20 Things to Do In Chesapeake VA

Set between the urban sprawl to the north and wilds to the south, Chesapeake is a scenic, modern city with a population of around just 250,000 residents. Offering a more laid-back atmosphere than larger cities could provide, it’s ideal if you want somewhere to spend a relaxing city break.

A relatively young city that was initially an extension of Norfolk, Chesapeake only gained its status as a city in its own right in 1963. It has grown into a cosy enclave of welcoming communities boasting a plethora of local cafes, restaurants and independent shops.

Chesapeake is a nature lover’s dream, as the city is filled with canals and rivers and surrounded by swampland and nature preserves teeming with life. So if you love spending time outdoors, Chesapeake is the perfect city.

Three other cities, Virginia Beach, Portsmouth, and Norfolk, surround Chesapeake, so you’ll have plenty more to explore. These are the best things to do in Chesapeake, Virginia, to help you plan an itinerary.

Chesapeake, Virginia

20 Things to Do In Chesapeake, Virginia

1- Learn About Nature At Chesapeake Arboretum

Sprawling over 45 acres (18 ha) and with miles of walking trails, Chesapeake Arboretum is nature’s classroom.

The various species of trees that call the arboretum home are well labelled, so you can explore the trails and learn at your own pace.

Those with kids can sign them up for one of the many classes held each year at ‘Nature’s Academy’.

Children (5 to 12 years) can learn about topics like taking care of our forests and the kinds of animals that make their homes in trees.

You do have to register in advance, so be sure to plan ahead.

Chesapeake Arboretum is at 624 Oak Grove Rd, Chesapeake, VA 23320, United States.

2- Step Back In Time At The Great Bridge Battlefield

If you want a taste of what life in Virginia was like in the 1700s, then pay a visit to the Great Bridge Battlefield and Waterways History Foundation.

Built on the Battle of Great Bridge site, the foundation hosts frequent re-enactments and immersive events.

The museum is housed within a Georgian manor at the heart of the foundation.

Along with its large permanent exhibition, there is also a large exhibition space that hosts an ever-changing rotation of special exhibits.

Great Bridge Battlefield and Waterways History Foundation is at 1775 Historic Way, Chesapeake, VA 23320, United States.

3- Take A Walk Through History In Battlefield Park

Right next to The Great Bridge Battlefield and Waterways History Foundation is Battlefield Park.

Many of the foundation’s outdoor events are held in the park, so you can often spot historical re-enactments or book tours around the historic grounds.

Even when no events occur, there’s still plenty to see within the park.

An educational walking trail, a monument to the soldiers of the American Revolution, and an amphitheatre are some of the amenities to enjoy.

Battlefield Park is at 1775 Historic Way, Chesapeake, VA 23320.

4- Enjoy A Refreshing Break In Great Bridge Lock Park

You’ll find Great Bridge Lock Park just downriver from the Great Bridge Battlefield and Waterways History Foundation.

With fishing docks, play areas, walking trails and sheltered picnic areas, it’s the perfect spot for the whole family to unwind for a couple of hours.

Along with being at the end of a decently busy canal, boat launching facilities are also here.

You can spend a lovely afternoon just relaxing by the water and watching the boats drift on by.

Great Bridge Lock Park is at 100 Locks Rd, Chesapeake, VA 23320, United States.

5- Watch The Raising Of Great Bridge Bridge

Built in 2004, Great Bridge Bridge is a bascule bridge crossing the Elizabeth River in Great Bridge.

Between 6 am and 7 pm, the bridge is raised every hour for boats to pass through.

Few bridges are raised quite as frequently, so if you’ve always wanted to watch a bridge open up, this is your chance.

Sailors can request additional openings outside those hours, but if you want to guarantee to see the bridge raised, it’s best to visit during the day.

Great Bridge Bridge is at S Battlefield Blvd, Chesapeake, VA 23320, USA.

6- Catch The Opening Of the Gilmerton Bridge

Gilmerton Bridge is another of Chesapeake’s bascule bridges.

