‘Widow’s Bay’ Season 2 Could Finally Fix Its Biggest Character Mistake

Published Aug 26, 2026, 5:44 PM EDT Taylor Vollman is a contributor at Collider. She has long quipped, “T.V. is my name, TV is my game.” Fortuitous initials aside, at the heart of a tired joke is a simple truth — she has a lifelong passion for television. And along with it, an affinity for movies, music and pop culture. In a childhood time capsule, she had listed Friends, PB&J Otter, and Days of Our Lives among her favorite shows. But her tastes have not narrowed with age. Her viewing habits span TV Land classics, network hits, buzzy reality shows and streamer critical darlings. Hoping to merge this passion with her love of writing, Taylor earned a bachelor’s in media arts and design with a minor in film studies from James Madison University. After working in marketing for years, she wanted to sharpen her skills and went on to graduate with a master’s in journalism from Georgetown University. Taylor has since pursued entertainment writing and reporting. The New England island at the heart of Widow’s Bay boasts the usual small town residents — the exasperated sheriff, the offbeat drug dealer, the local business owners, the rebellious teenagers, and the lifelong mean girls. But this isn’t a normal island. As if trapped in the past, the island doesn’t have the modern conveniences of Wi-Fi or cell phones. Rumors of a boogeyman, sea hag, and killer ghosts persist. And as local lore goes, any resident born on the island is unable to leave without risk of death. So, the island also has a kookier cast of characters. Among them, the disgruntled hotel owner too afraid to stay overnight, the unengaged waitress who never gets an order correct, and Wyck Crawford (Stephen Root), the conspiracy theorist who turns out to be right. Widow’s Bay was created by former Parks and Recreation writer Katie Dippold. The horror comedy follows the inhabitants of the titular cursed island, led by Mayor Tom Loftis (Matthew Rhys) and his staff at Town Hall. There’s the senile Ruth (K Callan), social outcast Patricia (Kate O’Flynn), and politically incorrect Rosemary (Dale Dickey). Among the smattering of other background employees is the show’s most underutilized character, Dale, played by Jeff Hiller. But it looks like Dale will finally get his due, with Apple TV announcing Hiller was promoted to a series regular ahead of the upcoming Season 2. Hiller was little more than an extra throughout most of Widow’s Bay, filling out the background staff of Town Hall. But throughout Season 1, Dale would have scene-stealing small moments or one-liners, like ineptly DJing Patricia’s cocktail party or donning an uncanny valley mask during Loftis’ mushroom trip. But it was during the storm that left the residents and vacationers trapped in an outdated shelter that Dale accidentally learned of the island’s sacrificial history. In one of the most popular memes from the show, he yelled, “This place is a death trap! Run! Run for your lives.” The comedian was a perfect fit for the show, with his deadpan delivery in small moments juxtaposing his iconic finale scream. The 50-year-old has made a career out of small movie roles, guest appearances, and the occasional short-lived series. But over the last year, Hiller has been hitting a career high. He was cast in Widow’s Bay before winning the Emmy for his role in HBO’s Somebody Somewhere.He is also a 2026 Emmy nominee for his guest appearance in another Apple TV series, Pluribus. Dale Was Originally Supposed to Die in Season 1 Image via Apple TV Dale was supposed to die in the first season, Hiller revealed to Deadline in August 2026. He explained that he submitted a self-tape without informing Dippold, someone he did improv with more than 20 years ago. So, the two had a short-hand despite it coming as a surprise when she called him with a question. According to Deadline, she asked, “Do you mind if I don’t kill you?” While Dale didn’t die, another Town Hall staffer did. Kenny was rather inconsequential throughout the season, but he tried to stop Loftis’ son Evan (Kingston Rumi Southwick) and his friends from messing around in the dark bunker. In the season finale, “We Hope You Enjoyed Your Time!,” he gets trapped in the room for sacrifices never to be seen again. Jeff Hiller and Dale Dickey Already Have Ideas for Season 2 Image via Apple TV With so much of Dale’s character left unexplored, the sky is really the limit in the upcoming season. As Deadline reported, Dippold has returned to the writer’s room but is remaining tight-lipped about the mystery’s next chapter. But that doesn’t mean the cast is without ideas. Dale and Rosemary made an unlikely duo throughout the season, often chatting in a corner or sharing knowing glances. She reinforced his concerns about skin cancer, and he went to her aid over Loftis during an accident with a frame. So, it makes sense the actors who play the pair, Hiller and Dickey, would like more time to explore this dynamic in the upcoming season. “I would love to do a boat scene where Rosemary and Dale are out searching for the sea hag to get some answers,” Dickey told Deadline in August 2026. “I thought that would be fun. And then we tip over and there’s only one life jacket. Who’s going to live?” Hiller would also like to explore more of Dale’s personal life, telling PauseRewind that he wants to see what creepy things he keeps in the basement or secret family members he keeps locked away in the vein of a hagsploitation film. Despite not being intended to live past Season 1, it is easy to see why Dippold course-corrected given Hiller’s performance as Dale. Much like the show, his character largely remains a mystery. But thankfully, with his recent addition to the core cast, audiences should get at least a few answers. Release Date April 28, 2026 Network Apple TV Showrunner Katie Dippold Cast Directors Sam Donovan, Andrew DeYoung, Hiro Murai, Ti West Writers Alberto Roldán, Neil Casey, Kelly Galuska, Colton Dunn, Dave Harris, Katie Dippold, Mackenzie Dohr Creator(s) Katie Dippold