As fall approaches, Chesapeake offers beautiful weather with warm September days, a mix of sweater weather and short sleeves in October, and peak fall foliage in early November. Enjoy a quick getaway with charming farms, pumpkin picking, corn mazes, and tractor rides. Discover a variety of fall festivals featuring delicious libations, seafood, music, and intriguing history and plan your fall getaway to Chesapeake, VA today.

Annual Blue Crab Festival

September

Steamed crabs, delicious BBQ, a fish fry, and more. Add live music to the mix and you can see why the Annual Blue Crab Festival is a local's favorite. Mark your calendars and get ready to crack some shells. Tickets can be purchased online and include food and beverages.

Great American Food Fest

October

If unlimited food and beverages don't interest you, you should probably sit the Great American Food Fest out. If you are interested in all-American favorites like BBQ, fried fish, corn on the cob, and more you should make plans to attend.

Chesapeake Restaurant Week

October 

Chesapeake Restaurant Week is when local restaurants offer fixed-priced menus showing off the best they have to offer for breakfast, lunch, and dinner. Keep an eye on the Restaurant week page for participating locations and while you're at it learn all about Chesapeake's ever-growing food scene.

Chesapeake Virginia Wine Festival

October

One of Coastal Virginia's most popular events is the Chesapeake Virginia Wine Festival. Enjoy unlimited tastings from 20 Virginia wineries while you take in live music and sample fares from local vendors. Private tables and chalets are available if you want to make the day extra special.

Chesapeake Jubilee Fall Craft Market

November

Over 100 vendors gather at Chesapeake City Park for this favorite local festival. With a Kid's Korner, crafts, and activities for all ages, the Chesapeake Jubilee Fall Craft Market is another great reason to get the entire family out in the fall weather.

Oyster & South Festival

November

All-you-can-eat oysters. Need we say more? Ok. We will. Attendees at the Oyster & South Festival will also have the option to feast on delicious BBQ, clam strips, hot dogs, and more. Live music and monster truck rides make this an event you won't want to miss!

Battle of Great Bridge

December

Whether you're a history buff or just want to learn more about Chesapeake - the reenactment of the Battle of Great Bridge is an amazing opportunity to see history come to life. This free, family friendly event will let you take a step back in time to see what life was like during the American Revolution.

TAs the leaves turn and the air cools, Chesapeake's fall events are not to be missed! Keep an eye on our events calendar for the latest updates on all the exciting autumn activities and celebrations.