To Travel the world is to travel within oneself. For all the adrenaline junkies out there are cool adventure events in Annapolis 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 Annapolis, we have got you covered.
Find your adventure and trips near Annapolis.
## Trips & Adventures Events in Annapolis - **Event Name**: Annapolis Sailboat Show - **Interested Audience**: - Count: 2 - **Date**: Wed Oct 07 2026 at 07:00 pm – Sun Oct 18 2026 at 12:00 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/annapolis-sailboat-show/2300027171578409 - **Venue**: Annapolis City Dock - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy82ZjFhMDZhMC1iMDY4LTExZjEtODAxMS03Mzk0ZjU3ZjcwMDQtcmltZy13MTIwMC1oNzQ2LWRjMDgxODI4LWdtaXIuanBnP3Y9MTc4OTQwOTgxMQ.avif - **Categories**: trips-adventures - **Event Name**: Navy Midshipmen vs. Tulsa Golden Hurricane - **Date**: Fri Oct 09 2026 at 07:00 pm – Sat Oct 10 2026 at 05:30 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/navy-midshipmen-vs-tulsa-golden-hurricane/2300029784416742 - **Venue**: Navy Marine Corps Memorial Stadium - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9hYWQxZGQ1MC1hZjllLTExZjEtOTRlMS00Mzg5ZmMwOGNhZGEtcmltZy13MTIwMC1oNTE0LWRjMDgwODA4LWdtaXIuanBnP3Y9MTc4OTMyMzE1MA.avif - **Categories**: trips-adventures - **Event Name**: Southern Culture On The Skids - **Date**: Fri Sep 25 2026 at 07:00 pm (-05:00) - **Event URL**: https://allevents.in/annapolis/southern-culture-on-the-skids/2300029867527241 - **Venue**: Rams Head On Stage - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy81YWUyZTQ3MC00OWVhLTExZjEtYWJiZC03M2M5YmVlZmQ5MDItcmltZy13MTIwMC1oMTIwMC1kY2MwYTc0Mi1nbWlyLmpwZz92PTE3NzgxNDA2MzI.avif - **Categories**: contests, trips-adventures - **Event Name**: Sean Hayes - **Date**: Tue Sep 22 2026 at 07:00 pm – Wed Sep 23 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/sean-hayes/2300030193670525 - **Venue**: Rams Head On Stage - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy80OTlkZTgyMC1hZmRiLTExZjEtOTRlMS00Mzg5ZmMwOGNhZGEtcmltZy13MTA4MC1oMTM1MC1kY2Y4ZjhmOC1nbWlyLmpwZz92PTE3ODkzNDkxNzk.avif - **Categories**: trips-adventures, contests - **Event Name**: Brett Dennen - **Date**: Thu Sep 24 2026 at 08:00 pm – Thu Sep 24 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/brett-dennen/2300030217273718 - **Venue**: Rams Head On Stage - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy8xY2E1MzJmMC1hZWRkLTExZjEtOTRlMS00Mzg5ZmMwOGNhZGEtcmltZy13MTIwMC1oNjc0LWRjZjhmOGU4LWdtaXIuanBnP3Y9MTc4OTI0MDAyOA.avif - **Categories**: trips-adventures - **Event Name**: Davy Knowles at Rams Head On Stage - **Date**: Fri Sep 18 2026 at 08:00 pm (-05:00) - **Event URL**: https://allevents.in/annapolis/davy-knowles-at-rams-head-on-stage/2400028084979255 - **Venue**: Rams Head On Stage - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9mMjk1NTM2MC1iMDJmLTExZjEtOTRlMS00Mzg5ZmMwOGNhZGEtcmltZy13MTIwMC1oNjAwLWRjZjhmOGY4LWdtaXIuanBnP3Y9MTc4OTM4NTU0MA.avif - **Categories**: trips-adventures - **Event Name**: Sean Hayes at Rams Head On Stage - **Date**: Wed Sep 23 2026 at 08:00 pm – Wed Sep 23 2026 at 10:00 pm (-05:00) - **Event URL**: https://allevents.in/annapolis/sean-hayes-at-rams-head-on-stage/2400030183357827 - **Venue**: Rams Head On Stage - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy9jZjRiOTI4MC01ZjQzLTExZjEtYjE2Zi0wZjlmNDY5NWIwYzQtcmltZy13MTA4MC1oMTM1MC1kY2YzZjNmMy1nbWlyLmpwZz92PTE3ODA0ODgwMjc.avif - **Categories**: trips-adventures - **Event Name**: Gerald Albright at Rams Head On Stage - **Date**: Wed Oct 14 2026 at 08:00 pm – Wed Oct 14 2026 at 10:00 pm (-05:00) - **Event URL**: https://allevents.in/annapolis/gerald-albright-at-rams-head-on-stage/2400029903107307 - **Venue**: Rams Head On Stage - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvNjBlZjg0YzAtYjA1My0xMWYxLTgwMTEtNzM5NGY1N2Y3MDA0LXJpbWctdzEyMDAtaDU1MC1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODk0MDA3NTk.avif - **Categories**: trips-adventures - **Event Name**: Chesapeake Bay Sunset Cruise - **Description**: Set sail on the Chesapeake Bay and enjoy a breathtaking sunset with friends on this fun cruise aboard Schooner Adventurer!About this EventChesapeake Bay Sunset CruiseJoin us for an unforgettable evening on th - **Date**: Sat Oct 03 2026 at 05:00 pm – Sat Oct 03 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/chesapeake-bay-sunset-cruise/100002000619344314 - **Venue**: Safe Harbor Port Annapolis - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9mNWJhZTBhOWQxNTJkODIxMzI2MDFkMDg3NGViMWE0ZjcwNTg4YmI0ZWM4MzE0YWRlZjkyOTVjY2IxMmQ3OGU5LXJpbWctdzEyMDAtaDE2MDAtZGM2ODc4ODgtZ21pci5qcGc_dj0xNzg5MjI4ODY3.avif - **Price**: USD 87 - **Categories**: trips-adventures - **Event Name**: Jim's Marine at the Annapolis Powerboat Show - **Description**: 🚤 Join Jim's Marine at the Annapolis Powerboat Show! 🚤 The countdown is on! October 8–11, head to City Dock in Annapolis and experience some of the most exciting boats on the water. Step aboard our lineup of Tidewater boats, explore innovative features, - **Interested Audience**: - Count: 23 - **Date**: Thu Oct 08 2026 at 10:00 am – Sun Oct 11 2026 at 05:00 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/jims-marine-at-the-annapolis-powerboat-show/200030402097018 - **Venue**: Annapolis City Dock - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9mZmY4NTQzNDVmYWU1ZGI5N2M3MWIwYmY2NzU1OTI0ZWJkMzM4YWZkY2FlZDQ2MjhhNWEwNmEzN2NiMTJhZTMzLXJpbWctdzEwMjQtaDQwMC1kY2I4YjhiOC1nbWlyP3Y9MTc4ODI5ODU2NQ.avif - **Categories**: trips-adventures - **Event Name**: Navy Midshipmen vs. North Texas Mean Green - **Date**: Fri Oct 23 2026 at 07:00 pm – Sat Oct 24 2026 at 05:30 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/navy-midshipmen-vs-north-texas-mean-green/2300029784416132 - **Venue**: Navy Marine Corps Memorial Stadium - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9hYWQxZGQ1MC1hZjllLTExZjEtOTRlMS00Mzg5ZmMwOGNhZGEtcmltZy13MTIwMC1oNTE0LWRjMDgwODA4LWdtaXIuanBnP3Y9MTc4OTMyMzE0Mw.avif - **Categories**: contests, trips-adventures - **Event Name**: Annapolis Powerboat Show - Sunday - **Date**: Sat Oct 17 2026 at 07:00 pm (-05:00) - **Event URL**: https://allevents.in/annapolis/annapolis-powerboat-show-sunday/2300029291437828 - **Venue**: Annapolis City Dock - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy83YmY3ZjFmMC1lYjg1LTExZjAtOTc4OC0wNTViN2ZhNDgxZjAtcmltZy13MTIwMC1oNjM0LWRjNzg5M2E1LWdtaXIuanBnP3Y9MTc2Nzc2MTg5OQ.avif - **Categories**: trips-adventures - **Event Name**: The Carole King & James Taylor Story - Tribute Show - **Interested Audience**: - Count: 1 - **Date**: Sat Oct 10 2026 at 07:00 pm – Sun Oct 11 2026 at 09:30 pm (-04:00) - **Event URL**: https://allevents.in/annapolis/the-carole-king-and-james-taylor-story-tribute-show/2300028776169149 - **Venue**: Rams Head On Stage - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9lMGQ3N2FmMC1iMDAxLTExZjEtOTRlMS00Mzg5ZmMwOGNhZGEtcmltZy13MTIwMC1oNjc1LWRjZjhmOGY4LWdtaXIuanBnP3Y9MTc4OTM2NTc3Ng.avif - **Categories**: trips-adventures, contests - **Event Name**: Annapolis Powerboat Show - Saturday - **Date**: Fri Oct 16 2026 at 07:00 pm (-05:00) - **Event URL**: https://allevents.in/annapolis/annapolis-powerboat-show-saturday/2300029291437025 - **Venue**: Annapolis City Dock - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvN2FiNTVmZDAtZWI4NS0xMWYwLWExNTctZGRiMjBhN2FkZjk3LXJpbWctdzEyMDAtaDYzNC1kYzc4OTNhNS1nbWlyLmpwZz92PTE3Njc3NjE4OTc.avif - **Categories**: trips-adventures - **Event Name**: Annapolis Murder Mystery: Solve the case! - **Description**: ⭐ Step into the shoes of a detective and solve a thrilling murder mystery at your own pace! Can you crack the case and catch the culprit before it’s too late? Highlights 🔍 Investigate a mysterious murder and follow the trail of clues. 🗝️ Interact with sus - **Interested Audience**: - Count: 10 - **Date**: Thu Oct 01 2026 at 12:00 am – Tue Dec 01 2026 at 12:00 am (-05:00) - **Event URL**: https://allevents.in/annapolis/annapolis-murder-mystery-solve-the-case/2700030036218101 - **Venue**: 101 State Cir, Annapolis, MD 21401, USA - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy8wZjU1MWRmMC1hZmY5LTExZjEtOTRlMS00Mzg5ZmMwOGNhZGEtcmltZy13NTUwLWg1NTAtZGMxODA4MDgtZ21pci5qcGc_dj0xNzg5MzYxOTY2.avif - **Price**: USD 10 - **Categories**: trips-adventures, ghost-hunts, contests ## Trending Events in Annapolis - **Event Name**: Improv Show - Reflex Improv 10th Anniversary - **Description**: Come join Reflex Improv Friday September 18th for a night of improv comedy performed by local improvisers! Reflex is celebrating our 10th Anniversary of holding classes and shows in Annapolis!Show starts at 8pm and runs around 90 mi - **Venue**: ArtFarm - **Banner**: https://cdn2.allevents.in/thumbs/thumb6a96290d22311.jpg - **Event Name**: BAYGRASS 2026: Annapolis Baygrass Music Festival 9/19-20 - **Description**: 🏖️ Beachfront music festival at Sandy Point State Park in Annapolis, MD 😎 September 19 & 20, 2026. 🎟️ baygrassfestival.com The 2026 Annapolis Baygrass Music Festival Lineup: Little Feat Yonder Mountain String Band Béla Fleck My Bluegrass Heart S - **Venue**: 1100 E College Pkwy, Annapolis, MD, United States, Maryland 21409 - **Banner**: https://cdn-az.allevents.in/events4/banners/43578ee6b027f9d3ced47fb24e53a83f12ce1d19fdcd44bd5a09223d6bccbabc-rimg-w1200-h628-dc2878a8-gmir?v=1787426581 - **Event Name**: 21st Annual Boatyard Beach Bash - **Description**: One Incredible Night. Lasting Impact. Join us for the 21st Annual Boatyard Beach Bash! on Saturday, September 19, 2026! Spend an unforgettable evening on the shores of the Chesapeake Bay enjoying incredible food, handcrafted