Make your life happening by enrolling to entertainment events in Gloucester. 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 Gloucester. 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 Gloucester.
## Entertainment Events in Gloucester - **Event Name**: Flat Iron Crossroads - **Description**: The band has had several private events recently, but looks forward to playing music for our regular fans in the Fall. Seems far away, but it will be here "before you know it"! We have a couple more private events, and then will be so pleased to entert - **Interested Audience**: - Count: 13 - **Date**: Sat Oct 10 2026 at 07:00 pm – Sat Oct 10 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/flat-iron-crossroads/200030466193050 - **Venue**: 7709 Flat Iron Rd, Gloucester, VA 23061-5120, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9iZmUwNjdlNzYwYmNhODRkY2Y5Y2RmMDg5YWMyMmIyZTc5ZTFhZDkxMDU1YjVmYjZhNWMzY2MxOTlmNzA4OTJjLXJpbWctdzQ1Ni1oNDc2LWRjMTgxODA4LWdtaXI_dj0xNzg4MTkzNjQz.avif - **Categories**: music, entertainment ## Trending Events in Gloucester - **Event Name**: Avery, Gottlieb & Rothko: By the Sea – Symposium - **Description**: Avery, Gottlieb & Rothko: By the Sea – Symposium ************ This program is sold out. Register for the livestream at https://www.capeannmuseum.org/event/livestream-avery-gottlieb-rothko-by-the-sea-full-day-symposium/. ************* Join us for Cap - **Venue**: 27 Pleasant St, Gloucester, MA, United States, Massachusetts 01930 - **Banner**: https://cdn-az.allevents.in/events9/banners/d81e3373b934ec744f816e18d411ad3c148882adaa705c8962a6af0ab7d04870-rimg-w1024-h614-dcf8f8f8-gmir?v=1788185397 - **Event Name**: Guitar Monsters feat. Jon Butcher, Johnny A. w/special guest Dave Amato - **Description**: Rockin’ 4 Vets presents Guitar Monsters as it makes its highly anticipated initial venture into The Cut Live for an electrifying night of world-class guitar rock. The show features ac - **Venue**: The Cut - Stage • Studio • Restaurant • Bar - **Banner**: https://cdn2.allevents.in/thumbs/thumb6a830db240886.jpg - **Event Name**: Tanya Donelly - **Description**: Doors 7:00pm Show 8:00pm 18+, Positive ID Required Premium Seating with cocktail service: $39.50 + $6.95 service fee Standard Seating with cocktail service: $34.50 + $6.95 service fee GA Standing: $24.50 + $6.95 service fee + $5 Day of Show Tanya Donell - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events3/banners/7a39289ef0791efad7270bad6b552f41f1e20d48bc27cf3337d9da6fcd44a525-rimg-w1200-h675-dc080808-gmir?v=1788530645 - **Event Name**: Guitar Monsters with Jon Butcher, Johnny A. and Dave Amato (formerly of REO Speedwagon) - **Description**: Thursday 9/24/26 Doors 7:30pm Show 8:00pm 18+, Positive ID Required Premium Seating with cocktail service: $44.50-$49.50 + $6.95 service fee Standard Seating with cocktail service: $34.50-$39.50 + $6.95 service fee Rear Floor Seating: $29.50 + $6.95 servi - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events7/banners/3b899698e9f4205e0432b946bb3dafb3ae56701fe3e404d177e53d8b765ad1ab-rimg-w1200-h675-dc080808-gmir?v=1788058313 - **Event Name**: Goblin King Ball at Hammond Castle Museum - **Description**: UPDATE: We are sold out for the 2026 Goblin King Ball! Thank you to all who purchased tickets, making this fundraiser a success. - **Venue**: 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 - **Banner**: https://cdn-az.allevents.in/events9/banners/e93fc6b957dd8c3debb360b3122fee4969c003c55d1f75bcf597e2541cd6bbfd-rimg-w1200-h628-dc282818-gmir?v=1788695011 - **Event Name**: Cape Ann Artisans