12 Best Things to Do in Chesapeake, Virginia

By VI Staff on October 10, 2021 - Updated

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There certainly isn’t a shortage of things to do in the city of Chesapeake, Virginia. From outdoor adventures and relaxing park to historic sites and attractions to shops and restaurants serving delicious food, the city is full of fun for both local residents and tourists alike. Chesapeake boasts many events and attraction found in a large city nestled within the heart of the dynamic coastal region of the state of Virginia. The city also serves as a base for a variety of outdoor activities, such as kayaking, hiking, biking, fishing, and much more. Certain attractions may be temporarily closed or require advance reservations. Some restaurants are currently offering pickup only. Hours/availability may have changed.

1.Dismal Swamp Canal Trail

The Dismal Swamp Canal Trail is an outdoor recreation, environmental, and historic park area with picnic areas, as well as multi-use trail that is open to horseback riding, hiking, running, walking, bicycling, and even boating. The north trailhead can be found at Old Route 17 and Dominion Boulevard in Chesapeake, Virginia and runs a little more than eight miles to the south along the Dismal Swamp Canal. This canal is also the site of the Paddle for the Border event in the spring, during which paddlers of all ages travel from the state of Maryland down to Georgia.

1200 Dismal Swamp Canal Trail, Chesapeake, VA 23322, Phone: 757-382-6411

2.Chesapeake Arboretum, Chesapeake, Virginia

The Chesapeake Arboretum is situated within the center of Chesapeake, Virginia and encompasses forty-eight acres that it calls “Nature’s Classroom,” promoting environmental and horticultural awareness through research, education, and plant displays. The arboretum is also designated as a “Virginia Treasure,” a state initiative for highlighting the important recreational, scenic, historic, and ecological lands throughout Virginia. The park includes around three miles of trails for walking and hiking, picnic areas, the three-acre Lake Hughes, a wide variety of plants, eight bridges, the Propagation Nursery, the historic Calem Williamson Farm House, and one of the finest trail systems in the state.

624 Oak Grove Rd, Chesapeake, VA 23320, Phone: 757-382-6411

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3.Hickory Ridge Farm, Chesapeake, Virginia

The Hickory Ridge Farm is a family-owned and operated farm in the Hickory area of the city of Chesapeake. The eighteen-acre farm consists of several acres of produce that is available to the public for picking during different parts of the year. During late April, throughout the month of May, and during early June, visitors can come to the Hickory Ridge Farm to pick strawberries. Summer produce is available between the months of June and August, as well as wholesale and you-pick pumpkins available during the autumn months. Hickory Ridge Farm is open from Tuesday to Sunday.

2928 S Battlefield Blvd, Chesapeake, VA 23322, Phone: 757-560-6763

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4.Things to Do in Chesapeake, Virginia: Great Bridge Lock Park

The Great Bridge Lock Park is located along the state of Virginia’s Intracoastal Waterway, where the Chesapeake Canal and the Albemarle Canal meet with the Elizabeth River’s Southern Branch. The park is named for the lock of the Corp of Engineers that separates the canal’s freshwater from the river’s saltwater. The Great Bridge Lock Park spans across nineteen acres of a small peninsula, surrounded by a river on one side and a canal on the other, and features interpretive signage about the lock system, fareas for fishing, picnic shelters, a playground area, and a boat ramp with two lanes.

100 Locks Rd, Chesapeake, VA 23320, Phone: 757-382-6411

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5.Greenbrier Mall, Chesapeake, Virginia

The Greenbrier Mall is made up almost nine hundred thousand square feet of shops in the state’s Hampton Roads area. This regional mall is set on a hillside terrain, which means mall entrances are located on both the lower and upper levels. Along with the city of Chesapeake, the Greenbrier Mall serves several communities along the east coast of Virginia, as well as some communities in North Carolina. The mall is home to more than one hundred retailers, including Macy’s, JCPenney, and Dillard’s, as well as the Cinema Cafe movie theater, and a number of different restaurants.

1401 Greenbrier Pkwy, Chesapeake, VA 23320, Phone: 757-424-7100

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6.Things to Do in Chesapeake, Virginia: South Norfolk Jordan Bridge

The South Norfolk Jordan Bridge, also known as the Jordan Bridge, is a fixed bridge and tolled highway that transports State Route 337 across the Southern Branch of the Elizabeth River, from Chesapeake, Virginia in South Hampton Roads to the city of Portsmouth, Virginia. The bridge was originally opened for traffic back in 1928, built by Carl and Wallace Jordan, two businessmen of South Norfolk. The South Norfolk Jordan Bridge was the state of Virginia’s oldest drawbridge, and closed in November of 2008 due to its amount of needed maintenance. The new, replacement bridge was finished in October of 2012.

