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**: Reckoners with Kevin James Graham - **Description**: Friday 10/16/26 Doors 7:00pm Show 8:00pm 18+, Positive ID Required Premium Seating with cocktail service: $39.50-$44.50 + $6.95 service fee Standard Seating with cocktail service: $34.50 + $6.95 service fee Rear Floor Seating: $29.50 + $6.95 service fee G - **Interested Audience**: - Count: 5 - **Date**: Fri Oct 16 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/reckoners-with-kevin-james-graham/200030496793531 - **Venue**: The Cut Live - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9lZjhiMTFiNWQ2M2IyYTZhYjA0Njc3NTNmNGM4MWM5M2RjOGJkMzBlMWQ5Y2ZmOTdjMmMxZDQxMGE4Y2IxYzc4LXJpbWctdzEyMDAtaDY3NS1kYzE4MTgwOC1nbWlyP3Y9MTc4ODUzMDY0NA.avif - **Categories**: music, entertainment, art - **Event Name**: Jimmy Tingle: The "Radical" Middle- Why Would a Comedian Run for Office? Film Screening + Q&A - **Description**: Sunday 10/11/26 Doors 7:00pm Show 7:30pm 21+, Positive ID Required Premium Seating with cocktail service: $39.50 + $6.95 service fee Standard Seating with cocktail service: $29.50 - $34.50 + $6.95 service fee Rear Floor Seating: $24.50 + $6.95 service fe - **Interested Audience**: - Count: 25 - **Date**: Sun Oct 11 2026 at 07:30 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/jimmy-tingle-the-radical-middle-why-would-a-comedian-run-for-office-film-screening-qanda/200030658452300 - **Venue**: The Cut Live - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy85YzdmY2UzYjAxNDc1NmZiNWY1MzM0OWRlYzU3M2M2ZTQ4ZTMyMmU0ZjU4OWYyOWJlZGRjMGM3Nzc3Y2M4MTIyLXJpbWctdzEyMDAtaDY3NS1kYzA4MDgwOC1nbWlyP3Y9MTc4ODUzMDY0MA.avif - **Categories**: entertainment, comedy, art, theatre, literary-art - **Event Name**: Takedown: K-Pop Dance Battle! Presented by No Sitter Necessary - **Description**: From the creators of the viral K-Pop Sing-A-Long and Dance Experience that toured nationwide in 2025–2026 comes a brand-new interactive sing-and-dance experience made for families! We're back at The Cut to kick off Fall! Get ready for No Sitter Necessar - **Interested Audience**: - Count: 2 - **Date**: Sun Oct 04 2026 at 01:00 am (-04:00) - **Event URL**: https://allevents.in/gloucester/takedown-k-pop-dance-battle-presented-by-no-sitter-necessary/200030623024101 - **Venue**: The Cut Live - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9lOGE4ODAwYzg2ZjEzNTcwYTQwZjZiNzYxZTFjNTE2MzE0ZDRkNjc4OTA2N2U4NjNkZjA2MzgyMDllZTViMDZmLXJpbWctdzEyMDAtaDY3NS1kYzI4MTg0OC1nbWlyP3Y9MTc4ODMwMjA0Mg.avif - **Categories**: kids, entertainment, dance, parties - **Event Name**: Oct 22nd: Gloucester, MA- MAGIC HUNKS® AUSTRALIAN TAKEOVER at Kitchen at The Cut - **Description**: Premier Ladies Night Event Is Coming to Kitchen at The Cut on Thursday October 22nd! Limited Tickets On Sale NOW! Open to Ages 18+ Doors open at 7:00pm Purchase tickets here: https://thecutlive.com/pages/events/magic-hunks-girls-night-out _______________ - **Interested Audience**: - Count: 8 - **Date**: Thu Oct 22 2026 at 08:00 pm – Thu Oct 22 2026 at 10:30 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/oct-22nd-gloucester-ma-magic-hunks-australian-takeover-at-kitchen-at-the-cut/200030623023958 - **Venue**: Kitchen at The Cut - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9hNTBiOTU1NTUxOWQ5NjZmMzg1YjMwMTAzNDBjNWZhZjEwNjZjOTM4OGQyMjE3NzI4ZjhjMWVjYjhmYjY4MWI0LXJpbWctdzEyMDAtaDc4My1kYzA4MDgwOC1nbWlyP3Y9MTc4ODMwMjA0Mw.avif - **Categories**: entertainment, parties, concerts, workshops, music - **Event Name**: Vyntyge Skynyrd - The Lynyrd Skynyrd Experience - **Description**: It's going to get loud in Gloucester! On October 24th, The Cut Live welcomes Vyntyge Skynyrd for a full-throttle night of classic Southern Rock! Travel back to 1977 and relive the legendary sound of Lynyrd Skynyrd with all the iconic hits — Sweet Home Ala - **Interested Audience**: - Count: 133 - **Date**: Sat Oct 24 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/vyntyge-skynyrd-the-lynyrd-skynyrd-experience/200029887011728 - **Venue**: The Cut Live - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9lYmNjMDFiOTlhYjJlMGI1MWE1NTRlMzI3MjYyMzg4NWE2MmExYzMyMzU2NDUyNDYwM2ZkNTQyMGE0ZGRmZTI0LXJpbWctdzEyMDAtaDY3NS1kYzE4MDgwOC1nbWlyP3Y9MTc4NzQ2NTMxOA.avif - **Categories**: music, entertainment, art, literary-art, workshops - **Event Name**: SAFETY 80'S - 21+ Halloween Show (The Late Show) - **Description**: Friday 10/30/26 Doors 7:00pm Show 8:00pm 21+ 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 SAFETY is not your - **Interested Audience**: - Count: 15 - **Date**: Fri Oct 30 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/safety-80s-21-halloween-show-the-late-show/200030496793631 - **Venue**: The Cut Live - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy9iNjE1ZDRmZTEwNzM3ZmU2YTEwNmY4Njg1NjNmY2EzNWNhMTFhYzI4NmIyYWY4MzYzNTg2YjU3YWNmNWU0YzdmLXJpbWctdzEyMDAtaDY3NS1kYzA4MDgwOC1nbWlyP3Y9MTc4ODYyMzY4Mg.avif - **Categories**: music, entertainment - **Event Name**: Flamenkora - **Description**: Thursday 10/1/26 Doors 7:00pm Show 8:00pm 18+, Positive ID Required Premium Seating with cocktail service: $44.50 + $6.95 service fee Standard Seating with cocktail service: $29.50 - $35.50 + $6.95 service fee Rear Floor Seating: $29.50 + $6.95 service fe - **Interested Audience**: - Count: 4 - **Date**: Thu Oct 01 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/flamenkora/200030722459701 - **Venue**: The Cut Live - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9iMzM0MGQ0YjNhM2MwZmQ5NzE4YTRmOWM0N2JiYTY3NWM4ZGMwZWFjOWVlODExOTJjY2VmYjVmMDdiNWY5ZDI3LXJpbWctdzEyMDAtaDY3NS1kYzA4MDgwOC1nbWlyP3Y9MTc5MDAwODQ0MQ.avif - **Categories**: music, entertainment, art, live-music, concerts - **Event Name**: Gloucester Electronics Recycling Event ♻️ - **Description**: Drop off your old gadgets and help clear out e-waste at our Electronics Recycling Event!About this EventJoin us for our Electronics Recycling Event! We're accepting all electronics, appliances, ANYTHING with a plug or bat - **Date**: Sat Oct 24 2026 at 09:00 am – Sat Oct 24 2026 at 02:00 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/gloucester-electronics-recycling-event/100002000642709199 - **Venue**: Our Lady of Good Voyage Church - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9kOTgzYzZhZGY1OTcyNDdlMzhhOTU2ZjFkN2JjZWQ1NDRhMjgwMzM1MGI1ZGRjMjZhYTFjZDExZmNiMTBmY2Y2LXJpbWctdzEyMDAtaDE1NTMtZGNmOGY4ZjgtZ21pci5qcGc_dj0xNzkwMDY0MDY4.avif - **Price**: Free - **Categories**: fitness, Entertainment, Music, Nonprofit, Sports ## Trending Events in Gloucester - **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**: Next Wave Event - **Description**: A Gloucester Harbor cruise, live music, bites, and the people shaping