30 Best Things to do in Chesapeake!

Nestled in the southeastern corner of Virginia, Chesapeake is a city full of natural beauty and modern conveniences. Known for its stunning waterways, vast forests, and rich history, Chesapeake offers a peaceful retreat without feeling too far from the hustle and bustle of nearby cities. Whether you’re an outdoor enthusiast looking to kayak along scenic rivers or a history buff ready to explore the past, we’ll showcase the best things to do in Chesapeake during your visit to Virginia.

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1. Must-See Attractions

Great Bridge Battlefield & Waterways Park

The Great Bridge Battlefield & Waterways Park reminds the Battle of Great Bridge, an important event in the American Revolution that shaped Virginia’s future. Walking through the park, visitors find informative signs detailing the battle, making it easy to follow the story. A boardwalk stretches over the waterways, offering scenic views and a calm atmosphere. Near the battlefield, the visitor center has exhibits with artifacts and information that bring the past to life without feeling overwhelming. The park is not just about history — it’s also a great spot for birdwatching, sunsets and enjoying nature.

Chesapeake Arboretum

Spanning 48 acres, Chesapeake Arboretum offers a quiet escape into nature where visitors can walk along peaceful trails surrounded by trees. The arboretum features different gardens highlighting native plants, making it an ideal spot for those who appreciate simple, natural beauty. A historic farmhouse is a highlight to the site, giving a glimpse into the past while being surrounded by greenery. The trails are simple to follow, making it great for a casual walk, photography, or just enjoying the fresh air. It’s a unique spot where families, couples, and solo visitors can spend time without feeling rushed.

Hickory Ridge Farm

The Hickory Ridge Farm is a place that brings families and anyone looking for a peaceful day outdoors will find something special here. The farm is best known for its fresh produce, including strawberries and pumpkins when they’re in season. Picking your own fruit straight from the field is a fun experience, especially for kids. There are open spaces where visitors can walk around and enjoy the surroundings. Farm animals adds a highlight to this place, with opportunities to see farm life up close. It’s the kind of spot where conversations happen naturally, whether it’s about farming or just everyday life.

Centreville–Fentress Historic District

In Chesapeake, the Centreville–Fentress Historic District quietly holds onto its past while standing in the present. Walking through the area, you notice old buildings that have been standing for years since 19th century, each telling a story about the people who lived and worked here. The structures here are simple, showing how the town evolved over time. Some have been restored, keeping their original charm, while others remain as reminders of an earlier era. This isn’t the kind of place with large museums or monuments, but rather one that lets history live through everyday surroundings.

Chesapeake Conference Center

The Chesapeake Conference Center is a well-known event space in Chesapeake, offering a large area for meetings, gatherings, and special occasions. It has over 39,000 square feet of space, making it a great choice for both small and large events. It is located close to hotels and restaurants, making it easy for visitors to find everything they need nearby. The building is designed to host different types of events, including business meetings, trade shows, and sports competitions. The center has advanced technology, including audio-visual equipment, to support presentations and performances.

Historic Greenbrier Church

Built on 1800s, Historic Greenbrier Church is more than just a place of worship — it’s a landmark with deep roots of history in the community. The church has stood through different eras, holding onto its history while continuing to welcome people. Walking around the church, you can feel a timeless charm, with its simple architecture. It has been an important part of the local community for years, serving as a gathering place for worship and special events. The church’s history is tied to the growth of Chesapeake, and its presence is a reminder of the traditions and values that have shaped the area.

2. Outdoor Adventures

Chesapeake City Park

The Chesapeake City Park is a large, open space where people come to relax, walk, play, or just enjoy the fresh air. The park has wide paths that make it easy to take a walk or go for a jog. There’s plenty of grassy space where families spread out for picnics or kids run around. One of the highlights is the playground, which always has children climbing, swinging, and having fun. Another big draw is the skate park, where skateboarders practice and show off their skills. For those who enjoy outdoor events, the park has an area that hosts concerts, festivals, and gatherings throughout the year.

Indian River Park South Side

The Indian River Park South Side is another peaceful place for walking, biking, and simply getting outside without distractions. The trails are well-kept and easy to follow, passing through a peaceful wooded area. Visitors looking for a break from busy city life will appreciate the calm atmosphere here. The park is known for its towering trees, which provide plenty of shade along the paths. Bikers often come here for the smooth trails, and hikers enjoy the simple beauty of the surroundings. There are open areas where visitors can take a break, sit for a while, or just enjoy the peaceful atmosphere.

