Explore VA’s Hidden Gem: Top Things To Do in Chesapeake

Explore VA’s Hidden Gem: Top Things To Do in Chesapeake


Nestled in the heart of Coastal Virginia, Chesapeake is a true hidden gem that often flies under the radar compared to its more famous neighbors.

This vibrant city not only offers a blend of lush landscapes and waterways but also serves as a gateway to the unique experiences of the Chesapeake Bay.

Just a stone’s throw from the bustling beachfronts of Virginia Beach and the rich maritime heritage of Norfolk, Chesapeake provides a perfect mix of tranquility and convenience.

Whether you’re a nature lover, history enthusiast, or just in search of a new adventure, Chesapeake promises a plethora of activities and sights that cater to all interests.

Discover why this charming city is worth more than just a stopover as you explore the myriad things to do in Chesapeake.

Book your flight with Skyscanner to Chesapeake and paddle along the serene waters of the Dismal Swamp Canal, rich in history and natural beauty.

Fast Facts About Chesapeake, VA

Sun through the trees

  1. Location: Chesapeake is located in the Hampton Roads region of Virginia, bordered by the cities of Virginia Beach, Norfolk, Suffolk, and Portsmouth.
  2. Size: Chesapeake is the third-largest city in Virginia by land area, covering approximately 353 square miles.
  3. Population: With a population of over 250,000 residents, Chesapeake is one of the most populous cities in the state.
  4. History: Chesapeake was formed in 1963 by the consolidation of the former Norfolk County and the city of South Norfolk.
  5. Geography: The city is characterized by its diverse geography, including waterfront areas along the Chesapeake Bay and Intracoastal Waterway, as well as rural and suburban neighborhoods.
  6. Outdoor Recreation: Chesapeake offers abundant opportunities for outdoor recreation, including boating, fishing, hiking, and birdwatching in its numerous parks, nature reserves, and waterways.
  7. Cultural Diversity: Chesapeake is known for its cultural diversity, with a vibrant community representing various ethnicities, cultures, and backgrounds.
  8. Economy: The city’s economy is driven by diverse industries such as agriculture, manufacturing, healthcare, and tourism, with a focus on preserving its natural resources and heritage.
  9. Quality of Life: Chesapeake consistently ranks as one of the best places to live in Virginia, offering residents a high quality of life, excellent schools, and ample recreational opportunities.

πŸ‘‰Stay in a cozy inn near the Dismal Swamp Canal to enjoy easy access to boat rentals and guided tours.

Discover the Natural Beauty of Chesapeake

Chesapeake, VA, is a nature lover’s paradise with stunning landscapes and waterways.

Kayak on the Chesapeake Bay or explore the Great Dismal Swamp.

For a serene day out, visit the Chesapeake Arboretum’s nature trails and blooming gardens.

Chesapeake offers the perfect blend of adventure and tranquility for those seeking to immerse themselves in nature.

Boating, Kayaking, and Paddle Sports in the Intracoastal Waterway


The Intracoastal Waterway in Chesapeake is an excellent location for water sports enthusiasts.

This scenic waterway not only offers vast and calm waters that are ideal for boating, kayaking, and paddleboarding, but also provides a picturesque backdrop of Virginia’s natural landscapes.

Whether you’re gliding through the water at dawn or enjoying a leisurely paddle at sunset, the waterway is a perfect setting for both relaxation and adventure.

Things to do:

  • Rent a kayak or paddleboard and explore the waterway at your own pace.
  • Join guided boating tours to learn more about the local ecosystem and history.
  • Participate in paddle sports events and competitions held throughout the year.

πŸ‘‰Find the best flights to Chesapeake on Skyscanner and explore the Great Dismal Swamp National Wildlife Refuge, home to diverse wildlife and scenic trails.

Fishing and Bird Watching at Northwest River Park

Northwest River Park and Campground

Photo by : City of Chesapeake

Northwest River Park is a beautiful and tranquil spot in Chesapeake that’s perfect for fishing and bird watching.

