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**: 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**: trips-adventures ## Trending Events in Leonardtown - **Event Name**: 40th Annual St Mary's County Crab and Music Festival - **Description**: Get ready to rock at the 40th Annual St. Mary's County Crab & Music Festival! 🦀🎶 📅 Date: Saturday, June 13, 2026 📍 Location: St. Mary's County Fairgrounds Join us for an unforgettable day packed with delicious seafood, family fun, and electrifying l - **Venue**: St. Mary's County Fairgrounds - **Banner**: https://cdn-az.allevents.in/events9/banners/b1dca218be17b5d41948cc89b33d4ce57ea8ba199922920d29b743b1a0584bec-rimg-w909-h1159-dcffffff-gmir?v=1775997687 - **Event Name**: St. Mary’s Freedom Fest - **Description**: St. Mary’s Freedom Fest will be held Friday, July 3, 2026, marking America’s 250th anniversary 🇺🇸 Free admission • Fireworks at dark - **Venue**: St. Mary’s Freedom Fest - **Banner**: https://cdn-az.allevents.in/events1/banners/63a8b8fa022ba524aa470fae6d90c380d6c730c082722d01829c4e97c4d6babe-rimg-w1200-h1189-dc0557ac-gmir?v=1776219646 - **Event Name**: Yung Joc LIVE at The Rex — It's Goin' Down in Leonardtown - **Description**: Grammy-nominated rap legend Yung Joc headlines a LIVE night at The Rex with The Future Band & DJ Papers. May 2 · Leonardtown, MD.About this EventSouthern Maryland, the wait is over.May 2, 2026, The Rex The - **Venue**: The Rex - **Banner**: https://cdn-az.allevents.in/events10/banners/6ee9b456b0a851ed88430555c0a76c204582712fe98b119fb0d905b5a3c60e74-rimg-w1200-h1466-dc020101-gmir.jpg?v=1773749838 - **Event Name**: Leprechaun Lilly's Kids Consignment Sale - 2026 Spring/Summer - **Description**: **Register NOW** **NO ENTRY FEE to shop** Leprechaun Lilly's 2026 Spring/Summer Kid's Consignment Sale April 16-18, 2026 St. Mary's County Fairgrounds Thu, Apr 16: 4PM-9PM – Presales (Helpers, Consignors, & Registered First Time Parents/Grandparents - **Venue**: 42455 Fairgrounds Rd, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events2/banners/81ba3ffbaf53b563bc316f07179baacc3971c29c2f45844c1510ddc6db0c1ea1-rimg-w1200-h628-dcffffff-gmir?v=1775670144 - **Event Name**: RenFest Southern Maryland - **Description**: An enchanted celebration of fun and feasting, live music and merriment, welcoming mystical creatures and noble characters to play along!About this EventStep Back in Time at RenFest Southern Maryland, vote - **Venue**: Brüdergarten (Brü) - **Banner**: https://cdn-az.allevents.in/events1/banners/425c8dc68783177291870571706e94823b7b8a19834036a342392197475e5ea0-rimg-w1200-h800-dcd9dfea-gmir.jpg?v=1770864487 - **Event Name**: Paint and Sip - **Description**: 🌸🎨 Let’s Welcome Spring with a Cherry Blossom Paint & Sip! 🍷🌸 Join us on April 18 at 6 PM at beautiful Port of Leonardtown Vineyard for a magical evening of creativity, wine, and springtime vibes! We’ll be painting a stunning cherry blossom masterpi - **Venue**: Port of Leonardtown Winery - **Banner**: https://cdn-az.allevents.in/events2/banners/ee23339e0e798ce7dfc0d4fb9f1dc0f67823a79ad9ba8999a381073fc505b869-rimg-w1200-h1592-dc63c5b8-gmir?v=1775819800 - **Event Name**: Rabies Clinic with SMAWL @ St. Mary's Fair Grounds - **Description**: Low-Cost Vaccination Clinics St. Mary’s Animal Welfare League, in partnership with St. Mary’s County Health Department, offers monthly low-cost rabies and distemper vaccinations, as well as microchipping to the public for their cats and dogs. Th - **Venue**: St. Mary's County Fairgrounds - **Banner**: https://cdn-az.allevents.in/events9/banners/78be2d11aae5384e52fb48dd5bddd2717cd4dbbf1227fe863a714fec032a1063-rimg-w1200-h628-dcffffff-gmir?v=1775202190 - **Event Name**: Spin It Again at RenFest Southern MD - **Description**: **SPONSORED BY BRUDERGARTEN BEER GARDEN** Medieval and Renaissance Life Festival: Live Music, demonstrations, vendors, food, drinks, petting zoo *THIS IS A TICKETED EVENT! Please visit www.renfestsomd.com FOR FURTHER INFORMATION* - **Venue**: Brudergarten Beer Garden at Shepherd’s Old Field Market - **Banner**: https://cdn-az.allevents.in/events2/banners/28c314a637a06b108d7057988628711d59489b123979791dbd29e81588d5ec71-rimg-w869-h425-dc56bbbd-gmir?v=1775921149 - **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-dcffffff-gmir?v=1774908171 ## 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 April in Leonardtown](https://allevents.in/leonardtown/trips-adventures--april) - [Trips & Adventures Events in May in Leonardtown](https://allevents.in/leonardtown/trips-adventures--may) ## 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**: 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 Coltons Point](https://allevents.in/coltons-point/trips-adventures)