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**: Free in Central Park: Monster House - **Description**: This film is a part of our Popcorn Flicks in the Park series in partnership with the City of Winter Park. These screenings occur in Central Park, Winter Park once a month and are FREE and open to the public! Presented with open captions. 20th Anniversa - **Interested Audience**: - Count: 40 - **Date**: Thu Oct 08 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/free-in-central-park-monster-house/200030429042548 - **Venue**: 1300 S Orlando Ave, Maitland, FL, United States, Florida 32751 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9mNjcxNDMzMGUzNWE5M2U3YTMwZjFjZWVlNDM1NTkzMWU4NTk1OWE3Yjg3ZmFkMjE4NjNkN2Q5YzMwNzRjMjc0LXJpbWctdzEyMDAtaDYzMy1kYzA4MDgwOC1nbWlyP3Y9MTc4NTgzNzUxOA.avif - **Categories**: entertainment, kids - **Event Name**: 14th Annual Best of The Best High School Showcase Orlando Edition - **Description**: 🚨 THE BEST OF THE BEST SHOWCASE SERIES IS BACK! 🚨 This year we're taking the action to TWO CITIES for one unforgettable weekend of basketball. 🏀 Saturday, September 5�📍 Orlando Edition – Southeastern Prep 🏀 Sunday, September 6�📍 Miami Edition – Overtow - **Interested Audience**: - Count: 3 - **Date**: Sat Sep 05 2026 at 10:00 am (-04:00) - **Event URL**: https://allevents.in/maitland/14th-annual-best-of-the-best-high-school-showcase-orlando-edition/200030356943958 - **Venue**: Southeastern Prep - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy8wN2MzODE3NWI3NTFlZTI1ZGY1MzA5MzQ3NTA1MTA3ZWIxZGE1M2E3YzVmOGM5ZmU3NDI1OWI2OWQ2M2VjZmNkLXJpbWctdzEyMDAtaDYyOC1kYzA4MDgwOC1nbWlyP3Y9MTc4NjU1MzI5Mw.avif - **Categories**: performances, entertainment, contests - **Event Name**: Next Stop Comedy at Good Times Bar & Grill! - Maitland, FL - **Description**: Next Stop! - A Comedy Show Near You! Join us at Good Times Bar & Grill for a brand new line-up of comedians each month!About this EventNext Stop Comedy brings top stand-up comedians to your favorite local venues! Each - **Date**: Fri Oct 02 2026 at 07:00 pm – Fri Oct 02 2026 at 08:30 pm (-04:00) - **Event URL**: https://allevents.in/maitland/next-stop-comedy-at-good-times-bar-and-grill-maitland-fl/100001994508385271 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9hMjk5ZjRlYWI1ZmZlNTFkY2FlOTgxOWY4Nzg1MGQ5YmQ2NmRiMDU5YmUzZmJlOGRkMDlkNDBlYTJjMGUwYjdlLXJpbWctdzEyMDAtaDgwMS1kYzA1MDQwOC1nbWlyLmpwZz92PTE3ODQ1MTc0NDM.avif - **Price**: USD 30 - **Categories**: fitness, comedy, Entertainment - **Event Name**: Dylan Williams In Concert - **Description**: Catch Dylan Williams live in concert for an unforgettable night of great music and good vibes!About this EventDylan Williams In ConcertExperience the smooth sounds of modern indep - **Date**: Sat Aug 29 2026 at 07:00 pm – Sat Aug 29 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/dylan-williams-in-concert/100001993580505959 - **Venue**: The Blue Goat - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy82ZjgxZDIzYjY4YmE3N2MzZDY0NjYwNTFiMDliMDdiMzcwMDEyMTJhMzE3YjMzYTg4ZTRkN2VlYjg5NWViMmE5LXJpbWctdzEyMDAtaDE2MDAtZGMxZTFkMTctZ21pci5qcGc_dj0xNzgzNzE4MTg3.avif - **Price**: USD 31 - **Categories**: music, entertainment, concerts, performances, live-music - **Event Name**: DEAD AND EXPERIENCED - A TRIBUTE TO THE GRATEFUL DEAD - MAITLAND, FL - **Description**: Six musicians. One night. No script. Come experience the next stop on the D&E journey as we bring the bus to Maitland, FLAbout this EventMaitland, are you Experienced? 