More funny women of a certain age return to Milford Theater

Milford. Comedian Carol Montgomery bring a new show on Jan. 24.

| 14 Jan 2026 | 03:59

Get ready to laugh your socks off on Jan. 24 because hilarious comedian, Carole Montgomery, is returning with a completely new show and she’s bringing two additional comedians with her to help you laugh your way through the aging process.

Montgomery is a powerhouse. She grew up watching comedy before she actually got into the game. Her father was a bartender in the Catskills and she used to watch and listen to comedians like Don Rickles and Rodney Dangerfield as they came through that world of standup comedy. She worked behind the scenes in summer stock as a crew member until one day it dawned upon her that she was funny. She did the clubs in New York and LA, like “The Improv” and “Catch a Rising Star,” but there wasn’t a huge call for women comedians which she and other women had to fight against.

After Covid and the growing importance of the internet, things began to change. She got older and it became even harder for older women comedians. Montgomery, who doesn’t easily take “no” for an answer, was able to make lemonade out of lemons. She embraced the comradery among women and started to embrace the joys of being older.

In 2019 she created, produced, and starred in the show “Funny Women of a Certain Age.” As if that weren’t enough, she became an entrepreneur, trademarked the show, and sold it to Showtime. At 67, she is proud of her age and accomplishments. There are now three specials streaming on Showtime extolling the wonders of growing old; “Funny Women of a Certain Age,” “More Funny Women of a Certain Age,” and “Even More Funny Women of a Certain Age.”

The show was created to give older comedians a chance to shine, to be seen and heard. Montgomery is fighting against ageism and sexism, one joke at a time.

There is also a live show touring the country and that is the one coming to Milford. Missy Hall and Vicky Kuperman will be joining Montgomery.

“Missy is my secret weapon. She always lifts me up. Vicky is a brilliant writer,” Montgomery said. “She’s my rock.”

The live show has a rotating cast in order to give more women more exposure.

”Getting older is my identity. I’ve had the biggest success in my career promoting and uplifting women of a certain age,” she said.

Montgomery has thousands of followers on Instagram and has more than 2,362 posts. This could not happen if she weren’t truly funny. It’s as if she has humor running through her veins and her immediate empathy with her audience finds its way to everyone’s funny bone. The show is non-stop laughter.

“Funny Women of a Certain Age” hits the Milford Theater stage (114 East Catharine St.) on Jan. 24 at 8 p.m. Tickets can be purchased at https://shorturl.at/2u4vb.