To Travel the world is to travel within oneself. For all the adrenaline junkies out there are cool adventure events in Chesapeake 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 itβs swimming, river rafting, rappelling , riding with motorcycle club or cycling with friends or just a weekend getaway near Chesapeake, we have got you covered.
Find your adventure and trips near Chesapeake.
## Trips & Adventures Events in Chesapeake - **Event Name**: π· Sundresses & Linen Wine Hop Bus Tour π - **Description**: π· Sundresses & Linen Wine Hop Bus Tour π Saturday, August 29, 2026 Get ready for a full day of good wine, good vibes, and unforgettable memories with Brooks Adventures! Grab your favorite sundress, linen fit, and your travel crew because we are headi - **Interested Audience**: - Count: 31 - **Date**: Sat Aug 29 2026 at 08:00 am (-04:00) - **Event URL**: https://allevents.in/chesapeake/sundresses-and-linen-wine-hop-bus-tour/200030185971044 - **Venue**: Chesapeake, Virginia - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy85NDAwNDE0MGY2ZTc4MTI5ZjZmZDg0ZTY4ZTg3MTkwYWEzNTE4MTRhYmY4MDk5NTViODBhNjEyYTNlZGM3ODQxLXJpbWctdzEyMDAtaDEyMDAtZGNlOGQ4YzgtZ21pcj92PTE3ODY1NzQ4MDY.avif - **Categories**: trips-adventures - **Event Name**: First Annual FloDo Golf Outing - FREE for Police, Fire, First Responders , and Active Military - **Description**: β³ Get ready for the First Annual FloDo Golf Outing β FREE for Police, Fire, First Responders , and Active Military β π Sign up here: https://form.jotform.com/260705899794174 Join us for a day of competition, camaraderie, and community. This event bring - **Interested Audience**: - Count: 42 - **Date**: Mon Aug 24 2026 at 08:00 am (-04:00) - **Event URL**: https://allevents.in/chesapeake/first-annual-flodo-golf-outing-free-for-police-fire-first-responders-and-active-military/200030142618708 - **Venue**: 1301 Volvo Pkwy, Chesapeake, VA 23320-9420, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy8xNTViYTdkZjBmNGY5NDI0YzBkNmVlZTcyYzk5OTg2ZTM2ODYyMjBkM2YzZjhkNWViNDdlYTMxZTY5ZjRjMWNjLXJpbWctdzEyMDAtaDY5OS1kYzM4OThkOC1nbWlyP3Y9MTc4NzIwNTI2OQ.avif - **Categories**: sports, trips-adventures, golf, contests - **Event Name**: Foodies + New Friends: Chesapeake - **Description**: Seeking new friends in your city? Connect with other locals over fun food and a relaxed atmosphere at our dinner series!About this Event40% of Americans are eating out at restaurants less thanks to the rise of food delive - **Date**: Fri Sep 11 2026 (-05:00) - **Event URL**: https://allevents.in/chesapeake/foodies-new-friends-chesapeake/100001967798673805 - **Venue**: Restaurant of the Week - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy85NTRmOTJkYWJjNzQ0ZGU5MjdmMzBiNzU2NDI0N2M4ZTIxY2M1YjY2NjExYjNiYTUyODNiMDA4ZmY3NjYwMWIzLXJpbWctdzEyMDAtaDIxMzMtZGNkN2Q5ZDgtZ21pci5qcGc_dj0xNzYyODgxNDg2.avif - **Price**: USD 18 - **Categories**: trips-adventures, nonprofit, calendar - **Event Name**: Snout and About - **Description**: Snout & About is a weekly field trip program that allows the local community to take a shelter dog out for the day. No experience is necessary, children are welcome, and all supplies are provided! - **Interested Audience**: - Count: 7 - **Date**: Sat Aug 22 2026 (-04:00) - **Event URL**: https://allevents.in/chesapeake/snout-and-about/200030259127033 - **Venue**: 2100 S Military Highway, Chesapeake, VA, United States, Virginia 23320 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9kNjYxYWQ5ODIyNDY2Y2M2NjZkZGJmMTRhOGFlNmM0MjkxNjI4ODJhY2FjYjljNzBiMWVjNDFlNzAyNTk1YjU4LXJpbWctdzg1MS1oMzE1LWRjMGRjMGRmLWdtaXI_dj0xNzgxNzM2NTEz.avif - **Categories**: dog - **Event Name**: Let's Conquer the Dragons - **Description**: Letβs Conquer the Dragons! π Friday Sept. 4th - Monday Sept. 7th π’ Meet Time & Safety Brief: 8:15 AM β Kickstands Up: Immediately after briefing