To Travel the world is to travel within oneself. For all the adrenaline junkies out there are cool adventure events in Gloucester like hiking in the forests, camping in mountains, hanging by the cliffs and a lot more. An adrenaline rush is sure to have when one is out there on adventure. Whether it’s swimming, river rafting, rappelling , riding with motorcycle club or cycling with friends or just a weekend getaway near Gloucester, we have got you covered.
Find your adventure and trips near Gloucester.
## 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**: Beauport Hotel Presents: The Halloween Soirée - **Description**: Step into a night of spooky surprises, light bites, and bewitching cocktails at Beauport Hotel’s Halloween Soirée on Saturday, October 31st!About this EventStep into a night of eerie elegance by the sea at Beauport Hotel’ - **Venue**: Beauport Hotel Gloucester - **Banner**: https://cdn-az.allevents.in/events4/banners/13cf740a5559b04f5397a58f3bfb8bb594e74a215fa31d6a5efc5bae2dd8f7bc-rimg-w1200-h675-dc080808-gmir.jpg?v=1788354976 - **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**: HOMECOMING starring Laila McQueen - **Description**: Doors 8:00pm Show 8:30pm 21+, Positive ID Required Premium Center Seating with Meet & Greet, bottle of bubbly, and cocktail service: $450 per table Premium Side Seating with Meet & Greet, bottle of bubbly, and cocktail service: $350 per table Stan - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events1/banners/5c8f7b0422e02813f73b356a24da51499982e729299401b16f9207edf821f886-rimg-w1200-h675-dcf898d8-gmir?v=1789624517 - **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 - **Venue**: The Cut Live - **Banner**: https://cdn-az.allevents.in/events7/banners/ebcc01b99ab2e0b51a554e3272623885a62a1c323564524603fd5420a4ddfe24-rimg-w1200-h675-dc180808-gmir?v=1787465318 - **Event Name**: Touch-A-Truck 2026 - **Description**: Mark your calendars! Touch-A-Truck 2026 is rolling into Gloucester on Sunday, November 1, from 12:00–4:00 PM at the Old Page Grounds! Get up close to the vehicles that keep Gloucester moving! Climb aboard police cars, fire trucks, heavy construction equi - **Venue**: 5644 George Washington Memorial Hwy, Gloucester, VA 23061-3749, United States - **Banner**: https://cdn-az.allevents.in/events5/banners/2e4c9ad44e46d7f659e88b62c7d275cdfadcbdacd7d52e3280f8da001dafcd87-rimg-w1200-h675-dc080808-gmir?v=1788048573 - **Event Name**: Witch Dance Flash Mob Downtown Gloucester - **Description**: The Witch Dance Flash Mob 2026 in Gloucester will happen! We will have weekly rehearsal starting Sundays in September at our shop location at 4pm. Everyone is welcome to come to practice and join in! Flash mob will take place Saturday (Halloween) October - **Venue**: 153 Main Street, Gloucester, MA - **Banner**: https://cdn-az.allevents.in/events4/banners/e4fa5e8dcdc7fde80b99d20a5d5d55eeb5860e3c4fd9a3b5103ec0f0d49a595c-rimg-w628-h318-dc081818-gmir?v=1787318205 - **Event Name**: 2026 Christmas & Holiday Parade & Annual Tree Lighting - **Description**: Experience the quaint charm of Gloucester Main Street under the glowing lights and twinkle of the holidays. The annual Christmas and Holiday Parade kicks off at 3:00 PM. Carols and the tree lighting, sponsored by The Cook Foundation, will follow at dusk - **Venue**: 6504 Main St, Gloucester, VA 23061-6103, United States - **Banner**: https://cdn-az.allevents.in/events4/banners/07bb87c4704f6ff16df3515f4ea7da3e6574b89df851ce75b2c6ac072c48be7a-rimg-w1200-h675-dce8f8f8-gmir?v=1787211311 - **Event Name**: Gloucester Classic Car Show - **Description**: Do you like classic cars? Who doesn't? Right? Come join the Virginia State Police HEAT Program and Gloucester Classic Cars Club for a car show, November 7th, 2026, 8AM-3PM. Browse all of the classic cars, get some FREE promo items, and learn ways to #Prot - **Venue**: 6920 Main St, Gloucester, VA 23061-5121, United States - **Banner**: https://cdn-az.allevents.in/events10/banners/e2c0d08aabbbcaec105863d42efb9361b53f916329f3df245c55035851f31998-rimg-w1200-h675-dc382828-gmir?v=1788269712 ## Browse Trips & Adventures Events by Date - [Trips & Adventures Events Today in Gloucester](https://allevents.in/gloucester/trips-adventures--today) - [Trips & Adventures Events This Weekend in Gloucester](https://allevents.in/gloucester/trips-adventures--this-weekend) - [Trips & Adventures Events in October in Gloucester](https://allevents.in/gloucester/trips-adventures--october) - [Trips & Adventures Events in November in Gloucester](https://allevents.in/gloucester/trips-adventures--november) ## FAQs - **Q**: How can I find Trips & Adventures events in Gloucester? - **A:** You can discover upcoming Trips & Adventures 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 Trips & Adventures 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**: Are there any online Trips & Adventures events available? - **A:** Yes, many Trips & Adventures 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 Trips & Adventures events in Gloucester? - **A:** Follow the Trips & Adventures category on AllEvents.in to get notified when new Trips & Adventures events are listed in Gloucester. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/d4/526b9c2f9443799c294c7c3b6e3343/freepik__candid-photography-with-natural-textures-and-highl__27226-1.webp ## Explore Events in Nearby Cities - [Trips & Adventurous Activities in Hayes](https://allevents.in/hayes-va/trips-adventures) - [Events in White Marsh](https://allevents.in/white-marsh-va) - [Events in Dutton](https://allevents.in/dutton-va) - [Events in Hayes](https://allevents.in/hayes-va)