Last season felt like a whirlwind. In spring 2025, they hosted a Beatles Tribute, raising money to buy a sousaphone for the marching band. 

Their second Woodstock event sent admission donations straight to St. David’s Jubilee and, again, toward that sousaphone. Charlie Foxtrot Brewing Co. jumped on board as a partner and became the heart of the new food court, with part of their sales covering festival expenses. 

For 2026-27, they’re planning six concerts split between winter and spring, all at Pioneer Plaza. The winter series kicks off with Oktoberfest on the 25th. Expect a mix of entertainment, a new “Kids’ Korner” filled with lawn games, and a food court offering German eats, capped off with a concert.

On November 22nd, they’re honoring veterans, servicemen, and their families with a Wizard of Oz theme: “There’s no place like Home.” They invite musicians who are vets or want to pay tribute to someone who served at the Open Mic: share a name, branch of service, introduce yourself or someone special. ROTC and veterans can join the cornhole tournament, and vet organizations may set up booths to showcase their services or sell merchandise. Bands like Rising Tide and Old Glory, with veteran musicians, will close out the event.

December 6th brings the Holiday Showcase. Local musicians deliver holiday tunes to get everyone in the spirit. The food court and Kids’ Korner return, along with another concert. Artists are welcome to display and sell their original work at every event.

Sydney, the founder of The Artist Colony, shares her story: “I was self-employed forever, organized and managed well. When I moved to Englewood, I started making concrete garden sculptures. Tried two-day art shows for two seasons. Honestly, I would’ve saved money staying home. So, I thought, why not start a local art group? A colony for artists to show and sell their original art: low costs, no travel, easy setup. We’re now in our fifth season for the Outdoor Gallery, twice a month in Pioneer Plaza. And it got bigger than I ever thought. We’re a 501c3 now and rolling out six Family Festivals and Benefit Concerts. We’ve partnered with the Englewood YMCA and created ‘The Artist Palette,’ offering classes for adults and kids at the YMCA. Supporting the arts and performing arts is what we do. And have I actually sold my garden art? Not yet, but I will, once the Artist Colony is truly established.”

She’s especially thrilled with their YMCA partnership. “Liz is the director. I asked if there was a room available for art classes. She gave us space, and we talked about how to use it. Now our artists can work there up to five days a week, evenings and weekends included. They can use it as a studio, set up areas to sell their work when teaching, and during monthly family events at the Y, we host mini art markets, putting a spotlight on our artists and their classes.”

As the Colony grows, Sydney’s bringing veterans into the fold. “I want them on the team. I have musicians, a group of artists, and now veterans.” She’s also looking for benefactors and supporters to help cover the costs for the sculptures that decorate Dearborn Street, a unique project they brought to Englewood.

Sydney adds, “We’re expanding our concert series: Kids’ Korner, artists during the day, aiming for true family festivals. There aren’t a lot of family events around here, and we want to change that.”

Admission is food or cash donations for causes listed in promotions and at the gates. This season, they’re still raising funds for sousaphones. They need another $25,000 to replace the three pvc and brass instruments the marching band started with. St. David’s Jubilee and Lotus Shadows, a veteran organization, also receive part of these donations.

The Colony’s partnership with the YMCA is growing. Their new ‘Artist Palette’ studio offers art and craft classes during the day, evening, and weekends, beginner and advanced students, for adults and kids, open to YMCA members and non-members.

Follow them on Facebook for updates. If you want to participate, volunteer, donate cash or instruments, or just ask questions, contact Sydney at i2garden@yahoo.com or 773-983-6190.

Events lineup:

Outdoor Gallery—1st and 3rd Wednesdays, October through April at Pioneer Plaza (325 W Dearborn)

The Artist Palette Studio—Classes at the YMCA

Six Family Festivals & Benefit Concerts—October, November, December, February, March, April

If you want to help with these family festivals, the Colony offers IRS letters for donors, patrons, and benefactors.

Be sure to check out their new art classes now available at the YMCA.

For information www.OldEnglewoodVillage.com or their Facebook page for details.

The post From Woodstock to Oktoberfest: Englewood’s The Artist Colony Celebrates 5 Years of Music and Meaning appeared first on Englewood Review.

The season opens Sunday, February 1, with the 2nd Spring Art Show relocated to Pioneer Plaza, followed by a Beatles Tribute benefit concert. Food donations for St. David’s Jubilee Center and cash donations for the Music Instruments for Students program will be collected at the gates. Charlie Foxtrot Brewing will provide beer and wine service during the event.

Family-focused programming continues Sunday, March 1, with the Mad Hatter Family Festival. The event will feature young performers, children’s activities, photo opportunities and opportunities for crafters to participate. Guests are encouraged to dress in themed attire.

On Sunday, March 8, the Artist Colony will host its second Salute to Woodstock benefit concert, again supporting St. David’s Jubilee Center. Nonperishable food donations will be collected, and Charlie Foxtrot Brewing will serve beverages.

The season resumes Sunday, April 12, with the Trop Roc benefit concert. Proceeds will help offset copyright fees for Lemon Bay High School Drama Department musicals. Organizers are planning an additional Spring Art Show earlier in the day at Pioneer Plaza leading into the concert.

In the fall, the Artist Colony and Charlie Foxtrot Brewing will collaborate on an Oktoberfest celebration on Sunday, October 18. The partnership continues Sunday, November 22, with the Wizard of Oz Family Festival, themed “There’s no place like Home.” The event will welcome families of servicemembers and veterans. Activities, entertainment and costumes will be encouraged, with Charlie Foxtrot Brewing providing service. A veterans organization will be selected to receive the event’s donations.

In addition to special events, the Outdoor Pioneer Plaza Galleries will be open from 10 a.m. to 3 p.m. on the first and third Wednesdays in February, March and April.

Artists, performers and community members interested in participating may contact Sydney at i2garden@yahoo.com.

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