Ladies Night Out Worcester: We Laughed, We Cried, We Shopped.

Friday, November 14, Maironis Banquets Ballroom- Ladies Night Out Worcester‘s exposition of women-owned businesses/shopping extravaganza was proof that women have a unique ability to lift each other up in support, in grace and in friendship. Women want to connect! And this year was particularly special. Unbeknownst to her, the event was also a celebration of Founder Allison Hale’s resilience in the face of breast cancer.

Why: Making Space for Female Entrepreneurs

Anyone who identifies as a woman, a woman in business or knows all-too-well that women in business are often the underdogs or feels that women tend to be “catty”, needs to go to Ladies Night Out Worcester. Meet the woman who cut through the BS with creativity and kindness and the community she has curated by just being a good person! Allison Hale said, “I started Ladies Night Out Worcester 8 years ago as a way to help promote a lot of my friends’ businesses”.

In 2017, she recognized her friends were meeting cost and marketing challenges starting out. Many new small businesses lack of seed money for comprehensive marketing campaigns and Chamber of Commerce membership fees. Online businesses have the unique challenges of physical distance from customers and competition with an infinite number of cyber market businesses. Additionally, corporate-focused events often do not make space for local entrepreneurs, particularly women.

A research panel that same year (2017) by Hult International School of Business found that women in traditional business settings still faced gender bias, lower pay, and lack of leadership opportunities, but predicted a boom in women-owned start-ups.

Recognizing that “women control up to 85% of all consumer purchasing decisions in the US,” said Hale, she found a creative way to help her friends: Inviting women to shop small businesses in one location. Toss in some drinks and entertainment, tolerance for all women, and hard work, and the recipe is perfect. That was eight years ago, and now Ladies Night Out Worcester is the place to be, with vendors returning year after year and new businesses at every event, not to mention hundreds of happy shoppers.

In sum, Hale has found a way to help local women come together, cut the red tape, minimize costs and crash through the glass ceiling all while having fun! And it’s not just “business as usual”. This event a safe space for ALL women because it is gender-affirming, celebrates diversity, makes shopping easy, and feels a lot hanging out with hundreds of new friends. A community of women helping women is without parallel.

What: Connecting and Empowering Women

What began as a Facebook campaign to run a women’s shopping event, has blossomed into the Premier Social Event of the year for female entrepreneurs and shoppers in Worcester County. Businesses and entertainment range from handmade goods like cosmetics and pet treats to drag shows and comedy. There is quite literally something for everyone, and isn’t it fun to dress up, go out for drinks and feel completely safe as a woman?!

This year, advanced ticket sales boomed and dozens of women in business set up shop as sponsors to the event, giving them a table to show their wares, an opportunity to be customer-facing, and shout outs on social media and at the event. Ladies Night Out wants to ensure cost is not a barrier for exciting new ventures. They offer variety of sponsorship levels and will work with businesses The Maironis Ballroom was a bustling hive of Wonder Woman energy on November 14, 2025.

Some ladies attended for the entertainment, which included drag and comedy performances, music, giveaways, and house-made cocktails. Some women went to shop fantastic local businesses (see complete list with links below), and some women went to support their friends. Many other women saw the event posted on social media and compelled by curiosity, they showed up not knowing what to expect and left raving.

Customers are saying…

Three generations of one local family (seen above) said they saw the event on social media and decided to make a “girls’ night out” of the event. They were gathered in the lobby getting ready to leave when the ever-effervesscent Diva D came out and broke into a full blown Mrs Doubtfire post-performance performance. Diva “did it” for them: They were already making plans to attend Femme Bar’s Santa’s Most Wanted Drag Brunch with another new female friend. Diva was one of three performers who had the audience cheering so loudly, it was likely heard across Lake Quinsig.

Jacqueline from Light hearted Healing and Messages said, “This was a great way for people to come together. We hear so much about the economic downfall, but seeing everybody work together to help each other, I don’t see it. Small businesses actually win this time.” She is just starting out in business and she said coming to this event was “empowering” and it makes her “not want to stop!” She and a friend came all the way out from the Boston area and said they can’t wait for the next event.

What women get from going to Ladies Night Out Worcester is so much more than a business gathering or Holiday Haul. It is a chance to make new friends, meet collaborators, get inspired by innovative ideas and empower each other. Hale said she was initially “blown away by the success of the event,” but it should be no surprise because she herself is inspiring and innovative. Not only does Hale have decades of business management on her CV, but this year she was honored by her friends, supporters and attendees for beating breast cancer. There may not be anything as moving as seeing 200 women stop mid-transaction and mid-conversation to honor the story of a remarkable woman who beat the odds and stands before them as a humble leader. Oh, the tears!

Who: True Friendship Allows Room for Laughter and Tears

Founder and Event Team

Ladies Night Out Worcester’s event team included Hale’s friend of 18 years Vanessa Williams and Jessica Whalen, who handled ticketing, greeting and personally welcoming every woman. In Hale’s words, “They are amazing ladies! This event wouldn’t run without them. They handle all things front of the house while I’m running around”. Everyone wants to meet and thank Hale for creating this safe space, and they are accepted with a smile and a hug. Her grace and kindness are infectious, and this year, her resilience in organizing an event while undergoing cancer treatment is quite a feat!

Allison Hale is humble and grateful. She speaks about her cancer battle openly to help other women and spread awareness of early detection. She does not ask for pity or compliments. Instead she compliments others, meaning everyone…genuinely. She credits her community for the success of Ladies Night Out Worcester, including her husband (who helped with the heavy lifting before he flees the estrogen-packed room!), her friends, the businesses and attendees. It is the easy task of others to speak about their friend Allison. Comedian Cindy Gray gave a wonderfully moving shout-out to Hale, when she didn’t have the crowd in “lol-tears” with menopause and ex-husband cracks. But it was Williams’ speech to her dear friend in the aftermath of Hale’s breast cancer that was a raw and beautiful public testament to the power of female friendship and the community Hale has created. The gratitude for a safe space to just be a woman was universal.

The spotlight isn’t required for Allison Hale to be pleased with Ladies Night Out Worcester’s success. She shared this highlight of her night:  

“I had a trans woman approach me the night of the event to introduce herself…She said Ladies Night Out Worcester was the first even that she truly felt welcomed, accepted and was comfortable.”

Hale said an inclusive community is exactly what she wants for Ladies Night Out Worcester. Readers should know that though the event has passed, the businesses are a community, a group of women who are open to dialogue, connection and support. LNOW is always open to questions and collaboration throughout the year via their website and social media. It was very clear by the turn out and reception at LNOW 2025 that women want and need to connect and support each other and Worcester needs champions of women, of diversity, and of small business. Allison Hale is all of those things.

Vendors and Performers

Betsey Taft Kennedy, Managing Editor, What’s Up Worcester, betsey@whatsupworcester.com

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