To Travel the world is to travel within oneself. For all the adrenaline junkies out there are cool adventure events in [CITY] 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 [CITY], we have got you covered.
Find your adventure and trips near [CITY].
## Trips & Adventures Events in Leonardtown - **Event Name**: 2026 Sultana Adult Paddling Experience-St. Mary's, MD - **Description**: Join the experienced staff of the Sultana Education Foundation for this four day kayaking expedition based from the Inn at Leonardtown.About this EventJoin the experienced staff of the Sultana Education Foundation for thi - **Date**: Tue Sep 08 2026 at 09:00 am – Fri Sep 11 2026 at 03:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/2026-sultana-adult-paddling-experience-st-marys-md/100001981367993004 - **Venue**: The Inn at Leonardtown, Ascend Hotel Collection - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8xZGIwMDBhYTEyNmZlYTA1MTg0MDI1OWY2YTY0YmJiNDcwODBmZjhlMjcwZjU0MTg3NTZiMmUzYTM2ZDRmNjI2LXJpbWctdzEyMDAtaDU1NC1kYzVjNjI0Ni1nbWlyLmpwZz92PTE3NjkxMTU3Mjk.avif - **Price**: USD 1,592 to 1,800 - **Categories**: fitness, trips-adventures - **Event Name**: Heroes on the Water, Maryland Chapter - Kayak Fishing at Saint Mary's Lake - **Description**: Come out and have an awesome day with the Heroes on the Water Maryland Chapter - it's kayak fishing time at St. Mary's Lake! It's free too!About this EventThis is a free kayak fishing event that will be held at Saint Mary - **Date**: Sat Aug 08 2026 at 07:00 am – Sat Aug 08 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/heroes-on-the-water-maryland-chapter-kayak-fishing-at-saint-marys-lake/100001980733708843 - **Venue**: Saint Marys River State Park - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy81YWZiZjJjYWI5YjYyYWZmZjcyOWY3Y2Q2MWRhNDc3YTdiMmZiZmE3NzRhMTEwNWVlZWZjZGMxMDUzMjUxYWM0LXJpbWctdzcyMC1oNzIwLWRjZGVmMWZlLWdtaXIuanBnP3Y9MTc2ODk2MDIwNg.avif - **Price**: Free - **Categories**: fitness, trips-adventures ## Trending Events in Leonardtown - **Event Name**: St. Mary's County Fair - 2026 - **Description**: St. Mary's County Fair for 2026 Please submit your items on Wednesday, 23 September 2026, from 1p-8p. *Important Note*: There should be a virtual system in place to submit your list of items this year! Please be on the lookout for this new entry method! - **Venue**: St Marys County Fair - **Banner**: https://cdn-az.allevents.in/events3/banners/47f43fa6e50b6d91d19da175fb419b7f31d664017217c10ff3cdc368a41b6942-rimg-w1200-h675-dc58a8e8-gmir?v=1786153849 - **Event Name**: Summer Smash 2.0 - **Description**: Powered By: @_iamlegendarytwain @divazincproductions @pheonix_always_risesAbout this EventLITTY ALERT‼This a Public Service Announcement 📣SUMMER SMASH 2.0(((Bounce & Crank Edition))) - **Venue**: The Rex - **Banner**: https://cdn-az.allevents.in/events6/banners/6892d48d9b73d4f0cc526fd20151875cb53f767fa06757516e62c399d48afa8e-rimg-w1054-h1494-dc181814-gmir.jpg?v=1783431187 - **Event Name**: Paws &Popcorn Movie Night: The Lion King - **Description**: Join us for a special showing of Disney’s The Lion King (animated)—a timeless story of friendship, courage, and finding your place in the circle of life… now with a few extra whiskers and purrs along the way. Whether you grew up with Simba or you’re intro - **Venue**: Meow Dyer Cat Cafe, LLC - **Event Name**: Blessing of the Fleet 2026 - **Description**: Celebration honoring Southern Maryland Watermen's heritage and community - a family-friendly day with fireworks at 8 pm! - **Venue**: Leonardtown Wharf - **Banner**: https://cdn-az.allevents.in/events5/banners/d8a35b0fcdcd833cb9a4864b6d21bc6ec57f1bb79857967d9afbc236c3fc27e0-rimg-w1200-h1200-dce8e8d8-gmir?v=1785763650 - **Event Name**: Home for The Holidays - A New St. Mary's County Holiday Tradition - **Description**: Home for the Holidays is a festive community event benefiting Christmas in April St. Mary's County, bringing families together to celebrate.About this EventHome for the Holidays is a festive community event benefiting Chr - **Venue**: Saint Mary's Fairgrounds - **Banner**: https://cdn-az.allevents.in/events8/banners/785d31d9df135c14bf14f433a0fe0d4cc612cb27d088d549ac2741a6c19a3f2d-rimg-w1054-h1492-dcf2ddb6-gmir.jpg?v=1784270780 - **Event Name**: Monster Mash Bash - **Description**: Get ready for a fang-tastic night of Halloween fun at the Monster Mash Bash, where ghosts, goblins, and ghouls of all ages are invited to join the festivities! This Halloween extravaganza is packed with activities, treats, and entertainment that will make - **Venue**: Leonardtown Wharf - **Banner**: https://cdn-az.allevents.in/events6/banners/77b81da018d8c9a39be14504d288b5d0418ebc8d23e569370a8cf489502a5ca2-rimg-w1200-h675-dcf8f8f8-gmir?v=1786153843 - **Event Name**: Arts & Entertainment Celebration First Friday - **Description**: Join us for a special First Friday