Witness the crazy comedy shows 2026 in Gloucester at the venues near you to laugh till your belly hurts. You cannot miss the chance to witness the popular names of the comedy scene. There are improv workshops, comedy class and comedy shows in Gloucester too where you can try your hands out.
Lighten yourself and laugh it out at a stand up comedy event happening near you in Gloucester.
## Comedy Events in Gloucester - **Event Name**: 3rd Annual So-Long-To-Summer Comedy Show with Paul D'Angelo - **Description**: Doors 7:00pm Show 8:00pm 21+, Positive ID Required Premium Seating with cocktail service: $34.50-$39.50 + $6.95 service fee Standard Seating with cocktail service: $29.50 + $6.95 service fee Rear Floor Seating: $24.50 + $6.95 service fee GA Standing: $19. - **Interested Audience**: - Count: 13 - **Date**: Sat Sep 12 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/3rd-annual-so-long-to-summer-comedy-show-with-paul-dangelo/200030461352531 - **Venue**: The Cut Live - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvYWY2NDFiZDk4ODU2NWY1NGFlMjhmMzgwMTg4ZjhiYjkyMGU0ODNlY2RlMjc2NzdiYWM5MDgwNmYxNGExNTE5YS1yaW1nLXcxMjAwLWg2NzUtZGMwODA4MDgtZ21pcj92PTE3ODc3NDQ4Mjk.avif - **Categories**: comedy, art, literary-art, entertainment - **Event Name**: Captains Dinner COMEDY NIGHT Monday 9/14 - **Description**: Wicked Fishin 2026 Captains Comedy Show featuring some of New England’s Best at Cape Ann Marina in Gloucester, MA. 7:30pm Monday 9/14About this EventJoin us after a day of - **Date**: Mon Sep 14 2026 at 07:30 pm – Mon Sep 14 2026 at 09:30 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/captains-dinner-comedy-night-monday-9-14/100001999707223135 - **Venue**: The Hotel at Cape Ann Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy80ZDBlZTdkZjY1YzU1YzdlZjE1ODhlODZiMjcwMTA3ZmRiOWUxOTEzN2VlN2FkYzRjMGM4NzI4NmRkYTk1Nzc5LXJpbWctdzEyMDAtaDYwMC1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODg0NjI5NzY.avif - **Price**: USD 55 - **Categories**: fitness, comedy, Entertainment - **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 ## Trending Events in Gloucester - **Event Name**: Gloucester Schooner Festival - **Description**: Be part of the action and join us onboard the When And If and Schooner Malabar X as we attempt to continue our winning streak at the spectacular Gloucester Schooner Festival. Race lunch included and beverages available for purchase onboard. Space is ver - **Venue**: Gloucester Schooner Festival - **Banner**: https://cdn-az.allevents.in/events2/banners/419df8b79bac74095773f87191bb0b8cd26af05f42ea3cd90214d7944b988d69-rimg-w960-h640-dc4878a8-gmir?v=1787008250 - **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**: Sunday, September 6th, Live Music at Birdseye Rooftop - **Description**: One last sunset. One last rooftop party. Join us for the final live music night on the rooftop on Sunday, September 6th from 6:00PM–9:00PMAbout this EventOne last sunset. One last rooftop party.Join us for the fina - **Venue**: Beauport Hotel Gloucester - **Banner**: https://cdn-az.allevents.in/events3/banners/6fc26dd9fd40d13c41a623c89df02427e3c70adecee6090f4b0f11841fb58ac9-rimg-w1200-h600-dc785848-gmir.jpg?v=1785796331 - **Event Name**: Parade of Sail - **Description**: Visit Beauport for some of the best views of the annual Gloucester Schooner Festival’s Parade of Sail. Watch from the terrace as schooners sail to the Eastern Point Light breakwater to begin the Mayor’s race for the Esperanto Cup. Bring blankets and/or ch - **Venue**: Beauport, the Sleeper-McCann House - **Banner**: https://cdn-az.allevents.in/events9/banners/89f449203544ffa173842edcb00e57a9a6a8eb7a8fab494d3bc3658dd8e85ff6-rimg-w1200-h900-dc98a8b8-gmir?v=1788464665 - **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**: 