If you’re dreaming of peaceful waterways, nature preserves, and easy family fun, I’d recommend Chesapeake, Virginia. I’ve wandered all over coastal Virginia, and Chesapeake has a way of slowing me down in the best way. You’ll find yourself paddling through cypress swamps one minute and shopping or relaxing the next. I love that it blends nature and convenience so well. Whether you’re heading out with kids or just need some quiet by the water, I think you’ll settle into the rhythm here like I always do.
Chesapeake, VA Highlights (My Picks Just for You):
- The Great Dismal Swamp always calls me back – You can hike, bike, or paddle through this wild, mysterious refuge. I’ve spotted otters and bald eagles out there—bring your camera!
- Chesapeake City Park is a favorite when I’m with family – You’ll find playgrounds, a skate park, open fields—something for everyone. I’ve even timed visits around seasonal events and had a blast.
- Northwest River Park is where I go to birdwatch and unwind – You can hit the trails or rent a paddle boat. I’ve spent peaceful mornings here with just the sound of birds and breeze through the trees.
- The Chesapeake Veterans’ Memorial always moves me – It’s a simple, powerful tribute, and I think you’ll find it worth the stop, right by City Hall.
- When I need some retail therapy, I hit Chesapeake Square or Greenbrier Mall – You’ll find big-name stores, plus some fun local spots for gifts or a bite.
Best Time to Visit Chesapeake, VA (When I Go and Why You Might Too)
I usually plan my visits for spring (April–June) or fall (September–October)—the weather’s perfect for hiking, kayaking, and hitting outdoor events. But I’ve also enjoyed summer days out on the water or even quiet winter weekends when everything slows down. You’ve got options year-round, depending on your vibe.
How I Get to Chesapeake (And How You Can Too)
- By car: I usually drive in via I-64 or US-17—it’s just 20 to 30 minutes from Norfolk or Virginia Beach. Super easy to reach.
- By air: I fly into Norfolk International Airport (ORF). It’s only about a 25-minute drive, and I’ve never had a problem renting a car there.
- By train or bus: I’ve used Amtrak and intercity buses to nearby Norfolk, then just connected locally. If you don’t want to drive, it works great.
Where I Stay (You’ll Be Comfy Here)
- Hyatt Place Chesapeake/Greenbrier – I love the roomy suites and indoor pool, especially when I’m traveling with family. You’ll be close to food and shopping too.
- Comfort Suites Chesapeake – If you’re watching your budget, this one’s solid. I’ve stayed here for quick trips and liked the free breakfast and highway access.
- Hilton Garden Inn Chesapeake/Greenbrier – For a little more comfort, I like this full-service hotel. The on-site restaurant is handy after a long day exploring.
Best Things to Do in Chesapeake, VA
Pedal, Walk, or Roll Through the Dismal Swamp Canal Trail - A peaceful, paved path lined with history, wildlife, and plenty of room to roam
Wander Woodland Beauty at the Chesapeake Arboretum - A hidden gem of gardens, trails, and tree-shaded serenity in the heart of the city
Pick Fresh and Play Freely at Hickory Ridge Farm - Strawberries, pumpkins, and kid-friendly fun on a family-run countryside escape
Watch the Water Flow at Great Bridge Lock Park - Boats, birdwatching, and breezy riverfront picnics define this tranquil green space
Shop, Sip, and Stroll at Greenbrier Mall - From big brands to tasty treats, this local retail hub offers indoor fun for all
Drive Above the Water on the South Norfolk Jordan Bridge - Soar across the river with sweeping skyline views and engineering marvel beneath your wheels
Step Back in Time at the Great Bridge Battlefield & Waterways Foundation - Explore the story of a pivotal Revolutionary War battle where land and water collided
Play Along the River at Elizabeth River Park - A family favorite for fishing, playground fun, and panoramic sunset strolls
Brunch Big and Bold at The Egg Bistro - Locally loved for creative comfort food, hearty portions, and morning-to-midday buzz
More Places to Eat in Chesapeake, VA (Here’s Where I Like to Dine)
- Recommended for Families: Baker’s Crust – I’ve taken the family here more than once. You’ll love the gourmet sandwiches, pizzas, and salads—all served in a relaxed, kid-friendly space that doesn’t skimp on quality.
- For Local Seafood: Wicker’s Crab Pot Seafood – I always recommend this place to seafood lovers. It’s a family-run gem where you can dig into crab legs, shrimp, and coastal favorites that taste like summer on a plate.
If You’re Interested in Local Events (These Are Worth Planning Around)
- For Families: Chesapeake Jubilee (May) – I’ve spent sunny afternoons here riding carnival rides and listening to live music. If you’re traveling with kids, you’ll love the fireworks, food, and family fun in City Park.
- For Food Lovers: Chesapeake Restaurant Week (October) – I always mark this on my calendar. You’ll get a chance to try local favorites at a great value—perfect if you like tasting your way through a destination.
- For Holiday Cheer: Chesapeake Holiday Brass Concert (December) – I’ve bundled up and joined the crowd for this festive concert. You’ll enjoy holiday music, sparkling lights, and that cozy small-town warmth.
Day Trip Itineraries I’ve Enjoyed Within 30–90 Minutes of Chesapeake, VA
- For Beaches: Virginia Beach (30–35 min) – I’ve hit the boardwalk on more than one sunny afternoon. You can surf, sunbathe, or stroll the oceanfront while soaking up a lively beach town vibe.
- For Culture: Norfolk (20–30 min) – I love how close this cultural hub is. From the Chrysler Museum of Art to Nauticus and live theater, you’ll find plenty to feed your curiosity.
- For History Buffs: Colonial Williamsburg (1 hr) – I always feel transported when I visit. You’ll walk cobblestone streets, meet costumed interpreters, and step straight into American history.
- For Outdoor Fun: First Landing State Park (45–50 min) – I’ve hiked and kayaked here and can’t recommend it enough. You’ll enjoy forested trails and peaceful waterways perfect for recharging.
- For Family Fun: Virginia Aquarium & Marine Science Center (45 min) – I’ve seen kids light up at the touch tanks and watched otters play here. If you’ve got little ones, this is a hands-on, nature-filled adventure they won’t forget.
Frequently Asked Questions (Here’s What I’ve Found Helpful to Know)
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What can visitors do in Chesapeake, Virginia?
- There’s always something going on here. I’ve hiked trails, explored historic sites, and eaten my way through town. Chesapeake, Virginia truly offers a little of everything.
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What types of activities are available in Chesapeake?
- Whether you’re into outdoor adventures, park picnics, historic stops, or trying new restaurants, I’ve done it all here—and I think you’ll find your own favorites, too.
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What makes Chesapeake unique?
- I’ve always felt that Chesapeake blends big-city amenities with that coastal Virginia charm. It’s in the heart of a vibrant region, yet it still feels personal and welcoming.
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In Summary...
(and if you want to revisit my photo journey)