in September, when we celebrate the anniversary of becoming the first Arts and Entertainment District in Southern Maryland. Enjoy live music, art activities & demonstrations, vendors and more! For more information, - **Venue**: Leonardtown Square - **Banner**: https://cdn-az.allevents.in/events7/banners/f9b4dbef7c10d2ba6ccf0cbaea40b1c8cfcbf3bce1c21e08ca1124929b07245b-rimg-w1200-h675-dcf8f8f8-gmir?v=1785808640 - **Event Name**: Outdoor Art & Movie Night - **Description**: Enjoy a magical evening under the stars with a free outdoor movie at the Town Market! Plus, we’ll have sidewalk chalk and art activities to participate in before the move starts! Grab your blanket or lawn chair, relax, and watch a family-friendly film (TB - **Venue**: Town Market LLC - **Banner**: https://cdn-az.allevents.in/events7/banners/c74ce57e47193c3ea24d9e7cd50326132856e621819b85603d00b10b2fa86369-rimg-w1200-h675-dcf8f8f8-gmir?v=1786153847 - **Event Name**: The Joe Cox Band LIVE @ The Rex Theatre - **Description**: One Night. One Stage. All Country. 🎶 Country music is coming to The Rex, and you won’t want to miss it. Join the Joe Cox Band on Saturday, August 29 from 7:00–10:00 PM for three hours of live country music 🤠, southern rock 🎸, and crowd-favorite singalong - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events2/banners/f6c47415231eb601583ea2448dd857f8c019cb8d9014625496a5602237728b2f-rimg-w1200-h1578-dc141217-gmir?v=1784306722 ## Browse Trips & Adventures Events by Date - [Trips & Adventures Events Today in Leonardtown](https://allevents.in/leonardtown/trips-adventures--today) - [Trips & Adventures Events This Weekend in Leonardtown](https://allevents.in/leonardtown/trips-adventures--this-weekend) - [Trips & Adventures Events in August in Leonardtown](https://allevents.in/leonardtown/trips-adventures--august) - [Trips & Adventures Events in September in Leonardtown](https://allevents.in/leonardtown/trips-adventures--september) ## FAQs - **Q**: What are the top Trips & Adventures events in Leonardtown? - **A:** 2026 Sultana Adult Paddling Experience-St. Mary's, MD (Tue Sep 08 2026 at 09:00 am at The Inn at Leonardtown, Ascend Hotel Collection), Heroes on the Water, Maryland Chapter - Kayak Fishing at Saint Mary's Lake (Sat Aug 08 2026 at 07:00 am at Saint Marys River State Park). - **Q**: What are the top free Trips & Adventures events in Leonardtown? - **A:** Heroes on the Water, Maryland Chapter - Kayak Fishing at Saint Mary's Lake (Sat Aug 08 2026 at 07:00 am at Saint Marys River State Park). - **Q**: What Trips & Adventures events are happening in Leonardtown today August 08, 2026? - **A:** Heroes on the Water, Maryland Chapter - Kayak Fishing at Saint Mary's Lake (Sat Aug 08 2026 at 07:00 am at Saint Marys River State Park). - **Q**: What Trips & Adventures events are happening in Leonardtown this weekend August 7–9, 2026? - **A:** Heroes on the Water, Maryland Chapter - Kayak Fishing at Saint Mary's Lake (Sat Aug 08 2026 at 07:00 am at Saint Marys River State Park). - **Q**: What Trips & Adventures events are happening in Leonardtown in August 2026? - **A:** Heroes on the Water, Maryland Chapter - Kayak Fishing at Saint Mary's Lake (Sat Aug 08 2026 at 07:00 am at Saint Marys River State Park). - **Q**: How can I find Trips & Adventures events in Leonardtown? - **A:** You can discover upcoming Trips & Adventures events in Leonardtown 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 Leonardtown? - **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 Leonardtown? - **A:** Some popular venues hosting Trips & Adventures events in Leonardtown include The Inn at Leonardtown, Ascend Hotel Collection, Saint Marys River State Park. - **Q**: What is the price range for Trips & Adventures events in Leonardtown? - **A:** Prices for Trips & Adventures events in Leonardtown range from USD 1,592 to USD 1,800. Many events also offer free entry. - **Q**: Who are the top organizers for Trips & Adventures events in Leonardtown? - **A:** Popular organizers hosting Trips & Adventures events in Leonardtown include Sultana Education Foundation Public Paddles, Heroes on the Water Maryland Chapter. - **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 Leonardtown? - **A:** Follow the Trips & Adventures category on AllEvents.in to get notified when new Trips & Adventures events are listed in Leonardtown. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/d4/526b9c2f9443799c294c7c3b6e3343/freepik__candid-photography-with-natural-textures-and-highl__27226-1.webp ## Trips & Adventurous Activities from nearby cities - [Trips & Adventurous Activities in Hollywood](https://allevents.in/hollywood-md/trips-adventures) - [Trips & Adventurous Activities in California](https://allevents.in/california-md/trips-adventures) - [Trips & Adventurous Activities in Coltons Point](https://allevents.in/coltons-point/trips-adventures)