3rd Annual So-Long-To-Summer Comedy Show with Paul D'Angelo - **Description**: Doors 7:00pm Show 8:00pm 21+, Positive ID Required Premium Seating with cocktail service: $34.50-$39.50 + $6.95 service fee Standard Seating with cocktail service: $29.50 + $6.95 service fee Rear Floor Seating: $24.50 + $6.95 service fee GA Standing: $19. - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events10/banners/af641bd988565f54ae28f380188f8bb920e483ecde27677bac90806f14a1519a-rimg-w1200-h675-dc080808-gmir?v=1787744829 - **Event Name**: Dead to the Core September Show presented by Ripple Effect Realty - **Description**: Friday 9/18/26 Doors 7:00pm Show 8:00pm 21+, Positive ID Required Premium Seating with cocktail service: $34.50 + $6.95 service fee Standard Seating with cocktail service: $29.50 + $6.95 service fee GA Standing: $15 + $6.95 service fee + $5 Day of Show - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events1/banners/6d831401e0d25241132214c98b8a4d5ad8034f985a293ea729f26fb060044130-rimg-w1200-h675-dcf8f8e8-gmir?v=1788530649 ## Browse Comedy Events by Date - [Comedy Events Today in Gloucester](https://allevents.in/gloucester/comedy--today) - [Comedy Events This Weekend in Gloucester](https://allevents.in/gloucester/comedy--this-weekend) - [Comedy Events in September in Gloucester](https://allevents.in/gloucester/comedy--september) - [Comedy Events in October in Gloucester](https://allevents.in/gloucester/comedy--october) ## FAQs - **Q**: What are the top Comedy events in Gloucester? - **A:** 3rd Annual So-Long-To-Summer Comedy Show with Paul D'Angelo (Sat Sep 12 2026 at 08:00 pm at The Cut Live), Captains Dinner COMEDY NIGHT Monday 9/14 (Mon Sep 14 2026 at 07:30 pm at The Hotel at Cape Ann Marina), 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), CrimeStery Fest 2026 (Fri, 09 Oct at 04:00 pm at DoubleTree by Hilton Hotel Boston North Shore, Ferncroft Road, Danvers, MA, USA). - **Q**: What Comedy events are happening in Gloucester in September 2026? - **A:** 3rd Annual So-Long-To-Summer Comedy Show with Paul D'Angelo (Sat Sep 12 2026 at 08:00 pm at The Cut Live), Captains Dinner COMEDY NIGHT Monday 9/14 (Mon Sep 14 2026 at 07:30 pm at The Hotel at Cape Ann Marina). - **Q**: How can I find Comedy events in Gloucester? - **A:** You can discover upcoming Comedy 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 Comedy 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 Comedy events in Gloucester? - **A:** Some popular venues hosting Comedy events in Gloucester include The Cut Live, The Hotel at Cape Ann Marina, DoubleTree by Hilton Hotel Boston North Shore, Ferncroft Road, Danvers, MA, USA. - **Q**: What is the price range for Comedy events in Gloucester? - **A:** Prices for Comedy events in Gloucester range from USD 30 to USD 90. Many events also offer free entry. - **Q**: Who are the top organizers for Comedy events in Gloucester? - **A:** Popular organizers hosting Comedy events in Gloucester include The Cut Live, PINKY RING COMEDY, CrimeStery-Fest. - **Q**: Are there any online Comedy events available? - **A:** Yes, many Comedy 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 Comedy events in Gloucester? - **A:** Follow the Comedy category on AllEvents.in to get notified when new Comedy events are listed in Gloucester. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/f3/0e051f4d9a4429ae6be27084e31353/comedy.png ## Comedy events from nearby cities - [Comedy events in Ipswich](https://allevents.in/ipswich-ma/comedy) - [Comedy events in Beverly](https://allevents.in/beverly-ma/comedy) - [Comedy events in Salem](https://allevents.in/salem-ma/comedy) - [Comedy events in Danvers](https://allevents.in/danvers-ma/comedy) - [Comedy events in Peabody](https://allevents.in/peabody-ma/comedy)