cocktails, live music, and b - **Venue**: 723 2nd St, Annapolis, MD, United States, Maryland 21403 - **Banner**: https://cdn-az.allevents.in/events1/banners/018231784bfc27e8c13b1f32af25d25cb98a340bf0a14557a9be696a680f59ec-rimg-w1200-h628-dc28a8e8-gmir?v=1787293332 - **Event Name**: 17th Annual Annapolis RUN for The Light House - **Description**: Half Marathon | 5K | Walk Scenic half-marathon and 5k routes along the trails of Quiet Waters Park and through the beautiful Chesapeake Bay-front community of Hillsmere Shores. This race event is unlike any other in the greater Annapolis area! Race rai - **Venue**: 600 Quiet Waters Park Rd, Annapolis, MD 21403-2700, United States - **Banner**: https://cdn-az.allevents.in/events7/banners/137333709802e04df5bddab9b2a46c87b48946d8963267488d538d2217468934-rimg-w1200-h675-dc182878-gmir?v=1787411793 - **Event Name**: The Annapolis Powerboat Show - **Description**: � Save the date! The Annapolis Powerboat Show returns October 8–11, 2026. It’s never too early to start planning for one of the biggest boating events of the year! https://www.annapolisboatshows.com/powerboat-show/ - **Venue**: Annapolis Boat Show - **Banner**: https://cdn-az.allevents.in/events1/banners/dd1f50cfdb5fa47a36ea085357af9a319f8fe1f75b5374a9ab7964e73cf8ec49-rimg-w1200-h628-dcf8f8f8-gmir?v=1788555470 - **Event Name**: Michael Franti Trio - **Venue**: Rams Head On Stage - **Banner**: https://cdn-az.allevents.in/events8/banners/e4115000-af8f-11f1-94e1-4389fc08cada-rimg-w1080-h1350-dce8e8f8-gmir.jpg?v=1789316811 - **Event Name**: Little Feat in Annapolis - **Description**: 🎶 Don't Miss this Out! Little Feat is Live at Sandy Point State Park on Saturday, September 19, 2026! 🎶 This is your moment. Little Feat is hitting Sandy Point State Park on Saturday, September 19, 2026 - **Venue**: Sandy Point State Park - **Banner**: https://cdn-az.allevents.in/events9/banners/eb66ffd0-12e6-11f1-acee-258006aecb7a-rimg-w1200-h675-dc192f2f-gmir.webp?v=1772091843 - **Event Name**: Annapolis Sailboat Show - October 2026 - **Description**: Save the Date — Annapolis Sailboat Show | October 15-18, 2026 Join Signature Catamarans at the renowned Annapolis Sailboat Show, taking place October 15–18, 2026 along the iconic City Dock in downtown Annapolis — widely recognized as one of the premier s - **Venue**: Annapolis City Dock - **Banner**: https://cdn-az.allevents.in/events7/banners/1a6daa133845d0ec328284b4eec37a5d79cf31579c326b2c12dbbea5ecdefa06-rimg-w1200-h899-dc080808-gmir?v=1787612446 - **Event Name**: Annapolis Fall Italian Festa 2026 - **Description**: 📍 620 Ridgely Avenue, Annapolis, MD 21401 🕙 Sunday, September 20 | 10 AM – 3 PM | Rain or Shine 🌎 Public Event · Everyone Welcome 🍁 Celebrate Fall – Italian Style! Join the Sons and Daughters of Italy Annapolis Lodge for a free, family-friendly Fall Itali - **Venue**: 620 Ridgely Avenue , Annapolis, MD, United States, Maryland 21401 - **Banner**: https://cdn-az.allevents.in/events7/banners/da4be76c5385f41d1d27c12644a8c22ae419583b59a3d1a80bd4f0fa2137a2cf-rimg-w1058-h430-dcc82828-gmir?v=1788301564 ## Browse Trips & Adventures Events by Date - [Trips & Adventures Events Today in Annapolis](https://allevents.in/annapolis/trips-adventures--today) - [Trips & Adventures Events This Weekend in Annapolis](https://allevents.in/annapolis/trips-adventures--this-weekend) - [Trips & Adventures Events in September in Annapolis](https://allevents.in/annapolis/trips-adventures--september) - [Trips & Adventures Events in October in Annapolis](https://allevents.in/annapolis/trips-adventures--october) ## FAQs - **Q**: What are the top Trips & Adventures events in Annapolis? - **A:** Annapolis Sailboat Show (Wed Oct 07 2026 at 07:00 pm at Annapolis City Dock), Navy Midshipmen vs. Tulsa Golden Hurricane (Fri Oct 09 2026 at 07:00 pm at Navy Marine Corps Memorial Stadium), Southern Culture On The Skids (Fri Sep 25 2026 at 07:00 pm at Rams Head On Stage), Sean Hayes (Tue Sep 22 2026 at 07:00 pm at Rams Head On Stage), Brett Dennen (Thu Sep 24 2026 at 08:00 pm at Rams Head On Stage). - **Q**: What Trips & Adventures events are happening in Annapolis this weekend September 18–20, 2026? - **A:** Davy Knowles at Rams Head On Stage (Fri Sep 18 2026 at 08:00 pm at Rams Head On Stage). - **Q**: What Trips & Adventures events are happening in Annapolis in September 2026? - **A:** Southern Culture On The Skids (Fri Sep 25 2026 at 07:00 pm at Rams Head On Stage), Sean Hayes (Tue Sep 22 2026 at 07:00 pm at Rams Head On Stage), Brett Dennen (Thu Sep 24 2026 at 08:00 pm at Rams Head On Stage), Davy Knowles at Rams Head On Stage (Fri Sep 18 2026 at 08:00 pm at Rams Head On Stage), Sean Hayes at Rams Head On Stage (Wed Sep 23 2026 at 08:00 pm at Rams Head On Stage). - **Q**: How can I find Trips & Adventures events in Annapolis? - **A:** You can discover upcoming Trips & Adventures events in Annapolis 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 Annapolis? - **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 Trips & Adventures events in Annapolis? - **A:** Some popular venues hosting Trips & Adventures events in Annapolis include Annapolis City Dock, Navy Marine Corps Memorial Stadium, Rams Head On Stage. - **Q**: What is the price range for Trips & Adventures events in Annapolis? - **A:** Prices for Trips & Adventures events in Annapolis range from USD 10 to USD 87. Many events also offer free entry. - **Q**: Who are the top organizers for Trips & Adventures events in Annapolis? - **A:** Popular organizers hosting Trips & Adventures events in Annapolis include Ticket Network Events, Vivid Events, Captain Duncan Hood. - **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 Annapolis? - **A:** Follow the Trips & Adventures category on AllEvents.in to get notified when new Trips & Adventures events are listed in Annapolis. ## 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 Severna Park](https://allevents.in/severna-park/trips-adventures) - [Events in Arnold](https://allevents.in/arnold-md) - [Events in Edgewater](https://allevents.in/edgewater-md) - [Events in Cape St Claire](https://allevents.in/cape-st-claire) - [Events in Mayo](https://allevents.in/mayo-md) - [Events in Crownsville](https://allevents.in/crownsville) - [Events in Severna Park](https://allevents.in/severna-park) - [Events in Davidsonville](https://allevents.in/davidsonville) - [Events in Lake Shore](https://allevents.in/lake-shore)