10 Fun Things To Do In and Around Chesapeake, Virginia
If you’re planning a trip to coastal Virginia, don’t skip
Chesapeake. Tucked between
Virginia Beach,
Norfolk, and the
North Carolina border, Chesapeake is the kind of place where you can hike a quiet trail in the morning, paddle a river in the afternoon, and sit down to fresh
seafood at night.
Whether you’re road-tripping down
I‑64, visiting family nearby, or looking for a relaxing weekend getaway, here are
10 great things to do in Chesapeake, VA and the surrounding area.
1. Explore the Great Dismal Swamp National Wildlife Refuge
Let’s start with Chesapeake’s wild side. The
Great Dismal Swamp National Wildlife Refuge sounds a little gloomy, but it’s actually one of the most beautiful and unique places on the East Coast.
Stretching across the
Virginia–North Carolina border, this refuge offers:
- Miles of flat walking and biking trails
- Boardwalks through quiet cypress swamps
- Birdwatching for warblers, herons, and hawks
- Wildlife viewing – you might spot deer, turtles, and even black bears
One of the highlights is
Lake Drummond, a roughly 3,100‑acre natural lake right in the middle of the swamp. On a still day, the water reflects the trees like a mirror. It feels almost otherworldly.
If you like history, this area is also powerful to walk through. The swamp was once a hiding place for freedom seekers escaping slavery on the
Underground Railroad.
Tip: Bring bug spray, especially in warmer months, and wear closed‑toe shoes. The trails are easy, but it still feels like real wilderness.
2. Paddle the Elizabeth River or Northwest River
Love being on the water but don’t want to deal with ocean waves? Chesapeake is packed with calm rivers and canals that are perfect for:
- Kayaking
- Canoeing
- Stand‑up paddleboarding
Popular spots include:
You can bring your own gear or look for local outfitters that rent kayaks and canoes near the launch areas.
On one of my visits, I set out on the Northwest River just after sunrise. The water was flat as glass, and the only sounds were birds calling and the dip of my paddle. It was hard to believe I was just a short drive from busy highways and shopping centers.
Tip: Early mornings and late afternoons are usually cooler and less crowded in summer.
3. Walk the Trails at Northwest River Park & Campground
If you want nature plus a few more comforts, head to
Northwest River Park & Campground, about 40 minutes from central Chesapeake.
This 763‑acre park offers:
- Wooded hiking and biking trails
- A scenic lake for paddleboats and canoe rentals (seasonal)
- Mini‑golf and playgrounds for the kids
- Camping and cozy cabins if you want to stay overnight
The trails are mostly flat and shaded, which is perfect on a hot Virginia day. You can do a short half‑mile stroll or put a few miles under your feet without much effort.
Thinking of a budget‑friendly family trip? A weekend of camping here, with s’mores by the fire and morning walks by the water, is hard to beat.
4. Take a Scenic Drive Along the Intracoastal Waterway
Chesapeake plays a big role in the
Atlantic Intracoastal Waterway, the protected route that boats use to travel up and down the East Coast without heading into the open ocean.
You don’t have to own a boat to enjoy it. You can:
- Drive along Route 17 and stop at public access points
- Watch sailboats and trawlers pass through locks and drawbridges
- Grab lunch at a nearby waterfront spot and just take in the view
If you time it right, you might see a drawbridge swing open or a line of boats waiting their turn to move through. For kids (and honestly, for adults too), it’s pretty cool to watch.
5. Visit the Chesapeake Arboretum
Right in the middle of the city, the
Chesapeake Arboretum feels like a hidden garden. It’s a 48‑acre “tree museum” with:
- Shady walking trails
- A small creek and footbridges
- Gardens with herbs and native plants
The trails here are easy and short, so it’s perfect for:
- Families with small kids
- Anyone who wants a gentle walk
- Visitors who don’t have time for a full‑day hike
It’s also a nice spot for photos, especially when the leaves change color in fall or flowers bloom in spring.
Tip: Parking is usually straightforward, and it’s free to explore, which makes this one of the best low‑cost things to do in Chesapeake, VA.
