Chesapeake, Virginia, is one of those underrated gems that packs a punch when it comes to fun, adventure, and relaxation.
Nestled between bustling cities and serene nature, this place offers everything from outdoor escapades to mouthwatering eats.
Whether you’re a local looking for a weekend escape or a traveler hunting for hidden treasures, Chesapeake won’t disappoint.
Ready to dive into the best this city has to offer? From kayaking through lush wetlands to savoring fresh seafood at a local hotspot, we’ve got the ultimate list of must-do activities.
Buckle up—you’re about to discover why Chesapeake should be your next go-to destination!
1. Explore the Great Dismal Swamp National Wildlife Refuge
If you think the name sounds intimidating, wait till you see how stunning this place really is.
The Great Dismal Swamp National Wildlife Refuge is a paradise for nature lovers, with over 112,000 acres of forests, wetlands, and wildlife.
Hike the scenic trails, paddle through the tranquil Lake Drummond, or keep your eyes peeled for black bears, bobcats, and rare birds.
This spot is perfect for those who love off-the-beaten-path adventures. The Dismal Swamp Canal Trail is a hit among bikers and walkers, offering a flat, easy route with gorgeous views.
Pro tip: Visit in the early morning or late afternoon for the best wildlife sightings. Don’t forget your camera—this place is Instagram gold!
2. Stroll Through the Chesapeake Arboretum
Need a peaceful escape without leaving the city? The Chesapeake Arboretum is a 48-acre oasis filled with lush gardens, walking trails, and towering trees.
It’s the perfect spot for a lazy afternoon picnic, a romantic walk, or even a solo recharge session.
The Native Plant Trail is a must-see, showcasing Virginia’s natural flora. If you’re into photography, the vibrant colors in spring and fall make for killer shots.
Best part? It’s free! So, grab your sneakers and enjoy some fresh air in this hidden green haven.
3. Get Adventurous at Northwest River Park
Calling all outdoor enthusiasts! Northwest River Park is where you go when you want to fish, camp, hike, or even try your hand at disc golf.
With over 763 acres of woodlands and waterways, this park is a dream for anyone who loves staying active.
The canoe and kayak rentals let you explore the Northwest River at your own pace. Prefer staying on land? The 8 miles of trails are perfect for biking or a leisurely stroll.
Families will love the playgrounds and picnic areas—this place is a one-stop fun zone!
4. Savor Fresh Seafood at The Butcher’s Son
Chesapeake’s food scene is no joke, and The Butcher’s Son is a local favorite.
This spot serves up juicy burgers, fresh seafood, and even vegan-friendly options, so everyone leaves happy. Their crab cakes? Absolute perfection.
The vibe here is casual and welcoming—think hearty meals in a cozy setting. Whether you’re craving a classic cheeseburger or a fresh catch of the day, this place nails it.
Pro tip: Come hungry, because the portions are generous!
5. Catch a Show at The Chesapeake Conference Center
Looking for some entertainment? The Chesapeake Conference Center hosts everything from live music and comedy shows to business expos and craft fairs.
Check their schedule—you might just catch a killer performance or a cool local event.
The venue is modern, spacious, and always buzzing with something exciting. Perfect for a fun night out without the hassle of big-city crowds.
6. Hit the Trails at Oak Grove Lake Park
For a quick nature fix, Oak Grove Lake Park is a winner. The 1.5-mile loop trail circles a serene lake, making it ideal for joggers, dog walkers, or anyone who just wants to unwind.
The park also has a fishing pier, so bring your gear if you’re into casting a line. It’s peaceful, well-maintained, and a great spot to clear your head.
7. Shop Local at the Chesapeake Farmers Market
If you love fresh produce, handmade crafts, and a lively atmosphere, the Chesapeake Farmers Market is a must-visit. Open seasonally, this market showcases the best of local vendors—think farm-fresh veggies, baked goods, and unique gifts.
Strolling through the stalls, chatting with vendors, and sampling goodies is a fantastic way to spend a Saturday morning. Plus, supporting small businesses? Always a win.
8. Tee Off at Chesapeake Golf Club
Golfers, listen up! The Chesapeake Golf Club offers a well-kept, 18-hole course that’s both challenging and scenic. Even if you’re not a pro, the lush fairways and relaxed vibe make it a great place to practice your swing.
Bonus: The club has a driving range and putting greens, so you can warm up before hitting the course. Fore!
9. Discover History at the Chesapeake Planetarium
For a dose of science and wonder, the Chesapeake Planetarium is a hidden gem. Their public shows explore space, astronomy, and mind-blowing cosmic phenomena.
It’s educational but far from boring—perfect for families or anyone who’s ever stared at the stars and wondered what’s out there.
10. Unwind at Fun Forest Playground
Traveling with kids? Fun Forest Playground is a dream come true for little ones. This massive, wooden castle-themed playground has slides, climbing structures, and plenty of space to run wild.
Parents can relax on the benches while the kids burn off energy. A total win for family fun!
11. Kayak the Elizabeth River
Adventure seekers, grab a kayak and hit the Elizabeth River. Paddling through these calm waters gives you a unique perspective of Chesapeake’s beauty.
You might even spot dolphins if you’re lucky! Rentals are available nearby, so no need to bring your own gear.
12. Dine at The Egg Bistro
Brunch lovers, rejoice! The Egg Bistro serves up fluffy pancakes, savory omelets, and gourmet coffee in a chic setting. Whether you’re craving sweet or savory, their menu has something delicious for every palate.
Weekend lines can get long, so arrive early—trust us, it’s worth it!
Final Thoughts: Chesapeake Awaits!
From outdoor adventures to mouthwatering eats, Chesapeake, Virginia, is packed with unforgettable experiences. Whether you’re kayaking through serene waters, exploring lush parks, or indulging in local flavors, this city has something for everyone.
So, what are you waiting for? Grab your friends, pack your bags, and get ready to explore the best things to do in Chesapeake. Your next adventure starts now!