Make your life happening by enrolling to entertainment events in Maitland. 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 Maitland. 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 Maitland.
## 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: 47 - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9mNjcxNDMzMGUzNWE5M2U3YTMwZjFjZWVlNDM1NTkzMWU4NTk1OWE3Yjg3ZmFkMjE4NjNkN2Q5YzMwNzRjMjc0LXJpbWctdzEyMDAtaDYzMy1kYzA4MDgwOC1nbWlyP3Y9MTc4ODY2NjgwNQ.avif - **Categories**: entertainment, kids - **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**: comedy, entertainment - **Event Name**: Rico Monaco Band Live at Good Times Bar & Grill - **Description**: Award-winning guitarist Rico Monaco and the Rico Monaco Band return to Good Times for a high-energy night of Rock, Latin Rock, Santana favs.About this EventRico Monaco Band — LIVE at Good Times Bar & G - **Date**: Fri Oct 16 2026 at 08:00 pm – Fri Oct 16 2026 at 10:30 pm (-04:00) - **Event URL**: https://allevents.in/maitland/rico-monaco-band-live-at-good-times-bar-and-grill/100001998798983566 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy8yMDNiNmI5MWU5MTg5M2EwNTVhNjE0NTdlYjI3Njk2YTJmYTRhY2Y2YjNiOTg0ZGZlY2JlYjY2ZmM2MDM0NGFjLXJpbWctdzEyMDAtaDE1NTMtZGMwODA4MDgtZ21pci5qcGc_dj0xNzg3NjA0NTQ0.avif - **Price**: USD 25 - **Categories**: fitness, Music, Entertainment, Concerts - **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**: DAUZAT ST. MARIE GRAMMY NOMINATED DUO DEBUTS GOOD TIMES BAR & GRILL - **Description**: Catch DAUZAT ST. MARIE Grammy-nominated duo live at Good Times Bar & Grill for an epic debut night back by popular demand to Central FloridaAbout this EventCatch the Grammy Nominated - **Date**: Thu Nov 12 2026 at 07:00 pm – Thu Nov 12 2026 at 09:00 pm (-05:00) - **Event URL**: https://allevents.in/maitland/dauzat-st-marie-grammy-nominated-duo-debuts-good-times-bar-and-grill/100002000220484313 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9kNWRlNWRiMTE1OTRlYTMwOTc5ZDhkYzYzMTZlMzRkZjZlZWZmZmJlYmEyZWM5NTA1NWE1MzgxMTM4ZjZmYzc1LXJpbWctdzEyMDAtaDE1NTMtZGMwODA4MDgtZ21pci5qcGc_dj0xNzg4OTk3NTYz.avif - **Price**: USD 19 to 36 - **Categories**: art - **Event Name**: TRIBUTE TO OZZY OSBORNE & RANDY RHOADS - THE RAILZ - **Description**: Rock out live with The Railz paying epic tribute to Ozzy Osbourne & Randy Rhoads—don’t miss this killer show!About this EventTRIBUTE TO OZZY OSBORNE & RANDY RHOADS - THE RAILZ - **Date**: Sun Oct 04 2026 at 04:00 pm – Sun Oct 04 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/maitland/tribute-to-ozzy-osborne-and-randy-rhoads-the-railz/100001999962895859 - **Venue**: Good Times Bar & Grill - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy81MTkxNWQxMDcwZjc4NGRlM2EwMzlhN2QzM2VmNDlmMjY0ZTU0OTc3ZTYzZjIzNjk1ZjViMTYwMjczMGQxZjgyLXJpbWctdzEyMDAtaDE1NTMtZGMwODA4MDgtZ21pci5qcGc_dj0xNzg4ODk1Mzg0.avif - **Price**: USD 19 to 42 - **Categories**: music, entertainment, performances - **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: 21 - **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_dj0xNzg4MTg0OTg1.avif ## Trending Events in Maitland - **Event Name**: Fiesta in Full Bloom hosted by The Wellness Sisterhood - **Description**: ✨ Orlando's girls' day brunch to meet new friends, enjoy amazing food, mimosas, margaritas, live DJs, and build your sisterhood.About this EventLooking to make genuine friendships in Orlando?Welcome to - **Venue**: Selva Rosa Cocina & Bar - **Banner**: https://cdn-az.allevents.in/events9/banners/52d8c0295f2a1d9e6296de1cc80ae97be3a8bafad411fc32035127e636bef0b0-rimg-w1200-h1200-dcf8e8c8-gmir.jpg?v=1786872734 - **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=1788666805 - **Event Name**: Free Fall Family Day at A&H + Paper Lantern Family Art Workshop - **Description**: Celebrate the colors of a new season with a family art workshop, face painting, scavenger hunt, and free admission to three museums!About this EventBring your whole family to say goodbye to summer and hell - **Venue**: Art & History Museums of Maitland - **Banner**: https://cdn-az.allevents.in/events5/banners/a34cf7d5542f2aedb40be9ea690575f836da40f72a9f7880bb853ef7ebbc93de-rimg-w1200-h795-dc8fa5ac-gmir.jpg?v=1782359034 - **Event Name**: Rollins Museum of Art presents A River Runs Through It @ the Enzian Theater - **Description**: Discover connections between art and the film with this Free movie on the Enzian lawn in conjunction RMA's exhibition Being