Join free

Virginia, United States

Chesapeake

Independent city of Hampton Roads; Great Dismal Swamp gateway; Home of Dollar Tree headqu…

Overall
6.3
Per day
$185 from $124
Season
Peak: Summer

Best for:Beaches

  • Drive
  • Bus
  • Airport
Directions

Best connected to Raleigh 3 h 31 min by car

Overview

Paddle a kayak or canoe across Lake Drummond and you see how Chesapeake spreads over a lot of ground, and a good chunk of it is wild. The Great Dismal Swamp National Wildlife Refuge and the lake are the headline draws, along with Northwest River Park and the Dismal Swamp Canal. Bring bug spray, because ticks and mosquitoes come with the territory. The rest of the city is mostly suburban and small-town, with Greenbrier for shopping, Deep Creek for a quieter feel and Great Bridge, where the Revolutionary battle site sits.

About 255,000 people live here, part of the Hampton Roads region of nearly 1.8 million. Norfolk is about 15 miles away and Virginia Beach about 25. A local ale trail and spring wine and kayak events give visitors a few extras. Housing sits near or a bit above the national norm, and the market is steady. Violent crime is close to the national average, and car break-ins are the most common problem. The bigger practical concern is water, with hurricane season from June to November and tidal flooding on low roads.

Trip planning at a glance

Peak season
Summer (Memorial Day to Labor Day)
Nearest airport
about 12-20 miles, 20-30 min drive (ORF), 20 miles

Highlights

  • Great Dismal Swamp National Wildlife Refuge
  • Dismal Swamp Canal and Welcome Center
  • Northwest River Park
  • Chesapeake City Park
  • Battle of Great Bridge historic site
  • Chesapeake Arboretum
  • Chesapeake Ale Trail breweries
  • Lake Drummond kayaking and paddling

Best connected to

Raleigh

North Carolina, United States ·

7.3
Distance
186 mi · 299 km
Drive
3 h 31 min est.
Bus
likely (not verified) · 4 h 36 min

adds national & state parks and museums & galleries

Durham

North Carolina, United States ·

7.0
Distance
195 mi · 314 km
Drive
3 h 42 min est.
Bus
likely (not verified) · 4 h 49 min

adds national & state parks and museums & galleries

Hampton

Virginia, United States ·

6.4
Distance
30 mi · 48 km
Drive
40 min

adds national & state parks and museums & galleries

Compare alternatives

Cities with a similar character, anywhere on the site.

Milwaukee

Wisconsin, United States

Overall
6.4
Connector
8.4
Per day (mid-range)
$208

Car-free travelBeaches

  • Drive
  • Train
  • Bus
  • Airport

Peak: In summer during Summerfest, State Fair…

View city

Pearland

Texas, United States

Overall
6.3
Connector
6.8
Per day (mid-range)
$173

FamiliesBeaches

  • Drive
  • Bus
  • Airport

Peak: Spring and fall (pleasant weather

View city

Evanston

Illinois, United States

Overall
6.0
Connector
7.6
Per day (mid-range)
$205

Beaches

  • Drive
  • Train
  • Airport

Peak: Northwestern graduation, move-in and fo…

View city

Compare all side by side

Scores

Out of 10. Open any score to see how it’s worked out. “Data-based” scores come from published figures; “Hey! En Route estimate” scores are worked out from what we know about the city; “Hey! En Route rating” scores were set by our editors.

