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20 Things to Do in Chesapeake, Virginia(VA)

Chesapeake, Virginia, is a hidden gem on the east coast, offering a delightful mix of natural beauty, rich history, and vibrant culture. Nestled between Norfolk and Virginia Beach, this charming city has become a popular destination for travelers seeking an escape from the hustle and bustle while still being close to major metropolitan areas. From its serene waterways and abundant wildlife to its family-friendly attractions, Chesapeake offers something for everyone. In this guide, we'll explore the best things to do in Chesapeake, VA, and why this city should be at the top of your travel list.

Why Visit Chesapeake, VA?

Chesapeake is a unique blend of history, nature, and modern amenities. Its convenient location in the heart of Hampton Roads makes it an ideal spot for a weekend getaway or a longer vacation, while also being a great starting point to explore things to do in Abingdon, Virginia (VA), known for its charming small-town vibe and rich cultural heritage. The city’s diverse offerings—ranging from beautiful parks to historical sites—appeal to a wide variety of travelers.

Key Attractions

One of Chesapeake's biggest draws is the Great Dismal Swamp National Wildlife Refuge, a vast and protected area filled with rich biodiversity, perfect for outdoor enthusiasts. The city is also home to a number of parks and historic sites, like the Chesapeake City Park and the Battlefield Park. Moreover, the city is brimming with cultural attractions like art galleries and museums, making it an ideal location for anyone interested in exploring both nature and history.

Cultural Significance

Chesapeake has a rich military history, reflected in the many historical landmarks and museums dedicated to its past. The city's deep-rooted connection with nature is evident in its commitment to preserving the Great Dismal Swamp, which has been a vital part of the local ecosystem for centuries. For those exploring the area, nearby things to do in Leesburg, Virginia (VA) also offer a variety of cultural and outdoor experiences.

Convenience for Travelers

Travelers from surrounding cities like Norfolk and Virginia Beach will find Chesapeake to be an easy-to-reach destination, making it perfect for a quick trip or an extended stay. With its proximity to other major cities, Chesapeake offers a unique and peaceful retreat without sacrificing access to urban amenities, as well as offering fun things to do in Virginia Beach nearby.

Infographic - 20 Things to Do in Chesapeake, Virginia

20 Things to Do in Chesapeake, Virginia

Chesapeake, Virginia, is a charming city located in the Hampton Roads region, offering a blend of rich history, scenic beauty, and outdoor adventure. Whether you're a history enthusiast, nature lover, or someone seeking a fun family outing, Chesapeake has plenty to offer. Below are some of the best things to do in Chesapeake, VA, each featuring a mix of cultural, historical, and recreational activities.

1. Explore Great Bridge Battlefield & Waterways Park

Short Description:
The Great Bridge Battlefield & Waterways Park is a historical site that commemorates the Battle of Great Bridge, a significant event during the American Revolution. The park offers interpretive trails, monuments, and scenic views of the surrounding waterway.

Pros:

  • Rich historical significance
  • Peaceful setting with waterfront views
  • Educational experience with interpretive signs

Cons:

  • Limited facilities for visitors
  • Best for history enthusiasts, may not appeal to all

Key Attractions and Events:

  • Annual reenactments of the Battle of Great Bridge
  • Scenic walking trails
  • Educational programs and guided tours

2. Visit the Chesapeake Arboretum

Short Description:
The Chesapeake Arboretum is a peaceful 48-acre green space showcasing a wide variety of native plants, trees, and flowers. It offers visitors an opportunity to enjoy nature while learning about local flora.

Pros:

  • Beautiful landscaping and peaceful atmosphere
  • Free admission
  • Ideal for nature walks, photography, and family outings

Cons:

  • Limited activities aside from walking and sightseeing
  • No major attractions or events

Key Attractions and Events:

  • Seasonal plant displays
  • Educational programs on native plants
  • Family-friendly nature trails

3. Spend the Day at Northwest River Park

Short Description:
Northwest River Park is a spacious 763-acre park that offers a range of outdoor activities like hiking, picnicking, fishing, and camping. It's a great spot for those who want to experience the beauty of nature in a serene environment.

