Chesapeake
Introduction
Chesapeake is an independent city in Virginia, part of the Hampton Roads region of the Mid-Atlantic. It is one of the larger cities in the commonwealth, and its size reflects a spread-out, suburban character rather than a dense urban core.
Getting there
Getting to Chesapeake is easiest by car, as the city sits within the Hampton Roads region of Virginia and is served by the area's major highways. Interstate 64 runs through the city, and Interstate 664 also passes through, connecting Chesapeake with neighbouring communities in the region.
- By car: Interstate 64 and Interstate 664 serve the city.
Getting around
Getting around Chesapeake is difficult without a car, and a personal vehicle is by far the most practical way to cover the city's spread-out districts and reach the surrounding Hampton Roads communities. Hampton Roads Transit does serve some areas of the city, but coverage is partial rather than comprehensive, so check the HRT network in advance to confirm whether your particular destination is served. Treat buses as a supplement to driving rather than a replacement for it. Chesapeake is not a walkable city in the way a dense urban center might be; walking is realistic for individual destinations once you have arrived, but not as a way to move between them.
Driving is the backbone of getting around, and understanding the road system will save you considerable time. The Hampton Roads Beltway is the most popular way in and out of the city, consisting of I-64 on the east side, I-664 on the west side, and I-464 along the Norfolk/Chesapeake border. US-13, US-460 and US-58 connect Chesapeake to Suffolk and provide access to other parts of Virginia: US-13 continues toward northeastern North Carolina, US-460 connects to Petersburg, and US-58 connects to Emporia and Southside Virginia. VA-168, known as the Chesapeake Expressway or simply the bypass to locals, serves south Chesapeake and continues toward the Outer Banks of North Carolina; it is the only toll road in the Hampton Roads area, with the toll on the border between Virginia and North Carolina, and you are not obligated to pay it unless you stay on the road that passes through the toll station. The area is known for its many bridges and tunnels, which can be confusing to anyone unfamiliar with the local roads. Chesapeake has several bridges over the Elizabeth River, and it is crucial to know which one to take to avoid long delays or getting lost.
Where to stay
Chesapeake's lodging is concentrated around the Greenbrier area and the Woodlake Drive conference corridor, so your choice of base is largely a choice between those two clusters. Both put you within easy reach of the city's business and meeting facilities, and both are geared toward travellers arriving by car.
- Greenbrier options include the Courtyard Chesapeake Greenbrier, the Fairfield Inn Chesapeake and the Residence Inn Chesapeake Greenbrier, all on or near Crossways Boulevard, plus the Hyatt Place Chesapeake/Greenbrier on Eden Way North, where rooms come with free Wi-Fi, a large work space, a refrigerator and a TV, and guests can use free parking, free breakfast, an indoor pool and a fitness centre.
- On Woodlake Drive you'll find the Norfolk Marriott Chesapeake and the Delta Hotels Chesapeake Norfolk, the latter described as the city's only full-service hotel, with business centres, express check-in and check-out, concierge services and high-speed internet for corporate events.
- Nearby, the Holiday Inn Express & Suites Chesapeake sits at the Conference Center, and the Chesapeake Staybridge Suites specialises in extended stays, offering all-suite accommodation and welcoming pets.
Food & drink
For breakfast, head to Broken Egg Bistro on Kempsville Road, which is known locally for turning out some of the best morning food in Hampton Roads. Beyond breakfast, it also serves a lunch menu with a wide range of specialty sandwiches and burgers. The source lists no bars, cafes or other drinking establishments for Chesapeake, so plan your evening drinks accordingly.What to see and do
For a dose of local history, head to the Great Bridge Battlefield & Waterways Historic Park, where the area's Revolutionary War past is interpreted alongside its waterways. If you'd rather spend your time outdoors, the Chesapeake Arboretum offers gardens and walking paths to explore.
- Great Bridge Battlefield & Waterways Historic Park
- Chesapeake Arboretum
- Cinema Cafe, 1864 Edinburgh Ln — movie watching with menu service
Three days in Chesapeake
Day one: Start by getting your bearings in Chesapeake, a city spread across Southside Virginia within Hampton Roads. Treat the day as an easy introduction rather than a rush between sights. If you arrive by air, you will likely come through Norfolk, and if you drive, Interstate 64 and the Hampton Roads Beltway make the city straightforward to reach from Norfolk, Suffolk, or down toward North Carolina via Petersburg and Emporia. Hampton Roads Transit, usually shortened to HRT, can help you move around without a car. Base yourself in Greenbrier, where several hotels sit along Woodlake Drive and Crossways Boulevard, including Courtyard Chesapeake Greenbrier, Fairfield Inn Chesapeake, Residence Inn Chesapeake Greenbrier, and Hyatt Place Chesapeake on Eden Way North. Settle in, then take a gentle drive to orient yourself along the Elizabeth River and the edges of the Great Dismal Swamp, and keep the evening simple with dinner near your hotel.
Day two: Give the day to the water and the wilder side of the city. Chesapeake sits beside the Elizabeth River and the Great Dismal Swamp, so plan around those landscapes rather than staying indoors. If you want a longer outing, the Chesapeake Expressway runs south toward the Outer Banks of North Carolina, making a day trip feasible, though you may prefer to stay closer and explore the city's own waterways and green edges. Mid-afternoon, return to Greenbrier for a break; the cluster of hotels along Woodlake Drive and Crossways Boulevard, such as Courtyard Chesapeake Greenbrier, Fairfield Inn Chesapeake, Residence Inn Chesapeake Greenbrier, and Hyatt Place Chesapeake, keeps you close to food and services. In the evening, eat locally and rest early.
Day three: Use your last day to see how Chesapeake connects to the wider region. Drive or take HRT toward Norfolk, or head west into Suffolk, to understand the shape of Hampton Roads and the Atlantic-facing coast. If you are continuing south, the route through Emporia and Petersburg leads on through Southside Virginia toward North Carolina. Before you leave, revisit the Greenbrier area along Woodlake Drive and Crossways Boulevard for any last errands, with the same cluster of hotels nearby if you need to extend your stay. Keep the pace light and let the region's waterways and roads set the rhythm of your final hours.