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 Chesapeake - **Event Name**: Striders Dismal Swamp 5 Miler and Kid's 1 Mile - **Description**: Course Information: 5 Miler: A 2.5-mile out and back course on the closed 2-lane roadway at the Dismal Swamp Trail Park in Chesapeake. 1 Miler: A .5 miles out and back on the same trail Start Times 5 Miler: 8:00 AM (Course will close at 10:30 AM) 1 Mi - **Interested Audience**: - Count: 144 - **Date**: Sat Apr 25 2026 at 08:00 am – Sat Apr 25 2026 at 11:00 am (-04:00) - **Event URL**: https://allevents.in/chesapeake/striders-dismal-swamp-5-miler-and-kids-1-mile/200029634622525 - **Venue**: Dismal Swamp Canal Trail - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9jYzdjNzJiYTJlZWY5OWRjNTQ2MmIyOWE3NDFhZjIzNWNlNTQwY2NkY2Q5ZjAzNmJmM2Q5ZDcyOGUyMzRiNDc0LXJpbWctdzEyMDAtaDQwMC1kYzczNzI3ZC1nbWlyP3Y9MTc3NTI2NzY4OQ.avif - **Categories**: trips-adventures, workshops, sports - **Event Name**: River Walk America 250 Picnic - **Description**: Let's Picnic and play games around the Clubhouse and in the field to celebrate the 250th anniversary of the United States of America! There will be plenty of room for pop-up tents to picnic and play games in the field -- come out with your Cornhole Board - **Interested Audience**: - Count: 7 - **Date**: Sun Jul 05 2026 at 11:00 am – Sun Jul 05 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake/river-walk-america-250-picnic/200029901136701 - **Venue**: 701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy81ZTFiYmNjNzY1MTlhODZkNWJiYTk4YzRiN2EwMTI3MTE1MmNjMmE3Zjg3NWEwZGViZTdiYzFmMjZmYmRkNWZmLXJpbWctdzEyMDAtaDYzMC1kY2MyMjc1MC1nbWlyP3Y9MTc3NTQ1OTUyMQ.avif - **Categories**: trips-adventures, food-drinks, pop-ups - **Event Name**: 🧭Adventures on the Northwest River - **Description**: 🧭Adventures on the Northwest River ✅️What's Available 🚣Kayak & Paddleboard Rentals 🚣♀️Kayak & Paddleboard Tours 🏄♂️Begginers Stand Up Paddleboard Class ⚠️All activities are by appointment only 🎟Spots are limited-reserve yours today! 📲757-2 - **Interested Audience**: - Count: 7 - **Date**: Thu May 14 2026 at 08:00 am – Thu May 14 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake/adventures-on-the-northwest-river/200029700237500 - **Venue**: Bob's Fishing hole - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy8xOTI5YjgxZTNjNTY4OTgxNDg0MDgzNzAxNWQwZGE3Y2U0OWUxMjM0ZTJkOWRhNzAzNWM1NDU4OGIyYWQzYmFhLXJpbWctdzEyMDAtaDE2MDAtZGMxOTE4MTctZ21pcj92PTE3NzYwNzYwMDc.avif - **Categories**: workshops, trips-adventures - **Event Name**: BikeFest - **Description**: This event is free and open to the public! Join us for a wonderful afternoon filled with giveaways, a food truck, a bike rodeo and bike-related vendors. Learn more about cycling and trails in Chesapeake. Bring your bike and personal safety equipment and - **Interested Audience**: - Count: 69 - **Date**: Sun May 03 2026 at 01:00 pm – Sun May 03 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake/bikefest/200029932132341 - **Venue**: 1246 Dismal Swamp Canal Trail - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy8xNzcwNTg2ZTRjNmM5MDRjYjI3NWRlN2NmZjQ0OGJmY2RlNjhmY2U0YjhlYzE5MjkxNzhiYTA5MmQ1YmI5NTQwLXJpbWctdzEyMDAtaDY3NS1kYzJlNDgxOS1nbWlyP3Y9MTc3NTk5MTgyMQ.avif - **Categories**: trips-adventures, sports, food-drinks, cycling, rodeo - **Event Name**: Mother’s Day Hike at Oak Grove Lake Park 💐🌿💗 - **Description**: Mother’s Day Hike 💐🌿 Sunday, May 10, 2026 | 8:00 AM – 10:00 AM 📍 Oak Grove Lake Park (Chesapeake) Let’s celebrate Mother’s Day with a fun, feel-good morning hike with East Coast Hikers! Moms, grandmas, bonus-moms, and anyone celebrating a mother figure