10 Best Year-Round Activities in Chesapeake, Virginia

Key Takeaways:

• Chesapeake, Virginia, is a destination that offers a mix of outdoor recreation, historical sites, and cultural experiences all year long.
• Whether you enjoy hiking, festivals, water activities, or local food, Chesapeake has something to offer every type of traveler.
• With free and affordable attractions, this city is a great place to visit for families, solo travelers, and adventure seekers alike.

Table of Contents

1. Explore the Great Dismal Swamp National Wildlife Refuge
2. Walk Along the Chesapeake Arboretum Trails
3. Visit Oak Grove Lake Park
4. Experience the Chesapeake Jubilee Festival
5. Discover Local History at the Chesapeake Veterans Memorial
6. Kayak on the Intracoastal Waterway
7. Enjoy Fresh Produce at the Chesapeake Farmers’ Market
8. Catch a Live Show at the Chesapeake Conference Center
9. Go Fishing or Boating at Northwest River Park
10. Take a Scenic Drive on the Chesapeake Bay Bridge-Tunnel

Located in the heart of coastal Virginia, Chesapeake is a city known for its natural beauty, rich history, and endless outdoor adventures. As one of the largest cities in the state, Chesapeake offers a perfect blend of urban convenience and scenic escapes, making it a fantastic year-round destination. Whether you’re exploring the stunning Great Dismal Swamp, strolling along peaceful waterfront parks, or attending lively festivals, there’s no shortage of things to do here.

People love Chesapeake for its charming small-town feel mixed with easy access to some of Virginia’s most breathtaking landscapes. From hiking trails and water activities to historical sites and seasonal events, there’s always something happening. If you’re planning a trip, here are ten exciting activities that you can enjoy in Chesapeake no matter the season.

1. Explore the Great Dismal Swamp National Wildlife Refuge

One of Chesapeake’s most famous natural wonders, the Great Dismal Swamp National Wildlife Refuge is a must-visit for outdoor enthusiasts. Covering over 112,000 acres, this vast wilderness is home to stunning landscapes, diverse wildlife, and incredible hiking and kayaking opportunities. Visitors can explore miles of trails, including the popular Dismal Swamp Canal Trail, where you’ll see towering cypress trees and serene waterways. The area is also a great spot for birdwatching, with bald eagles, owls, and woodpeckers frequently spotted.

For those who prefer a water adventure, the Dismal Swamp Canal is perfect for kayaking and canoeing. The peaceful waters provide a unique way to experience the beauty of the swamp while spotting turtles, deer, and even black bears along the shoreline. Whether you’re hiking, paddling, or simply taking in the views, this hidden gem offers a one-of-a-kind experience in Chesapeake.

2. Walk Along the Chesapeake Arboretum Trails

For a relaxing day outdoors, the Chesapeake Arboretum offers beautifully maintained walking trails surrounded by lush greenery. Known as a “nature classroom,” this 48-acre park is home to a variety of native trees, gardens, and scenic boardwalks. Visitors can take self-guided tours through themed gardens, including the Butterfly Garden and the Camellia Cove, where vibrant flowers bloom year-round.

The arboretum’s trail system winds through a picturesque forest, making it a great spot for an easy hike or a peaceful escape from city life. The park also hosts seasonal events, including guided nature walks and educational programs for all ages. Whether you’re an avid nature lover or just looking for a quiet place to unwind, the Chesapeake Arboretum is a hidden treasure.

3. Visit Oak Grove Lake Park

One of the most popular parks in Chesapeake, Oak Grove Lake Park is a favorite destination for both locals and visitors. The park features a 1.5-mile loop trail that circles a scenic lake, perfect for walking, jogging, or biking. With picnic shelters, fishing spots, and plenty of shaded areas, it’s an ideal location for a family outing or a peaceful afternoon in nature.

The lake itself provides a stunning backdrop for photography and wildlife spotting, with ducks, herons, and turtles frequently seen near the shoreline. During the fall, the park’s trees explode with vibrant colors, making it one of the best places in Chesapeake to enjoy autumn foliage. Whether you’re looking to get some exercise or simply relax by the water, Oak Grove Lake Park is a great year-round destination.

4. Experience the Chesapeake Jubilee Festival

If you’re visiting Chesapeake in the spring, don’t miss the annual Chesapeake Jubilee Festival. This multi-day event is one of the city’s biggest celebrations, featuring carnival rides, live music, food vendors, and a spectacular fireworks display. The festival highlights local culture with performances from regional musicians, arts and crafts showcases, and delicious Southern cuisine.

The Chesapeake Jubilee also includes a barbecue cook-off, where top chefs compete to serve up the best ribs, brisket, and pulled pork. Families will love the kid-friendly activities, including face painting, pony rides, and interactive games. With so much to see and do, this festival is a fun way to experience the lively spirit of Chesapeake.

5. Discover Local History at the Chesapeake Veterans Memorial

For those interested in history, the Chesapeake Veterans Memorial is a moving tribute to the men and women who have served in the U.S. military. Located near City Hall, this beautifully designed memorial features engraved plaques honoring veterans from different wars and conflicts. Visitors can take a quiet moment to reflect while walking through the site, which is surrounded by well-manicured gardens and flags representing each branch of the military.

Throughout the year, the memorial hosts ceremonies for Veterans Day and Memorial Day, drawing members of the community together to pay their respects. Whether you have a personal connection to the military or simply want to learn more about Chesapeake’s history, this site is a meaningful stop on any trip to the city.

