Things To Do
in Chesapeake
Chesapeake sits in the Hampton Roads region of southeastern Virginia, a large independent city defined by waterways, suburban neighborhoods, and large tracts of preserved natural land. It blends maritime and agricultural heritage with modern suburban amenities, providing easy access to Norfolk, Virginia Beach, and the Chesapeake Bay. Outdoor recreation—boating, fishing, hiking and birdwatching—is a major draw thanks to the Great Dismal Swamp and miles of rivers and creeks.
The city is family-friendly and practical for visitors who want a quieter base with day-trip access to the region’s cultural and beach scenes.
Day Trips
Spend a day exploring around
Start your day with a visit to the Chesapeake City Park, where you can enjoy a peaceful walk by the water and take in the beautiful views of the Elizabeth River. Afterward, head to the historic downtown area to explore charming shops and local art galleries. Don't forget to stop by a local café for a delicious breakfast featuring fresh pastries and locally brewed coffee.
In the afternoon, take a guided tour of the Chesapeake Museum to learn about the city's rich history and maritime heritage. Following the museum visit, enjoy a leisurely lunch at one of the waterfront restaurants, where you can savor fresh seafood dishes while admiring the river views. Afterwards, stroll along the scenic paths of the nearby Deep Creek Park, where you can appreciate the area’s natural beauty.
As the sun sets, head to the Great Bridge Locks to witness the fascinating process of boats navigating through the locks. For dinner, indulge in a hearty meal at a local steakhouse, taking advantage of Chesapeake's vibrant dining scene. Cap off the evening with a cozy visit to a nearby bar for live music and a taste of local craft beers.
Begin your morning with a trip to the Northwest River Park, where you can embark on a peaceful hike or rent a kayak to paddle through the serene waters. The park is known for its diverse wildlife, so keep an eye out for birds and other animals as you explore the beautiful surroundings. Enjoy a packed breakfast amidst nature, taking in the sounds of chirping birds and rustling leaves.
After your morning adventure, spend the afternoon at the Chesapeake Arboretum, where you can wander through beautifully landscaped gardens and learn about various plant species. Participate in a guided nature walk to deepen your appreciation of the local flora and fauna. For lunch, find a quaint picnic spot within the arboretum and enjoy a light meal surrounded by the tranquility of nature.
As dusk approaches, head to the nearby Dismal Swamp National Wildlife Refuge for a unique evening experience. Join a guided night hike to discover the nocturnal wildlife that inhabits this lush ecosystem. Afterward, return to the city for dinner at a cozy diner, enjoying comfort food that warms your soul after a day outdoors.
Prices
| Item | Price |
|---|---|
| 🍔Meal at inexpensive restaurant | $10-15 |
| ☕Coffee (regular) | $3-5 |
| 🚕Taxi / short rideshare | $8-20 |
| 🏨Mid-range hotel (per night) | $100-180 |
| 🍺Domestic beer (restaurant/bar) | $5-8 |
Strengths and Weaknesses
- Easy access to abundant natural areas like the Great Dismal Swamp and waterfronts
- Lower-key, family-friendly atmosphere with affordable amenities compared with bigger nearby cities
- Good base for day trips to Norfolk, Virginia Beach and other Hampton Roads attractions
- Strong local seafood and growing farm-to-table and craft brewery options
- Limited nightlife and cultural attractions within the city compared with nearby Norfolk and Virginia Beach
- Hot, humid summers and occasional severe weather (tropical storms/hurricanes)
- Car-dependent in many neighborhoods; public transit options are limited
- Some pockets may experience suburban sprawl and heavy commuter traffic during rush hour
Places to Visit in Chesapeake
Visit one of these nice places.
Vast wetlands and cypress-lined waterways offer misty sunrises, boardwalk views, and abundant birdlife for landscape and wildlife photography.
Historic canal with rustic locks, reflections and wooded banks ideal for moody water scenes and history-infused compositions.
Well-maintained trails, formal plantings and river overlooks provide colorful seasonal shots and intimate nature details.
Riverfront vistas, marshes and kayak launch areas give opportunities for wildlife and sunset photography.
Small marinas, creeks and bay vistas capture boating life, dock reflections and dramatic cloudscapes during golden hour.
Food in Chesapeake
Chesapeake Famous Food
Signature dishes, delicacies and famous food
Seasonal blue crabs steamed with Old Bay and served whole; best at seafood houses and crab shacks along local waterways.
Must-Try!
A creamy, crab-forward soup sometimes finished with a splash of sherry; available at mid-range seafood restaurants.
Assorted locally caught fish, shrimp and oysters served with fries and coleslaw; a casual staple.