a - **Interested Audience**: - Count: 160 - **Date**: Sun May 10 2026 at 08:00 am – Sun May 10 2026 at 10:00 am (-04:00) - **Event URL**: https://allevents.in/chesapeake/mother’s-day-hike-at-oak-grove-lake-park/200029413554649 - **Venue**: Oak Grove Lake Park - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvODZkNmE2MDFiOGYyMzAyNWFhNmExZjVjODdjN2M5YjE2N2JlZWY2OGVlODI2MjRmNWNiYmQ1Yjk1N2E3Y2MyMC1yaW1nLXcxMjAwLWg5MDAtZGNhYmMxZDgtZ21pcj92PTE3NzU3NjQ1NDc.avif - **Categories**: trips-adventures, meetups - **Event Name**: The Gothic Market - **Description**: 🎉 Welcome to The Gothic Market, where the impossible becomes possible and dreams take flight! 🏛️ Join us at Chesapeake Conference Center in the heart of Chesapeake, VA for an event that w - **Date**: Fri May 29 2026 at 07:00 pm (-05:00) - **Event URL**: https://allevents.in/chesapeake/the-gothic-market/2300029788981353 - **Venue**: Chesapeake Conference Center - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvZjU4ODcyMDAtMzUyOC0xMWYxLWFlNWUtMzVmMmRmNmU5N2M4LXJpbWctdzEyMDAtaDU0Ny1kYzI4MmUzNC1nbWlyLmpwZz92PTE3NzU4NTg1NDY.avif - **Categories**: business, trips-adventures, conferences - **Event Name**: Trail Therapy: Hidden Gem Hike at Indian River Park South Side (2–4 Miles) 🍄🪵🌿 - **Description**: Trail Therapy: Hidden Gem Hike at Indian River Park South Side (2–4 Miles) 🍄🪵🌿 Short, flexible, and full of nature. 🌞🥾 We’re heading into the hidden wooded side of Indian River Park where it’s all about winding trails, tree cover, and that peaceful “off- - **Interested Audience**: - Count: 54 - **Date**: Sat Apr 25 2026 at 08:30 am – Sat Apr 25 2026 at 10:30 am (-04:00) - **Event URL**: https://allevents.in/chesapeake/trail-therapy-hidden-gem-hike-at-indian-river-park-south-side-2-4-miles/200029895060309 - **Venue**: Indian River Park - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvZDdlOTJhYjIzYjk5YzkwNmMwM2Y4Y2JmNDM1NzM3OTI3YzA5YjgzMmI1YWM1MzBiMjY5MTI0N2FjMjlkYmRkMS1yaW1nLXcxMjAwLWg5MDAtZGNkMWQyZGEtZ21pcj92PTE3NzYwNzUyMjg.avif - **Categories**: trips-adventures, trekking, kids, dog - **Event Name**: D & D Adventures League - **Description**: Join the Sons for game night. - **Interested Audience**: - Count: 6 - **Date**: Fri Apr 17 2026 at 06:30 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake/d-and-d-adventures-league/200029917018152 - **Venue**: 469 N Battlefield Blvd, Chesapeake, VA, United States, Virginia 23320 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy82NTY2NjZhYjgyYTNjODgxMzE5MWFkZDUxNjQ3NzZiYWFlYWViMWUwMWU1OGJkOGI3M2NhNzI4OGI4MjYwY2FkLXJpbWctdzk4OS1oMTI4MS1kY2ZmZmZmZi1nbWlyP3Y9MTc3NTc4MjMxMg.avif - **Categories**: trips-adventures ## Trending Events in Chesapeake - **Event Name**: The 43rd Annual Chesapeake Jubilee - **Description**: 2026 CHESAPEAKE JUBILEE DATES FOOD, VENDOR & CRAFTER APPLICATIONS ARE LIVE! Vendors interested in joining our event are welcome to reach out to Capp98907@gmail.com. vendor apply(https://forms.gle/HJ8Yc2UDmFNZD4699) We now have additional openings ava - **Venue**: 900 Greenbrier Pkwy, Chesapeake, VA 23320-3677, United States - **Banner**: https://cdn-az.allevents.in/events10/banners/7d565f2f0ef8437a331c87fb387b11181a0046adcbab7c6f4ebfe4f3db5325f0-rimg-w1200-h1200-dc010101-gmir?v=1775956972 - **Event Name**: Chesapeake Spring Arts Festival - **Description**: Experience the vibrant heart of Chesapeake at our Spring Art Festival, where over 170 artists bring the city to life with their creativity. The Rotary Club of Chesapeake, in conjunction with the Chesapeake Fine Arts Commission, is having our sixth annual - **Venue**: Chesapeake City Park - **Banner**: https://cdn-az.allevents.in/events5/banners/e8eed3b08786fbd5ece4b965ca5794342d173c6482a377d527a9fc2a39a12205-rimg-w1200-h540-dc785c48-gmir?v=1776128836 - **Event Name**: Chesapeake Virginia Wine Festival - **Description**: 16th Annual Chesapeake Virginia Wine Festival Presented by Atlantic Union Bank Join us for a day of premier tastings and community impact! All proceeds benefit the Chesapeake Rotary Club Community Charities. ✨ What to Expect: Unlimited Sampling: Sip you - **Venue**: Chesapeake City Park - **Banner**: https://cdn-az.allevents.in/events4/banners/e51858834b3803265f2801a1d7554534e7ef81a060966711e3d366a8275c9fb6-rimg-w1200-h628-dcf1f1f0-gmir?v=1776032776 - **Event Name**: Pride in the 'Peake 2026 - **Description**: We are excited to announce the date and location for the 5th Annual Pride in the 'Peake celebration! This year, we will be headed back to Chesapeake City Park on June 14th, 2026 from 12:00pm to 5:00pm for five wonderful hours of love, inclusion, and com - **Venue**: Chesapeake City Park - **Banner**: https://cdn-az.allevents.in/events4/banners/be228832368b941cd9a1fa8aac7273f4a9e66e07f3c5d8d8a5f78d7f9587b3ff-rimg-w640-h360-dc010101-gmir?v=1775480011 - **Event Name**: 11th Annual Touch-a-Truck - **Description**: Touch-a-Truck™ is a hands-on learning experience for children to explore, climb and touch their favorite big trucks and vehicles as well as meet the professionals who protect, build and serve the South Hampton Roads community. We will have fire trucks, - **Venue**: Greenbrier Mall - **Banner**: https://cdn2.allevents.in/thumbs/thumb69a3a5422be08.jpg - **Event Name**: Tidewater Strider Spring Marathon and Half Marathon - **Description**: Course Information: The Marathon (26.2 mi) and Half Marathon (13.1 mi) take place on the closed 2-lane roadway at the Dismal Swamp Trail Park in Chesapeake. The Full Marathon course is a USATF Certified Course—this means this is a great Boston Qualifyin - **Venue**: Dismal Swamp Canal Trail - **Banner**: https://cdn-az.allevents.in/events10/banners/9a7d626bbb3442357e9c6665a20655c223e727dce88784e810c69f783368d454-rimg-w1200-h400-dc74727d-gmir?v=1775783116 - **Event Name**: Chesapeake Polish Fest - **Description**: St. Mary Catholic Church in Chesapeake will host its annual Polish Festival on Saturday, April 25th 10am - 5pm. All are invited to celebrate more than a century of this Catholic community's Polish heritage! Come enjoy Polish music, a Polish goods store, a - **Venue**: 536 Homestead Rd , Chesapeake, VA, United States, Virginia - **Banner**: https://cdn-az.allevents.in/events4/banners/aa3534a07dbc3615636a4e6899e51dca25b994ef83cc6529e274c4fa8b944870-rimg-w1200-h676-dcffffff-gmir?v=1775765276 - **Event Name**: South Norfolk Ruritans 19th Annual Blue Crab Festival - **Description**: WE ARE EXCITED TO ANNOUNCE TICKETS FOR OUR ANNUAL CRAB FEST ARE NOW ON SALE Hope to see you there ! ������������ https://events.humanitix.com/south-norfolk-ruritans-19th-annual-blue-crab-festival - **Venue**: Chesapeake City Park - **Banner**: https://cdn-az.allevents.in/events2/banners/b175085ba6d8983406b9ef4fd766fbef489130d573f1f89e061492128ef20e1d-rimg-w500-h250-dc2e1914-gmir?v=1775928193 - **Event Name**: The Gothic Market (May 30, 2026) Chesapeake/Virginia Beach Area - **Description**: Entry: In order to attend this event, you must have tickets in advance. Not only is it cheapest to get tickets earlier, but there is no cash entry. Ticket prices increase towards the event date ($15+), so why reserve later and pay more? Same Event & - **Venue**: Chesapeake Conference Center | 700 Conference Center Dr, Chesapeake, VA 23320 - **Banner**: https://cdn-az.allevents.in/events6/banners/423d4171b9cb6e9c514afebc5fe7982be564b57ce3248dd1972dbbb7df803485-rimg-w1024-h1024-dc1b1314-gmir?v=1775922637 ## Browse Trips & Adventures Events by Date - [Trips & Adventures Events Today in Chesapeake](https://allevents.in/chesapeake/trips-adventures--today) - [Trips & Adventures Events This Weekend in Chesapeake](https://allevents.in/chesapeake/trips-adventures--this-weekend) - [Trips & Adventures Events in April in Chesapeake](https://allevents.in/chesapeake/trips-adventures--april) - [Trips & Adventures Events in May in Chesapeake](https://allevents.in/chesapeake/trips-adventures--may) ## FAQs - **Q**: What are the top Trips & Adventures events in Chesapeake? - **A:** Striders Dismal Swamp 5 Miler and Kid's 1 Mile (Sat Apr 25 2026 at 08:00 am at Dismal Swamp Canal Trail), River Walk America 250 Picnic (Sun Jul 05 2026 at 11:00 am at 701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States), 🧭Adventures on the Northwest River (Thu May 14 2026 at 08:00 am at Bob's Fishing hole), BikeFest (Sun May 03 2026 at 01:00 pm at 1246 Dismal Swamp Canal Trail), Mother’s Day Hike at Oak Grove Lake Park 💐🌿💗 (Sun May 10 2026 at 08:00 am at Oak Grove Lake Park). - **Q**: What Trips & Adventures events are happening in Chesapeake this weekend April 17–19, 2026? - **A:** D & D Adventures League (Fri Apr 17 2026 at 06:30 pm at 469 N Battlefield Blvd, Chesapeake, VA, United States, Virginia 23320). - **Q**: What Trips & Adventures events are happening in Chesapeake in April 2026? - **A:** Striders Dismal Swamp 5 Miler and Kid's 1 Mile (Sat Apr 25 2026 at 08:00 am at Dismal Swamp Canal Trail), Trail Therapy: Hidden Gem Hike at Indian River Park South Side (2–4 Miles) 🍄🪵🌿 (Sat Apr 25 2026 at 08:30 am at Indian River Park), D & D Adventures League (Fri Apr 17 2026 at 06:30 pm at 469 N Battlefield Blvd, Chesapeake, VA, United States, Virginia 23320). - **Q**: How can I find Trips & Adventures events in Chesapeake? - **A:** You can discover upcoming Trips & Adventures events in Chesapeake 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 Chesapeake? - **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 Chesapeake? - **A:** Some popular venues hosting Trips & Adventures events in Chesapeake include Dismal Swamp Canal Trail, 701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States, Bob's Fishing hole. - **Q**: Who are the top organizers for Trips & Adventures events in Chesapeake? - **A:** Popular organizers hosting Trips & Adventures events in Chesapeake include Tidewater Striders Club, River Walk Family Events, Adventure Kayak & SUP Tours. - **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 Chesapeake? - **A:** Follow the Trips & Adventures category on AllEvents.in to get notified when new Trips & Adventures events are listed in Chesapeake. ## 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 Washington](https://allevents.in/washington/trips-adventures) - [Trips & Adventurous Activities in Baltimore](https://allevents.in/baltimore/trips-adventures) - [Trips & Adventurous Activities in Raleigh](https://allevents.in/raleigh/trips-adventures) - [Trips & Adventurous Activities in Richmond](https://allevents.in/richmond/trips-adventures) - [Trips & Adventurous Activities in Virginia Beach](https://allevents.in/virginia-beach/trips-adventures) - [Trips & Adventurous Activities in Norfolk](https://allevents.in/norfolk/trips-adventures) - [Trips & Adventurous Activities in Alexandria](https://allevents.in/alexandria/trips-adventures) - [Trips & Adventurous Activities in Durham](https://allevents.in/durham-nc/trips-adventures)