what comes next across the North Shore.About this EventThis October, Northshore Magazine brings its signature fall celebration to Gloucester Harbor. - **Venue**: Beauport Cruiselines - **Banner**: https://cdn-az.allevents.in/events8/banners/d85e40ca23751f2dfb0351374f0876763a9e92ed9e01d2da9863270413ed31f4-rimg-w1200-h600-dc080808-gmir.jpg?v=1787627715 - **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**: Around Cape Ann Half Marathon - **Description**: USATF Certified Half Marathon! Since 1933, the Around Cape Ann Road Race has been a running tradition. Considered one of the best and oldest races in America, the Around Cape Ann Road Race is also among the most beautiful race courses in New England. The - **Venue**: 32 Cherry Street Gloucester, MA 01930 - **Banner**: https://cdn-az.allevents.in/events10/banners/5ab0b58b21191cd327b7d5960c02ca26db951697701618e115026e6f28d668e8-rimg-w1200-h1222-dcf8f8f8-gmir?v=1787298647 - **Event Name**: Reckoners with Kevin James Graham - **Description**: Friday 10/16/26 Doors 7:00pm Show 8:00pm 18+, Positive ID Required Premium Seating with cocktail service: $39.50-$44.50 + $6.95 service fee Standard Seating with cocktail service: $34.50 + $6.95 service fee Rear Floor Seating: $29.50 + $6.95 service fee G - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events1/banners/ef8b11b5d63b2a6ab0467753f4c81c93dc8bd30e1d9cff97c2c1d410a8cb1c78-rimg-w1200-h675-dc181808-gmir?v=1788530644 - **Event Name**: Chelsea Berry - Peace Soldier Album Release - **Description**: Doors 6:30pm Show 7:00pm ALL AGES Premium Seating with cocktail service: $44.50 + $6.95 service fee Standard Seating with cocktail service: $34.50 - $39.50 + $6.95 service fee GA Standing: $29.50 + $6.95 service fee + $5 Day of Show Chelsea Berry is a M - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events3/banners/c9dcff67b7e9e8d8bce361735b457dd58eeae408ccb92c76d589fb96966fd6ee-rimg-w1200-h675-dcd8a8a8-gmir?v=1788374420 - **Event Name**: The North Shore's Own Renaissance Faire at Hammond Castle Museum - **Description**: TICKET ALERT: Member-Only Presale begins this Monday, June 15th. Remaining tickets go on sale on Monday, June 22nd. Rain or Shine. Saturday, November 7 & Sunday, November 8 Step into a world of knights, artisans, performers, and merriment as Hammond - **Venue**: 80 Hesperus Ave, Gloucester, MA, United States, Massachusetts 01930 - **Banner**: https://cdn-az.allevents.in/events2/banners/0961d2f5cfa273256566811a31be2c30c7b842d8401ffb40e510fd597c939a00-rimg-w1200-h628-dcf8f8f8-gmir?v=1788211116 - **Event Name**: Hogwarts Comes To The Apothecary - **Description**: Bring the magic of Hogwarts to your October at our apothecary this year with a crafting collection of enchanting potions and wizarding flair. Each potion created by your children is crafted with care, featuring ingredients inspired by the wizarding world - **Venue**: 153 Main Street Gloucester MA 01930 - **Banner**: https://cdn-az.allevents.in/events3/banners/d19f6ecf1a2884d09616ac586ddb120912fc67cb6cc3c577c5a583e38086309e-rimg-w512-h512-dc080808-gmir?v=1787577077 - **Event Name**: Dueling Pianos - **Description**: Doors 7:00pm Show 8:00pm 21+, Positive ID Required Premium Seating with cocktail service: $29.50-$34.50 + $6.95 service fee Standard Seating with cocktail service: $24.50 + $6.95 service fee Rear Floor Seating: $19.50 + $6.95 service fee GA Standing: $12. - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events10/banners/2205714418e9fe79f4f285f2235b5fe3552fce45d13d5e2ce8062fa0c20df8d0-rimg-w1200-h675-dc080808-gmir?v=1788212381 ## 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 October in Gloucester](https://allevents.in/gloucester/entertainment--october) - [Entertainment Events in November in Gloucester](https://allevents.in/gloucester/entertainment--november) ## FAQs - **Q**: What are the top Entertainment events in Gloucester? - **A:** Reckoners with Kevin James Graham (Fri Oct 16 2026 at 08:00 pm at The Cut Live), Jimmy Tingle: The "Radical" Middle- Why Would a Comedian Run for Office? Film Screening + Q&A (Sun Oct 11 2026 at 07:30 pm at The Cut Live), Takedown: K-Pop Dance Battle! Presented by No Sitter Necessary (Sun Oct 04 2026 at 01:00 am at The Cut Live), Oct 22nd: Gloucester, MA- MAGIC HUNKS® AUSTRALIAN TAKEOVER at Kitchen at The Cut (Thu Oct 22 2026 at 08:00 pm at Kitchen at The Cut), Vyntyge Skynyrd - The Lynyrd Skynyrd Experience (Sat Oct 24 2026 at 08:00 pm at The Cut Live). - **Q**: What are the top free Entertainment events in Gloucester? - **A:** Gloucester Electronics Recycling Event ♻️ (Sat Oct 24 2026 at 09:00 am at Our Lady of Good Voyage Church). - **Q**: What Entertainment events are happening in Gloucester today October 01, 2026? - **A:** Flamenkora (Thu Oct 01 2026 at 08:00 pm at The Cut Live). - **Q**: What Entertainment events are happening in Gloucester this weekend October 2–4, 2026? - **A:** Takedown: K-Pop Dance Battle! Presented by No Sitter Necessary (Sun Oct 04 2026 at 01:00 am at The Cut Live). - **Q**: What Entertainment events are happening in Gloucester in October 2026? - **A:** Reckoners with Kevin James Graham (Fri Oct 16 2026 at 08:00 pm at The Cut Live), Jimmy Tingle: The "Radical" Middle- Why Would a Comedian Run for Office? Film Screening + Q&A (Sun Oct 11 2026 at 07:30 pm at The Cut Live), Takedown: K-Pop Dance Battle! Presented by No Sitter Necessary (Sun Oct 04 2026 at 01:00 am at The Cut Live), Oct 22nd: Gloucester, MA- MAGIC HUNKS® AUSTRALIAN TAKEOVER at Kitchen at The Cut (Thu Oct 22 2026 at 08:00 pm at Kitchen at The Cut), Vyntyge Skynyrd - The Lynyrd Skynyrd Experience (Sat Oct 24 2026 at 08:00 pm at The Cut Live). - **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 The Cut Live, Kitchen at The Cut, Our Lady of Good Voyage Church. - **Q**: What is the price range for Entertainment events in Gloucester? - **A:** Prices for Entertainment events in Gloucester range from USD 30 to USD 90. Many events also offer free entry. - **Q**: Who are the top organizers for Entertainment events in Gloucester? - **A:** Popular organizers hosting Entertainment events in Gloucester include The Cut Live, NSN: The Family Dance Party, Girls Night Out The Show. - **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 ## Entertainment events from nearby cities - [Entertainment events in Rockport](https://allevents.in/rockport/entertainment) - [Entertainment events in South Hamilton](https://allevents.in/south-hamilton/entertainment) - [Entertainment events in Beverly](https://allevents.in/beverly-ma/entertainment) - [Entertainment events in Marblehead](https://allevents.in/marblehead/entertainment) - [Entertainment events in Salem](https://allevents.in/salem-ma/entertainment)