6. Kayak on the Intracoastal Waterway

For those who love water adventures, kayaking on the Intracoastal Waterway is one of the best ways to experience Chesapeake’s natural beauty. This network of rivers, canals, and bays provides calm, scenic waters perfect for paddlers of all skill levels. Rent a kayak or bring your own to explore the winding waterways surrounded by lush forests and wetlands. Along the way, you may spot dolphins, herons, and other wildlife that thrive in this coastal ecosystem.

In addition to kayaking, visitors can also enjoy fishing or boating in the area. Several launch points make it easy to start your journey, whether you’re looking for a short paddle or an all-day adventure. Whether you’re seeking relaxation or an active day on the water, the Intracoastal Waterway offers a peaceful escape from city life.

7. Enjoy Fresh Produce at the Chesapeake Farmers’ Market

For a taste of local flavor, stop by the Chesapeake Farmers’ Market, where you can find fresh produce, homemade baked goods, and handcrafted items from local vendors. Open year-round, this market is the perfect place to pick up seasonal fruits and vegetables, locally made honey, and fresh seafood straight from the Chesapeake Bay. The friendly atmosphere and variety of goods make it a fun and rewarding shopping experience.

Beyond food, the market often hosts live music, cooking demonstrations, and special events showcasing Chesapeake’s agricultural roots. Whether you’re looking to grab ingredients for a picnic or just browse for unique souvenirs, this market is a great way to support local businesses while enjoying the charm of Chesapeake.

8. Catch a Live Show at the Chesapeake Conference Center

For those who love entertainment, the Chesapeake Conference Center is a top venue for concerts, comedy shows, and cultural performances. Throughout the year, the center hosts a variety of live events, including theatrical productions, tribute bands, and seasonal festivals. The intimate setting ensures that every seat offers a great view of the stage, making it a fantastic place to enjoy live entertainment.

In addition to music and theater, the venue also holds expos, conventions, and community events that draw locals and visitors alike. Whether you’re in town for a weekend or a longtime resident, checking out a show at the Chesapeake Conference Center is a great way to add some excitement to your trip.

9. Go Fishing or Boating at Northwest River Park

For outdoor lovers, Northwest River Park is one of Chesapeake’s top spots for fishing, boating, and hiking. The park features a large lake stocked with bass, catfish, and bluegill, making it a popular spot for anglers. If you don’t have your own boat, canoe and kayak rentals are available, allowing you to paddle through the peaceful waters surrounded by stunning greenery.

The park also has over 7 miles of scenic trails, perfect for a refreshing hike or a quiet nature walk. Families can enjoy picnic areas, playgrounds, and even a mini-golf course, making it an excellent destination for a full day of fun. Whether you’re casting a line or just soaking in the natural beauty, Northwest River Park is a fantastic year-round getaway.

10. Take a Scenic Drive on the Chesapeake Bay Bridge-Tunnel

For a breathtaking coastal experience, take a scenic drive on the Chesapeake Bay Bridge-Tunnel, one of the most impressive engineering marvels in the country. Spanning over 17 miles, this bridge-tunnel system connects Chesapeake to Virginia’s Eastern Shore, offering incredible views of the Chesapeake Bay along the way. Whether you’re driving for the experience or heading to a new destination, the journey itself is a memorable adventure.

Along the route, visitors can stop at scenic overlooks and observation areas to take in the vast ocean views. Birdwatchers and photographers will appreciate the unique vantage points, where seabirds and marine life are often visible. If you’re looking for a road trip with stunning scenery, this drive is a must-do while visiting Chesapeake.

What to Do if You Have Kids?

Chesapeake is a great destination for families, with plenty of kid-friendly attractions to explore. Fun Forest Playground, located at City Park, is one of the largest playgrounds in the region, offering exciting climbing structures, slides, and open spaces for children to run and play. If your kids love animals, the nearby Lions Bridge Petting Zoo allows them to interact with friendly farm animals.

For an educational experience, visit the Children’s Museum of Virginia, just a short drive away in Portsmouth. This interactive museum features hands-on exhibits about science, space, and history, making learning fun for kids of all ages. Whether your family enjoys outdoor adventures or engaging indoor activities, Chesapeake has plenty of options to keep little ones entertained.

Where Can I Find Free Events in Chesapeake Virginia Taking Place This Weekend?

If you’re looking for free events in Chesapeake this weekend, check out PlanMyWeekend.ai. This tool helps you discover local festivals, concerts, outdoor movie nights, and community gatherings—all without spending a dime. Whether you’re looking for something family-friendly or just a fun outing with friends, this site makes it easy to find great activities happening nearby.

Many of Chesapeake’s parks and public spaces also host free events throughout the year, from farmers’ markets to holiday parades. Simply enter your location on PlanMyWeekend.ai to explore the best upcoming events that match your interests.

Final Thoughts

Chesapeake, Virginia, is a destination that offers a little bit of everything—natural beauty, historical landmarks, and exciting entertainment. Whether you’re hiking through the Great Dismal Swamp, attending a festival, or exploring the city’s vibrant arts scene, there’s always something happening year-round. With a mix of outdoor adventures, cultural experiences, and free activities, Chesapeake is a great place to visit for travelers of all types.

Whether you’re planning a weekend getaway or an extended stay, this city has something to offer in every season. Start planning your trip today and experience the charm, history, and adventure that Chesapeake has to offer!