Autumn in Chesapeake is magical. The air is crisp. Sunlight bounces off the water and people travel from far and wide for our farmers’ markets, wine festivals and art shows. Visitors and residents alike delight in some of the best kayaking and paddle boarding in the region – complete with 22 miles of waterways adorned in a rainbow of red, orange and gold. We’ve got corn mazes of every size to get lost in, a famous Ghost train in beautiful Northwest River Park (select weekends) – and eateries, craft beer and live music at every turn.

The warm weather is perfect for hiking and biking your way through 8.5 miles of wildlife on the Great Dismal Swamp Canal Trail. You can even take an Adventure Kayak Tour through the sprawling Cyprus tree groves.

Shoppers come to unearth buried treasure at an array of eclectic shops, while foodies imbibe on artisanal beers, fresh crab and more! And there’s an autumn event to suit every taste!

Festive festivals:

The Dismal Swamp Art Festival
October 27-28, 2018 | 10 a.m. – 4 p.m.
At The Canal Trail of the Great Dismal Swamp Wildlife Refuge
Free Admission
Explore our local art and fill up on Brunswick stew, craft brews, hot apple cider and a host of harvest-themed activities!

The Great American Food Fest
October 3, 2018 | Chesapeake City Park | 3 – 7 p.m.
The 39th Annual Great American Food Festival
Hosted by Chesapeake Sheriff’s Department Charities Inc. and the South Norfolk Ruritan Club.

Come hungry and ready to have fun at this all-inclusive charity event featuring live entertainment, BBQ, and beer.

Chesapeake Virginia Wine Festival
October 13, 2018 | Chesapeake City Park | Noon – 6 p.m.
This favorite outdoor event features wine from 20 premier Virginia Wineries as well as craft beer, specialty food vendors, and live entertainment. Get your tickets here: https://www.cheswine.com/

Farmers Markets and Pick-your-own

No matter why you love fall, Chesapeake has you covered!

Fan of a farmer’s market?

Chesapeake City Park and Battlefield Park South host Farmers’ Markets every Wednesday and Saturday from 8 a.m. – 1 p.m.

How about working farms?

There are a number of working farms open to the public that offer produce, fresh honey, and seasonal fun like corn mazes, and pumpkin picking.

Bergey’s Breadbasket Bakery & More offers fresh, delicious homemade ice cream from their very own cows. Children are invited to see the animals, explore their giant corn maze, take wagon rides and play in their sunflower patch. The fun begins mid-September at 2207 Mount Pleasant Road, Chesapeake, VA, 23322.

Greenbrier Farms hosts the Oyster & South Festival – and hayrides, pumpkin picking, hiking and horseback riding. 225 Sin Pine Road, Chesapeake, VA, 23322.

Lilley Farms has an enormous and challenging maze as well as fresh produce for picking, including pumpkins and squash. 2800 Tyre Neck Road, Chesapeake, VA, 23321

Mount Pleasant Farms offers fresh farm eggs, raw local honey, sweet corn, baked goods, fresh dairy, and lots of pumpkins, gourds and squash. There’s also a petting zoo, corn maze, straw pile and playground. And beginning in October, wagon rides through the orchard. 2201 Mount Pleasant Road, Chesapeake, VA 23322

Gum Tree Farm also provides petting zoos, fresh produce and pumpkins for purchase. 1900 Pocaty Road, Chesapeake, VA 23322.

This autumn, leave your cares at home – and let the moments begin in Chesapeake.