There’s nothing like autumn in Chesapeake, Va., and it all comes alive in September. Located in the heart of Coastal Virginia, the water is warm, the weather is mild and the trees are transforming to a rainbow of vibrant colors.

Get your paddle on


Our breathtaking Intracoastal Waterway is accessible by the Deep Creek Lock Park, where you can put in kayaks, canoes and paddleboards, or try your hand at crabbing and fishing, when in season. In addition to our Intracoastal Waterway, Chesapeake has thousands of acres of parkland with waterways such as the Northwest River Park and Campground. This enormous forested park features Lake Lesa, a 6-acre freshwater lake where you can fish for trout or catfish, depending on the season. Here you can rent a canoe or paddleboat. If you are interested in paddling the Northwest River, there is an easy put-in at Bob’s Fishing Hole.

The Elizabeth River Park is located next to the South Norfolk Jordan Bridge. Locals and visitors alike enjoy walking the bridge and then paddling the Elizabeth River. There is a two-lane boat ramp with launch as well as a dog park, multiple shelters, a store and a playground.


The Dismal Swamp Canal Trail offers 8.5 miles of flat paved surface. This is the perfect place for hiking or biking with the whole family. You might even spot a bald eagle, osprey, bluebird or other wildlife while enjoying the hundreds of acres of natural beauty.

If you are looking for a daylong excursion, Adventure Kayak Tours can lead you on a guided tour of the Dismal Swamp Canal into Lake Drummond. Owner Kevin Fonda is a history and nature aficionado and can regale you with stories about the park. Here the Underground Railroad flourished with runaway slaves and Maroons living deep in the swamp. The Native Americans revered Lake Drummond for its naturally clean water. Don’t be fooled by its brown color. The tannins in the cypress trees kill the bacteria.


If you only have an hour, the Chesapeake Arboretum offers easy walking trails through this 48-acre natural classroom. Here, you’ll find theme gardens and trails that meander through a mature hardwood forest with many varieties of native plants and trees.

Fall is the time to visit one of Chesapeake’s many working farms. Bergey’s Breadbasket, Mount Pleasant Farms, Greenbrier Farms and Hickory Ridge Farm all offer corn mazes, pumpkin picking, fresh produce, baked goods and honey. Bergey’s Breadbasket makes their own fresh ice cream, and Hickory Ridge Farm’s petting zoo and tractor-train ride is always a hit with children.

Always an event


If you time your visit right, you can join in the celebration during one of the city’s many events and festivals. Coming up on Saturday, Oct. 12, at Chesapeake City Park, is the Chesapeake Wine Festival, featuring live music, great food and wine sampling from a variety of vintners. Restaurant Week, Oct. 18-25, is a great opportunity to experience Chesapeake’s flourishing culinary scene, where a variety of local restaurants serve delicious offerings from $10 to $50.

Breweries abound

Want to check out some breweries? Visit Chesapeake’s Big Ugly Brewing, where you can sample their “big, bold beer” varieties along with great eats, bands and events. Or stop by , the city’s newest brewery, offering a tasting room, wraparound bar and patio.

It’s all close to home

With Virginia Beach and Norfolk just a short drive away, Chesapeake makes a great base for any getaway, offering an abundance of affordable accommodations catering to families and even pets.

So plan your next getaway in Chesapeake. And let the bounties of fall begin.

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