Live music in Fruitland Park, FL

Settle in for jazz and blues from The Mudds at Barons Creek Vineyards Tasting Room in The Villages as part of First Fridays. Situated in the heart of Spanish Springs Town Square, this wine lounge offers guided tastings, bites, and a place to gather. Guests can enjoy live music while sampling wines in a relaxed, social setting.

Wind down after work in Baldwin Park as the village center transforms into a lively open air market experience. Explore a curated mix of local vendors for unique finds, enjoy food and drinks from neighborhood favorites, and take in live entertainment while relaxing with friends and family. Admission is free and everyone is welcome. The event is kid friendly and leashed pets are invited. Whether planning a date night or a casual outing with the whole crew, expect shopping, dining, music, and an easygoing community vibe in a beautiful setting. Vendor applications are available.

The Highway 41 Band brings an energetic mix of country, Southern rock, and danceable favorites to Brownwood Paddock Square in The Villages. Bring lawn chairs, dancing shoes, and friends for a fun Florida evening filled with live music and good company.

Funtastic Depot transforms into a neon themed celebration for families, teens, and friends, featuring live DJs, arcade games, climbing walls, and a grand finale show. Guests can jump, dance, and compete while neon lights set the mood across the park, and unlimited attractions are included. More than a trampoline park, it offers a Friday night tradition in the making.

Frank’s Rack & Grill in historic downtown Leesburg hosts a Red Shirt Friday karaoke night presented by Son-Rae Entertainment. The evening celebrates the Remember Everyone Deployed tradition and offers a warm salute to U.S. military service members and veterans. DJ Jeff-fa-fa, a singer with the local cover band Rock Hard, leads open karaoke and takes song requests, with performers heard through a Bose L1 Pro 8 system for clear, room-filling sound. The venue is indoor and smoke free, with smoking and vaping permitted outside under cover. Guests can enjoy a full bar, a billiards hall with APA leagues, and a selection of food and snacks. Bikers are welcome, and Frank’s is back open under new owners and new management, previously known as Frank’s Place.

AEG Presents brings Too Much, Not Enough to The Plaza Live, featuring Daði Freyr with Bríet. This is an all ages event.

Recommended for ages 17 and up, this cult-favorite stage show fuses audacious comedy, horror movie nostalgia, and high-octane rock into a wild night at the theater. Evil Dead The Musical reimagines the beloved franchise with demons, chainsaws, familiar musical moments, and gleefully over-the-top fun, arriving right in time for spooky season. Central Florida Vocal Arts and Opera del Sol work to build a kinder, more connected community by expanding access to the performing arts through quality productions and transformative education, changing lives, one voice at a time.

Food, drinks, and music await on the patio.

Five-time Grammy winner Lalah Hathaway appears in an intimate lounge setting for four shows over two nights. As the daughter of Donny Hathaway, her musical roots run deep, and her collaborations span Pharrell Williams, Kendrick Lamar, and Dr. Dre. She has also shared stages with Prince, Stevie Wonder, and Herbie Hancock. Hathaway is tied with Beyoncé for the most Grammy wins in Best Traditional R&B Performance, with three each. Expect an evening of rich vocals and timeless songs, with sounds grounded in R&B, jazz, and soulful expression.

A soundtrack of rock and roll sets the tone for an upbeat evening with a groovy vibe. Enjoy ice cream made by hand, including options with alcohol. Expect plenty of fun and the chance to win prizes. There is no charge to play.

Spanish Springs in The Villages features an afternoon of acoustic classics and familiar songs.

A ballroom dance party offers music, dancing, and a friendly atmosphere for participants of every level. Admission is $20 per person. For more information or to verify the schedule, call or text (352) 533-7400. Schedule is subject to change.

A weekly open karaoke night brings singers and music fans together at Frank's Rack & Grill in Leesburg, presented by Son-Rae Entertainment and hosted by DJ Jeff-fa-fa, vocalist with the local cover band Rock Hard. Participants can take the mic, request favorite songs, and perform in a smoke-free indoor setting, with vocals carried by a Bose L1 Pro 8 sound system. The venue has reopened under new ownership and management with a new bar team, and it was formerly known as Frank's Place. On-site amenities include a full bar, a billiards hall with APA leagues, and a selection of food and snacks. Smoking and vaping are permitted outside under cover. Bikers are welcome, and Linda is behind the bar.

Orlando’s #1 ladies night turns downtown into a late-night block party across Room 22 and Sidebar. Built for keeping the evening going after Wine Down Wednesdays, R&B Wine Down, and other after-work plans, it mixes that unwind-to-nightlife transition with a lively crowd and steady momentum. Two rooms offer different atmospheres while top DJs drive the soundtrack from start to finish. Capacity is frequently reached, so early arrival is recommended.

Bike Night takes over downtown Leesburg at Great Chicago Fire Brewery & Tap Room, presented with support from Gator Harley-Davidson. Look for live music, cold beer, a full bar, and gift cards. The kitchen features an authentic Chicago-style menu that now includes Chicago thin crust pizzas. An on-site brewery offers 10 house beers, complemented by a selection of domestic and imported options and a full range of spirits. A happy hour provides one dollar off all beer, wine, and liquor.

An open jam night welcomes local musicians and music fans for spontaneous collaborations and lively performances. Bring an instrument if you want to play, invite friends, or simply enjoy the vibe. A full backline will be available. The cover charge is $10. Guests may bring their own beverages and snacks.

Vibe Tribe offers a weekly, family-friendly gathering centered on connection, self expression, and music. It begins with a facilitated support circle where people can check in, listen, and be heard in a respectful, judgment-free setting. Speaking is optional, and there is no fixing or preaching, only space for authenticity. Afterward, the focus turns to a collaborative music session. Instruments come out, ideas mingle, and whatever you are carrying can be expressed through sound. No prior experience is required, and all instruments and skill levels are welcome. Participants can talk, listen, make music, or simply be present, with an inclusive, community-centered spirit that moves from conversation to creation.

A lively spot with friendly faces, live music, and plenty of good food and drinks. A cheerful place to spend a fun evening.

Jeru the Damaja brings authentic Golden Era hip-hop to Iron Cow in Orlando with a performance that honors boom bap, 90s classics, and the culture. The Brooklyn MC is known for the DJ Premier produced album The Sun Rises in the East and standout tracks like Come Clean, D. Original, and You Can’t Stop the Prophet. Music from DJ Heron and The Throwback Champ sets the tone for an intimate night centered on beats, bars, and lyrical skill. Presented by Addictive Affairs in collaboration with Thirstin Howl The 3rd and Big Earl Promotions.