It boasts a freshwater lake and several trails, making it a favourite of both novice and seasoned anglers, as well as bird lovers.

This park’s varied habitat supports a wide range of wildlife, providing plenty of opportunities for photography and nature observation.

Things to do:

  • Enjoy freshwater fishing from the pier or bank, with bass, catfish, and bluegill in abundance.
  • Walk the nature trails and use the provided birding stations to spot local and migratory birds.
  • Rent a boat for a quiet day on the water, perfect for family outings or solo trips.

πŸ‘‰Book a family-friendly hotel near the Great Dismal Swamp Wildlife Refuge for convenient access to nature walks and wildlife spotting.

Hiking in the Great Dismal Swamp

Lake Drummond

The Great Dismal Swamp in Chesapeake is a fascinating wilderness area that offers a beautiful combination of history and natural splendor.

It spans over 112,000 acres, making it one of the largest swamps in the United States.

The swamp’s thick forests and mysterious waters create a unique hiking experience that feels like stepping back in time.

It is a place where nature and history are intertwined, providing visitors with a peaceful escape and an opportunity to explore a crucial wildlife habitat.

Things to do:

  • Trek along the extensive network of trails that offer varying levels of difficulty and scenic views.
  • Visit Lake Drummond, one of only two natural lakes in Virginia, located within the swamp.
  • Participate in a ranger-led tour to learn about the swamp’s ecology and its role in the Underground Railroad.
  • Bird watching for a chance to see various species, including the bald eagle and the barred owl.
  • Photograph the diverse flora and fauna, capturing the unique beauty of this rare ecosystem.

πŸ‘‰Use Skyscanner to plan your visit to Chesapeake for a round of golf at one of the city’s premier courses, like the Chesapeake Golf Club.

Visiting Chesapeake Arboretum

The Chesapeake Arboretum, also known as “Nature’s Classroom,” is a 48-acre natural sanctuary located at the heart of Chesapeake.

This well-maintained arboretum features thematic gardens and miles of walking trails, showcasing both native and exotic plants.

It is a perfect destination for nature enthusiasts, garden lovers, and families looking for a serene day out.

The tranquil environment fosters education, conservation, and recreation, making it an ideal spot to spend quality time.

Things to do:

  • Stroll through various gardens that display a mix of ornamental and utility plants.
  • Walk the wooded trails, which are well-marked and suitable for all ages.
  • Attend workshops and guided tours to learn more about horticulture and local wildlife.
  • Enjoy picnicking in designated areas surrounded by lush greenery.
  • Participate in seasonal events like plant sales and educational programs.

πŸ‘‰Find accommodations near the Chesapeake Golf Club to enjoy morning rounds and evening dining in a scenic setting.

Oak Grove Lake Park

Oak Grove Lake Park is a 65-acre park that surrounds a breathtaking 8-acre lake.

The park is ideal for individuals looking for outdoor activities and picturesque views.

Its well-maintained paths and facilities make it a go-to spot for joggers, bikers, and families.

The park’s loop trail provides an accessible route that offers stunning vistas of the lake, making it a popular choice for photographers and nature enthusiasts.

Things to do:

  • Walk or bike around the lake on the 1.5-mile loop trail, which is fully paved and accessible.
  • Fish from the lakeside pier or launch a non-motorized boat to enjoy the water.
  • Utilize the playgrounds and picnic areas for family gatherings.
  • Watch for wildlife, including turtles, ducks, and geese, which are common sights around the lake.
  • Visit in the early morning or late evening for a spectacular view of the sunrise or sunset over the lake.

πŸ‘‰Secure your flight with Skyscanner and enjoy a family picnic at Northwest River Park, offering fishing, hiking, and star-gazing opportunities.

Chesapeake’s Cultural Attractions and History 

Chesapeake, VA, is a city rich in history and culture. 

Visitors can explore museums, historic homes, and remnants of early American life.

The city also offers modern-day culture through art, music, and community events.

