Top 10 Best Things to do in Chesapeake, Virginia

Chesapeake Channel Tunnel Photo By Famartin – Wikimedia Commons

Top 10 best things to do in Chesapeake, Virginia

Chesapeake is a city in Virginia that operates on its own.  It is one of the largest cities in the area and was formed as an independent city in 1963 by a merger of the city of South Norfolk and Norfolk County.

It is located on the Tidewater coastal plain along the Elizabeth River, adjacent to Suffolk, Portsmouth, Norfolk, and Virginia Beach, and extends southward from Hampton Roads to the North Carolina border. 

The area, which was once inhabited by Chesapeake Indians, was settled by colonists in the early 1630s. During the American Revolutionary War, British and American forces clashed in the area in December 1775 in the Battle of Great Bridge.

Even though Union troops occupied and destroyed parts of the Chesapeake region during the American Civil War, it quickly recovered and urban development began in the early 1900s. 

It is now a diverse city with a few urban areas, as well as many square miles of protected farmland, forests, and wetlands, including a significant portion of the Great Dismal Swamp National Wildlife Refuge.

Here are the top 10 best things to do in Chesapeake, Virginia

1. Take a walk-through Dismal Swamp Canal Trail

Dismal Swamp Canal Visitor Center Rest Area Photo By WhisperToMe – Wikimedia Commons

The Dismal Swamp Canal Route is a multi-use trail that is available for horseback riding, hiking, running, walking, bicycling, and even rowing, as well as outdoor recreation, environmental, and historic park area with picnic sites.

The north trailhead is located at Old Route 17 and Dominion Boulevard in Chesapeake, Virginia, and goes for about eight miles along the Dismal Swamp Canal to the south.

This canal is also the site of the Paddle for the Border event, which takes place in the spring and involves paddlers of all ages travelling from Maryland to Georgia.

2. Explore the Chesapeake Arboretum

The Chesapeake Arboretum, located in the heart of Chesapeake, Virginia, is a forty-eight-acre “Nature’s Classroom” that promotes environmental and horticultural awareness via research, teaching, and plant exhibits.

The arboretum is also a “Virginia Treasure,” a governmental program that recognizes the state’s valuable recreational, scenic, historic, and ecological assets.

Don’t forget to meander through a mature hardwood forest full of native plants and trees!

3. Learn about the great Hickory Ridge Farm

The Hickory Ridge Farm is family-owned and runs the farm in Chesapeake’s Hickory neighbourhood. Several acres of food on the eighteen-acre farm is accessible for picking by the public at various times of the year.

Visitors may harvest strawberries at the Hickory Ridge Farm starting in late April and continuing through May and early June. Summer food is available from June through August, as well as wholesale and you-pick pumpkins in the fall. From Tuesday through Sunday, Hickory Ridge Farm is open.

4. Breeze at the Great Bridge Lock Park.

The Chesapeake Canal and the Albemarle Canal intersect with the Elizabeth River’s Southern Branch at the Great Bridge Lock Park, which is located along Virginia’s Intracoastal Waterway.

The Corp of Engineers lock that divides the canal’s fresh water from the river’s saltwater is the inspiration for the park’s name.

Aside from the main attraction of watching boats pass through the lock which can hold up to 20 boats at once, there is plenty of space for fishing along the canal, a boat ramp, a playground, a short hiking path, and the eponymous Great Bridge, which is quite impressive in its own right.

5. Shopping at the Greenbrier Mall

In the Hampton Roads region of Virginia, the Greenbrier Mall has about 900,000 square feet of retail space. Because this regional mall is built on a hillside, mall entrances may be found on both the lower and upper floors.

The Greenbrier Mall serves various villages along Virginia’s east coast, as well as some localities in North Carolina, in addition to the city of Chesapeake. The mall contains multiple department stores, including Macy’s, JCPenney, and Dillard’s, and speciality stores selling jewellery, home furnishings, and accessories, as well as men’s and women’s clothing.

It is also home to Cinema Cafe movie theatre and a variety of eateries.

6. Take a thrilling walk on the South Norfolk Jordan Bridge

The new South Norfolk Jordan Bridge Photo By Neilbert – Wikimedia Commons

The South Norfolk Jordan Bridge, also known as the Jordan Bridge, connects Chesapeake, Virginia in South Hampton Roads and Portsmouth, Virginia across the Southern Branch of the Elizabeth River.

Carl and Wallace Jordan, two South Norfolk industrialists, built the bridge, which opened to traffic in 1928. The South Norfolk Jordan Bridge, Virginia’s oldest drawbridge, was decommissioned in November 2008 owing to a lack of upkeep. In October of 2012, the new replacement bridge was completed.

You can see for miles in every direction from the top of the South Norfolk Jordan Bridge. Beautiful bird species can be seen flying across the skyline. If you’re lucky, wisps of clouds will float past you from above.

The view from below is even more spectacular!  The walk across is electrifying and for a moment you may forget the existence of the Elizabeth River which stretches as far as the eyes can see.

7. Great Bridge Battlefield and Waterways Foundation

The Great Bridge Battlefield and Waterways Foundation is the owner and operator of the Great Bridge Battlefield and Waterways Historic Park, Museum, and Visitor Center in Chesapeake, Virginia.

The foundation’s mission is to preserve American history, and it has decided to open a museum and visitor centre along the Intracoastal Waterways to highlight the history of the nation’s waterways, as well as the Battle of Great Bridge during the American Revolution, for visitors travelling by land or by water.

The museum has a permanent gallery, a gallery for rotating exhibits, and a one-hundred-seat theatre.

Visitors will be immersed in 18th century Virginia, learning about the water that defined the landscape, visiting a Three Tun Tavern, and standing in the middle of the Battle of Great Bridge, which set Virginia on the path to independence.

8. Site seeing at the Elizabeth River Park

The Elizabeth River Park is a waterfront park in Chesapeake, Virginia that offers spectacular views of the river and is an excellent place to picnic or participate in outdoor recreational activities including walking routes or a cardio training area.

The Elizabeth River Park is easily accessible by both water and land for boat owners. The pedestrian walkway provides excellent views from the city’s South Norfolk Jordan Bridge. 

Tourists can also enjoy a free fishing/crabbing pier, gazebos and shelters, a dog park, and refreshments at the Snack Shack.

9. Experience the mouthwatering food at the Cutlass Grille

Grilled steak with baked potato and gravy Photo By hiwarz – Wikimedia Commons

The name Cutlass Grille pays homage to the owner’s Jamaican background since the cutlass is a typical farming tool in the Caribbean.

On Chesapeake, Virginia, The Cutlass Grille specializes in American barbecue and Jamaican food. The restaurant is run by a family and provides a range of fresh and tasty home-cooked meals.

The Cutlass Grille is open from 11:00 a.m. to 9:00 p.m. on Tuesdays, Wednesdays, and Thursdays, as well as 11:00 a.m. to 10:00 p.m. on Fridays and Saturdays, and is particularly popular with Chesapeake locals for both lunch and dinner. On Sundays and Mondays, the restaurant is closed.

10. Eating and dining at the Egg Bistro in Virginia.

The Egg Bistro is a Chesapeake, Virginia-based neighbourhood bistro with additional locations in Virginia Beach and Suffolk’s Harbor View. In a hip family setting, the restaurant delivers unique and fresh dishes.

The staff strives to provide the best service and food possible to guests dining at The Egg Bistro, with an expansive bar and food menu, twelve different craft beers available on tap, and event space accommodating up to 150 guests.

Each of the bistro’s locations offers off-site catering and can accommodate gatherings seven days a week.