Live music in Winter Garden, FL

Day’s Trips presents an outing to Winter Park Playhouse for Rat Pack Lounge, a musical comedy that sends Frank, Dean, and Sammy back for one night to make amends and keep a long-standing promise to the lounge’s owner. Expect signature hits like My Way, Come Fly with Me, Ain’t That a Kick in the Head, Everybody Loves Somebody Sometime, and more. The itinerary includes a bus departure from PSL with an additional pickup in Vero, travel to the theater for the performance, and time afterward to enjoy dinner in Winter Park at one of several restaurants before returning home. The price is $105 per person. Payment is due at booking. Tickets are nonrefundable but may be transferred to another person. Day’s Trips, LLC is a Florida Seller of Travel, Ref. No. ST44375.

Enjoy a Taylor Swift themed music bingo brunch at Teak Neighborhood Grill. Songs from across her eras set the soundtrack as participants sing along, mark their cards with familiar hits, and aim for a winning bingo. A fun outing for Swifties who love turning favorite tracks into game time excitement.

Music Under the Oaks returns to VanderLey Park with SWITCH!, presented by the Town of Oakland and Advent Health. The band will play classic songs from the 60s and 70s. Attendees may bring blankets and lawn chairs, and dinner and drinks will be available before the performance.

Wine O’Clock Bistro hosts Southern Night, featuring live country music by Mark Houghton and a special Southern menu. Enjoy a fun evening with family and friends as great tunes pair with Southern-inspired dishes.

Experience the beauty of Florida’s crystal clear springs at Wekiva Island with a mix of outdoor fun and live music. Paddle a canoe or try stand-up paddle boarding, join a volleyball match, take a swim, and connect with new friends. Adults can relax with a beverage while the Sandy Back Porch band plays.

After a hint in a story last week, the news is now official. Black Country, New Road will be at The Beacham.

Scott Bradlee’s Postmodern Jukebox brings a new production to Steinmetz Hall, featuring a versatile ensemble of singers, dancers, and musicians. With a vintage twist, they reinterpret favorites ranging from 70s rock and 80s Britpop to today’s hits, beloved movie themes, and even video game soundtracks. Brimming with lively, dance-ready numbers and showstopping moments, this performance suits both a night on the town and a fun outing for families.

Central Florida’s long-running International Food & Drink Festival marks its 11th anniversary with a first-ever stop in Clermont at Waterfront Park. This outdoor celebration spotlights global flavors and gourmet dishes from area restaurants and food vendors, along with wines, beers, cocktails, and piña coladas. Live music and entertainment run throughout the event, a food eating contest adds a competitive edge, and prizes and giveaways keep the energy high. The experience is family friendly, and both admission and parking are free. Vendor participation is very limited, with two spots remaining on a first come, first served basis. For details, text 213-218-5017 or email vfapply@gmail.com.

A vibrant outdoor celebration of Haitian Fritay, music, and culture fills Wall Street Plaza in Downtown Orlando, turning the plaza into a lively gathering for the Haitian and Caribbean community, families, friends, and anyone eager to explore Haiti’s flavors and sounds. Food vendors serve beloved specialties such as griot, fried plantains, pikliz, tassot, patties, accra, fried chicken, and other Haitian favorites, offering a rich taste of the island’s culinary traditions. The music sets the tone with Kompa, Zouk, Gouyad, Raboday, Afrobeats, and other Caribbean selections, with live DJs and special guests keeping energy high. Festival highlights include Haitian cuisine at the forefront, drinks available across the plaza, local vendors and businesses, and plenty of photo-ready moments, all in an all-ages, open-air setting in the heart of Downtown Orlando.

A candlelit tribute to the film music of Hans Zimmer comes to The Abbey in Orlando, performed by the Listeso String Quartet. The program includes selections from Inception, The Lion King, Madagascar, Dunkirk, The Pacific, The Dark Knight, Wonder Woman, Gladiator, Interstellar, Dune, Sherlock Holmes, and Pirates of the Caribbean. The concert lasts about 60 minutes, doors open 45 minutes beforehand, and late entry is not allowed. Seating is assigned on a first come, first served basis within each zone. Attendees must be at least 8 years old, and anyone under 16 must be accompanied by an adult. The venue is ADA compliant. This is a tribute performance and is not affiliated with or endorsed by the composer, their estate, or official representatives.

Weezer, The Shins, and Silversun Pickups perform at the Kia Center in Orlando. The lineup brings all three bands together on one stage.

Michael Jackson takes center stage at Hurricane Grill & Wings Longwood with a music bingo night in Longwood, FL. Enjoy a playlist of classic hits, sing along, and mark off your card as each song plays. The aim is to complete a bingo before anyone else for a lively evening built around the King of Pop’s greatest tracks.