This blend of old and new makes Chesapeake a captivating destination for history buffs and culture enthusiasts alike.

Great Bridge and the Battle of Great Bridge Site

The Battle of Great Bridge is a historically significant location in Chesapeake.

This battle played a crucial role during the American Revolutionary War, as it marked a significant victory for the American forces and helped establish control over the Virginia colony.

Presently, the site features several markers and exhibits that explain the battle’s importance, as well as the tactics employed by both sides.

Things to do:

  • Visit the battlefield to learn about the events of December 1775 through informative displays.
  • Walk across the modern Great Bridge to reflect on the strategic significance of the original structure.
  • Attend annual reenactments of the battle, where history comes to life with soldiers in period uniforms.
  • Explore nearby historical markers and plaques that provide further insight into the area’s past.
  • Visit the Great Bridge Battlefield & Waterways History Museum to see artifacts and exhibits related to the battle and local history.

πŸ‘‰Choose a campsite or cabin at Northwest River Park for a natural retreat perfect for family bonding and outdoor activities.

Dismal Swamp Canal with its Ties to the Underground Railroad

Dismal Swamp Canal

The Dismal Swamp Canal is not only an engineering marvel as one of the oldest operating artificial waterways in the United States but also a site of profound historical depth.

It served as a refuge for escaped slaves, becoming part of the Underground Railroad.

This hidden history makes the canal a poignant site for reflection on the struggle for freedom.

Things to do:

  • Kayak or boat along the canal to experience the same secluded waterways that provided shelter centuries ago.
  • Participate in guided tours that focus on the canal’s role in the Underground Railroad.
  • Visit the nearby Dismal Swamp State Park to explore more of the swamp’s vast and historic landscape.
  • Birdwatching and wildlife photography are popular here, thanks to the area’s rich biodiversity.
  • Attend special presentations and educational programs about the history and ecology of the canal and swamp.

πŸ‘‰Fly into Chesapeake with Skyscanner and delve into local history at the Chesapeake Veterans’ Memorial, honoring those who have served.

Local Galleries and Summer Concerts

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A post shared by Chesapeake Arts Center (@chesapeakeartscenter)

Chesapeake boasts a lively art scene with many local galleries showcasing the works of established and emerging artists.

The city’s vibrant and creative atmosphere offers a platform for visual storytelling and cultural expression.

During the summer, Chesapeake also hosts a variety of concerts, ranging from classical music to contemporary hits, creating a lively atmosphere for all to enjoy.

Things to do:

  • Visit local galleries to view and purchase unique art pieces.
  • Attend gallery openings and meet-the-artist events to engage with the local art community.
  • Enjoy outdoor summer concerts at city parks and other venues, featuring a mix of genres and performers.
  • Participate in art workshops and classes offered by local artists and galleries.

πŸ‘‰Secure a room near Chesapeake City Park to be close to festivals, concerts, and community events throughout the year.

Chesapeake City Park Events and Cultural Festivities

Fun Forest Playground

Photo by: City of Chesapeake

Chesapeake City Park is a popular venue that hosts a variety of cultural events all year round.

From food festivals to cultural heritage days, the park offers a diverse range of activities that celebrate the community’s spirit and diversity.

With its modern facilities and expansive green spaces, the park not only provides a beautiful backdrop but also encourages community engagement and cultural exchange.

Things to do:

  • Attend various cultural festivals that celebrate different heritages and traditions.
  • Enjoy family-friendly events like movie nights and children’s festivals.
  • Participate in or watch sporting events and tournaments held at the park.
  • Visit during special holiday events, which often include fireworks, live music, and more.

πŸ‘‰Book through Skyscanner for a trip to Chesapeake and shop at the Greenbrier Mall or the unique boutiques along Battlefield Boulevard.

Chesapeake’s Top Attractions and Must-Sees

Chesapeake, VA offers an array of attractions for all. Its rich history, scenic spots, cultural & recreational activities make it a standout destination.

Discover the premier places & activities that define Chesapeake’s charm and ensure a memorable visit.

