Outdoor Events

Outdoor Events

For Virginia travelers interested in festivals, events, and celebrations that take place in the great outdoors, you’ve come to the right locale. Chesapeake, VA offers adventures and gatherings all year long on the many bodies of water and within the parks of the region, so you can get out there and be active in nature.


Sprinters and sweet fanatics alike will love January’s Cookie Classic Run. The 5K and 10K races around the Dismal Swamp Canal Trail are ideal for both runners and walkers and help support local Girl Scout troops.

Break out your binoculars for February’s Great Backyard Bird Count at the Indian River Community Center. This guided walk through the park will help bird watchers spot some of the most gorgeous singing creatures in the county.


May is Bike Month, and for those outdoor enthusiasts who prefer to glide on two wheels, there’s Bike Fest. In addition to the 12 miles of paved paths for you and your friends and family to enjoy along the Dismal Swamp Canal Trail, Bike Fest has visits with bike mechanics, a bike rodeo, and maintenance demos to get you rolling.

Chesapeake's Paddle for the Border, an event where kayakers can paddle the Dismal Swamp Canal, is also each May. Bring your own vessel, or reserve a kayak online before the gathering. Registration for Paddle for the Border opens in January, so make sure to pre-register as this event fills up quickly.


Also for kayak-lovers, Chesapeake offers KayaXpedition each June. This yearly festival for aquatic aficionados provides classes, races, and lots of other fun for paddlers. 

Cyclists, get ready to compete during the annual Chesapeake Criterium Bike Race. The closed-circuit race begins a weekend of racing that also includes the Virginia Senior State Championship, Peter and Gerald Teeuwen Memorial Time Trial, and the Virginia Age-Graded State Championship. Participants of all ages—even those requiring training wheels—are welcome to join.


In search of ways to celebrate your perfect pup? Come out in October for the Bark in the Park fundraiser. Organized by the Chesapeake Humane Society, this is the ideal event to spend the day outside with your dog, meet canine companions, or even adopt a new pet. 

October also brings a host of family-friendly events that celebrate the fall harvest season. These yearly events showcase nature-based activities, like trail tours, corn mazes, skywatches, and pumpkin picking. Find all this and more here.

All Year

These are just some of the annual outdoor events to experience in Chesapeake. Look out for more events popping up while you’re in town.

Filter by:
Show Events between


  • Show More
  • No available filters


More Things to Do

Restaurants Discover renowned local restaurants in Chesapeake,...More
History From historic trails to museums, learn about...More
Shopping With a wide spectrum of shops, services and...More