Chesapeake, Virginia, offers the perfect hub with spokes for the vacation of your dreams just 20 minutes from Norfolk Airport or Virginia Beach. But centralize your wheel so it centers squarely on Chesapeake herself, and you’ll find just how many places the spokes reach within the region. Revel in watersports, hike and bike to your heart’s desire, spend a night stargazing, or camp under the stars. All options are available in Chesapeake.
They don’t call it Wanderlust here, they call it WanderLove. Love focuses your trip on reconnecting with yourself, friends, and family through shared activities that make for an itinerary as packed as you’d like, and memories bound to be treasured for years to come. Explore the outdoors as you did as a child. Enjoy seasonal harvests for the freshest food and excellent restaurants that prepare them in old and new ways. Top it off with a stop at an old-fashioned candy factory three generations in the making, and you may decide you’ll want to stay for longer than a visit.
Wear your bug repellent, hat, and sunscreen, and prepare for an amazing ride. And don’t forget to check the city’s website for frequent community celebrations.
We visited Chesapeake, Virginia on a press trip and enjoyed more activities than I could’ve ever expected. All opinions contained herein are my own.
It’s no surprise that water can be a prime focus of activity in Chesapeake. After all, you’ll find Chesapeake at Virginia Mile Marker 12 on the Atlantic Intracoastal Waterway, the 3,000-mile waterway along the Atlantic and Gulf Coasts of the Eastern United States. What may surprise you are the many types of waterways that exist. This unique ecosystem includes the Intracoastal, rivers, streams, and lakes (natural and manmade), where salt water from the Elizabeth River and fresh water from the Albemarle and Chesapeake Canal mix as the lock system does its job propelling vessels to their next location.
1. Paddle For The Border
For a 3-hour paddle trip from North Carolina to Chesapeake, Virginia, choose your paddle — kayak, canoe, stand-up paddle board, shell — all are allowed. Go with your family or friends to join 300 vessels that launch into the 7.5-mile journey through Dismal Swamp Canal each spring.
The event begins with a traditional pre-launch breakfast. One insider took a separate kayak from her husband, enjoying a leisurely ride with a friend as he sped ahead and was one of the first to finish. Paddle through Atlantic white cypress-lined banks that once hid escaping slaves along the Underground Railroad. If you’re lucky, you’ll be joined by river otters sliding through the water or hopping to shore. Black bears have been spotted, but not as often as the birds migrating north for summer.
Afterward, partake in a festive, fun, and friendly pancake breakfast with the early arrivers welcome to nap until the rest of their group catches up to them.
Pro Tip: Registration for Paddle For The Border — officially limited to the first 300 applications — begins in January and fills fast, so sign up early.
2. Kayak From A Pontoon Boat
You may be accustomed to traveling to a location to kayak, but how’s this for a twist? Travel to the dock with a pontoon boat with attached kayaks, and it’ll take you to different locations based on your interest. Flora? They’ve got it. Fauna? In abundance. Specify your desire, and River Dogs Kayaking gladly shares knowledge and sites before your trip through the locks.
Great news for the less active members of your party: Anyone who can’t kayak can sit on the pontoon and enjoy the views.
When you go, be sure to check out the City of Chesapeake’s website for ongoing events. Adventure Kayak & SUP Tours offers “Paddle In Trash Out” events as well as “Paddle Under the Stars” and “Full Moon” paddles.
Pro Tip: Always wear a life vest when engaged in any water activity.
Each June, join KayaXpedition at 65-acre Oak Grove, Lake Park’s family festival where you can learn to kayak or practice canoeing across the lake with music, food trucks, and even a 1.5-mile trail when you’re ready to stretch your legs. What a great way to spend quality time with family and meet new friends.
Fish from shore or from your own (or rented) boat along the Elizabeth River or Albemarle Sound. Anglers tell me that the 763-acre Northwest River Park is the best place to catch winter striper and yellow perch. In the winter, expect to find catfish. In spring, flounder. And in summer, spadefish, striped bass, and cobia.
