned an Instagram carousel post shared Aug. 24. "Lots of tears not gonna lie wow."
"So happy and proud and excited for you Wildman!!" she added. "Couldn’t love you more and counting the days til I can hug you and annoy you again."
Along with throwback photos of their son, Erinn—who also shares son Bodhi, 16, and daughter Rio, 13, with Oliver—included several pictures of them moving Wilder into his dorm room, which they decked out with a gray, black and white color scheme and TVs at the end of his and his roommate's bed.
In one of the snaps, the proud parents are all smiles as they pose with the teen in his new accommodations and, in another, they stand outside the dorm building together.
The couple's milestone moment with their firstborn comes after they celebrated their 20th wedding anniversary earlier this summer, which Oliver made sure to immortalize on his social media.
"20 years of marriage with this incredible being who blessed me with everything that is her!” the 49-year-old wrote on Instagram in June. "How lucky I am."
"I could go on and on about this bubbly bright light who has changed my life but I won’t," he added at the time, "because she made me use this picture where she looks amazing and I look like you could wring tequila out of my eyelids. 2 nights at @elencanto.sb in Santa Barbara was incredible. Perfect getaway! Love you poop!!"
Erinn also shared a tribute of her own to commemorate the occasion.
"I know it should make sense but it does not," she captioned a slideshow of photos of them together from over the years posted to Instagram. "20. Wow. I Love you. I love us. I love this life we’ve worked hard to create."
"We had no idea what was ahead of us in some of these photos," Erin added, "and I can’t believe how much fun we’ve had, the adventures we’ve taken, the babies we made and for what lies ahead. Cheers to us Poop."
Oliver and Erinn aren't the only stars with kids going back to school this fall. Keep reading for more famous tots who are preparing to hit the books again...
Hoda Kotb
The former Today anchor and her ex Joel Schiffman celebrated daughters Haley Joy and Hope Catherine kicking off their studies.
"It’s here! First day of school," she wrote on Instagram Sept. 8. "4th and 2nd grade! Whaaaatttt?"
Kate Middleton & Prince William
Prince George was escorted by his parents to his first day at Eton College on Sept. 8.
Khloe Kardashian
The Kardashians star kept up with tradition, snapping a photo of son Tatum and daughter True on their first day of school.
“I canNOT believe Tatum started school today! And my True is in THIRD GRADE!” she wrote on Instagram Sept. 2. “Both of my babies are officially in school and I truly don’t know how we got here.”
LeBron James
The NBA icon's daughter Zhuri's first day of sixth grade on Sept. 1 was complete with a Herschel Supply backpack full of books and a ride to school.
Al Roker
The Today anchor's son Nick returned to college to pursue a bachelor's degree after earning an associate degree in communication in 2025.
"Another drop off for my young man," he wrote on Instagram Aug. 29. "Gonna miss him but as Al Roker Sr. always said, #cantmissyouifyoudontleave. So very proud of him."
Craig Melvin & Lindsay Czarniak
The morning show host and his sports journalist wife sent their kids Sybil and Delano back to school on Aug. 26.
"So proud of these two," Melvin wrote on Instagram, "and can’t wait to see all they accomplish this year."
Jamie Lynn Spears
College 101. The Zoey 101 alum helped her daughter Maddie set up her dorm room at University of Southern Mississippi in mid-August. A few days later, she and her husband Jamie Watson sent their daughter Ivey off to third grade.
As the actress put it in an Aug. 19 Instgram post, "Definitely crying."
Kendra Wilkinson
On Aug. 19, the Girls Next Door alum shared a dropoff selfie with her daughter Alijah, who she shares with ex-husband Hank Baskett.
"First day of 7th grade and i couldn’t be more proud of Alijah," she captioned the photo. "Made her a chicken quesadilla for lunch lol. Time to fly my love. Good luck my amazing daughter. I love you."
Mia Talerico
Good luck to the Good Luck Charlie alum, who started her senior year of high school on Aug. 19.
Richard Blais
The Top Chef: All-Stars winner was served a plate of emotions while sending off his daughter Riley to her freshman year at Indiana University Bloomington, writing on Instagram Aug. 18, "Gonna miss you kiddo."
Trista Sutter & Ryan Sutter
The longtime Bachelor couple dropped their son Maxwell off at the University of Colorado Boulder, with Trista writing on Instagram Aug. 17, "He’s gonna go so far and we’re definitely not angry. Emotional, yes, but so insanely excited and proud - which is a very strange place to be…caught between 2 drastic emotions."
And if that wasn't already a bittersweet moment, the parents of two also saw their daughter Blakesley off to her senior year of high school.
Sheryl Crow
The singer made sure to soak up the sun with her son Wyatt before sending him off to his freshman year of college.
"Where does the time go?" whe wrote in an Aug. 17 Instagram post. "For any parent who just went through this, I know how you are feeling! So proud of the young man he has become, and sure am missing him around here!"
Teyana Taylor
On Aug. 13, the Oscar nominee and her ex Iman Shumpert celebrated their daughters Junie Shumpert and Rue Shumpert's "first day" while showing there's one resemblance after another between the actress and her kids.
Giada De Laurentiis
The Food Network star reunited with her ex Todd Thompson on Aug. 8 at a college send-off party for their daughter Jade.
Tristan Thompson
The NBA star escorted his son Prince—who he shares with ex Jordan Craig—to his first day of fourth grade, joking in an Aug. 12 Instagram, "Man I’m getting old."
Melissa Joan Hart
The Sabrina the Teenage Witch alum enchanted to see her and husband Mark Wilkerson's sons Braydon and Tucker head back to school on Aug. 12.
"Last first day of school for our Brady," she wrote on Instagram. "Senior year for him and 7th grade for Tucker. May God bless and protect all the children as they head back to school!"
Kelly Stafford
Matthew Stafford's wife snapped this photo of the NFL quarterback sending their twins Chandler and Sawyer off to their first day of fourth grade. As she captioned the photo on Instagram Aug. 12, "New school, same girls."
Lindsay Arnold
The former Dancing With the Stars pro waltzed her and husband Sam Cusick's daughters Sage and June to class on Aug. 12, writing on her Instagram Story, “I can’t believe they are both starting school now.”
Jana Kramer
Summer is winding down. The Whine Down podcaster sent her kids Jolie and Jace—who she shares with ex Mike Caussin—as well as her and husband Allan Russell's son Roman off to their first day of school on Aug. 10.
"First day of Pre-K3, 5th grade & 2nd grade," she captioned a photo of their blended family. "So proud of these three and excited for all this school year will bring."
Brittany Aldean
Jason Aldean's wife shared photos of their kids Navy and Memphis heading back to school on Aug. 11, calling it an "emotional Tuesday."
DeAnna Pappas
She's going to school for all the right reasons. The Bachelorette alum saw her daughter Addison start seventh grade on Aug. 11.
"You are incredible Tiny," she wrote on Instagram. "Praying for a great year in middle school!"
Taylor Selfridge
The Ex on the Beach alum helped her and Cory Wharton's oldest daughter Mila get ready for elementary school. As she wrote on Instagram Aug. 12, "My little first grader."