🚌⚡🌹 - **Date**: Sun Sep 13 2026 at 04:00 pm – Sun Sep 13 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/dead-and-experienced-a-tribute-to-the-grateful-dead-maitland-fl/100001993178496538 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy9mYmVlMmQ1OGNlYTVmZjQzYzdkZThiM2FmYTVkZmFhNDNiZTYxZDg0ZTYzNWJhZjM0NWVmMDRiZTdhYzg0MGIyLXJpbWctdzEyMDAtaDYwMC1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODYwODM5NzA.avif - **Price**: USD 19 - **Categories**: fitness, Music, Entertainment, performances, Art - **Event Name**: Laughing Stock Comedy Showcase at Good Times Bar - **Description**: Laughing Stock Comedy is bringing an evening with local standup comedians to Maitland!About this EventLaughing Stock Comedy is coming back to Maitland at Good Times Bar & Grill.Come for the comedy, stay for the - **Date**: Thu Aug 20 2026 at 07:00 pm – Thu Aug 20 2026 at 08:30 pm (-04:00) - **Event URL**: https://allevents.in/maitland/laughing-stock-comedy-showcase-at-good-times-bar/100001995469919245 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9jNmRlNjJlMGQ1NDA1M2NkNDEyMzRmMWJjNWE3NjQ1ZTUzZjcyZDdhNGFkZWU2MmMzNjk5ZWQ0NGMyMTA4ZjY2LXJpbWctdzEwODAtaDEzNTAtZGMwMjEzMTUtZ21pci5qcGc_dj0xNzg1MzMxMzQ4.avif - **Price**: Free - **Categories**: fitness, comedy, Entertainment - **Event Name**: DEAD & EXPERIENCED LIVE - GOOD TIMES BAR & GRILL - MAITLAND, FL - **Description**: Dead & Experienced is rolling into Good Times Bar & Grill in Maitland, FL, on Sunday, September 20th! This show will feature D&E’s second unique lineup, reuniting Eric Ryan and Tom Marcellis alongside an incredible group of musicians drawn fr - **Interested Audience**: - Count: 124 - **Date**: Sun Sep 20 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/dead-and-experienced-live-good-times-bar-and-grill-maitland-fl/200030408852747 - **Venue**: Good Times Bar & Grill - Maitland FL - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9mNWU3ZDk3Y2I4M2Y4NTc2ZjFiNjJjMGI1NmM2NWUzMjJkMWJiMDZlYmVjMmYwYmMxMGMwY2VhYTNiOTE0MDY3LXJpbWctdzEyMDAtaDc3MS1kYzA4MDgwOC1nbWlyP3Y9MTc4NTY5NDMzNw.avif - **Categories**: music, entertainment - **Event Name**: Be Great Gala - **Description**: In celebration of the 10th Anniversary of the Be Great Gala, we invite you to an inspiring evening benefiting youth in our Seminole County Clubs. Enjoy dinner, entertainment, powerful stories, and live and silent auctions as we celebrate great futures in - **Interested Audience**: - Count: 17 - **Date**: Fri Sep 18 2026 at 06:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/be-great-gala/200030281388408 - **Venue**: 1217 Trinity Woods Ln, Maitland, FL 32751-3159, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy83MTgyNTdiY2U1N2UxOGZlMzVlMmM3ODBkMzA3MWU3NDNlMmY4YzI5YTBmZTI1NTkyNGVlZGZiYzA3OGMwM2NjLXJpbWctdzg0MC1oNDAwLWRjMDgwODA4LWdtaXI_dj0xNzg2MzgxNzQw.avif ## Trending Events in Maitland - **Event Name**: Free in Central Park: Monster House - **Description**: This film is a part of our Popcorn Flicks in the Park series in partnership with the City of Winter Park. These screenings occur in Central Park, Winter Park once a month and are FREE and open to the public! Presented with open captions. 