Elizabeth River Trail

Stretching over 10 miles, Elizabeth River Trail is a great spot for anyone who enjoys walking, biking, or simply being outdoors. It’s a long, scenic path that follows the river, giving visitors peaceful views as they move along. The trail connects different areas, making it useful for both exercise and casual walks. The path is well-maintained, making it easy to navigate from any starting point. Along the way, there are benches and open spaces where people can take a break and enjoy the surroundings. Some parts of the trail go through wooded areas, offering shade and a nice escape from busy city life.

Boating Tours

In Chesapeake, boating tours offer a fantastic way to experience the waterways. Many tours companies like Top Rack Marina or Ocean Yacht Marina take visitors through rivers, creeks, and marsh areas, giving a close look at the landscapes and wildlife. Nature-focused tours often include guides who share details about the local environment, while other tours focus on fishing, giving visitors a chance to head out into deeper waters with expert captains who know where to find the best spots. Kayak and paddle tours allow visitors to explore at a slower pace while moving through narrow channels.

Western Branch Park

The Western Branch Park has a spacious area with plenty of room for different activities, whether someone wants to play sports, take a walk, or just relax. The park has open fields where kids and adults can run around, making it a good spot for casual games. There are trails that offer a simple way to enjoy nature, with trees providing shade along the way. Many visitors appreciate the laid-back atmosphere, which makes it a good place to take a break from the busy day-to-day routine. The park has courts and fields for people who like to stay active, but it’s also a great spot to enjoy the surroundings.

Deep Creek Park

The Deep Creek Park has open fields where families gather for picnics, kids run around, and visitors take time to enjoy nature. Walking trails takes you through the area, providing an easy way to explore without feeling rushed. For those who enjoy staying active, there are fields for sports, where local teams and groups often meet to play. The park’s layout makes it simple to navigate, whether someone wants to take a short walk or spend a longer time outside. People come here to jog, bike, or enjoy the outdoors. There are benches in different areas, perfect for resting and enjoying a peaceful moment.

Paradise Creek Nature Park

The Paradise Creek Nature Park offers a quiet escape into nature while also highlighting conservation efforts that protect the local environment. The park has peaceful trails that takes you through open spaces, making it easy for visitors to explore at their own pace. Along the way, signs provide information about the land and water, helping people understand the importance of preservation. The creek itself is a key feature, offering a calm place where birds and other wildlife can be seen. The park’s conservation efforts make it more special, showing how nature can thrive with care and attention.

3. Family-Friendly Activities

Children’s Museum of Virginia

Located in nearby Portsmouth, the Children’s Museum of Virginia is filled with hands-on activities that encourage creativity and curiosity, from science experiments to pretend play areas. Kids can explore spaces set up like a grocery store, bank, or fire station, helping them understand everyday life in a fun way. There’s also an area dedicated to science, where simple experiments and interactive displays make learning about concepts like electricity or gravity enjoyable. One of the highlights is the train exhibit, which captures the attention of children and adults with detailed models and displays.

Sky Zone Trampoline Park

The Sky Zone Trampoline Park is a fun indoor space where visitors can jump, flip, and move freely in a safe environment. It features wall-to-wall trampolines give people a place to bounce, whether they’re trying tricks or just enjoying the movement. Some sections have angled trampolines, letting jumpers push off the walls for extra excitement. Dodgeball on trampolines adds a fun twist to the classic game, making players jump while aiming for their targets. The foam pit is a favorite spot, giving visitors a soft landing when trying flips or dives, while basketball hoops allow people to dunk while jumping.

Golfing Courses

Golfing in Chesapeake is a great way to enjoy the outdoors while playing on well-kept courses designed for all skill levels. Some courses like Chesapeake Golf Club or Battlefield Golf Club have well-kept fairways, making the experience more scenic while requiring players to plan their shots carefully. Many courses like Greenbrier Country Club or Bide-A-Wee Golf Course also have clubhouses, offering food, seating, and a comfortable place to rest after a game. Some locations provide guided lessons, helping beginners improve their skills while making sure they feel comfortable on the course.