Mixed Hits Music Bingo arrives at Gators Dockside Apopka with a soundtrack that spans throwbacks and today’s favorites. Enjoy a game centered on songs you know and love, with prizes available.

Puzzles Entertainment brings a weekly Jukebox Bingo experience to The Friar Tuck, blending a Name That Tune style challenge with classic bingo. Participation is free, and the vibe centers on music, singing, dancing, and friendly competition. The game runs through four rounds that produce four winners, with prizes such as complimentary drinks and gift certificates.

Puzzles Entertainment hosts a weekly Jukebox Bingo night at The Friar Tuck, blending a name that tune style challenge with classic bingo. The event features lively music, singing, and dancing, with four rounds and four winners. Prizes include free drinks and gift certificates.

Jukebox Bingo brings a music-fueled twist to classic bingo at 4Corners Tavern in Davenport, FL. Instead of numbers, participants listen for songs, mark them on a digital card, and race to be the first to call bingo. The action unfolds across four rounds with four distinct playlists, creating four winners and four prizes. The soundtrack spans decades and genres, so each card feels fresh and unpredictable. Bingo cards are digital, which means a charged phone or tablet is needed. Enjoy food and drinks while you play. Presented by Puzzles Entertainment.

Freya Skye brings a distinctive mix of genres to House of Blues Orlando, delivering a compelling live set crafted to engage both longtime followers and those discovering her for the first time. The performance guides audiences through a wide-ranging journey across her sound, with genre-blending moments that showcase her artistry.

An acoustic open mic hosted by Pete Prieto invites performers to sign up and share a few songs. Bring an acoustic guitar or hand percussion to participate, since amplifiers and drum sets are not part of this event. All styles are welcome, including original music and covers. Those who prefer to listen can enjoy a relaxed, low-volume evening of local music, with food and drink available from The Friar Tuck.

A concert at the Kia Center in Orlando brings the Red Clay Strays, the Revivalists, and Haley Reinhart together on one stage. Attendees can experience live sets from all three acts in a single show.

Country Music Bingo at Froggers Grill & Bar Altamonte in Altamonte Springs features country classics and today’s biggest hits, with sing along moments as players mark their cards to the music and race to call bingo. It is a boot scootin night filled with music, laughs, and bingo.

A late-night block party takes over Room 22 and Sidebar in downtown Orlando, offering a grown, elevated ladies night that kicks in once Wine Down Wednesdays, R&B Wine Down, and other after-work events wind down. Top DJs keep the music moving across two rooms with distinct atmospheres, so the crowd can choose the vibe that fits the moment. The experience balances the easygoing feel of early evening wine-downs with full-on nightlife, creating a dependable weekly tradition where the energy runs strong from start to finish. It is a popular stop when early plans wrap up and the night is still calling, and it often reaches capacity.

Downtown Leesburg’s Cool Cars Under the Stars brings car and truck enthusiasts together at Great Chicago Fire Brewery for a showcase of standout vehicles, live entertainment, and laid-back hospitality. Explore rows of classics, customs, modern muscle, trucks, and imports while enjoying Chicago style food and pizza, craft brews, domestic favorites, a full bar, sweet tea, and soda. The atmosphere is family friendly with plenty of indoor and outdoor seating, and beverages are welcome as you stroll among the displays. There is no entry fee, and participants can compete for awards that often include a Best of Show plaque along with recognitions for classic cars, trucks, custom builds, modern muscle, imports, and the occasional playful wildcard. Ample parking is available for those bringing their rides.

Arch Enemy and The Black Dahlia Murder bring the Wrath Across North America Tour to The Beacham, promising an intense show from beginning to end.

Old Town’s Karaoke Nights turns the Main Stage next to Southern Breeze into a welcoming spotlight for singers of every level. Whether pitch perfect or a little off-key, performers step to center stage, have fun, and enjoy a brief moment of fame under the lights.

At Paddy’s Pub Altamonte Springs, music bingo takes center stage with a playlist that jumps from nostalgic throwbacks to current favorites. Each new track keeps the energy up and the cards filling, all leading to that satisfying moment of calling bingo. Expect a sing-along atmosphere with music lovers in mind and a playful nod to trivia-style fun.

Leslie Mendelson, a Brooklyn singer and songwriter, channels a Laurel Canyon spirit with a blend of folk rock and pop Americana. The Grammy-nominated artist counts Jackson Browne among her admirers, and she has been praised for timeless vocals, melodies, and craft. Coverage from music publications highlights her ability to connect across generations and scenes, often pointing to 1970s influences in the tradition of artists like Carole King and Carly Simon. Her songs focus on graceful melodies and openhearted storytelling.