20th Anniversa - **Venue**: 1300 S Orlando Ave, Maitland, FL, United States, Florida 32751 - **Banner**: https://cdn-az.allevents.in/events3/banners/f6714330e35a93e7a30f1ceee4355931e85959a7b87fad21863d7d9c3074c274-rimg-w1200-h633-dc080808-gmir?v=1785837518 - **Event Name**: Cooking con Omi: A Celebration of Puerto Rican Food, Culture & Community - **Description**: Join Writer's Block Bookstore in celebrating the release of Cooking con Omi: A Love Letter to Puerto Rican Home Cooking!About this EventMeet Author & TikTok Sensation, Omi Hopper!We're thril - **Venue**: Venue on Lake Lily / Maitland Civic Center - **Banner**: https://cdn-az.allevents.in/events5/banners/ab065fe4e05b06f046b7f9ebb20b985221723a8c6707e861fb24996aefcd0d57-rimg-w1200-h600-dceeeeee-gmir.jpg?v=1781649035 - **Event Name**: Gala Monte Carlo in Maitland, Fl - **Description**: The Venue on Lake Lily will bring the elegance and excitement of Monte Carlo to Maitland on Saturday, October 17, 2026, for its upcoming Gala Monte Carlo, an unforgettable evening designed to entertain, connect and make a meaningful difference. Guests w - **Venue**: 641 Maitland Avenue S., Maitland, FL, United States, Florida 32751 - **Banner**: https://cdn-az.allevents.in/events10/banners/c3fefceb788eb165076d9fa923e2449cb94a67c35b31c270e60a154eda96a9af-rimg-w1200-h620-dc080808-gmir?v=1786290717 - **Event Name**: FREE Earth Day Family Day at A&H + Printed Tote Bag Family Art Workshop - **Description**: Get ready to celebrate Earth Day with a family art workshop, craft stations, face painting, scavenger hunt and free admission to 3 museums!About this EventFamilies are invited to celebrate our "home sweet - **Venue**: Art & History Museums of Maitland - **Banner**: https://cdn-az.allevents.in/events3/banners/67a41b29a64e108dc5ba938dd3c07d9778156e757eab88f389c6b02921a5e466-rimg-w1200-h795-dc97a4aa-gmir.jpg?v=1782359093 - **Event Name**: 14th Annual Best of The Best High School Showcase Orlando Edition - **Description**: 🚨 THE BEST OF THE BEST SHOWCASE SERIES IS BACK! 🚨 This year we're taking the action to TWO CITIES for one unforgettable weekend of basketball. 🏀 Saturday, September 5�📍 Orlando Edition – Southeastern Prep 🏀 Sunday, September 6�📍 Miami Edition – Overtow - **Venue**: Southeastern Prep - **Banner**: https://cdn-az.allevents.in/events8/banners/07c38175b751ee25df5309347505107eb1da53a7c5f8c9fe74259b69d63ecfcd-rimg-w1200-h628-dc080808-gmir?v=1786553293 - **Event Name**: Fall Open House 2026 - **Description**: Join us for a cozy, FREE celebratory evening filled with local art, live music, and creative inspiration in our gardens.About this EventJoin us for a cozy, FR - **Venue**: Art & History Museums of Maitland - **Banner**: https://cdn-az.allevents.in/events5/banners/4f41d586e085a3075499b27a557fc7622a56c4adabf74c0f7e0f14c551a86155-rimg-w1175-h985-dcd7dddd-gmir.jpg?v=1782627076 - **Event Name**: A POKÉ CELEBRATION! indoor market - **Description**: Applications open for: Vendors Food trucks Itasha vehicles Mascot volunteers Cosplayers Content Creators INDOOR MARKET! Come celebrate 30yrs of Pokémon and our first anniversary!!!! - **Venue**: Venue on the Lake - Maitland Civic Center - **Event Name**: Next Stop Comedy at Good Times Bar & Grill! - Maitland, FL - **Description**: Next Stop! - A Comedy Show Near You! Join us at Good Times Bar & Grill for a brand new line-up of comedians each month!About this EventNext Stop Comedy brings top stand-up comedians to your favorite local venues! Each - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-az.allevents.in/events9/banners/a299f4eab5ffe51dcae9819f87850d9bd66db059be3fbe8dd09d40ea2c0e0b7e-rimg-w1200-h801-dc050408-gmir.jpg?v=1784517443 - **Event Name**: Sip + Social - A Wine Pop-up - **Description**: Come sip tasty wines and mingle at our fun pop-up social—good vibes and great sips await!About this EventCome join us for Sip + Social - A Wine Pop-up!Get ready to unwind and mingle in person at this laid-bac - **Venue**: The Parker at Maitland Station Apartments - **Banner**: https://cdn-az.allevents.in/events7/banners/1dc353c7106e9d64a860892e3aea188dc627b93ec51b1a5c9850ab56c817efb8-rimg-w940-h470-dce8d8c8-gmir.jpg?v=1786083847 ## 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 August in Maitland](https://allevents.in/maitland/entertainment--august) - [Entertainment Events in September in Maitland](https://allevents.in/maitland/entertainment--september) ## FAQs - **Q**: What are the top Entertainment events in Maitland? - **A:** Free in Central Park: Monster House (Thu Oct 08 2026 at 08:00 pm at 1300 S Orlando Ave, Maitland, FL, United States, Florida 32751), 14th Annual Best of The Best High School Showcase Orlando Edition (Sat Sep 05 2026 at 10:00 am at Southeastern Prep), Next Stop Comedy at Good Times Bar & Grill! - Maitland, FL (Fri Oct 02 2026 at 07:00 pm at Good Times Bar & Grill), Dylan Williams In Concert (Sat Aug 29 2026 at 07:00 pm at The Blue Goat), DEAD AND EXPERIENCED - A TRIBUTE TO THE GRATEFUL DEAD - MAITLAND, FL (Sun Sep 13 2026 at 04:00 pm at Good Times Bar & Grill). - **Q**: What are the top free Entertainment events in Maitland? - **A:** Laughing Stock Comedy Showcase at Good Times Bar (Thu Aug 20 2026 at 07:00 pm at Good Times Bar & Grill), Florida Kids and Family Expo (Sat, 22 Aug at Orange County Convention Center). - **Q**: What Entertainment events are happening in Maitland in August 2026? - **A:** Dylan Williams In Concert (Sat Aug 29 2026 at 07:00 pm at The Blue Goat), Laughing Stock Comedy Showcase at Good Times Bar (Thu Aug 20 2026 at 07:00 pm at Good Times Bar & Grill), 3rd Annual Tanoshii Con: An All Fandom Con (Sat, 22 Aug at 10:00 am at Ocean Center Convention Daytona Beach), Florida Kids and Family Expo (Sat, 22 Aug at Orange County Convention Center), Cooking con Omi: A Celebration of Puerto Rican Food, Culture & Community (Wed, 19 Aug at 06:00 pm at Venue on Lake Lily / Maitland Civic Center). - **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 1300 S Orlando Ave, Maitland, FL, United States, Florida 32751, Southeastern Prep, Good Times Bar & Grill. - **Q**: What is the price range for Entertainment events in Maitland? - **A:** Prices for Entertainment events in Maitland range from USD 19 to USD 90. 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 Enzian Theater, Marcus McGee Basketball, How Bout Comedy. - **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 Casselberry](https://allevents.in/casselberry/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 Pine Hills](https://allevents.in/pine-hills-fl/entertainment)