AMF Indian River Lanes

The AMF Indian River Lanes is a great place for casual bowling, whether you’re visiting with friends, family, or just looking for a relaxed way to spend time indoors. Some come to compete, while others just roll for fun, making it a welcoming space for beginners and experienced bowlers. The scoring system is easy to follow, so players can focus on enjoying the game rather than worrying about complicated rules. There’s also an arcade with classic games for those who want a break between rounds. The snack bar serves food and drinks, making it easy to grab something without leaving the building.

FunVille Playground

The FunVille Playground is designed especially to keep children active by jumping or climbing, while making sure they have fun in a space full of different play areas. The setup includes slides, obstacle courses, climbing structures, and open areas where kids can run freely. Some sections are made for younger children, giving them smaller spaces to play without worrying about bigger kids rushing past. There’s also an arcade area where visitors can play games before heading back to the main play area. Families often visit for birthday parties or group outings, making it a popular choice for celebrations.

4. Natural Attractions

Stumpy Lake Natural Area

The Stumpy Lake Natural Area is surrounded by trees, has a unique look with sections of tree trunks emerging from the water, creating a scenic backdrop that feels undisturbed. Walking trails around the lake provide an easy way to explore, offering shade and quiet spaces to pause and enjoy the view. Many visitors come just to sit by the water and breathe in the fresh air. Kayaking is a popular activity, allowing people to paddle across the lake and explore the area from a unique perspective. Some enjoy fishing, while others simply appreciate the quietness that makes this area feel like a hidden escape.

Great Dismal Swamp National Wildlife Refuge

The Great Dismal Swamp National Wildlife Refuge is a place where nature feels wild and untouched, offering visitors a unique outdoor experience. Explore the 8.5 miles Lake Drummond trail to see dense forests and the large, mysterious lake. The swamp has a deep history, once serving as a hiding place for freedom seekers and playing a role in early American life. Walking through the refuge, visitors can follow trails that lead deeper into the natural landscape, surrounded by towering trees. The large lake Drummond is one of its highlights, offering a quiet place to paddle or take in the views.

Northwest River Park

The Northwest River Park is a peaceful space with walking trails, water views, and plenty of open areas to explore. The river is one of the highlights, offering a quiet spot for fishing, kayaking, or just watching the water move. The park has campsites, making it a great option for those who want to spend more time outdoors. Many visitors enjoy biking or hiking along the trails, taking in the fresh air and relax under trees. There’s also a disc golf course, a fun activity for anyone looking for something different. Unlike busy parks with attractions, this one keeps things simple, focusing on outdoor enjoyment.

Oak Grove Lake Park

The Oak Grove Lake Park is a peaceful spot where visitors can enjoy nature without distractions. The lake sits at the center, surrounded by trees and well-maintained trail circles the lake, making it easy for people to walk, jog, or bike while taking in the scenery. Benches along the path provide spots to rest, allowing visitors to pause and enjoy the quiet surroundings. Fishing is popular along the shore, with people casting lines and enjoying the slow pace of the water. The shade from the trees makes it comfortable, even on warmer days, and the breeze off the lake adds to the peaceful atmosphere.

Hoffler Creek Wildlife Preserve

The Hoffler Creek Wildlife Preserve is a quiet place where visitors can explore nature and enjoy the outdoors at their own pace. The trails takes you through forests, open fields, and along the water, giving plenty of space to walk and take in the surroundings. Birds are a big part of the experience, making it a great spot for birdwatchers looking to see different species up close. The water areas attract turtles, fish, and other animals, adding to the natural feel. Kayaking is a great way to see the preserve from a different angle, allowing visitors to paddle through and experience the beauty of the area.

Northwest River Natural Area Preserve

The Northwest River Natural Area Preserve is a kind of place where visitors can take slow walks, enjoy the fresh air, and feel more connected to nature. The trails passing through forests and wetlands, making each step feel like a part of the natural environment. Many people visit for birdwatching, as the area is home to different species throughout the year. The flowing river adds as highlight, with sections where visitors can sit and watch the water move quietly. Some parts of the preserve feels wild and being untouched, giving visitors a chance to experience nature without any distractions.

