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 Gloucester - **Event Name**: SIPE, HADDEN, STERNBERG, COMBS August 29, 2026 - **Description**: Jeff Sipe, Isaac Hadden, Quinn Sternberg, and Daniel Combs are recognized as eclectic and virtuosic musical voices in the southeastern U.S. For select dates, they are teaming up to deliver a set of music that is dance-ably delicate and effortlessly electr - **Interested Audience**: - Count: 60 - **Date**: Sat Aug 29 2026 at 06:30 pm (-04:00) - **Event URL**: https://allevents.in/gloucester/sipe-hadden-sternberg-combs-august-29-2026/200030441394902 - **Venue**: 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy80Y2JkZWEyNjNiZjE2NzY2MDk5MzJiZmVmYWY2ZGRjZjc1ODM5ZDkxYWFlZDY1YTZjNDg4MDMwODE2ZWQ1YjcyLXJpbWctdzEwNzctaDg5OC1kYzA4MDgwOC1nbWlyP3Y9MTc4NjY3NDU5MQ.avif - **Categories**: music, live-music, entertainment, performances, volunteering - **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_dj0xNzg2NjkyNzU3.avif - **Categories**: music, entertainment ## Trending Events in Gloucester - **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=1786382027 - **Event Name**: 2026 Boat Parade of Lights - Gloucester - **Description**: Boats Parade on Annisquam River to Gloucester Boulevard, Harbor and inlets of the inner harbor during the Schooner Festival weekend. - **Venue**: Central Gloucester - **Banner**: https://cdn-az.allevents.in/events6/banners/cadcd7356a033611c2e042d055d27b3331082751ea4785e68c961260e742779b-rimg-w1200-h799-dc080808-gmir?v=1785441521 - **Event Name**: Schooner Festival (Labor Day Weekend) Viewing Cruises - **Description**: Gloucester Schooner Festival Schedule of Events 2024 Calendar - Cruise Schedule aboard WEJACK to View the Schooners, Schooner Races, Boat Parade of Lights, Gloucester Fireworks, and Parade of Sail Plan ahead. Purchase tickets below to ensure your spot abo - **Venue**: 63 Rogers Street, Gloucester, MA, United States, Massachusetts 01930 - **Banner**: https://cdn-az.allevents.in/events6/banners/52bc64118e0cdc4619cc3c03817019b0178df231f6b3e2798cc2945186198452-rimg-w1200-h1200-dcf8e8d8-gmir?v=1786382025 - **Event Name**: Friday, August 28th, Sunset Sessions at Beauport Hotel - **Description**: Spend your weekend nights on Beauport Hotel's Birdseye Rooftop with stunning views, lively tunes and handcrafted cocktails!About this EventEnjoy the weekend in style at Sunset Sessions. An evening of vibrant energy, coast - **Venue**: Beauport Hotel Gloucester - **Banner**: https://cdn-az.allevents.in/events3/banners/feb30db23689705d8456ed455a1374a0f0892df35cf8990fb355ff0173fcc54b-rimg-w1200-h600-dc7a6349-gmir.jpg?v=1777853768 - **Event Name**: Saturday, September 5th, Sunset Sessions: Summer's Grand Finale - **Description**: Celebrate Labor Day Weekend with a front-row seat to Gloucester Harbor fireworks during Beauport's 10th summer by the sea.About this EventSaturday, September 5 | 7:00 PM–10:00 PM | Birdseye Rooftop | 21+ - **Venue**: Beauport Hotel Gloucester - **Banner**: https://cdn-az.allevents.in/events1/banners/3dd13239e353c9adf3e1afe85a061fd2db4b83158dc9f3c50fc15a79359e3fac-rimg-w1200-h675-dc082848-gmir.jpg?v=1785538084 - **Event Name**: Sunday, August 30th, Rooftop Evening Access at Beauport Hotel - **Description**: Bringing live coastal music every Sunday-Thursday on Birdseye Rooftop at Beauport Hotel with craft cocktails and unbeatable views.About this EventElevate your weeknight above Gloucester Harbor. - **Venue**: Beauport Hotel Gloucester - **Banner**: https://cdn-az.allevents.in/events3/banners/c5a11ca0da25245fc2c7048b2014118e0564cbff583e8d0d3f4d31b303e72c9b-rimg-w1200-h600-dc77615d-gmir.jpg?v=1777792257 - **Event Name**: Saturday, August 29th, Sunset Sessions at Beauport Hotel - **Description**: Spend your weekend nights on Beauport Hotel's Birdseye Rooftop with stunning views, lively tunes and handcrafted cocktails!About this EventEnjoy the weekend in style at Sunset Sessions. An evening of vibrant energy, coast - **Venue**: Beauport Hotel Gloucester - **Banner**: https://cdn-az.allevents.in/events1/banners/2668c0c9192bebd64c05b6de23731c5e217f1af15a71e7d80b8ed3cd85486f03-rimg-w1200-h600-dc7a6349-gmir.jpg?v=1777853707 - **Event Name**: Sunday, August 23rd, Rooftop Evening Access at Beauport Hotel - **Description**: Bringing live coastal music every Sunday-Thursday on Birdseye Rooftop at Beauport Hotel with craft cocktails and unbeatable views.About this EventElevate your weeknight above Gloucester Harbor. - **Venue**: Beauport Hotel Gloucester - **Banner**: https://cdn-az.allevents.in/events1/banners/82f622de3b15890fd5503659e3fe2e1d93e068f8702f93fb3e102eaff84a82b6-rimg-w1200-h600-dc77615d-gmir.jpg?v=1777792600 - **Event Name**: Bordellos At The Gloucester Waterfront Festival!! Sun. 8/16 2-5pm - **Description**: C’mon down for the Gloucester Waterfront Festival! Always a fun time at beautiful Stage Fort Park. We’re on 2-5pm Come find us!! - **Venue**: Stage Fort Park - **Banner**: https://cdn-az.allevents.in/events1/banners/e63f1327fadf5ebdf0fc20f64e20a820ef2a9532d0eafb945bbdd60123a2a640-rimg-w1200-h1200-dc080808-gmir?v=1786236095 ## 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 August in Gloucester](https://allevents.in/gloucester/entertainment--august) - [Entertainment Events in September in Gloucester](https://allevents.in/gloucester/entertainment--september) ## FAQs - **Q**: What are the top Entertainment events in Gloucester? - **A:** SIPE, HADDEN, STERNBERG, COMBS August 29, 2026 (Sat Aug 29 2026 at 06:30 pm at 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061), Flat Iron Crossroads (Sat Oct 10 2026 at 07:00 pm at 7709 Flat Iron Rd, Gloucester, VA 23061-5120, United States). - **Q**: What Entertainment events are happening in Gloucester in August 2026? - **A:** SIPE, HADDEN, STERNBERG, COMBS August 29, 2026 (Sat Aug 29 2026 at 06:30 pm at 7709 Flat Iron Road, Gloucester, VA, United States, Virginia 23061). - **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 Road, Gloucester, VA, United States, Virginia 23061, 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 Flat Iron Crossroads, 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 - [Events in White Marsh](https://allevents.in/white-marsh-va) - [Events in Hayes](https://allevents.in/hayes-va)