6.3/10Good
  • Connector Score6.5

    7 worthwhile cities within three hours; reachable by road, intercity bus, air, and local transit; lodging and sights for an overnight stop. Hey! En Route estimate

  • Safety7.3

    About 339 violent crimes per 100,000 people a year; the US average is about 370. Data-based

  • Affordability6.2

    Cost of living index about 103, where the national average is 100. Data-based

  • Transportation8.0

    Reachable by: road, intercity bus, air, and local transit. Hey! En Route estimate

  • Car-free friendliness5.0

    Intercity train or bus, plus local transit and walkability. Hey! En Route estimate

  • Walkability5.2

    Estimated from city size and transit; no walkable downtown noted. Hey! En Route estimate

  • Things to do5.7

    Known for 6 kinds of attraction, with 7 annual events listed. Hey! En Route estimate

  • Food & dining6.6

    A known food scene, weighted by city size. Hey! En Route estimate

  • Places to stay6.3

    Lodging at budget, mid-range and luxury prices. Hey! En Route estimate

  • Nature & outdoors5.0

    Known for beaches, lakes & rivers. Hey! En Route estimate

  • Scenic value5.5

    From its landscape: coast, mountains, lakes and parks. Hey! En Route estimate

  • Family friendliness5.0

    Zoos, aquariums, theme parks and museums, weighted by safety. Hey! En Route estimate

  • Solo-traveler friendliness5.3

    Safety, getting around without a car, hostels, and things to do. Hey! En Route estimate

  • Nightlife4.5

    Estimated from city size and live music. Hey! En Route estimate

  • Remote-work friendliness6.0

    City size, affordability, cafés and connections. Hey! En Route estimate

  • Road-trip convenience6.4

    7 worthwhile cities within three hours’ drive, plus parking, EV charging and RV options. Hey! En Route estimate

  • Train-trip convenience1.0

    No intercity train service noted. Hey! En Route estimate

  • Bus-trip convenience7.3

    Intercity buses, with 7 nearby cities reachable by bus. Hey! En Route estimate

City info

Country
United States
State / province
Virginia
Population
255,332
Metro area
1,797,213
Area
909 km²
Density
281 / km²
Elevation
3 m
Currency
USD
Local time
7:54 pm UTC-04:00
Power
Type A/B, 120V 60Hz
Drives on the
Right
Known as
Independent city of Hampton Roads; Great Dismal Swamp gateway; Home of Dollar Tree headquarters
Founded
1691 Norfolk County established; 1919 South Norfolk incorporated; 1963 consolidated as Chesapeake
Languages
English; Spanish and Tagalog spoken by smaller communities
Airports
Norfolk International ORF (about 12-20 miles, 20-30 min drive); Newport News/Williamsburg PHF (about 35-40 miles, 45-55 min); Richmond RIC (about 90 miles, 1.5 hr)
Tipping
Restaurants 18-20% for table service; bars $1-2 per drink; taxis and rideshare 15-20%; hotel housekeeping $3-5 per night; bellhop $1-2 per bag; hair and spa 15-20%; counter service optional

Community signals

Not enough responses yet to show a trend.

Chesapeake City Circle

For people considering Chesapeake, visiting soon, living there for a while, or comparing it with somewhere else.

Sign up to join

No discussions yet. Be the first to share something useful.

Open the circle

About this data

Population is Census V2025 (July 1, 2025). Metro is Virginia Beach-Chesapeake-Norfolk MSA 2025 estimate (Wikipedia); Chesapeake shares this MSA with larger Virginia Beach and Norfolk. Area total 351 sq mi per Wikipedia (land 338.46 sq mi per Census). Elevation about 3 m (10 ft) is from memory and not verified by search. Coordinates from Wikipedia. Home value and rent from Census ACS 2020-2024. Crime from OpenCrime (2024). Cost of living, hotel rates, listing prices and tipping are approximate and unverified. Event months are typical and unconfirmed for 2026. visitchesapeake.com verified to load.

Last verified September 25, 2026 · Source: Research spreadsheet · Editorial ·

Neighborhoods

8 areas to know, and who each one suits.

Great Bridge

Historic

    South Norfolk

    Revitalizing

      Western Branch

      Suburban

        Hickory

        Rural

          Indian River

          Residential

            Grassfield

            Family

              Where to base yourself

              • Greenbrier area for chain hotels and shopping
              • Great Bridge for restaurants
              • Norfolk or Virginia Beach oceanfront for a broader tourist base. Tiers: budget motels near I-64/I-464
              • mid-range chain hotels in Greenbrier
              • luxury options mostly in Norfolk and Virginia Beach

              Suburbs and neighboring towns

              Portsmouth (8 mi; car, HRT bus); Norfolk (10 mi; car, HRT bus); Virginia Beach (15 mi; car, HRT bus); Suffolk (15 mi; car); Camden County NC (20 mi; car); Currituck County NC (25 mi; car)

              What a visit costs

              Per person per day, with a room shared by two. Change anything below to fit your trip.