Pros:

  • Extensive recreational options
  • Ideal for both relaxation and adventure
  • Family-friendly with picnic areas and campgrounds

Cons:

  • Limited amenities (e.g., no major stores or restaurants nearby)
  • Requires a vehicle for easier access

Key Attractions and Events:

  • Fishing and boating on the Northwest River
  • Seasonal events and programs
  • Campsites for overnight stays

4. Take a Scenic Walk at Dismal Swamp Canal Trail

Short Description:
The Dismal Swamp Canal Trail is a 3-mile long walking trail located along one of the oldest man-made canals in the U.S. The trail offers a unique opportunity to experience wildlife and the natural beauty of the Dismal Swamp.

Pros:

  • Scenic views and peaceful surroundings
  • Rich biodiversity for nature enthusiasts
  • Accessible for walking, running, and biking

Cons:

  • Limited amenities along the trail
  • Can be buggy during warmer months

Key Attractions and Events:

  • Birdwatching and wildlife viewing
  • Historical landmarks along the canal
  • Guided tours during the summer months

5. Tour the Chesapeake Planetarium

Short Description:
The Chesapeake Planetarium offers visitors a chance to explore the wonders of the night sky through educational shows and interactive exhibits. It's a fantastic destination for astronomy lovers and families looking to learn more about space.

Pros:

  • Educational and interactive exhibits
  • Affordable family-friendly experience
  • Various programs for different age groups

Cons:

  • Limited to certain showtimes and events
  • Small facility compared to larger planetariums

Key Attractions and Events:

  • Planetarium shows focusing on constellations and astronomy
  • Special events for children and school groups
  • Stargazing nights with local astronomers

6. Check Out the Chesapeake Ice Rink

Short Description:
The Chesapeake Ice Rink is the go-to location for ice skating and other ice-related activities. Whether you're a seasoned skater or a beginner, this rink offers fun for all ages.

Pros:

  • Indoor ice rink for year-round skating
  • Rental equipment available
  • Family-friendly and affordable

Cons:

  • Can get crowded during peak hours
  • Limited to skating-related activities

Key Attractions and Events:

  • Public ice skating sessions
  • Ice hockey leagues and events
  • Birthday parties and private events

7. Visit the Chesapeake Bay Bridge-Tunnel

Short Description:
The Chesapeake Bay Bridge-Tunnel is a unique and iconic structure that spans the Chesapeake Bay, offering a thrilling and scenic drive. It's considered one of the seven engineering wonders of the modern world.

Pros:

  • Breathtaking views of the Chesapeake Bay
  • A once-in-a-lifetime experience
  • Great photo opportunities

Cons:

  • Tolls required to cross the bridge
  • Not a traditional tourist attraction with amenities

Key Attractions and Events:

  • Scenic drive with spectacular bay views
  • Observation areas for photos and sightseeing
  • Educational exhibits about the bridge’s construction

8. Discover the Chesapeake Virginia Historical Society Museum

Short Description:
The Chesapeake Virginia Historical Society Museum is dedicated to preserving the rich history of Chesapeake. With exhibits that showcase everything from the city’s Native American heritage to its role in the American Revolution, the museum provides a comprehensive look at the area’s past.

Pros:

  • Well-curated exhibits for history buffs
  • Educational and informative
  • Accessible location

Cons:

  • Small museum size
  • Limited interactive exhibits for children

Key Attractions and Events:

  • Permanent exhibits about Chesapeake’s history
  • Special events like history tours and speakers
  • Local history workshops

9. Explore the Chesapeake City Park

Short Description:
Chesapeake City Park is a well-maintained park featuring walking trails, a large lake, picnic areas, and playgrounds. It’s perfect for a day of outdoor fun, whether you’re looking to relax or stay active.