Step into a neon-charged Friday night at Funtastic Depot, where families, teens, and friends can dive into a high-energy mix of music and play. The venue glows with vibrant lighting as live DJs set the soundtrack, turning the park into a bright, buzzing party. Spend the evening jumping, dancing, and competing, then try arcade games and take on the climbing walls. Access to attractions is included, so the fun keeps going without limits. A showstopping finale wraps up the celebration with extra flair. More than a typical trampoline park, this Orlando experience turns Friday into a tradition.

Set on a National Historic Landmark campus, this opening reception for a new contemporary art exhibition features music, a food truck, and a cash bar, with a moment to honor the featured artist. The exhibition showcases the art of Soude Dadras.

Gators Dockside Eustis hosts an upbeat night of 80s hits music bingo. Expect a nostalgia-packed soundtrack with classic tracks that capture the decade’s spirit and a bright, neon-inspired vibe. It is a lively throwback evening in Eustis, FL for fans of 80s music and a friendly game of bingo.

Soccer Mommy and Snail Mail share the spotlight in Orlando, bringing together two artists known for candid, incisive songwriting. Sophie Allison’s project grew from intimate bedroom recordings into music that preserves its raw honesty while embracing wider production possibilities. Her album Evergreen was shaped by a profound personal loss, balancing frank reflection with moments of wit, including a playful nod to a purple-haired spouse from Stardew Valley, and it stays close to the spirit of her demos. Lindsey Jordan arrives with Ricochet, her first Snail Mail release in five years, created with a careful focus on melody after a period that included vocal surgery and recovery. The record marries clear-eyed introspection with expansive hooks, luminous guitars, and subtle string textures, exploring themes of mortality, connection, and the pull of distance. Together, they set the stage for an evening of heartfelt lyrics, richly layered sounds, and indie rock that resonates long after the last note.

Scott Fish takes the stage for a live performance at HFV Speakeasy.

Denzel Curry delivers high-voltage hip-hop powered by precise wordplay and intensity that ignites the crowd. With a fluid flow that blends styles, he turns the stage into a charged experience for rap fans.

Polyphia delivers a boundary blurring sound with virtuosic guitar work and razor sharp ensemble playing, putting the spotlight on pure musicianship. Expect labyrinthine riffs, bursts of intensity, and a show that stretches the possibilities of modern instrumental and progressive rock. Look for a tightly executed, guitar driven set packed with energy from start to finish.

At Blue Bamboo Center For The Arts, Walter Parks & The Unlawful Assembly present a live concert that celebrates and reframes historic spirituals and hymns that inspire, empower, and bring people together. The group is led by guitarist and vocalist Walter Parks, a longtime sideman to Woodstock icon Richie Havens. The lineup appears as either a six piece band or a trio, with featured artists including drummer and producer Steven Williams, vocalist Ada Dyer, who is currently touring worldwide with Bruce Springsteen, and trombonist Andrae Murchison. The program weaves together roots traditions from different backgrounds, interlacing spirituals, gospel, blues, and prison work songs with swamp hollers, shaped note hymns, and Appalachian reels tied to white homesteader heritage. The performance aims to both entertain and inform by revealing the shared musical threads that run through American history.

Frank’s Rack & Grill in downtown Leesburg hosts a smoke-free, open karaoke night presented by Son-Rae Entertainment and led by DJ Jeff-fa-fa. Singers and music lovers can take the mic and request favorite tracks, with clear, room-filling sound from a Bose L1 Pro 8 system that helps spotlight local talent. The venue has recently reopened under new ownership and management and was previously known as Frank’s Place. Guests can enjoy a full bar, a billiards hall with APA leagues, and a selection of food and snacks. The establishment is non-smoking and non-vaping inside, with covered outdoor areas available for those who need them, and bikers are welcome. The evening embraces the Red Shirt Friday theme, standing for Remember Everyone Deployed, and expresses appreciation for United States service members and veterans.

A candlelit tribute celebrates the iconic catalogs of Queen and ABBA at Azalea Lodge in Mead Botanical Garden, bringing an intimate, multi-sensory live music experience to Orlando. A string quartet performs favorites like Dancing Queen, SOS, Money, Money, Money, Bohemian Rhapsody, I Want to Break Free, Waterloo, Super Trouper, Mamma Mia, Don't Stop Me Now, We Will Rock You, and We Are the Champions. The program lasts 60 minutes. Doors open 45 minutes before the music begins, and late entry is not permitted. Seating is assigned within each zone on a first come, first served basis. The venue meets ADA accessibility standards. Recommended for ages 8 and up, with an adult required for attendees under 16. This is a tribute performance and is not affiliated with, endorsed by, or sponsored by the original artists, their estates, or official representatives. On select dates, ensembles such as the Listeso String Quartet and the Fernwood String Quartet take the stage.