Greenbrier Parks and Playgrounds

Greenbrier Sports Park

Photo by: City of Chesapeake

The Greenbrier area in Chesapeake is famous for its meticulously maintained parks and extensive playground facilities, which make it a preferred destination for outdoor enthusiasts and families.

These parks are designed to cater to all age groups, providing a diverse range of recreational activities in a secure and welcoming environment.

The lush green spaces, coupled with modern amenities, ensure a fun and relaxing day out for everyone.

Things to do:

  • Enjoy the diverse playgrounds, each offering different fun setups for kids of various ages.
  • Walk or jog along the scenic paths that wind through the parks.
  • Use the sports facilities, including baseball fields and basketball courts, for a day of active fun.
  • Host a picnic at one of the many shaded picnic areas, complete with tables and grills.
  • Participate in community events and activities often held in the park areas.

πŸ‘‰Opt for a hotel near Greenbrier Mall for a comfortable stay with ample shopping and dining options at your doorstep.

Western Branch with its Outdoor Play Areas and Picnic Spots

Photo by: City of Chesapeake

Western Branch is a beautiful location in Chesapeake that offers vast outdoor play areas and picturesque picnic spots.

It’s a perfect spot for family gatherings, casual outings, and leisurely days spent in nature.

The area has plenty of space and a variety of recreational options, making it an ideal place to unwind and have fun outdoors.

Things to do:

  • Explore the large play areas, which are equipped with modern and safe playground equipment.
  • Enjoy a family picnic at the well-equipped picnic spots overlooking beautiful natural views.
  • Take advantage of the walking and biking trails for some exercise or a peaceful stroll.
  • Engage in water activities at nearby access points if available.
  • Watch local sports games or participate in recreational leagues.

πŸ‘‰With Skyscanner, reach Chesapeake and experience the local flavors at the city’s annual BBQ festival or other culinary events.

Unique Local Experiences

Chesapeake, VA offers unique experiences that set it apart. Visitors can explore historic waterways, local cuisine, and natural beauty.

From paddling through the Dismal Swamp to tasting fresh seafood, there’s something for everyone to enjoy in Chesapeake.

Chesapeake City’s C&D Canal Museum

Chesapeake and Delaware Canal (C&D Canal)

The C&D Canal Museum is located in the heart of Chesapeake City and provides an intriguing insight into the history and importance of the Chesapeake and Delaware Canal.

The museum is housed in a historic building and showcases exhibits and artifacts that depict the canal’s construction, its impact on regional commerce, and its role in shaping the local community.

Visitors can explore interactive displays, watch informative videos and even step aboard a replica canal boat to experience life on the waterway firsthand.

Things to do:

  • Explore exhibits detailing the history and engineering of the Chesapeake and Delaware Canal.
  • Learn about the canal’s importance as a vital transportation artery and its role in shaping regional development.
  • Participate in guided tours led by knowledgeable museum staff.
  • Visit the museum gift shop to purchase unique souvenirs and gifts related to canal history.
  • Enjoy scenic views of the canal and surrounding waterfront from the museum’s observation deck.

πŸ‘‰Discover a bed and breakfast near Chesapeake’s historic district for a charming and intimate experience of the city’s heritage.

Scenic Drives and Fresh Seafood Markets


Chesapeake presents an opportunity for visitors to enjoy scenic drives along picturesque routes that wind through the city’s diverse landscapes.

These drives offer breathtaking views and a chance to connect with nature, whether it’s meandering along the waterfront or cruising through rolling countryside.

Along the way, travelers can explore the city’s thriving seafood markets, where they can sample and purchase a variety of locally caught seafood, including Chesapeake Bay blue crabs, oysters, and fresh fish.