Pros:

  • Variety of outdoor activities for all ages
  • Beautiful lake for picnicking and fishing
  • Safe and family-friendly environment

Cons:

  • Can be busy on weekends and holidays
  • Limited seating at some areas

Key Attractions and Events:

  • Playground and sports courts for children and families
  • Fishing and canoeing on the park’s lake
  • Seasonal events and concerts

10. Take a Boat Tour of the Intracoastal Waterway

Short Description:
A boat tour of the Intracoastal Waterway offers an opportunity to experience the beauty of the waterway, wildlife, and local landmarks from the comfort of a boat. This is a great activity for nature lovers and anyone interested in maritime history.

Pros:

  • Beautiful water views and wildlife sightings
  • Educational experience about the waterway’s history
  • Relaxing and scenic tour

Cons:

  • Limited availability during off-season months
  • Can be pricey compared to other activities

Key Attractions and Events:

  • Guided boat tours with expert commentary
  • Chance to spot dolphins and other wildlife
  • Scenic routes through the Chesapeake Bay area

11. Experience a Live Performance at the Chesapeake Conference Center

Short Description:
The Chesapeake Conference Center is a premier venue for hosting a wide range of events, from live performances and concerts to conventions and banquets.

Pros:

  • Versatile event space accommodating large audiences.
  • Regular performances and events cater to different tastes.
  • Great acoustics and modern facilities.

Cons:

  • Limited events depending on the time of year.
  • Parking can get crowded during major events.

Key Attractions and Events:

  • Live concerts, comedy shows, and theater performances.
  • Annual conventions and trade shows.
  • Special community events held throughout the year.

12. Visit Oak Grove Lake Park

Short Description:
Oak Grove Lake Park is a beautiful, tranquil park perfect for those looking to enjoy the outdoors. It features a serene lake, walking trails, picnic areas, and much more.

Pros:

  • Ideal for fishing, boating, and picnicking.
  • Scenic walking and biking trails.
  • Family-friendly atmosphere.

Cons:

  • Can get crowded on weekends, especially during peak seasons.
  • Limited facilities for large groups or events.

Key Attractions and Events:

  • Beautiful lake with paddle boats available.
  • Walking and cycling trails surrounded by nature.
  • Annual outdoor events, including family picnics and bird-watching tours.

13. Explore the Chesapeake Regional Park

Short Description:
Chesapeake Regional Park offers a range of outdoor activities including camping, hiking, and water sports. It’s an ideal spot for nature lovers.

Pros:

  • Offers various recreational activities like kayaking, fishing, and hiking.
  • Campground facilities for those who want to stay overnight.
  • Peaceful natural setting perfect for relaxation.

Cons:

  • Limited amenities for those looking for luxury accommodations.
  • Popular during holiday weekends, so plan ahead.

Key Attractions and Events:

  • Year-round fishing tournaments and outdoor festivals.
  • Wildlife observation and nature walks.
  • Seasonal camping experiences for families and groups.

14. Attend Local Festivals Like the Chesapeake Jubilee

Short Description:
The Chesapeake Jubilee is one of the city’s most beloved annual events, offering a variety of live entertainment, food, and fun for all ages.

Pros:

  • Family-friendly with something for everyone, including rides, music, and games.
  • Great opportunity to sample local cuisine and cultural traditions.
  • Free entry for most events within the festival.

Cons:

  • Can get crowded, especially on the weekends.
  • Limited parking around the event grounds.

Key Attractions and Events:

  • Live music performances by local and regional bands.
  • Carnival rides and games for kids.
  • Local food vendors offering a variety of cuisine.

15. Go Shopping at Greenbrier Mall

Short Description:
Greenbrier Mall is the place to go if you're looking for a shopping spree. With a variety of retail stores, restaurants, and entertainment options, it’s a great spot for both locals and tourists.

Pros:

  • Wide variety of retail stores and services.
  • Ample dining options, from casual to more upscale.
  • Family-friendly atmosphere with a play area for kids.

Cons:

  • Can become crowded during peak shopping seasons.
  • Limited parking spots during holidays or major sales events.

Key Attractions and Events:

  • Popular retail stores like Macy's and Dillard’s.
  • Special events like holiday sales and community events.
  • Restaurants offering diverse cuisines, including fast food and sit-down options.

16. Explore the Western Branch Nature Trail

Short Description:
For those who enjoy outdoor activities, the Western Branch Nature Trail provides an excellent opportunity to experience Chesapeake's natural beauty.

