
Where waterways weave through history and modern living
Things to know

Explore over 112,000 acres of forested wetlands on the historic Dismal Swamp Canal. Hike or bike the trails, paddle the waterways, and spot black bears, bobcats, and over 200 bird species in this unique ecological treasure.

Walk through history at this preserved Civil War site, part of the 1862 Battle of Great Bridge. The park features interpretive trails, earthworks, and a museum that tells the story of this pivotal early-war engagement.

A true community hub held at City Park, featuring local produce, meats, baked goods, and artisan crafts from Chesapeake and surrounding Tidewater farms. It's the perfect Saturday morning stop for fresh, seasonal flavors.

The city's premier recreational space, featuring a massive playground, skate park, fitness trail, and the iconic Fun Forest. It's a favorite for family picnics, festivals, and enjoying the outdoors.

The commercial heart of Chesapeake, centered around Greenbrier Mall. This bustling district offers everything from major retailers and department stores to local boutiques and a wide array of dining options.

Chesapeake is the landward anchor of the incredible Chesapeake Bay Bridge-Tunnel. While the engineering marvel itself is just south, the city is the perfect base for exploring the seafood shacks and maritime culture of the lower Bay.
things to do
Chesapeake offers a blend of outdoor adventure, historical exploration, and family-friendly entertainment, all connected by its extensive waterways and green spaces.
Rent a kayak or canoe and explore the calm, cypress-lined waters of the Northwest River. The river is perfect for spotting osprey, turtles, and other wildlife in a serene, natural setting just minutes from the city.
More than just books, this modern library is a community centerpiece with art exhibits, a local history room, and regular events. Its architecture and peaceful grounds make it a worthwhile stop.
Tee off at this well-maintained public course known for its friendly atmosphere and challenging layout. It's a local favorite for golfers of all skill levels looking to enjoy a day on the links.
Get your hands messy at a local seafood joint like The Crab Shack on Military Highway. Summer and fall are prime time for steaming piles of spicy, seasoned blue crabs, a true Chesapeake tradition.
Enjoy a peaceful 1.8-mile loop around the scenic 65-acre Oak Grove Lake. The paved trail is popular with walkers, runners, and cyclists, and features fishing piers and plenty of shaded benches.
Just over the border in Virginia Beach, this premier attraction features zip lines and aerial adventure courses through the maritime forest. It's an exhilarating outdoor challenge for older kids and adults.
neighborhoods
Chesapeake's vast land area encompasses distinct communities, from historic villages and waterfront properties to bustling suburban centers and quiet rural stretches.
Centered around the historic Battlefield Park and the Intracoastal Waterway, this area blends history with modern convenience. It features a charming main street with local shops and restaurants, and is known for its annual Christmas parade.
The bustling economic and retail core of Chesapeake. Anchored by the mall, it's a maze of shopping centers, chain restaurants, hotels, and business parks, offering the most concentrated urban conveniences in the city.
A largely residential area named for the Western Branch of the Elizabeth River. It offers a mix of established neighborhoods, good schools, and community parks, with many homes having access to canals and waterways.
Experience Chesapeake's rural roots in this southeastern area. Known for farm stands, open fields, and the unique Fentress Airfield (a former naval auxiliary landing field), it provides a quiet, country atmosphere.
A historic community with a strong sense of identity, centered around the Deep Creek Lock and the Intracoastal Waterway. It features older, tree-lined neighborhoods, local marinas, and a tight-knit community feel.
Browse by category
Local salons and spas offering relaxed, friendly service with Southern hospitality.
Find everything from major retailers in Greenbrier to unique local finds.
From fresh Chesapeake Bay seafood to classic Southern comfort food.
Trusted local contractors and services for maintaining your Chesapeake home.
Outdoor trails and parks invite an active lifestyle in a natural setting.
A growing hub for business services in the South Hampton Roads region.
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