Things to do:

  • Take a leisurely drive along scenic routes such as the Chesapeake Bay Bridge-Tunnel or the Dismal Swamp Canal Scenic Byway.
  • Stop at roadside overlooks and parks to take in panoramic views of the Chesapeake Bay and surrounding countryside.
  • Visit local seafood markets to browse a wide selection of fresh seafood caught daily by local fishermen.
  • Enjoy a seafood feast at one of Chesapeake’s many waterfront restaurants, where chefs expertly prepare the day’s catch.
  • Purchase fresh seafood to take home and enjoy, ensuring a taste of Chesapeake’s culinary delights long after your visit.

πŸ‘‰Find your flight to Chesapeake on Skyscanner and take the family to Fun Forest, the ultimate children’s playground sprawling over three acres.

 Plan Your Visit

Locks at Deep Creek, Chesapeake, Virginia along the Atlantic Intracoastal Waterway

By taking advantage of seasonal planning and various transportation options, you can fully enjoy all that Chesapeake has to offer.

When to Visit

Chesapeake is an ideal destination for outdoor activities and sightseeing throughout the year with its mild weather.

 However, different seasons offer unique advantages for various activities.

  • Spring (March to May): Mild temperatures and blooming flowers make spring an excellent time for outdoor adventures like hiking, biking, and birdwatching.
  • Summer (June to August): Warm weather beckons visitors to enjoy water sports, beach outings, and outdoor festivals. Be prepared for higher humidity levels during this season.
  • Fall (September to November): Crisp, cool air and vibrant foliage make fall perfect for scenic drives, hiking, and exploring outdoor attractions. It’s also a great time to visit local farms for pumpkin picking and apple harvesting.
  • Winter (December to February): While winters are mild in Chesapeake, with occasional snowfall, indoor attractions like museums and art galleries are popular during this time. It’s also an excellent season for birdwatching and wildlife observation.

πŸ‘‰Select a vacation rental near Fun Forest to ensure the kids have plenty to do right outside your door.

Getting Around Chesapeake

Navigating Chesapeake and its surrounding areas is relatively easy thanks to its well-connected roadways and public transportation options.

  • Car Rental: Renting a car is the most convenient way to explore Chesapeake and its neighboring attractions. Several rental agencies operate in the city, offering a variety of vehicles to suit different needs and budgets.
  • Public Transportation: Chesapeake Transit System (CTS) provides bus services within the city, offering convenient transportation to popular destinations and attractions. Additionally, intercity buses and trains connect Chesapeake to nearby cities like Norfolk and Virginia Beach.
  • Ridesharing: Services like Uber and Lyft operate in Chesapeake, providing an alternative mode of transportation for travelers who prefer not to drive.

Tips for Navigating:

  • Familiarize yourself with the main roads and highways in Chesapeake, such as Interstate 64, Route 168, and Route 17. These provide access to major attractions and neighboring cities.
  • Use navigation apps like Google Maps or Waze to plan your routes and avoid traffic congestion.
  • Keep an eye out for signage and directional markers, especially when exploring natural areas and parks.
  • For shorter trips within the city, consider biking or walking, especially in pedestrian-friendly areas like downtown Chesapeake and City Park.

πŸ‘‰Book your flight with Skyscanner to Chesapeake and paddle along the serene waters of the Dismal Swamp Canal, rich in history and natural beauty.

Conclusion: Discover the Charm of Chesapeake


Chesapeake, Virginia is a great destination for travelers who are looking for adventure and relaxation.

The city offers a diverse range of attractions, natural beauty, and rich cultural heritage, making it suitable for everyone’s taste.

From exploring historic sites such as the Battle of Great Bridge to immersing yourself in the tranquility of the Great Dismal Swamp, Chesapeake provides endless opportunities for discovery and adventure.

The hidden gem of Virginia awaits you, ready to enchant and inspire you with its beauty and charm.

Come and discover all that Chesapeake has to offer, and create memories that will last a lifetime. Your adventure begins here!

πŸ‘‰Stay in a cozy inn near the Dismal Swamp Canal to enjoy easy access to boat rentals and guided tours.

The post Explore VA’s Hidden Gem: Top Things To Do in Chesapeake appeared first on Take More Adventures.