Slow-smoked pork or brisket with tangy or vinegary sauces served at BBQ joints across the city.
Food Markets
Explore local food markets
Seasonal markets deliver fresh produce, baked goods and sometimes prepared foods—excellent for picnic supplies and local specialties.
Small local fish markets and takeout counters near the water where you can buy steamed crabs, oysters, or fresh fillets to cook yourself.
Weather
How to Behave
Tips on cultural norms and respectful behavior
Politeness and friendliness are customary—use please and thank you, hold doors for others, and expect friendly small talk. A relaxed pace and helpful locals are typical.
The Hampton Roads area has a significant military presence—show respect for service members and installations, and follow posted rules near bases and military facilities.
When visiting natural areas, follow leave-no-trace principles: pack out trash, stay on trails, and observe wildlife from a distance.
Safety
Tipping in Chesapeake
Ensure a smooth experience
Standard U.S. tipping applies: 15–20% at sit-down restaurants, $1–2 per drink at bars, $2–5 for valet or bell services, and rounding up or 10–15% for taxis and rideshares. Tip more for exceptional service and expect tip prompts on card machines.
Credit and debit cards are widely accepted, and contactless/mobile payments are common. Carry some cash for small vendors, farmers markets, or if you’re visiting remote areas where card signals may be patchy.
Best Time to Visit
And what to expect in different seasons...
Mild temperatures and blooming vegetation make it an ideal time for hiking, birdwatching and visiting farmers markets; be aware of muddy trails after rains and strong insect activity as it warms.
Hot, humid weather with frequent afternoon thunderstorms; perfect for boating, swimming and beach trips—bring sun protection and stay hydrated, and expect peak tourist activity on nearby beaches.
Comfortably cool temperatures and colorful foliage in the swamp and river corridors; this is prime time for outdoor activities and photography with fewer bugs and lower humidity.
Generally mild winters with occasional cold snaps and rare snow; outdoor activities are still possible, though some services may have reduced hours and marshy areas can be soggy in thaw cycles.
Chesapeake at Night
Hiking in Chesapeake
Immerse in an unforgettable hike.
Extensive trail network and boardwalks through wetlands and pine forests; good for long hikes, wildlife viewing and serene photography—bring insect repellent and water.
Riverside trails, picnic areas and canoe launches with varied terrain and good birdwatching opportunities.
Well-marked paths through curated plant collections and native woodlands—ideal for shorter walks and educational outings.
Diverse coastal trails across maritime forest, dunes and marshes with historical sites and beach access—popular for longer day hikes and nature exploration.
Remote and undeveloped coastal park with backcountry trails, dunes and pristine maritime habitats—access requires parking at designated lots or arranging a shuttle or water access.
Airports
How to reach Chesapeake by plane.
The closest major airport (about 20–30 minutes by car depending on location) with domestic flights and rental car services; convenient for most travelers to the Hampton Roads area.
Smaller regional airport to the northwest offering limited commercial flights and general aviation; useful for some regional connections.
Approximately 1 hour drive west—offers more flight options and carriers for broader domestic travel.
Major airport at a longer distance (roughly 2–2.5 hours drive) with many domestic and international connections; an option for budget flights or routing alternatives.
Walkability
Demographics
Explore demographics in this area.
Large portion of the population lives in single-family neighborhoods and suburbs—family-oriented amenities and schools are important.
Due to proximity to several bases in the Hampton Roads area, many residents are active-duty military, veterans, or civilian defense contractors.
A multicultural community with significant African American population, growing Hispanic and Asian communities, and a blend of long-time locals and newer residents.
Popular Sports
Explore popular sports in region.
Football is a regional passion at high school and college levels; nearby Norfolk and the Tidewater region also follow collegiate and professional teams.
Recreational boating, crabbing and fishing are hugely popular due to rivers, creeks and the bay—local culture revolves around time on the water.
Little league, youth sports and community baseball/softball leagues are active and central to family life in suburbs.
Traffic
Accomodations
Find the best place to stay when visiting Chesapeake.
Dietary Restrictions
Tips for restricted diets.
Vegetarian options are widely available at cafés, farm-to-table restaurants and many chain outlets; ask for vegetable or grain bowls, salads, and farm-market specials—seafood-heavy places will often accommodate meatless dishes with advance notice.
Vegan options are growing but can be limited at traditional seafood-centric spots; look for dedicated vegan-friendly cafés, ethnic restaurants, or larger eateries with plant-based entrées.
Many restaurants offer gluten-free menus or can adapt dishes; communicate allergies clearly and consider calling ahead for pronounced cross-contamination concerns.
Shellfish is common—notify servers about allergies and avoid seafood-focused establishments if cross-contact risk is high.