Make your life happening by enrolling to entertainment events in [CITY]. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in [CITY]. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in [CITY].
## Entertainment Events in Maitland - **Event Name**: Smile City Comedy Show & Good Times Bar & Grill - **Description**: See the best headliners from Nateland Live, K*ll Tony, Bet, Florida's Funniest at Smile City comedy show a night of hilarious stand up!About this EventSmile City Comedy - **Date**: Thu May 28 2026 at 07:00 pm β Thu May 28 2026 at 09:30 pm (-04:00) - **Event URL**: https://allevents.in/maitland/smile-city-comedy-show-and-good-times-bar-and-grill/100001988626429182 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvMzc1ODE5MjYzM2RjNDVmMjIzN2E5MTdkODBjNjY2ZWMyOWI1OTBiMjAxZWUxN2MyNGVjMWJkN2VjY2UyZWQzMi1yaW1nLXc1ODktaDY2OS1kYzAxMDEwMS1nbWlyLmpwZz92PTE3Nzc3NDU4NzM.avif - **Price**: USD 5 to 16 - **Categories**: comedy, Entertainment - **Event Name**: Hedwig and the Angry Inch - Film with John Cameron Mitchell - **Description**: π Venue: Enzian Theater π Address: 1300 South Orlando Avenue, Maitland, FL 32751 π City: Maitland π Location: 28.62, -81.36β¨ Discover the extraordinary at Hedwig and the Angry Inch - Film with John Cameron Mitchell, where magic meets rea - **Date**: Mon Jun 15 2026 (-05:00) - **Event URL**: https://allevents.in/maitland/hedwig-and-the-angry-inch-film-with-john-cameron-mitchell/3200030064685044 - **Venue**: Enzian Theater - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=Hedwig+and+the+Angry+Inch+-+Film+with+John+Cameron+Mitchell&date=Mon+Jun+15+2026&bg=5 - **Categories**: entertainment, art, theatre - **Event Name**: Earlybirds Club Dance Party - **Description**: What better way to care for your mental health than a dance party with all of the fun, none of the judgement and home by 10:30 "for ladies who have sh*t to do in the morning". Tickets go on sale for this party April 2 at 10AM! Get yours at www.early-bir - **Interested Audience**: - Count: 2 - **Date**: Fri Jun 05 2026 at 06:00 pm β Fri Jun 05 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/earlybirds-club-dance-party/200029960548839 - **Venue**: The Beacham 46 N Orlando Ave, Orlando - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy8xMGE0MWQwZWVhNzViNDllNGEyOTdlMDRiZDg1YjZjODZkZDBmOGRhYTRhYTI0MjZjZGQ2OTIxZjlkOGJlMWNjLXJpbWctdzEyMDAtaDE1MDAtZGMwNjAxMDItZ21pcj92PTE3NzkxNjUzOTU.avif - **Categories**: parties, entertainment, health-wellness, mental-health - **Event Name**: Ozzy Osbourne & Randy Rhoads Tribute - The Railz 07/19/2026 - **Description**: Get ready to rock out with The Railz paying tribute to the Prince of Darkness himself in a night full of epic tunes!About this EventGet ready for a SUNDAY FUNDAY of high-energy rock, crowd favorites, and n - **Date**: Sun Jul 19 2026 at 04:00 pm β Sun Jul 19 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/ozzy-osbourne-and-randy-rhoads-tribute-the-railz-07-19-2026/100001988942794439 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy8xYTI2NjUyNzc4MmUwMWFlZDEyYTlhNzg0OTcxZGJjZGNjMzIxOTZlNzY0ZjYzZWZkZWIzODExZmY2M2JjNGYyLXJpbWctdzEyMDAtaDYwMC1kYzE3Mjg3Ni1nbWlyLmpwZz92PTE3NzgxMzUxNjg.avif - **Price**: USD 25 to 36 - **Categories**: entertainment, performances, music - **Event Name**: Music in the Gallery (collab. with Howey Music + CFCF) - **Description**: Free event: Live music inspired by the art inside the gallery!About this EventIn this rare event in Maitland, the Art & History Museums of Maitland (A&H) invites the Central Florida Composerβs Forum (CFCF) a - **Date**: Wed May 27 2026 at 05:30 pm β Wed May 27 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/music-in-the-gallery-collab-with-howey-music-cfcf/100001968846204999 - **Venue**: Art & History Museums of Maitland - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy82NWQ0YzJkZGQ2N2RhYjc1OTVmYTk0M2U0NmY3OTllZjUxYTA4YmRjMTBmYmIwZjQ4MmEzZjM0MWQ2MGY3MDI2LXJpbWctdzcwNS1oNTkxLWRjZGNkOWQ1LWdtaXIuanBnP3Y9MTc2MzM4MjI3OA.avif - **Price**: Free - **Categories**: music, art, entertainment, business, exhibitions, live-music, performances, nonprofit - **Event Name**: MJ Fitness Party - **Description**: RSVP ASAP: www.mjfitnessparty.com Youβre Invited to the MJ Fitness Party πΆπΊ Join The Orlando Moonwalkers for a high-energy, feel-good experience inspired by the music and movement of the King of Pop π Date: Saturday, May 30th, 2026 β° Time: 1:00β4:00 PM - **Interested Audience**: - Count: 15 - **Date**: Sat May 30 2026 at 01:00 pm β Sat May 30 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/mj-fitness-party/200030029481600 - **Venue**: Genesis Health Clubs - Orlando Sportsplex - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9kNzlhZGIyNWIxMjA4YmRjOTNmMDkwZGYzZmYxZmVhYmVmZDFlMGYxNTI4YzVhN2MzNGFkYmQ5M2Q4NGMzZjZhLXJpbWctdzEyMDAtaDYyOS1kY2ZlZmVmZS1nbWlyP3Y9MTc3ODYwNTk5OQ.avif - **Categories**: parties, entertainment, business, workshops, health-wellness - **Event Name**: BEATLES TRIBUTE - TOPPERMOST returns to Good Times Bar & Grill - **Description**: Get ready to rock out with #1 Beatles Tribute - Toppermost bringing Beatles hits and vibes like never before!About this EventBEATLES TRIBUTE - TOPPERMOST returns to Good Times Bar & Grill! - **Date**: Sun Jun 21 2026 at 04:00 pm β Sun Jun 21 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/beatles-tribute-toppermost-returns-to-good-times-bar-and-grill/100001985915573941 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy82YjkwOTI3YmIwYjA0NjZkMDdjNGY0OGE0OGIyZWViYzcxNzdjMzEwNWZiM2Q3NTE5ZThiM2Q3YThhMjIwM2U2LXJpbWctdzEwODAtaDEwODAtZGNmZGQxMDEtZ21pci5qcGc_dj0xNzc0NjI2Mzcy.avif - **Price**: USD 25 to 42 - **Event Name**: 50's, 60's, 70's & 80's Music Bingo @ Good Times Bar & Grill - **Description**: πΆβ¨ Take a trip through the decades at Good Times Bar & Grill with 50βs, 60βs, 70βs & 80βs Music Bingo! Classic hits, great vibes, and a night of nonstop fun! #MusicBingo #ThrowbackHits #GoodTimesBarAndGrill #GameNight #GoodVibes #DecadesNight - **Interested Audience**: - Count: 51 - **Date**: Wed May 27 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/50s-60s-70s-and-80s-music-bingo-good-times-bar-and-grill/200030018131349 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9lMDQ0NDRlZjA4MGE4OWRlNmRhZTA1ZDM0NmM4MDI5OTFiZDFkNmFiMWJhOWY2OGFlNDMxNWZiYjg5YjUxZDIyLXJpbWctdzEwODAtaDEzNTAtZGMwMDAwMDEtZ21pcj92PTE3Nzg0Mzg1ODg.avif - **Event Name**: OBC Concert Season Kick-off / Guest Night - **Description**: Do you love to sing? Come to our concert season kickoff event! It's a great time to join the chorus as we prepare for our concert on September 26th. We welcome new members any time! We also welcome guests who just want to check things out and learn about - **Interested Audience**: - Count: 55 - **Date**: Tue May 26 2026 at 07:00 pm β Tue May 26 2026 at 09:30 pm (-04:00) - **Event URL**: https://allevents.in/maitland/obc-concert-season-kick-off-guest-night/200030049917801 - **Venue**: 331 Lake Ave, Maitland, FL, United States, Florida 32751 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy8xOWNjNjE2OTgyZjFlNWVjMzI2MzNhMWVjMzJlOWJlMzVkOTkyOTQzNzY2ODY4ZjFmZGQxODgzNjQ1NTNiODNlLXJpbWctdzEyMDAtaDgwMC1kYzA1MDUwNS1nbWlyP3Y9MTc3ODY4MjYwMA.avif - **Categories**: music, entertainment, concerts, live-music ## Trending Events in Maitland - **Event Name**: Central FL Juneteenth Celebration β Talent & Performer Casting Call 2026 - **Description**: Perform at Central FLβs biggest Juneteenth! Bands, dancers & creatives apply now for stage spots + gala opportunities.About this EventCALLING ALL TALENT β THIS IS YOUR STAGEThe - **Venue**: Maitland - **Banner**: