When autumn rolls around, tourists and leaf-peepers flock to the hills. But why should the mountains get all the glory? Fall is just as gorgeous in Coastal Virginia, and this year, the city of Chesapeake should be on your to-visit list.

Virginia - Chesapeake - biking in autumn VERTICAL

Chesapeake, Virginia, offers plenty of outdoor recreational opportunities year-round.

Chesapeake, Virginia, is just 90 minutes from Richmond and is an easy three-hour drive from Washington, D.C., making it an ideal destination for a weekend getaway. Situated on the Atlantic Intracoastal Waterway, just minutes from Virginia Beach and Norfolk, Chesapeake has a vibe all of its own.

That’s because Chesapeake is noted for its many outdoor attractions, from the shady trails of the Chesapeake Arboretum (named one of Virginia’s Treasures) to the wildlife haven of the Dismal Swamp Canal (trust someone who’s been there—there’s nothing dismal about this incredible spot!). 

Explore Chesapeake, VA’s Waterways With Paddle the Peake

Chesapeake has miles of wonderful waterways for stand-up paddleboarding, kayaking, and canoeing. Along the way, you’ll take in scenic views and learn about the history of the area. You’ll also spot some of the abundant wildlife.

If you plan on exploring the Chesapeake area’s waterways, download the Visit Chesapeake app and sign up for the Paddle the Peake Passport. This free passport is your guide to the best places to paddle, as well as teaching you about the local flora and fauna. You’ll win prizes for check-ins, including stickers, dry bags, hats, and an exclusive Paddle the Peake Nalgene water bottle.

Your Destination for Outdoor Festivals

Every fall, Chesapeake hosts a variety of outdoor events that are enjoyed by locals and visitors alike. 

On September 11, the 15th Annual Blue Crab Festival will feature live music, BBQ, and all the steamed crabs you can eat. The crabs are caught fresh and provided by local legend Ray Wicker, owner of long-time favorite Wicker’s Crab Pot Seafood.

On October 5, the Great American Food Fest at Chesapeake City Park celebrates the finger-licking-good food heritage of the region. Expect to find favorites like BBQ pork and chicken, fried fish, hush puppies, and corn on the cob. Tickets are available through EventBrite.

Also at Chesapeake City Park, the Chesapeake Wine Fest Virginia offers attendees the chance to sample Virginia wines from more than 20 wineries and enjoy delicious food provided by local restaurants. Of course, there will also be live music as you sip and dine on October 8.

Virginia - Chesapeake - Oyster and South Festival

The Oyster and South Festival at Greenbrier Farms is a long-time favorite among locals and visitors alike.

And expect to plan a return trip on November 19 for the Oyster and South Festival held at historic Greenbrier Farms. A local favorite, the festival offers delicious food from local restaurants, as well as live music and games for the whole family.

Working Farms Offer Fall Fun

Fall is also a great time to explore Chesapeake’s charming working farms. Many of them offer seasonal pick-your-own opportunities, so you can load up on the freshest farm-grown produce and fruit.

Virginia - Chesapeake - pumpkin patch

Enjoy the best of Nature’s bounty at Chesapeake, Virginia’s many working farms this fall.

In addition, in the fall, these farms offer fun for kids and adults: corn mazes, pumpkin patches, tractor rides, and petting zoos. They also sell fresh jams, jellies, pickles, pies, breads, and more. (Click here for a complete list of working farms.)

Also visit Greenbrier Farms and enjoy the brand-new farm-to-table casual dining experience at The Hive Bar and Grill. The whole family will enjoy eating outside on the patio and listening to live music. 

For More Information

Visit Chesapeake, Virginia: visitchesapeake.com

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