Pros:

  • Peaceful environment perfect for hiking or nature walks.
  • Ideal for bird watching and photography.
  • Well-maintained trail system for all skill levels.

Cons:

  • Limited facilities for picnicking or large groups.
  • Some sections of the trail may be less accessible for people with mobility issues.

Key Attractions and Events:

  • Scenic trail through wooded areas and wetlands.
  • Guided nature walks and wildlife viewing.
  • Seasonal events focused on local flora and fauna.

17. Visit the Hunt Club Farm

Short Description:
Hunt Club Farm offers a unique experience with a variety of farm animals, seasonal events, and petting zoos, perfect for a family outing.

Pros:

  • Family-friendly with activities for children and adults.
  • Seasonal events such as corn mazes, hayrides, and pumpkin patches.
  • Opportunity to interact with farm animals.

Cons:

  • Limited hours during off-peak seasons.
  • Can be crowded during special events like Halloween or Christmas.

Key Attractions and Events:

  • Petting zoo with a variety of farm animals.
  • Seasonal attractions like the haunted forest and Christmas light displays.
  • Educational farm tours and animal shows.

18. Enjoy the Western Branch Community Park

Short Description:
Western Branch Community Park is a well-maintained public park that offers sports facilities, walking paths, and playgrounds.

Pros:

  • Great for sports enthusiasts with fields for soccer, baseball, and more.
  • Spacious playground areas for children.
  • Well-maintained walking paths and picnic areas.

Cons:

  • Can get busy during weekends or special events.
  • Limited indoor facilities during inclement weather.

Key Attractions and Events:

  • Local sports leagues and tournaments.
  • Seasonal community events like outdoor movie nights.
  • Playground and splash pad for children.

19. Explore the Arts at the Chesapeake Art Gallery

Short Description:
The Chesapeake Art Gallery is the perfect place for art lovers to explore local and regional artwork, with rotating exhibitions and unique installations.

Pros:

  • Features a wide variety of art forms, from painting to sculpture.
  • Great way to support local artists.
  • Regular art workshops and community events.

Cons:

  • Limited space, so exhibitions are often small-scale.
  • Can be closed for installation or between exhibits.

Key Attractions and Events:

  • Rotating exhibits featuring regional artists.
  • Art classes and workshops for both beginners and advanced artists.
  • Community events celebrating art and culture.

20. Enjoy a Family Day at the Chesapeake Family YMCA

Short Description:
The Chesapeake Family YMCA is a fantastic destination for families looking to stay active and engaged. With facilities for swimming, fitness classes, and more, it’s perfect for a fun day out.

Pros:

  • Variety of recreational activities, including swimming and fitness classes.
  • Family-friendly environment with programs for all ages.
  • Well-maintained and safe facilities.

Cons:

  • Membership or daily fees may apply for certain activities.
  • Can become crowded during peak hours.

Key Attractions and Events:

  • Swimming pools and fitness centers.
  • Youth sports leagues and educational programs.
  • Family-oriented community events and classes.

Best Time to Visit Chesapeake

The ideal time to visit Chesapeake depends on the type of activities you’re looking to enjoy. Each season offers something special.

Spring and Fall

These seasons are the most pleasant for outdoor activities. The mild weather makes it perfect for hiking, boating, and exploring the city’s parks and wildlife areas. Fall is particularly charming with the beautiful foliage, while spring is ideal for visiting the area’s many gardens and outdoor festivals.

Summer

Summer in Chesapeake can be warm, but it's also the most active time of the year. This is when you’ll find a variety of events, including the Chesapeake Jubilee, a popular festival with music, food, and rides for all ages. For beachgoers, the city’s proximity to Virginia Beach also makes it an easy destination for some fun in the sun.

Winter

Although winter is cooler, it's still a great time to explore the city’s indoor attractions and take part in seasonal events like holiday markets and winter festivals. Chesapeake’s quieter atmosphere during the colder months makes it ideal for those looking to avoid the crowds.

Local Cuisine and Dining Spots

No visit to Chesapeake is complete without sampling some of its delicious local cuisine. Whether you’re in the mood for seafood, Southern comfort food, or casual bites, Chesapeake has plenty to offer.

Top Restaurants and Cafes

  • The Butcher’s Block: A fine dining experience known for its excellent steaks and fresh seafood, perfect for a romantic dinner or special occasion.
  • Cedar Point Country Club: Ideal for a relaxed afternoon, this venue offers a beautiful setting along with a fantastic menu featuring local seafood.
  • Mill House Restaurant: A local favorite that blends Southern flavors with modern twists. Perfect for families and anyone craving hearty meals.

Casual Dining

For those seeking more casual dining options, The Greenbrier Grill and El Toro Mexican Restaurant offer a welcoming atmosphere and great food at affordable prices. These are ideal for travelers on the go or families looking for a relaxed dining experience.

Local Delicacies

Make sure to try Chesapeake’s local specialties like Virginia ham, seafood dishes (especially crabs and oysters), and Southern-style biscuits. These are the perfect way to savor the taste of Chesapeake.

Family-Friendly Activities in Chesapeake

Chesapeake is a fantastic destination for families, offering a wide variety of activities that cater to all ages.

Parks and Museums

  • Chesapeake City Park: This 90-acre park is home to a large playground, picnic areas, and trails. It’s perfect for a family day out with plenty of room for kids to run and play.
  • Children’s Museum of Virginia: Just a short drive away, this museum is packed with interactive exhibits that kids will love. From science to art, it’s an educational experience that’s fun for the whole family.

Seasonal Events

Chesapeake hosts family-friendly events year-round, such as the Chesapeake Jubilee, where families can enjoy games, carnival rides, and live music. There are also various seasonal festivals celebrating the city’s history and culture, providing fun opportunities for family bonding.

Outdoor and Nature Adventures

For nature lovers and outdoor enthusiasts, Chesapeake has an abundance of options to explore the great outdoors.

Hiking and Boating

Chesapeake is home to numerous parks and trails, including those in the Great Dismal Swamp National Wildlife Refuge. Visitors can explore the swamp's scenic beauty while hiking or taking a boat tour. Whether you’re an experienced kayaker or someone who simply enjoys a leisurely boat ride, the swamp offers endless opportunities for outdoor fun.

Birdwatching and Wildlife

Chesapeake’s natural beauty is also a haven for birdwatching. The Great Dismal Swamp is home to over 200 species of birds, making it a prime location for bird watchers. The area also hosts a variety of wildlife, including deer, foxes, and turtles.

FAQs

What is the best time of year to visit Chesapeake, VA?

The best time to visit is during the spring or fall, when the weather is mild and perfect for outdoor activities. Summer is also a great time for festivals, while winter is quieter but still enjoyable for indoor attractions and seasonal events.

Are there any pet-friendly places in Chesapeake?

Yes! Chesapeake offers several pet-friendly parks, walking trails, and outdoor spaces. Many of the area’s outdoor attractions welcome pets, making it a great destination for travelers with furry friends.

How can I get around Chesapeake?

Chesapeake is best explored by car. The city is well-connected by highways, and most of its attractions are a short drive away from each other. Public transportation is limited, so renting a car is recommended.

Are there any free attractions in Chesapeake, VA?

Yes! Many of the parks, including the Great Dismal Swamp National Wildlife Refuge, are free to visit. You can also explore some of Chesapeake’s historic sites and nature trails without any admission fee.

Is Chesapeake a family-friendly destination?

Absolutely! Chesapeake is known for its family-friendly atmosphere, offering numerous parks, museums, and seasonal events that kids and adults will enjoy.

Conclusion

Chesapeake, VA, is an underrated travel destination that offers a rich mix of history, nature, and fun activities for all types of travelers. Whether you’re looking to explore the outdoors, learn about the city’s past, or enjoy some delicious local cuisine, Chesapeake has something for everyone. From its family-friendly attractions to its stunning natural landscapes, this city should be on your travel list. So pack your bags, and get ready to discover all the wonderful things to do in Chesapeake, VA!

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