A little different from other bridges of its type, Gilmerton Bridge allows boats to pass through by lifting the entirety of the middle section of the bridge straight up,

Unlike Great Bridge Bridge, Gilmerton doesn’t have a regular opening schedule, rather opening only upon request.

As such, you’ll have to rely more on the chance if you hope to see the bridge being raised.

It’s worth noting, though, that the bridge will not open during the weekday rush-hour periods between 6:30 to 9:30 am and 3:30 to 6:30 pm, so don’t bother waiting around during those times.

7- Sample Local Flavour At Back Bay’s Farmhouse Brewing 

Just tripping across the border into Virginia Beach, Back Bay’s Farmhouse Brewing Co. is worth the travel.

Tucked away inside an old manor house, Back Bay’s farmhouse has been a brewery since 1938.

Back Bay also boasts a large and lovely beer garden along with its beautiful building.

The brewery is best known for its red ales, but it also offers a wide range of specialty beers, wines, and ciders, so there will be something for everyone.

Visitors can also take tours of the brewery, complete with guided tastings of some of Back Bay’s beverages.

Back Bay’s Farmhouse Brewing Co. is at 1805 Kempsville Rd, Virginia Beach, VA 23464, United States.

8- Indulge Your Tastebuds At Branches Tasting Room

Consider an evening at Branches Tasting Room if you want to indulge in some adult-only time.

Boasting an array of wines to suit every preference, along with a decadent variety of sandwiches, snacks, and desserts, you’re sure to leave feeling satisfied.

Wine tasting classes are held frequently, though you must make sure to reserve a space.

Branches also host various other events, including regular live music evenings.

Branches Tasting Room is at 2125 Starmount Pkwy Suite 105, Chesapeake, VA 23321, United States.

9- Soak In River Views At Elizabeth River Boat Landing

With water on three sides, Elizabeth River Boat Landing and Park is the perfect spot to relax and enjoy those river views.

With playgrounds and plenty of sheltered picnic areas, you’ll have everything you need for a chilled family day out.

Located at the east end of the South Norfolk Jordan Bridge, you can also enjoy impressive views of the towering structure.

It’s also lovely at night when the bridge’s lights illuminate the area and reflect off the water.

Elizabeth River Boat Landing is at 1400 Elizabeth River Way, Chesapeake, VA 23324, United States.

10- Admire The Soaring South Norfolk Jordan Bridge

Crossing the Elizabeth River and connecting Chesapeake and Norfolk, South Norfolk Jordan Bridge soars through the air at 145 feet (44 metres) tall.

The original bridge was opened in 1938, when Chesapeake was still known as South Norfolk, thus the name.

Open to both cars and pedestrians, you can enjoy stunning views as you cross the river.

Bear in mind that it is a toll bridge, though, so make sure to check ahead for relevant fees.

South Norfolk Jordan Bridge is at 100 Poindexter St, Chesapeake, VA 23324, United States.

11- Enjoy The Tranquillity At Stumpy Lake

One of the many areas of natural beauty around Chesapeake, Stumpy Lake is a great place to go to unwind and enjoy nature.

The 278-acre lake has plenty of space for fishing, kayaking, and paddleboarding, without getting overcrowded.

Stumpy Lake is surrounded by lush forests riddled with hiking and biking trails.

Keep your eyes peeled for the plentiful birds and animals that call the area home.

Stumpy Lake is at 4797 Indian River Rd, Virginia Beach, VA 23456, United States.

12- Visit The Unknown and Known Afro-Union Civil War Soldiers Memorial

Just around the corner from Great Bridge Bridge, you can find the Unknown and Known Afro-Union Civil War Soldiers Memorial.

This memorial, specifically honouring the contributions of black Americans to the United States’ independence, is an important slice of the area’s history.

The memorial consists of thirteen stone plaques engraved with the names, ranks, and birth and death dates of the known soldiers.

A U.S. flag is also erected at the memorial in their honour.

The Unknown and Known Afro-Union Civil War Soldiers Memorial is at 1001 Bells Mill Road, Chesapeake, VA, United States.