              Budget

              $124/day

              Lodging about $88 a night

              Mid-range

              $185/day

              Lodging about $140 a night

              Luxury

              $333/day

              Lodging about $275 a night

              Budget calculator

              Vehicle
              mpg

              These are estimates from typical prices, not quotes. Real costs vary with season, events, booking time and your own habits; taxes and fees are approximate.

              Cost of living

              For longer stays and relocation.

              Cost of living index
              103 (national average = 100)
              Typical 1-bedroom rent
              $1,500 a month
              Median home price
              $378,400
              Research notes

              Roughly 100-105 vs US=100 (approximate); typical 1BR rent about $1,400-1,600; Census median gross rent $1,586

              Real estate

              Buying or renting long-term: prices, trends and the rules.

              Median home

              $378,400

              Mortgage calculator

              Census median owner-occupied home value $378,400 (2020-2024); recent listing medians about $400,000-$450,000 (approximate); median gross rent $1,586; market steady to modest appreciation

              Research notes on prices and seasons

              Hotels per night approx: budget $70-105; mid $110-170; luxury $200-350 (Hampton Roads region). Peak season is summer (Memorial Day to Labor Day); military events can raise rates. Rough daily visitor budget excluding lodging $80-150

              Where to stay

              Which part of town suits which kind of trip.

              • Greenbrier area for chain hotels and shopping
              • Great Bridge for restaurants
              • Norfolk or Virginia Beach oceanfront for a broader tourist base. Tiers: budget motels near I-64/I-464
              • mid-range chain hotels in Greenbrier
              • luxury options mostly in Norfolk and Virginia Beach

              Places to stay

              7 listings in Chesapeake, ranked by traveller reviews. Featured listings are marked.

              Top sights

              • Great Dismal Swamp National Wildlife Refuge
              • Dismal Swamp Canal and Welcome Center
              • Northwest River Park
              • Chesapeake City Park
              • Battle of Great Bridge historic site
              • Chesapeake Arboretum
              • Chesapeake Ale Trail breweries
              • Lake Drummond kayaking and paddling

              Known for: BeachesLakes & riversHistoric sitesFood sceneWineries & breweriesShopping

              Things to do

              7 listings in Chesapeake, ranked by traveller reviews. Featured listings are marked.

              See what’s on: events and festivals

              Known for: Food sceneWineries & breweries

              Food & nightlife

              10 listings in Chesapeake, ranked by traveller reviews. Featured listings are marked.

              Events

              Dated events will appear here as they’re added.

              Every year

              • Chesapeake Restaurant Week (January and summer editions)
              • Chesapeake Jubilee (spring)
              • Chesapeake Wine Festival (spring)
              • Bergey's Breadbasket Corn Maze (fall)
              • Chesapeake Christmas Bird Count (December)
              • KayaXpedition (spring)
              • Deep Creek Yuletide and holiday parades (December)

              Official events calendar ↗

              Safety information is a guide from public data and our research, not a guarantee. Conditions change; check local news and official advice before you go.

              7.3

              Very good · Data-based

              About 339 violent crimes per 100,000 people a year; the US average is about 370.

              Safety overview

              Violent crime about 339 per 100k (2024, OpenCrime; near the US average of about 359); property theft and vehicle break-ins are most common visitor risks; hospitals include Chesapeake Regional Medical Center and Sentara Careplex-area facilities; hurricane season June-November, nor'easter and tidal flooding on low roads, ticks and mosquitoes in swamp areas, summer heat and humidity

              Local notes

              Specific places where extra care is worthwhile, especially at night. Most visits are trouble-free.