6. Shop, Dine, and People‑Watch at Town Place at Greenbrier
Chesapeake isn’t just woods and water. If you’re in the mood for shopping and food, head to the
Greenbrier area, especially
Town Place at Greenbrier and the nearby
Greenbrier Mall and shopping centers.
In this part of the city you’ll find:
- Plenty of chain and local restaurants
- Cafés where you can grab coffee and recharge
- Big‑name stores mixed with smaller shops
- Movie theaters to wind down in the evening
After a day of hiking the Great Dismal Swamp or paddling the river, it’s nice to clean up and enjoy a sit‑down meal or catch a movie. The Greenbrier area is also a handy base if you’re staying in Chesapeake and doing day trips to Norfolk or Virginia Beach.
7. Spend a Peaceful Morning at Oak Grove Lake Park
If you ask locals about relaxing things to do in Chesapeake,
Oak Grove Lake Park comes up a lot.
This 65‑acre park features:
- A 1.5‑mile loop trail around the lake
- Fishing spots along the shoreline
- Benches and open areas for picnics
The trail is wide and flat, so it’s an easy walk or jog. On weekday mornings you’ll see people walking dogs, pushing strollers, or just getting their steps in before work.
If you like to fish, bring your rod. You might catch bass, catfish, or sunfish right from the bank.
Tip: Sunrise and sunset are especially pretty here, when the sky reflects off the lake.
8. Take a Day Trip to Nearby Virginia Beach
One of the best parts of staying in Chesapeake is how close you are to the ocean.
Virginia Beach is usually about a 30‑ to 40‑minute drive, depending on traffic and where you start in Chesapeake.
Once you get there, you can:
- Walk the famous Virginia Beach Boardwalk
- Swim, sunbathe, or play volleyball on the beach
- Rent bikes and cruise along the oceanfront
- Try local seafood – especially crab cakes and fresh fish
If you like history and nature, you can also swing by
First Landing State Park, where English settlers first landed in 1607. There are easy trails through cypress swamps and dunes just a short drive from the main strip.
Staying in Chesapeake often means more affordable hotels and quieter nights, while still giving you quick access to the beach scene when you want it.
9. Discover History and Harbor Views in Norfolk
Another easy day trip from Chesapeake is
Norfolk, home to the world’s largest naval base. It’s usually a 20‑ to 30‑minute drive, again depending on traffic and your starting point.
Popular things to do in Norfolk include:
If you like ships, history, or just harbor views, Norfolk is worth at least an afternoon. Then you can head back to the quieter pace of Chesapeake for the night.
10. Taste Chesapeake’s Local Flavors
You can’t talk about things to do in Chesapeake, VA without talking about food. Being so close to the water, the area has plenty of
seafood and Southern‑style comfort dishes.
When you’re in town, keep an eye out for:
You’ll find a mix of:
- Casual, family‑friendly spots
- Hidden local joints in small strip malls
- Chain restaurants if you want something familiar
One fun way to explore is to pick a different part of Chesapeake each day – Greenbrier, Western Branch, Deep Creek – and try a local place for lunch or dinner. It turns each meal into a mini adventure.
Planning Your Chesapeake, VA Getaway
Chesapeake may not shout as loudly as some nearby destinations, but that’s part of its charm. It’s a place where you can:
- Enjoy quiet nature in the Great Dismal Swamp and local parks
- Get out on calm rivers and lakes
- Shop, eat, and relax without heavy crowds
- Make easy day trips to Virginia Beach and Norfolk
If you’re planning a trip to coastal Virginia and want a base that’s less hectic, Chesapeake is a smart, comfortable choice.
What Did We Miss? Share Your Chesapeake Favorites!
Have you been to Chesapeake, Virginia?
- Do you have a favorite park, trail, or restaurant?
- Is there a hidden gem activity more people should know about?
Drop your tips and experiences in the comments so other travelers can discover new things to do near Chesapeake, VA.
And if you found this guide helpful, please
share it with friends or family planning a trip to coastal Virginia. Your share might be the nudge they need to explore this underrated corner of the state.
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