Open Studios - Fall Event - **Description**: The Cape Ann Artisans are a juried group of diverse makers that host the oldest Open Studios in the country.About this EventThe Cape Ann Artisans are a juried group of diverse makers that host the oldest Open Studios in t - **Venue**: Gloucester and Rockport MA - **Banner**: https://cdn-az.allevents.in/events5/banners/22433dffa7851e9823e39788d309ea0cede39111a4eed8eb6651ad8300a1d9ff-rimg-w1200-h625-dc161d2d-gmir.jpg?v=1770241582 - **Event Name**: Davy Knowles And His Band Sept 19, 2026 - **Description**: Since bursting on to the scene with his band Back Door Slam’s critically acclaimed album ‘Roll Away’ in 2007 (“I heard the spirit of Jimi Hendrix” Patrick McDonald - Seattle Times), Davy’s star has only risen. His sophomore release ‘Coming Up For Air’ was - **Venue**: 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 - **Banner**: https://cdn-az.allevents.in/events9/banners/f2beb8f2773f6bb7dd7c646beb26c8a8fc258aa2980f5de1f116486084b0cbd8-rimg-w1200-h800-dc28280e-gmir?v=1784212130 - **Event Name**: 2026 Gloucester Wine Festival Attendee & Vendor Tickets - **Description**: Featuring top Virginia Wineries, live music, fine foods, art and retail vendors. There will also be Wine Tasting and Educational Seminars.About this EventSeptember 19, 2026: Saturday 11-5pm - **Venue**: Brent & Becky's - **Banner**: https://cdn-az.allevents.in/events6/banners/5b2af218a17ac0e9514ccedd96bf41743945ef28d9e74e4ad58987a8affb2098-rimg-w1200-h800-dcf0f3f0-gmir.jpg?v=1778296527 - **Event Name**: Third World in Gloucester - **Description**: 🎶 Don't Miss this Out! Third World is Live at The Cut on Sunday, September 20, 2026! 🎶 This is your moment. Third World is hitting The Cut on Sunday, September 20, 2026, and with chart-topping hits - **Venue**: The Cut - **Banner**: https://cdn-az.allevents.in/events6/banners/e52ad320-860a-11f1-a8a4-631b175f3d78-rimg-w1200-h675-dcbfd9e9-gmir.webp?v=1784751677 ## Browse Entertainment Events by Date - [Entertainment Events Today in Gloucester](https://allevents.in/gloucester/entertainment--today) - [Entertainment Events This Weekend in Gloucester](https://allevents.in/gloucester/entertainment--this-weekend) - [Entertainment Events in September in Gloucester](https://allevents.in/gloucester/entertainment--september) - [Entertainment Events in October in Gloucester](https://allevents.in/gloucester/entertainment--october) ## FAQs - **Q**: What are the top Entertainment events in Gloucester? - **A:** Flat Iron Crossroads (Sat Oct 10 2026 at 07:00 pm at 7709 Flat Iron Rd, Gloucester, VA 23061-5120, United States). - **Q**: How can I find Entertainment events in Gloucester? - **A:** You can discover upcoming Entertainment events in Gloucester 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 Gloucester? - **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 Gloucester? - **A:** Some popular venues hosting Entertainment events in Gloucester include 7709 Flat Iron Rd, Gloucester, VA 23061-5120, United States. - **Q**: Who are the top organizers for Entertainment events in Gloucester? - **A:** Popular organizers hosting Entertainment events in Gloucester include Dana Newsome. - **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 Gloucester? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Gloucester. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Explore Events in Nearby Cities - [Entertainment events in Hayes](https://allevents.in/hayes-va/entertainment) - [Events in White Marsh](https://allevents.in/white-marsh-va) - [Events in Hayes](https://allevents.in/hayes-va)