13- Have Fun In The Fresh Air At Northwest River Park

Venture a little way south of Chesapeake’s urban area to find Northwest River Park.

Running along Northwest River, plenty of activities are on offer, and being further from the city keeps it relatively quiet.

Activities you can enjoy in Northwest River Park include fishing and boating, horse riding and mini golf.

There are also campgrounds here, so you can enjoy spending the night under the stars.

Northwest River Park is at 1733 Indian Creek Rd, Chesapeake, VA 23322, United States.

14- Escape Into The Wilds Of Northwest River Natural Area Preserve

Also running along the Northwest River is the Northwest River Natural Area Preserve.

Boasting 2,774 acres (1122 ha) of largely untouched nature for you to explore, the Natural Area Preserve is ideal for those who prefer outdoor activities to be a little more adventurous.

With few formal trails running through the preserve, the area is best explored by boat.

There are several landings along the riverbank for you to hop ashore and explore.

15- Wander The Trails Of Great Dismal Swamp

A little easier to explore on foot, the Great Dismal Swamp National Wildlife Refuge boasts plenty of clearly marked trails to follow through the lush groves.

Don’t let the name put you off, Dismal Swamp is a beautiful location that is home to an abundance of animals and plants for you to spot.

Great Dismal Swamp National Wildlife Refuge is at 3100 Desert Rd, Suffolk, VA 23434, United States.

16- Cruise Along The Dismal Swamp Canal

This man-made canal was constructed in 1805 and has been in constant usage ever since, making it the USA’s oldest of its kind.

Taking a boat out onto the Dismal Swamp Canal lets you explore this area of natural beauty without worrying about bears or getting lost amongst the trees.

Dismal Swamp Canal is in Chesapeake, VA, 23323.

17- Explore The Dismal Swamp Canal Welcome Centre

Start off any visit to Dismal Swamp and Dismal Swamp Canal with a stop by the welcome centre.

Along with informative guides on the local wildlife to spot and maps of the swamp’s hiking and biking trails, this is also the place to go to hire adventurous equipment.

Canoes and kayaks are both available to rent from the welcome centre. Various launch points are available nearby, and there are guides to point you in the direction of the various paddling routes you can take.

Dismal Swamp Canal Welcome Centre is at 2356 Hwy 17, South Mills, NC 27976, United States.

18- Discover Nature In Comfort At Paradise Creek Nature Park

If you want to enjoy nature without leaving the comforts of civilisation, head to Paradise Creek Nature Park.

Covering 40 acres (16 ha) of forest and wetlands at the city’s heart, the nature park is the best of both worlds.

There’s plenty to do, such as walking trails through the trees and across the wetlands, launch points for kayaks and canoes, picnicking spots, and the occasional art installation.

Paradise Creek Nature Park is at 1141 Victory Blvd, Portsmouth, VA 23702, United States.

19- Take A Break At Judge Eileen Olds Courtyard Park

Wrapping around Chesapeake City Hall and various other municipal buildings, Judge Eileen Olds Courtyard Park is a lovely expanse of manicured lawns and walking trails.

There are plenty of shaded areas and seating for when you want to take a break.

Various events are hosted in the park, from markets to fairs.

On sunny days, the wide-open fields are ideal for picnicking.

One of the primary features of Judge Eileen Olds Park is the Chesapeake LOVE Letters installation.

The 6-foot-tall sign is cut from loblolly pine, and each letter is carved in the image of various animal species native to the area.

20- Explore The Skies At Chesapeake Planetarium

On the edge of Judge Eileen Olds Courtyard Park is the Chesapeake Planetarium.

A fulfilling attraction for the whole family, the Chesapeake Planetarium hosts exhibits and displays extolling the wonders of space and the universe.

Educational programs throughout the year are interesting for both children and adults, along with interactive experiences.

Take a look through their powerful telescope to view the stars and planets like you never have before.

Judge Eileen Olds Courtyard Park is at 310 Shea Dr, Chesapeake, VA 23322, United States.