In need of supplies? Check out Gail’s Bait & Tackle (sadly, no relation) for gear, and know you’re hitting autumn’s prime time in Chesapeake with the Urban Trout Fishing Program. The Virginia Department of Game and Inland Fisheries stocks more than 2,500 brown and rainbow trout in Northwest River Park’s Lake Lesa each fall. The season is from November 1 through April 30, so be certain to have both trout and freshwater fishing licenses before you reach the lake.
Some kayak companies offer kayak fishing. If you’re a confident kayaker, try it yourself.
Hike, Bike, Skate, Run, Or Stroll
A remarkable thing about Chesapeake is that many of the places available for hiking are also amenable to biking or even skating. This makes many accessible for people in wheelchairs or who use walkers.
5. South Norfolk Jordan Bridge
This scenic South Norfolk Jordan Bridge, a mile-long toll bridge, at 169 feet over the water, connects Chesapeake to Portsmouth and provides gorgeous views of the Elizabeth River Park. Pedestrian traffic has an 8-foot-wide, 5 percent grade, ADA-compliant path open during daylight hours. If you’re on foot, plan for about an hour.
Pro Tip: Locals think this is one of the best places for selfies.
6. The Great Bridge Guard Lock
The Great Bridge and her lock create “The Liquid Highway,” a central feature of the town. With a lovely park below laced with blue heron statues, an anchor, and the most incredible Revolutionary War Great Bridge Battlefield & Waterways Museum, it’s a must-do during your trip to Chesapeake.
The lock is a feat in both architectural and ecological terms. It allows auto traffic above, and at the top of the hour, opens for 10 minutes to allow boat traffic to pass below.
As an outdoor enthusiast, you can cross the Great Bridge bridge and lock by land or sea vessel, on foot, by bike, or by skating. While horses are allowed at Dismal Swamp, we didn’t see any horses on the Great Bridge during our visit.
7. Hike Or Run Dismal Swamp
Dismal Swamp Canal Park and The Great Dismal Swamp National Wildlife Refuge contain some of the purest water in the world surrounded by bald cypress trees but it’s impossible to ignore the region’s historic importance. There’s nothing dismal about this region George Washington once surveyed. Independent Virginia’s first governor, Patrick Henry, urged the creation of the canal to connect the Chesapeake Bay and North Carolina’s Albemarle Sound. It took 12 years of backbreaking human (hired) labor to complete the 22-mile border, which continues as the country’s oldest continually operating man-made canal.
Start your hike of the Dismal Swamp Canal Trail at the northern trailhead at the statue of Chessie the Bear (aka Ches A. Peake). While bears are sighted (stay away from them), birds, white-tailed deer, and flora can keep your eyes engaged the entire trip. The Chesapeake Arboretum on the American Camellia Trail is the best place to see a specific floral species.
8. Dismal Swamp Stomp
The annual April Dismal Swamp Stomp half marathon and Children’s Cub Run are entertaining ways to welcome spring. Temperatures range from 54 to 70 Fahrenheit, very comfortable for running.
If you’re a lover of links, both the Chesapeake Golf Club and the Battlefield Golf Club have 18-hole courses recommended by the local visitor center. There are many mini-golf courses available and even a disc golf course.
If paintball is your game, Chesapeake Paintball should be on your to-do list. With 40 acres of woods, you can paint your opponents as you attempt to avoid welts.
11. Produce Picking
My first trip to Chesapeake happened during strawberry season in May. Fresh strawberries made their way into many of the foodie scene offerings, true to their farm-to-table roots. In summer, peaches take the forefront. And in the fall, apples, pumpkins, and corn collaborate with the riot of autumnal colors to celebrate your group spending a few hours picking your own produce of the season.
Join birders with sightings of 213 species of birds including the elusive Swainson’s warbler and the great blue heron. You’ll feel doubly blessed in this unspoiled nature if you take the opportunity to visit the Virginia Birding and Wildlife Trail.
Though I’ll admit I really enjoyed our stay at Marriott’s Delta Hotel, if you’re up for more rugged adventures sleeping under the stars, check out the campgrounds and watch the city website for stargazing events.
When your sweet tooth starts to beckon, the more than 100-year-old H.E. Williams Candy Company is a short drive away.
Chesapeake, Virginia, is a great place to work and live and visit, and “with so much to find here, you may just lose yourself…”