100 Poindexter St, Chesapeake, VA 23324

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7.Great Bridge Battlefield and Waterways Foundation, Chesapeake, Virginia

The Great Bridge Battlefield and Waterways Foundation owns and operates The Great Bridge Battlefield & Waterways Historic Park & Museum / Visitor Center in the city of Chesapeake, Virginia. The foundation works to preserve the history of the United States and has decided to open the museum and visitor center in a gorgeous Georgian-style building along the Intracoastal Waterways to highlight the history of the nations waterways and the Battle of Great Bridge during the American Revolution, for visitors traveling by land or by water. The museum features a permanent gallery, a changing exhibit gallery, an an auditorium that seats one hundred people.

1775 Historic Way, Chesapeake, Virginia 23320, Phone: 757-482-4480

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8.Things to Do in Chesapeake, Virginia: Elizabeth River Park

The Elizabeth River Park is a waterfront park in Chesapeake, Virginia that boasts amazing views of the river and serves as a great spot for picnicking or taking part in outdoor recreational activities, such as the walking paths or the area for cardio fitness. Boat owners can easily access the Elizabeth River Park by both water and land. The pedestrian walkway offers spectacular views from the city’s South Norfolk Jordan Bridge. There is also a fishing/crabbing pier available for visitors to use free of charge, gazebos and shelters, a dog park, and snacks available at the Snack Shack.

1400 Elizabeth River Way, Chesapeake, VA 23324, Phone: 757-382-6411

9.Things to Do in Chesapeake, Virginia: Cutlass Grille

The Cutlass Grille in Chesapeake, Virginia specializes in American barbeque dishes and Jamaican cuisine. The family-owned and operated restaurant serves a variety of fresh and delicious food cooked home-style. Particularly popular among the local residents of Chesapeake for both lunch and dinner, the Cutlass Grille is open on Tuesdays, Wednesdays, and Thursdays from 11:00am until 9:00pm, as well as on Fridays and Saturdays from 11:00am until 10:00pm. The restaurant is closed on Sundays and Mondays. The name of “Cutlass Grille” honors the Jamaican heritage of the owner, Shawn, as the cutlass is a common farming tool in Jamaica.

805 N Battlefield Blvd, Chesapeake, VA 23320, Phone: 757-382-0015

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10.Things to Do in Chesapeake, Virginia: The Egg Bistro

The Egg Bistro is a neighborhood bistro that is independently owned in Chesapeake, Virginia, with other locations in Virginia Beach and in Suffolk’s Harbour View. The restaurant serves innovative and fresh food within a hip family atmosphere. The staff strives to provide the best service and food possible to guests dining at The Egg Bistro, with an expansive bar and food menu, twelve different craft beers available on tap, and event space that can accommodate up to 150 guests. Off-site catering is available at each of the bistro’s location and can host events seven days a week.

501 Kempsville Rd, Chesapeake, VA 23320, Phone: 757-410-8515

11.Wicker's Crab Pot Seafood, Chesapeake, Virginia

Wicker's Crab Pot Seafood boasts a heritage within the seafood industry for more than sixty years and has become a popular establishment of the city of Chesapeake. The family-owned and operated restaurant is ran by Ray Wicker, Jr., who is a fourth-generation waterman with more than thirty years of experience working the Chesapeake Bay’s waters and specializes in harvesting oysters, Virginia Blue Crabs, and other types of fresh, locally sourced seafood. Ray and his wife opened Wicker’s Crab Pot Seafood in 2008, sharing their family tradition and passion for fresh seafood with every guest of the restaurant.

4201 Indian River Rd, Chesapeake, VA 23325, Phone: 757-351-2724

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12.Things to Do in Chesapeake, Virginia: Abuelo's Mexican Restaurant

The Abuelo's Mexican Restaurant started out with Dirk Rambo, Chuck Anderson, and James Young opening the first location in Amarillo, Texas in 1989 with a simple goal of opening a restaurant that serves made-from-scratch, delicious Mexican food at affordable prices. The founders are wanted to create a place where people of all ages can enjoy a meal together and experience the culture, art, and unique flavors of Mexico. Thirty years later, Abuelo’s Mexican Restaurant has expanded to include locations in thirteen states throughout the country. The restaurant is designed to be an open-air Mexican courtyard featurings a mix of traditional and modern decor.

1712 Ring Rd, Chesapeake, VA 23320, Phone: 757-961-7610

13.Black Pelican Seafood Co. Greenbrier, Chesapeake, Virginia

The Black Pelican Greenbrier serves Mid-Atlantic coastal cuisine in the heart of the city of Chesapeake, Virginia within an inviting and casual atmosphere. Some people may recognize the name of the restaurant from the iconic Outer Banks location featured on the popular show “Diners, Driver-Ins, and Dives.” Crystal and Jason offer the same tried-and-true food as the original Black Pelican restaurant, along with a coastal setting and elevated service. The Black Pelican Greenbrier is open 11:00am until 9:00pm Sunday to Thursday and 11:00am until 10:00pm on Fridays and Saturdays. Sunday brunch is served 9:00am until 2:00pm.

1625 Ring Rd, Chesapeake VA, Phone: 757-424-3171