π MeetβUp Location: Wawa 720 Woodlake Dr, Chesapeake, VA, 23320 (Off Greenbrier Parkway) Lead RC - George - **Interested Audience**: - Count: 15 - **Date**: Fri Sep 04 2026 at 08:15 am β Mon Sep 07 2026 at 04:30 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake/lets-conquer-the-dragons/200030247778010 - **Venue**: Wawa (720 Woodlake Drive, Chesapeake, VA) - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9kNGY5MTZjM2I2MTg1NjU2YjY5MWRhZGIwNTAxMTY2NTc5ZDQwZmUxZmNmMzBiYWM0ZGQwOGY2ZGUyYTZjMDY4LXJpbWctdzEyMDAtaDY3My1kYzE4MjgyOC1nbWlyP3Y9MTc4Njc0NDM3OA.avif - **Categories**: trips-adventures, contests, food-drinks - **Event Name**: Mackey's Marina Run to Roper - **Description**: Mackey's Marina Run to Roper Sunday September 13th 8:00 AM Meet at Wawa 720 Woodlake Dr Chesapeake, VA Second meeting place: Duck Thru 6125 Whaleyville Blvd Suffolk, VA Road Captain: George B Sweep RC: Regie F Estimated Mileage: 200 miles Estimated ret - **Interested Audience**: - Count: 9 - **Date**: Sun Sep 13 2026 at 08:00 am β Sun Sep 13 2026 at 03:30 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake/mackeys-marina-run-to-roper/200030539455250 - **Venue**: Wawa (720 Woodlake Drive, Chesapeake, VA) - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy8wMjk2MTZkZTBmOGM5NzZhNjc2ZTRmNGQ0ZjM1YjAxZjg4ZWFiYWQ3MTY1YzNjNzAyMWFhOTJjMzI2ZDljNjNkLXJpbWctdzYyMi1oNDkzLWRjZjhmOGY4LWdtaXI_dj0xNzg2NDM5Mjc1.avif - **Categories**: meetups, trips-adventures ## Trending Events in Chesapeake - **Event Name**: Combat Sports Challenge 46 at Chesapeake Conference Center - **Venue**: Chesapeake Conference Center - **Banner**: https://cdn-az.allevents.in/events1/banners/ed6254c0-9a58-11f1-9bc6-8b4f56db6c43-rimg-w1008-h977-dc180808-gmir.png?v=1786984215 - **Event Name**: The Craft Beer Social - **Description**: Hops of Reese & The Garage Brewery Present: πΊ ππ‘π ππ«πππ ππππ« ππ¨ππ’ππ₯ π Saturday, August 29th from 12-5pm π The Garage Brewery Taproom π΄ Big Mikeβs Q & Derpy Dogs ποΈ $45 ticket gets you a commemorative glass & unlimited tastings!! This isnβt y - **Venue**: 1011 Eden Way N, Chesapeake, VA - **Banner**: https://cdn-az.allevents.in/events7/banners/e8cba645d3f7166f5811df7f70064e37e3cc66b726d812f10ef27e6188aecced-rimg-w1080-h1350-dc102944-gmir?v=1785131398 - **Event Name**: Dear Summer All White Labor Day Party β 3rd Annual Edition - **Description**: Dear Summer All White Labor Day Party β 3rd Annual Edition Sunday, September 6th | 4PM β 11PM Cutlass Grille Jamaican Jerk Barbeque 725 EdenAbout this EventThe summer isn't officially over until we celeb - **Venue**: Cutlass Grille - **Banner**: https://cdn-az.allevents.in/events5/banners/bf0ea85f6b30a4545a0ebbd26ce39da98a8923976986ab2d3a9bd939328b529e-rimg-w1200-h593-dcffffff-gmir.jpg?v=1781557565 - **Event Name**: 6th Annual Somewhere Over The Rainbow Gala - **Description**: Join us for the 6th Annual Somewhere Over The Rainbow Gala, a fun in-person night celebrating hope and color!About this EventThe 6th Annual "Somewhere Over the Rainbow" Gala Prese - **Venue**: Delta Hotels Chesapeake Norfolk - **Banner**: https://cdn-az.allevents.in/events7/banners/0e8c73431ff6e8eb63ff139b5e94146904086e0f36ccbd535d625e7da2811a5b-rimg-w1200-h675-dc015da3-gmir.jpg?v=1777380071 - **Event Name**: Symphony Under the Stars - **Description**: Join us for a free, family-friendly concert with the Virginia Symphony Orchestra on the Bagley Stage! Free parking. A variety of food trucks will be available for an evening picnic. Bring your own chairs or blanket. Pop-up tents and oversized umbrellas ar - **Venue**: City Park Dr, Chesapeake, VA 23320, United States - **Banner**: https://cdn-az.allevents.in/events1/banners/68b993a1976caae0e8dbbf3bae726979281d9e66acdf740f321e41d046e30880-rimg-w800-h800-dc080808-gmir?v=1787030071 - **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 ! οΏ½οΏ½οΏ½οΏ½οΏ½οΏ½οΏ½οΏ½οΏ½οΏ½οΏ½οΏ½ 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-dc180808-gmir?v=1786753577 - **Event Name**: Seafood Fest - **Description**: π¦π¦πΆ KHEDIVE SHRINE CENTER SEAFOOD FEST 2026 πΆπ¦π¦ Get ready for an afternoon of amazing food, live music, and great company at the Khedive Shrine Center Seafood Fest! Bring your family and friends and enjoy an all-you-can-eat seafood feast packed with favo - **Venue**: 645 Woodlake Dr, Chesapeake, VA - **Banner**: https://cdn-az.allevents.in/events5/banners/95be5f3779ec281b7f7a742409783412f6c027c7ebec2ff16c364de0d3da2646-rimg-w945-h2048-dc080808-gmir?v=1787162410 - **Event Name**: The Gathering Table | Premium Cellar Bottle Share - **Description**: An intimate, premium bottle share featuring exceptional wines, great conversation, and a community of fellow wine lovers.About this EventJoin us for an intimate evening of exceptional wine, meaningful conversation, and wo - **Venue**: WineStyles Chesapeake - **Banner**: https://cdn-az.allevents.in/events1/banners/73349b680bb2edd9bdf3061eabfabaef614bd721ed7113c31c78baa8494d90ba-rimg-w1200-h600-dc080808-gmir.jpg?v=1785585194 - **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. β¨ 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=1776692423 ## 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 August in Chesapeake](https://allevents.in/chesapeake/trips-adventures--august) - [Trips & Adventures Events in September in Chesapeake](https://allevents.in/chesapeake/trips-adventures--september) ## FAQs - **Q**: What are the top Trips & Adventures events in Chesapeake? - **A:** π· Sundresses & Linen Wine Hop Bus Tour π (Sat Aug 29 2026 at 08:00 am at Chesapeake, Virginia), First Annual FloDo Golf Outing - FREE for Police, Fire, First Responders , and Active Military (Mon Aug 24 2026 at 08:00 am at 1301 Volvo Pkwy, Chesapeake, VA 23320-9420, United States), Foodies + New Friends: Chesapeake (Fri Sep 11 2026 at Restaurant of the Week), Snout and About (Sat Aug 22 2026 at 2100 S Military Highway, Chesapeake, VA, United States, Virginia 23320), Let's Conquer the Dragons (Fri Sep 04 2026 at 08:15 am at Wawa (720 Woodlake Drive, Chesapeake, VA)). - **Q**: What Trips & Adventures events are happening in Chesapeake this weekend August 21β23, 2026? - **A:** Snout and About (Sat Aug 22 2026 at 2100 S Military Highway, Chesapeake, VA, United States, Virginia 23320). - **Q**: What Trips & Adventures events are happening in Chesapeake in August 2026? - **A:** π· Sundresses & Linen Wine Hop Bus Tour π (Sat Aug 29 2026 at 08:00 am at Chesapeake, Virginia), First Annual FloDo Golf Outing - FREE for Police, Fire, First Responders , and Active Military (Mon Aug 24 2026 at 08:00 am at 1301 Volvo Pkwy, Chesapeake, VA 23320-9420, United States), Snout and About (Sat Aug 22 2026 at 2100 S Military Highway, 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 Chesapeake, Virginia, 1301 Volvo Pkwy, Chesapeake, VA 23320-9420, United States, Restaurant of the Week. - **Q**: What is the price range for Trips & Adventures events in Chesapeake? - **A:** Prices for Trips & Adventures events in Chesapeake range from USD 18 to USD 18. Many events also offer free entry. - **Q**: Who are the top organizers for Trips & Adventures events in Chesapeake? - **A:** Popular organizers hosting Trips & Adventures events in Chesapeake include Brooks Adventures Tours, FloDo Access, Ermantourage Sports. - **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 Norfolk](https://allevents.in/norfolk/trips-adventures) - [Trips & Adventurous Activities in Virginia Beach](https://allevents.in/virginia-beach/trips-adventures) - [Trips & Adventurous Activities in Hampton](https://allevents.in/hampton/trips-adventures) - [Trips & Adventurous Activities in Newport News](https://allevents.in/newport-news/trips-adventures)