https://cdn-az.allevents.in/events4/banners/68fa04a7e38c4d8c1c744ba9f63d554ee1271789fdca6b464a3f741b5118a1d7-rimg-w1200-h625-dc151619-gmir.jpg?v=1774845380 - **Event Name**: Meet Tea on the Mat at Mercedes-Benz - **Description**: Wellness workout by Olympic medalist Teahna Daniels + vendors at Mercedes-Benz Orlando with guest nutritionist on healthy eating habits!About this EventMeet Tea on the Mat is a curated we - **Venue**: Mercedes-Benz of Orlando - **Banner**: https://cdn-az.allevents.in/events4/banners/c3422c099183af5d4462a6d25b6614968e257d80f0e0b0ca515f3e6e1ec970ce-rimg-w1200-h800-dcf2f4ef-gmir.jpg?v=1777382018 - **Event Name**: Smile City Comedy Show & Good Times Bar & Grill - **Description**: See the best headliners from Nateland Live, K*ll Tony, Bet, Florida's Funniest at Smile City comedy show a night of hilarious stand up!About this EventSmile City Comedy - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-az.allevents.in/events10/banners/3758192633dc45f2237a917d80c666ec29b590b201ee17c24ec1bd7ecce2ed32-rimg-w589-h669-dc010101-gmir.jpg?v=1777745873 - **Event Name**: Hedwig and the Angry Inch - Film with John Cameron Mitchell - **Description**: π Venue: Enzian Theater π Address: 1300 South Orlando Avenue, Maitland, FL 32751 π City: Maitland π Location: 28.62, -81.36β¨ Discover the extraordinary at Hedwig and the Angry Inch - Film with John Cameron Mitchell, where magic meets rea - **Venue**: Enzian Theater - **Event Name**: Ultimate Santana Tribute at Good Times Bar & Grill in Maitland, FL - **Description**: Enjoy live music, dinner, dancing and a tribute to Carlos Santana with Ultimate Santana Tribute Band! VIP Available! Doors 6pm. Show 7pm.About this Event10% OFF PRESALE NOW for - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-az.allevents.in/events5/banners/cac5db55eb2ca05166360eff2c661803c57ae69f77e4cd47821e718c2dbbf43b-rimg-w1200-h601-dc293243-gmir.jpg?v=1773185664 - **Event Name**: FREE Summer Family Art Workshops - Week 1: Friendship Sculptures - **Description**: Kids can stay creative all summer long at A&H's FREE Summer Family Art Workshops on our National Historic Landmark campus!About this EventAt the Art & History Museums of Maitland, kids can stay creative and artist - **Venue**: Art & History Museums of Maitland - **Banner**: https://cdn-az.allevents.in/events6/banners/ddca939f08053fe38e00150269bc22d6e8e94174ad10173e292203ee5fbd7c2a-rimg-w1200-h795-dc041519-gmir.jpg?v=1769227155 - **Event Name**: Corks & Forks - **Description**: Mark your calendar for another extraordinary evening under the stars β Corks and Forks returns to Lake Lilyβ¦ with unlimited food tastings, fine wines, craft beer, spirit samplings, specialty cocktails, live entertainment and more, hosted by the Venue On L - **Venue**: 641 Maitland Avenue S., Maitland, FL, United States, Florida 32751 - **Event Name**: FREE Summer Family Art Workshops - Week 3: Soft Sculpture Bugs - **Description**: Kids can stay creative all summer long at A&H's FREE Summer Family Art Workshops on our National Historic Landmark campus!About this EventAt the Art & History Museums Maitland, kids can stay creative and artistica - **Venue**: Art & History Museums of Maitland - **Banner**: https://cdn-az.allevents.in/events1/banners/08ee86b421c60dc27c90b1ddc27ae6b41b18e10041d5eee4cf94c67ac549bc08-rimg-w1200-h695-dc46ab48-gmir.jpg?v=1769227245 - **Event Name**: FREE Summer Family Art Workshops - Week 4: Printmaking Party! - **Description**: Kids can stay creative all summer long at A&H's FREE Summer Family Art Workshops on our National Historic Landmark campus!About this EventAt the Art & History Museums Maitland, kids can stay creative and artistica - **Venue**: Art & History Museums of Maitland - **Banner**: https://cdn-az.allevents.in/events3/banners/5196dbdb6964683e83149c77036b99127201b4cb699e8bc16305827a2ec10fb0-rimg-w1200-h833-dcdfecfd-gmir.jpg?v=1769353503 ## Browse Entertainment Events by Date - [Entertainment Events Today in Maitland](https://allevents.in/maitland/entertainment--today) - [Entertainment Events This Weekend in Maitland](https://allevents.in/maitland/entertainment--this-weekend) - [Entertainment Events in May in Maitland](https://allevents.in/maitland/entertainment--may) - [Entertainment Events in June in Maitland](https://allevents.in/maitland/entertainment--june) ## FAQs - **Q**: What are the top Entertainment events in Maitland? - **A:** Smile City Comedy Show & Good Times Bar & Grill (Thu May 28 2026 at 07:00 pm at Good Times Bar & Grill), Hedwig and the Angry Inch - Film with John Cameron Mitchell (Mon Jun 15 2026 at Enzian Theater), Earlybirds Club Dance Party (Fri Jun 05 2026 at 06:00 pm at The Beacham 46 N Orlando Ave, Orlando), Ozzy Osbourne & Randy Rhoads Tribute - The Railz 07/19/2026 (Sun Jul 19 2026 at 04:00 pm at Good Times Bar & Grill), Music in the Gallery (collab. with Howey Music + CFCF) (Wed May 27 2026 at 05:30 pm at Art & History Museums of Maitland). - **Q**: What are the top free Entertainment events in Maitland? - **A:** Music in the Gallery (collab. with Howey Music + CFCF) (Wed May 27 2026 at 05:30 pm at Art & History Museums of Maitland). - **Q**: What Entertainment events are happening in Maitland this weekend May 22β24, 2026? - **A:** Ultimate Santana Tribute at Good Times Bar & Grill in Maitland, FL (Sun, 24 May at 07:00 pm at Good Times Bar & Grill). - **Q**: What Entertainment events are happening in Maitland in May 2026? - **A:** Smile City Comedy Show & Good Times Bar & Grill (Thu May 28 2026 at 07:00 pm at Good Times Bar & Grill), Music in the Gallery (collab. with Howey Music + CFCF) (Wed May 27 2026 at 05:30 pm at Art & History Museums of Maitland), MJ Fitness Party (Sat May 30 2026 at 01:00 pm at Genesis Health Clubs - Orlando Sportsplex), 50's, 60's, 70's & 80's Music Bingo @ Good Times Bar & Grill (Wed May 27 2026 at 07:00 pm at Good Times Bar & Grill), OBC Concert Season Kick-off / Guest Night (Tue May 26 2026 at 07:00 pm at 331 Lake Ave, Maitland, FL, United States, Florida 32751). - **Q**: How can I find Entertainment events in Maitland? - **A:** You can discover upcoming Entertainment events in Maitland on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Entertainment events in Maitland? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for Entertainment events in Maitland? - **A:** Some popular venues hosting Entertainment events in Maitland include Good Times Bar & Grill, Enzian Theater, The Beacham 46 N Orlando Ave, Orlando. - **Q**: What is the price range for Entertainment events in Maitland? - **A:** Prices for Entertainment events in Maitland range from USD 5 to USD 58. Many events also offer free entry. - **Q**: Who are the top organizers for Entertainment events in Maitland? - **A:** Popular organizers hosting Entertainment events in Maitland include Rob smiles, Seat Geek, Kindred Counseling. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Entertainment events in Maitland? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Maitland. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in Altamonte Springs](https://allevents.in/altamonte-springs/entertainment) - [Entertainment events in Winter Park](https://allevents.in/winter-park-fl/entertainment) - [Entertainment events in Goldenrod](https://allevents.in/goldenrod/entertainment) - [Entertainment events in Longwood](https://allevents.in/longwood/entertainment) - [Entertainment events in Bertha](https://allevents.in/bertha-fl/entertainment) - [Entertainment events in Orlando](https://allevents.in/orlando/entertainment) - [Entertainment events in Azalea Park](https://allevents.in/azalea-park/entertainment) - [Entertainment events in Conway](https://allevents.in/conway-fl/entertainment)