OutdoorsAbout this EventFree movie on the Enzian lawn! In conjunction with the Rollins Mus - **Venue**: Enzian Theater - **Banner**: https://cdn-az.allevents.in/events6/banners/e18693f879a501bb10cefa8ea212033599d9379ebf7164baf4a62b57c33bcbfa-rimg-w800-h400-dc182818-gmir.jpg?v=1788895570 - **Event Name**: 5th Annual Not So Spooky HallowFest - **Description**: Join us for a magical day filled with shopping local, tasty bites, and festive fall excitement! Bring the whole family — kids are encouraged to dress in their favorite costumes and strike a pose at our adorable fall photo opportunities 📸🍂 for the cutest - **Venue**: Venue on Lake Lily - Maitland Civic Center - **Banner**: https://cdn-az.allevents.in/events5/banners/44d00b38db89c5f189ec0cb0ac103b7435a976a1a1d06830f0d8215475cd1c22-rimg-w1200-h676-dc8828b8-gmir?v=1787125428 - **Event Name**: Nature's Neighbors Monthly Hiking Series - **Description**: Hike and learn about Florida's diverse environment with a new monthly educational series at Maitland Community Park.About this EventHike and learn in Maitland.The Maitland Parks and Recreation Department is partner - **Venue**: Maitland Community Park - **Banner**: https://cdn-az.allevents.in/events6/banners/6a06f9c7bbed964dd9477a414b78b38a24710973e4110b5824aea1436903b647-rimg-w1200-h1541-dc483828-gmir.jpg?v=1787862629 - **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**: DisruptHR 25.0: Destination Unknown - **Description**: Can you handle the lack of control? Come take a ride to a Destination Unknown, and get disruptive with DisruptHR OrlandoAbout this EventLike all DisruptHR Orlando events, we have created a memorable experience for our com - **Venue**: 601 S Lake Destiny Dr - **Banner**: https://cdn-az.allevents.in/events1/banners/8de61402a12df0e1f00da3e6857fd3321dc7f3d45dd1644b9d1f336d145c28b3-rimg-w200-h200-dc010101-gmir.jpg?v=1784240302 - **Event Name**: Film and Conversation with Deeyah Khan - **Description**: Emmy Award-Winning Documentary Film Maker and Human Rights AdvocateAbout this EventDoors Open 10:30 AM | Food and refershments available for purchaseEvent 11:00 AM - 1:00 PM | Film & Real-Time Virtual Conversat - **Venue**: Enzian Theater ## 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 September in Maitland](https://allevents.in/maitland/entertainment--september) - [Entertainment Events in October in Maitland](https://allevents.in/maitland/entertainment--october) ## 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), Next Stop Comedy at Good Times Bar & Grill! - Maitland, FL (Fri Oct 02 2026 at 07:00 pm at Good Times Bar & Grill), Rico Monaco Band Live at Good Times Bar & Grill (Fri Oct 16 2026 at 08:00 pm at Good Times Bar & Grill), DEAD & EXPERIENCED LIVE - GOOD TIMES BAR & GRILL - MAITLAND, FL (Sun Sep 20 2026 at 04:00 pm at Good Times Bar & Grill - Maitland FL), DAUZAT ST. MARIE GRAMMY NOMINATED DUO DEBUTS GOOD TIMES BAR & GRILL (Thu Nov 12 2026 at 07:00 pm at Good Times Bar & Grill). - **Q**: What Entertainment events are happening in Maitland this weekend September 18–20, 2026? - **A:** DEAD & EXPERIENCED LIVE - GOOD TIMES BAR & GRILL - MAITLAND, FL (Sun Sep 20 2026 at 04:00 pm at Good Times Bar & Grill - Maitland FL), Be Great Gala (Fri Sep 18 2026 at 06:00 pm at 1217 Trinity Woods Ln, Maitland, FL 32751-3159, United States). - **Q**: What Entertainment events are happening in Maitland in September 2026? - **A:** DEAD & EXPERIENCED LIVE - GOOD TIMES BAR & GRILL - MAITLAND, FL (Sun Sep 20 2026 at 04:00 pm at Good Times Bar & Grill - Maitland FL), Be Great Gala (Fri Sep 18 2026 at 06:00 pm at 1217 Trinity Woods Ln, Maitland, FL 32751-3159, United States). - **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, Good Times Bar & Grill, Good Times Bar & Grill - Maitland FL. - **Q**: What is the price range for Entertainment events in Maitland? - **A:** Prices for Entertainment events in Maitland range from USD 19 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 Enzian Theater, How Bout Comedy, Ricmon Productions LLC. - **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 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 Orlando](https://allevents.in/orlando/entertainment) - [Entertainment events in Conway](https://allevents.in/conway-fl/entertainment) - [Entertainment events in Lake Mary](https://allevents.in/lake-mary/entertainment) - [Entertainment events in Oviedo](https://allevents.in/oviedo-us/entertainment)