              No major visitor no-go zones. Use standard caution at night in parts of South Norfolk and areas along Military Highway near the Norfolk border; the Great Dismal Swamp requires preparation (trail conditions, insects) rather than avoidance

              Safety & health

              Health

              • Hospital (ER)Chesapeake Regional Medical Center
              • Hospital (ER)Sentara Careplex-area facilities
              Official visitor information
              visitchesapeake.com

              Last verified September 25, 2026 · Source: Research spreadsheet · Editorial ·

              Local directory

              28 listings in Chesapeake, ranked by traveller reviews. Featured listings are marked.

              Nearby cities and connections

              Find the next city worth adding to your trip from Chesapeake: how far, how long, and how to get there.

              Elizabeth City NC

              Distance
              45 mi · 72 km
              Drive
              1 h

              Richmond

              Distance
              95 mi · 153 km
              Drive
              1 h 30 min

              Outer Banks NC

              Distance
              85 mi · 137 km
              Drive
              1 h 45 min

              Raleigh

              North Carolina, United States ·

              7.3
              Distance
              186 mi · 299 km
              Drive
              3 h 31 min est.
              Bus
              likely (not verified) · 4 h 36 min

              Cary

              North Carolina, United States ·

              6.5
              Distance
              194 mi · 313 km
              Drive
              3 h 41 min est.
              Bus
              likely (not verified) · 4 h 48 min

              Durham

              North Carolina, United States ·

              7.0
              Distance
              195 mi · 314 km
              Drive
              3 h 42 min est.
              Bus
              likely (not verified) · 4 h 49 min

              Washington DC

              District of Columbia, United States ·

              5.8
              Distance
              197 mi · 317 km
              Drive
              3 h 44 min est.
              Bus
              likely (not verified) · 4 h 52 min

              Lynchburg

              Virginia, United States ·

              6.2
              Distance
              209 mi · 336 km
              Drive
              3 h 58 min est.
              Bus
              likely (not verified) · 5 h 8 min

              Baltimore

              Maryland, United States ·

              6.6
              Distance
              224 mi · 360 km
              Drive
              4 h 14 min est.
              Bus
              likely (not verified) · 5 h 29 min

              Greensboro

              North Carolina, United States ·

              6.1
              Distance
              253 mi · 407 km
              Drive
              4 h 48 min est.
              Bus
              likely (not verified) · 6 h 9 min

              Times marked “est.” are estimates: drives use typical road distances at highway speeds, and train or bus times assume both cities have service. Always check a route planner and timetables before you travel.

              Route ideas

              Suggested by Hey! En Route from the best-connected next stops. Save one to your routes and make it your own.

              2-day trip

              Chesapeake (1 night)

              3-day trip

              Chesapeake (1 night) → Raleigh (1 night)

              About 188 mi, 3 h 49 min of travel

              5-day trip

              Chesapeake (2 nights) → Raleigh (1 night) → Durham (1 night)

              About 212 mi, 4 h 24 min of travel

              7-day trip

              Chesapeake (2 nights) → Raleigh (1 night) → Durham (1 night) → Charlotte (1 night)

              About 354 mi, 7 h 9 min of travel

              10-day trip

              Chesapeake (2 nights) → Raleigh (2 nights) → Durham (1 night) → Charlotte (1 night) → Winston-Salem (1 night)

              About 431 mi, 8 h 45 min of travel

              Suggested city pairs

              Building your own routes is part of Hey! En Route Plus. See what’s included

              Community signals

              Not enough responses yet to show a trend.

              Chesapeake City Circle

              For people considering Chesapeake, visiting soon, living there for a while, or comparing it with somewhere else.

              Sign up to join

              No discussions yet. Be the first to share something useful.

              Share experience, not guesses presented as fact, and keep contact details out of posts. Community guidelines

              The newsletter

              Postcards from the road, every other week

              New city guides, events worth planning a trip around, and the places worth the detour. Pick your topics, or leave them all unticked for everything.