5. Day Trips & Excursions

Williamsburg

Start a day trip to Williamsburg takes about 45 minutes drive from Chesapeake, making it an easy getaway. Most visitors start from Colonial Williamsburg, where history comes to life with old streets, preserved buildings, and people dressed like they’re from the 1700s. Walking through the area feels like stepping into the past, with small shops selling handmade goods and places offering traditional meals. The historic sites tell the story of early America, making it a great spot for those who enjoy learning. Nearby, Merchants Square has cafes where visitors can grab a bite to eat or find souvenirs.

Back Bay National Wildlife Refuge

From Chesapeake, a day trip to Back Bay National Wildlife Refuge takes about 30 minutes, and the reward is a peaceful area filled with wetlands, forests, and open water. The refuge is home to all kinds of wildlife, including deer, foxes, and different species of birds, making it a great spot for nature lovers and photographers. One of the best ways to explore is by walking the trails that lead through different areas, offering views of both land and water. Many visitors bring binoculars to get a closer look at the wildlife, while others come just to enjoy a quiet moment away from the city.

Pocosin Lakes National Wildlife Refuge

Planning a day trip to Pocosin Lakes National Wildlife Refuge from Chesapeake, is a great way to step into nature and experience a quiet, untouched landscape. This refuge is a special place for wildlife, known for its mix of birds, black bears, and other animals that thrive in its protected environment. Walking along the trails, visitors get a chance to see the land up close, with open fields and waterways stretching in different directions. Birdwatchers especially love this area, since many species stop here throughout the year, making it an ideal spot to bring binoculars and spend time watching the sky.

Cape Charles

From Chesapeake, a day trip to Cape Charles takes about 1.5 hours, crossing the Chesapeake Bay Bridge-Tunnel, which itself is an experience with long stretches over the water. The pier is a great spot to stop and watch the boats, and the view of the bay is stunning. The town is full of small shops, many selling handmade goods, art, and coastal-themed items. Local restaurants offer fresh seafood and simple meals, making lunch a treat no matter where you choose to eat. Walking through the town, there’s a mix of historic buildings and colorful homes, giving Cape Charles a warm and welcoming look.

Petersburg

Start early from Chesapeake and drive about 1.5 hours to reach Petersburg that offers a good mix of history and a local charm. Petersburg is best known for its deep Civil War history, and one of the first stops for many visitors is Petersburg National Battlefield. Walking through the site gives a sense of the past, with old cannons, trails, and signs explaining the events that took place there. Downtown Petersburg is filled with historic buildings, small shops, and restaurants that offer tasty meals. Many people enjoy walking in the streets, stopping at antique stores, or checking out local art galleries.

How to Reach Chesapeake

Reaching Chesapeake, Virginia, is simple, with several travel options depending on where you’re coming from. The nearest airport is Norfolk International Airport (ORF), located about 20 minutes away by car, offering direct flights to several U.S. cities. Upon arrival, visitors can rent a car or take a taxi to Chesapeake for an easy transfer. For those who prefer trains, Amtrak stops in nearby Norfolk and Newport News, making it a convenient alternative before continuing with a short drive.

Road trips are a great way to arrive, with Chesapeake well-connected through major highways such as I-64, U.S. Route 17, and Interstate 464, allowing smooth travel from North Carolina and Maryland. Bus services like Greyhound also have routes that stop nearby, giving travelers additional options to reach the city without driving. While Chesapeake is not directly accessible by train, the nearby stations make rail travel an option. Some visitors coming from the coast may arrive through boat services or marinas, though this is less common.

Local Transportation

Chesapeake is spread out, with parks, shopping areas, and neighborhoods that aren’t always connected by public transit. Many visitors and locals rely on their own vehicles, and major roads like Interstate 64 and Route 17 make driving smooth. For those who prefer public transportation, Hampton Roads Transit (HRT) operates bus services that connect parts of Chesapeake to nearby cities like Norfolk and Virginia Beach. The buses are useful for getting around, but they don’t reach every area, so planning ahead is important.

Taxis and rideshare services are also available in Chesapeake, making it easy to get where you need to go without worrying about parking. Some areas have bike-friendly paths, especially around parks and nature trails, offering another option for getting around in good weather. Chesapeake doesn’t have its own train system, but Amtrak stations in Norfolk and Newport News are close enough for those traveling longer distances. While public transit is limited compared to bigger cities, making driving the best option for most people.

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FAQ’s (Frequently Asked Questions)

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