Bruce Hornsby and others celebrate 20 years of The Ridgefield Playhouse

Photo of TinaMarie Craven

The COVID-19 pandemic has forced the arts and entertainment industry to get creative in 2020 after social distancing protocols forced them to close their doors, but it won’t stop the Ridgefield Playhouse from celebrating its 20th anniversary.

“We were hoping to have a big gala celebration for our 20th anniversary season,” said Ridgefield Playhouse executive director Allison Stockel. “But I think we have turned lemons into lemonade and have come up with a great way to have a really fun 20th Anniversary Gala!”

This year’s gala fundraiser, which will be held in person and virtually, is certainly different from the galas the Playhouse has held in the past. On Saturday, Oct. 3, the Playhouse will mark its milestone season by having performers from the past 20 years make special virtual guest appearances including Graham Nash, Stephen Schwartz, Todd Rundgren and more, as well as a live performance on the indoor stage at the Playhouse with Bruce Hornsby.

“We are really excited to have someone perform on our stage again!” Stockel said.

The annual fall gala has traditionally kicked off the Playhouse’s new season, but this year Stockel said the fundraiser is more important than ever as it celebrates not only its 20th anniversary milestone, but it’s also the theater’s biggest fundraiser. After having to cancel its annual summer gala, Stockel said she’s not sure if the Playhouse will be able to hold its Valentine’s Day event in February.

“As a nonprofit, this is so necessary to keep us going during this incredibly difficult and unprecedented time,” she said.

When asked if the Playhouse has a specific fundraising goal Stockel joked that she would like to raise “as much as humanly possible” before noting how strange this year is for the nonprofit theater financially. “Honestly, this is an odd year for us. We don’t know if this is our only fundraiser of the year and we don’t know when the state is going to allow shows and at what capacity yet, so we are basically hoping that people who come, celebrate with us and bid on the auction items to support us,” Stockel said. “And, people who don’t come, will hopefully donate and bid on the auction items.”

According to Stockel, the Playhouse lost $3 million in ticket sales when it had to cancel more than 130 shows due to the pandemic, but has managed to maintain its staff by holding outdoor shows and screening films while working with “the new normal.”

As part of its fundraiser, the Playhouse will be holding a virtual auction that includes plenty of items including a vintage American Girl doll, items signed by Willie Nelson, Charlie Daniels, Buddy Guy and others. Stockel said that patrons that make a donation of $200 or more will receive autographed posters.

For the gala itself, the Playhouse is offering a variety of ways to participate depending on its patrons comfort level. There will be a limited number of sponsor tickets inside the theater, as well as outdoor tented seating for gala ticket holders, both include an open bar and a sit down dinner with food from Bernard’s and Gallo and virtual streaming tickets for those who want to stay at home.

“We want everyone to be able to celebrate with us,” Stockel said. For the in-person event, the fundraiser will kick off at 6:30 p.m. with a red-carpet arrival hosted by comedian Christine O’Leary in the tent on the field next to the Playhouse. Gala and sponsor ticket holders can also get their grub to go and view the stream from home as well. Gala tickets are $175 while virtual tickets are available for $44.

“I think when the Playhouse opened its doors 20 years ago, no one ever thought that we would have gotten to the point where we would be presenting more than 200 shows annually,” Stockel said. “And in addition to that, doing 33 Arts in Education performances, giving away more than $90,000 in free tickets to Title 1 schools and people from low-income areas and have some of the most iconic performers from all genres like Willie Nelson, Smokey Robinson, Blondie, Stephen Sondheim, Jay Leno and so many more.”

When asked if Stockel has any standout moments from the Playhouse’s 20 years of performances, she said going through the Playhouse’s auction items brought back many memories and mentioned having Natalie Cole at the 10th anniversary gala was a special experience.

“Another memorable one was Willie Nelson — he was amazing, fun and super kind. And then, of course was last year’s gala with Kristen Chenowith. Stephen Schwartz, who wrote “Wicked” and lives here in Ridgefield, got on stage with her and they sang songs together from the Broadway show, which was amazing and not something they normally do together. I love those special moments that just sort of happen,” she said.

As a nonprofit, the Playhouse works to give back to the community through its free ticket offers to Title 1 schools, its Arts and Education series and acting as a venue for different fundraisers.

Even though the Playhouse isn’t quite sure when it’ll be able to hold shows at half capacity, much less full capacity again, Stockel remains optimistic about how the venue will move forward.

“We have wonderful and loyal sponsors, members and donors. This gala is as much for them as it is for us,” Stockel said. “And even though we’re doing it a little differently during these unprecedented times, we’re here and we’re not going anywhere. We have been through a lot over the past 20 years, and we’ve stood the test of time. I know we will be okay and come out on the other end, it’ll just be a bit of a journey to get there.”

She also promised that plans are underway for future shows. “The arts are so important in our lives right now. Once we can resume and have a season, we will have a killer season, with everyone from Rosanne Cash and Kenny Wayne Shepherd to comedians like Jim Breuer and Jay Leno to people like Theresa Caputo and Masters of Illusion,” she said. “We can’t wait to be able to do it with a full audience again!”

For more information about the gala, visit or call 203-438-5795.