Chesapeake Travel and Things to Do Guide
Chesapeake, a city within the unique Coastal Virginia region, is a meeting destination that features more than two million square feet of entertainment and retail options in three upscale malls - Greenbrier Mall, Chesapeake Square, and Towne Place at Greenbrier - as well as easy access to popular area attractions like beaches and historic sites.
While the city certainly benefits from proximity to Norfolk, Hampton, and other nearby cities, Chesapeake meeting venues offer affordable and well-equipped alternatives for small to moderate-sized groups seeking variety in accommodations, meeting facilities and activities.
Chesapeake is within a 15-minute drive from Norfolk International Airport. Situated just 20 minutes from the Virginia Beach oceanfront, 45 minutes from Virginia's "Historic Triangle" of Yorktown, Williamsburg, and Jamestown, and 3.5 hours from Washington, DC, Chesapeake also makes an excellent drive-to destination. The largest of Chesapeake meeting venues is the Chesapeake Conference Center, with 39,000 square feet of function space and room for up to 200 exhibit booths. It is within a one-mile distance of 650 hotel rooms, including 350 adjacent rooms. The center combines with meeting spaces in area hotel properties to bring Chesapeake's group facilities portfolio to nearly 40,000 square feet of function space. Other event venues include Greenbrier Country Club and Chesapeake Arboretum.
Dining options include The Butcher's Son Chop House offering a classic American steakhouse feel and Passion the Restaurant offering creative, innovative cuisine with space for any special event.
Groups can enjoy Chesapeake's local golf courses, but the particularly adventurous will find an array of after-business and team-building outdoor activities along Chesapeake's 22 miles of fresh and salt waterways, such as canoeing, kayaking, and fishing on the Great Dismal Swamp Canal, Lake Drummond or the Atlantic Intracoastal Waterway. Birdwatching is also popular around Chesapeake, and it's easy to spot rare species along the Great Dismal Swamp National Wildlife Refuge, especially during spring migrations.
For the culturally inclined, Chesapeake has pleasing outdoor cultural activities almost year-round, such as the annual "Shakespeare in the Grove," outdoor theater production by the Chesapeake Campus of Tidewater Community College. From May through September, the Chesapeake Fine Arts Commission and the Virginia Arts Festival present "Symphony Under the Stars," by the Virginia Orchestra Symphony. The Chesapeake Wine Festival is held every October featuring the best of Virginia wineries.
While the city certainly benefits from proximity to Norfolk, Hampton, and other nearby cities, Chesapeake meeting venues offer affordable and well-equipped alternatives for small to moderate-sized groups seeking variety in accommodations, meeting facilities and activities.
Chesapeake is within a 15-minute drive from Norfolk International Airport. Situated just 20 minutes from the Virginia Beach oceanfront, 45 minutes from Virginia's "Historic Triangle" of Yorktown, Williamsburg, and Jamestown, and 3.5 hours from Washington, DC, Chesapeake also makes an excellent drive-to destination. The largest of Chesapeake meeting venues is the Chesapeake Conference Center, with 39,000 square feet of function space and room for up to 200 exhibit booths. It is within a one-mile distance of 650 hotel rooms, including 350 adjacent rooms. The center combines with meeting spaces in area hotel properties to bring Chesapeake's group facilities portfolio to nearly 40,000 square feet of function space. Other event venues include Greenbrier Country Club and Chesapeake Arboretum.
Dining options include The Butcher's Son Chop House offering a classic American steakhouse feel and Passion the Restaurant offering creative, innovative cuisine with space for any special event.
Groups can enjoy Chesapeake's local golf courses, but the particularly adventurous will find an array of after-business and team-building outdoor activities along Chesapeake's 22 miles of fresh and salt waterways, such as canoeing, kayaking, and fishing on the Great Dismal Swamp Canal, Lake Drummond or the Atlantic Intracoastal Waterway. Birdwatching is also popular around Chesapeake, and it's easy to spot rare species along the Great Dismal Swamp National Wildlife Refuge, especially during spring migrations.
For the culturally inclined, Chesapeake has pleasing outdoor cultural activities almost year-round, such as the annual "Shakespeare in the Grove," outdoor theater production by the Chesapeake Campus of Tidewater Community College. From May through September, the Chesapeake Fine Arts Commission and the Virginia Arts Festival present "Symphony Under the Stars," by the Virginia Orchestra Symphony. The Chesapeake Wine Festival is held every October featuring the best of Virginia wineries.

Weather and Seasonality
With winters milder than the north, and more seasons than the south, Chesapeake, VA offers weather you can play, dine, and enjoy year round.
| Month | High/Low °F | Seasonality |
|---|---|---|
| January | -/- | - |
| February | -/- | - |
| March | -/- | - |
| April | -/- | - |
| May | -/- | - |
| June | -/- | - |
| July | -/- | - |
| August | -/- | - |
| September | -/- | - |
| October | -/- | - |
| November | -/- | - |
| December | -/- | - |
