WanderLove in Chesapeake

Whether it’s a weeklong vacation or a quick day trip, the fall season in Virginia evokes a desire in all of us to just hop in the car and explore the amazing locations this state has to offer. In other places, people might call this strong need for travel Wanderlust, but here in Chesapeake, Virginia, we call it WanderLove. Easily accessible from Richmond and NOVA via I-64 and the rest of Coastal Virginia via US-158, it is impossible not to fall in love with Chesapeake in autumn. Walk through any of the beautiful parks and you’ll see vibrant leaves changing colors and waving in the crisp air. Visit one of our amazing cafes or restaurants and sample delicious ciders and craft hot chocolate. Talk to any local and hear about the magic of slipping on a comfy sweater and visiting a working farm. There are so many things to do – check out why Chesapeake is a perfect road trip destination to WanderLove this fall.


There’s a reason why professional guide Kevin Fonda of Adventure Kayak Tours calls the route through Chesapeake’s Northwest River Natural Area Preserve the “paddle of paradise.” These beautiful, cypress-tree speckled waterways, like the ones you’ll find at the Dismal Swamp Canal Trail and Elizabeth River Park, display a natural beauty that can hold their own against any nature preserve in the world.

Chesapeake has miles of tidal and non-tidal waterways perfect for kayaking, canoeing, and stand up paddleboarding. Whether you want to launch out with your own gear, rent a vessel for the day, or even book an excursion, there’s always a way for you to get out on the water.

Oak Grove Lake Park

Nature Trails

The great outdoors has been a saving grace for so many of us in 2020, and Chesapeake’s parks and trails are some of the best Virginia has to offer. With miles of walking paths and acres of green space, there really is something for everyone.

You can grab your bike and peddle the 16-mile bike loop at the Dismal Swamp Canal Trail, which is also great for kids due to its lack of elevation, or experience history when you visit the recently opened Great Bridge Battlefield & Waterways Museum. Take in the manicured, themed gardens of the Chesapeake Arboretum or simply enjoy the present with a mindful walk in any of the natural escapes you can find scattered throughout town. 

South Norfolk Jordan Bridge

South Norfolk Jordan Bridge

Most people are surprised to find such a unique piece of engineering tucked away in a corner of Chesapeake, making The South Norfolk Jordan Bridge one of Chesapeake’s true hidden gems. The two-mile round-trip walking path is a popular spot for locals to get out and about, and when you take in gorgeous panoramic views of the Elizabeth River from a 167-feet high bridge, you can literally see why. Whether you traverse the bridge on foot, bike or by car, it’s a way to enjoy the outdoors that is uniquely Chesapeake.

Big Ugly Brewing

Breweries and Tasting Rooms

One of the best ways to celebrate changing seasons is to sample local produce. But, stay with us for a second, what if instead of local produce, you sampled local beer? Big Ugly Brewing and The Garage Brewery are Chesapeake breweries with unique, local and seasonal beers on tap. It’s not just their “gotta try” beverages like Big Ugly’s S’mores Brown Ale or The Garage’s Sunkissed Strawberry Blonde that makes both of these spots worth the visit. They also present opportunities to celebrate local, open spaces that allow the community to thrive and come together while still being safe and mindful of others.  

Grilled salmon food photography recipe idea

Restaurant Week

In between hiking, kayaking and sampling local beverages, you’re going to build up an appetite. Chesapeake is regionally famous for its food scene, and with Restaurant Week coming up October 16-23, there’s never been a better time to indulge. From fine dining over seafood and steaks, to authentic Caribbean cuisine and woodfired pizzas, Chesapeake’s most delicious restaurants are offering prix fixe menus in socially distanced settings for lunch and dinner.

LoveWorks Sign

What better way to wrap up your WanderLove experience than by stopping by Chesapeake’s LOVEworks sign at Courtyard Square Park. There are almost 100 LOVEworks signs all over Virginia, and every one of them is different. Chesapeake’s sign celebrates local wildlife, with each letter representing a different indigenous species. Take a selfie or pose with your friends and family to commemorate the time you spent exploring.    

Now is the perfect time to hop in the car, road trip to Chesapeake and let the WanderLove take hold.

Share this post:

Discover more in the Blue Ridge: