Chesapeake, Virginia: Best Things to Do – Top Picks

Did you know Chesapeake has more miles of deepwater canals than Venice, Italy? This underrated Virginia gem offers a perfect blend of natural beauty, outdoor recreation, and small-town charm that makes it an ideal destination for travelers seeking authentic experiences. With over 22 miles of waterways winding through the city, Chesapeake provides unique perspectives and adventures that many visitors overlook when traveling through Virginia’s coastal region.

Getting to Chesapeake

Chesapeake is conveniently located in the Hampton Roads area of southeastern Virginia, making it easily accessible by various transportation methods. The Norfolk International Airport (ORF) serves as the primary air gateway to the region, located just 15 minutes from downtown Chesapeake.

If you prefer driving, Chesapeake is accessible via Interstate 64, which connects to major cities like Richmond and Washington D.C. The city is also served by Interstate 464 and U.S. Routes 17, 58, and 460, making it a convenient road trip destination from many East Coast locations.

Best Time to Visit Chesapeake

Chesapeake enjoys a moderate climate with four distinct seasons, each offering its own unique experiences. The best time to visit depends on your preferred activities and tolerance for different weather conditions.

Spring and fall are generally considered the best times to visit Chesapeake, with comfortable temperatures and beautiful scenery. Summer offers the most opportunities for water activities but can be hot and humid. Winter provides a quieter experience with fewer tourists and mild temperatures compared to northern states.

Fall brings spectacular colors to Northwest River Park’s hiking trails

Getting Around Chesapeake

Chesapeake is a sprawling city covering over 340 square miles, making personal transportation essential for exploring the area effectively. While there is some public transportation available through Hampton Roads Transit (HRT), having your own vehicle provides the most flexibility.

For those interested in exploring Chesapeake’s waterways, kayak and canoe rentals are available at several locations, including Northwest River Park and the Great Dismal Swamp. These water routes offer unique perspectives of the city’s natural beauty and wildlife.

Exploring Great Dismal Swamp by kayak offers a unique perspective of Chesapeake’s natural beauty

Where to Stay in Chesapeake

Chesapeake offers a variety of accommodation options to suit different preferences and budgets. From well-known hotel chains to charming bed and breakfasts, you’ll find comfortable places to rest after a day of exploration.

Many Chesapeake accommodations offer scenic water views

Top Attractions and Activities in Chesapeake

Chesapeake offers a diverse range of attractions and activities, from outdoor adventures to cultural experiences. Here are the top things to do during your visit:

1. Great Dismal Swamp National Wildlife Refuge

Despite its ominous name, the Great Dismal Swamp is a breathtaking natural wonder spanning over 112,000 acres. This ancient wetland ecosystem is home to diverse wildlife, including over 200 bird species, black bears, and the elusive bobcat. Visitors can explore miles of hiking trails, paddle through pristine waterways, or fish in Lake Drummond, one of only two natural lakes in Virginia.

The refuge’s boardwalk trail provides an accessible way to experience this unique ecosystem without getting your feet wet. For a more immersive experience, to learn about the swamp’s fascinating history as a sanctuary for escaped slaves on the Underground Railroad.

The boardwalk trail at Great Dismal Swamp offers accessible exploration of this unique ecosystem

2. Chesapeake Arboretum

Known as “Nature’s Classroom,” the 48-acre Chesapeake Arboretum features beautiful gardens, a mature hardwood forest, and over 3 miles of trails. The arboretum is home to the Caleb Williamson Farm House, a historic structure dating back to the 1700s that offers a glimpse into the area’s agricultural past.

Don’t miss the impressive collection of camellias and the peaceful Japanese garden. The arboretum hosts seasonal events and educational programs throughout the year, making it worth checking their calendar before your visit.

The Chesapeake Arboretum features beautiful garden paths and native plant collections

3. Northwest River Park

This 763-acre park offers something for everyone, from outdoor enthusiasts to families seeking a relaxing day in nature. Northwest River Park features camping facilities, picnic areas, playgrounds, and an 18-hole disc golf course. The park’s crown jewel is the Northwest River, perfect for kayaking, canoeing, and fishing.

Hikers can explore over 7 miles of trails winding through diverse habitats, while birdwatchers will appreciate the variety of species that call the park home. Equipment rentals are available on-site, including kayaks, canoes, and fishing gear, making it easy to enjoy water activities even if you didn’t bring your own equipment.

Northwest River Park offers perfect spots for family picnics and outdoor recreation

4. Chesapeake City Park

This expansive community park hosts many of the city’s major events, including the Chesapeake Jubilee and the Symphony Under the Stars. Even when there’s no event scheduled, the park offers plenty of recreational opportunities with its playgrounds, walking trails, and sports facilities.

The Fun Forest, a large wooden playground complex, is particularly popular with families. The park also features a skate park, volleyball courts, and ample green space for informal games and activities.

The central fountain at Chesapeake City Park is a popular gathering spot for families

5. Oak Grove Lake Park

This serene 65-acre park centers around a beautiful 65-acre lake, offering a peaceful retreat from the bustle of everyday life. A 1.5-mile trail encircles the lake, providing excellent opportunities for walking, jogging, and wildlife observation.

The park is a paradise for birdwatchers, with numerous species visible throughout the year. Fishing is permitted from the shoreline and the park’s pier, with the lake stocked with various fish species. Picnic facilities and a playground make this an ideal spot for a family outing.

The boardwalk at Oak Grove Lake Park is a prime spot for birdwatching enthusiasts

6. Intracoastal Waterway

The Atlantic Intracoastal Waterway runs through Chesapeake, offering unique perspectives of the city from the water. Several companies offer cruises and boat tours, allowing you to experience the waterway’s beauty while learning about its historical and ecological significance.

For a more personalized experience, consider a guided kayak eco-tour that explores the waterway’s hidden corners and introduces you to the diverse wildlife that inhabits these waters.

A sunset cruise on the Intracoastal Waterway offers breathtaking views and a peaceful experience

Local Dining Scene

Chesapeake’s culinary landscape reflects its coastal location and Southern heritage, offering everything from fresh seafood to comfort food classics. Here are some top dining spots to try during your visit:

She-crab soup is a local delicacy found on many Chesapeake restaurant menus

For those seeking a unique dining experience, consider visiting during the Chesapeake Restaurant Week, typically held in March, when many local establishments offer special menus at fixed prices. This is an excellent opportunity to sample the city’s diverse culinary offerings at a value.

Practical Tips for Visitors

Make the most of your Chesapeake visit with these helpful tips:

Safety Information

Chesapeake is generally a safe destination, but it’s always wise to take standard precautions:

• Be aware of your surroundings, especially when visiting remote natural areas
• When hiking or kayaking, let someone know your planned route and expected return time
• During summer, be mindful of heat and humidity – stay hydrated and take breaks in shaded areas
• If exploring waterways, always wear a life jacket and check weather conditions before heading out
• Keep an eye out for wildlife, including snakes and insects, when exploring natural areas

The Military Aviation Museum showcases an impressive collection of vintage aircraft

Plan Your Chesapeake Adventure

With its mix of wild wetlands and Southern charm, Chesapeake isn’t just a stopover – it’s a destination where adventure whispers from every cypress tree. From paddling through the mysterious waters of the Great Dismal Swamp to enjoying fresh seafood along the Intracoastal Waterway, Chesapeake offers experiences that connect you with both nature and local culture.

Whether you’re seeking outdoor adventures, historical discoveries, or simply a peaceful retreat from everyday life, Chesapeake welcomes you with open arms and endless possibilities. Pack your sense of adventure and prepare to be charmed by this hidden gem of coastal Virginia.