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.


We recommend that you call the attractions and restaurants ahead of your visit to confirm current opening times.

1.Dismal Swamp Canal Trail

Dismal Swamp Canal Trail
© fotoforfun/stock.adobe.com

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


Fun day trip ideas: Ohio, From San Francisco, From NYC, Texas, Florida -- You are reading "12 Best Things to Do in Chesapeake, Virginia" Back to Top

2.Chesapeake Arboretum, Chesapeake, Virginia

Chesapeake Arboretum, Chesapeake, Virginia
© crystalseye/stock.adobe.com

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


Things to do near me today: Sarasota, From Boston, OR, NC, From Houston, NJ, GA -- You are reading "12 Best Things to Do in Chesapeake, Virginia" Back to Top

3.Hickory Ridge Farm, Chesapeake, Virginia

Hickory Ridge Farm, Chesapeake, Virginia
© Hickory Ridge Farm

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



Our experts' top picks for a long weekend getaway: Poconos, NY, TN, MI, OC, All Inclusive, Family weekend getaways, NJ, NC, VA, TX, OH -- You are reading "12 Best Things to Do in Chesapeake, Virginia" Back to Top

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

Things to Do in Chesapeake, Virginia: Great Bridge Lock Park
© buharina/stock.adobe.com


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


More places we like: Cincinnati, MD, OR Beaches, HI, Indoor Amusement Parks, Things to Do in Gatlinburg, WI, Orlando, Texas Beaches -- You are reading "Fun Things to Do in Chesapeake, Virginia this Weekend with Friends" Back to Top

5.Greenbrier Mall, Chesapeake, Virginia

Greenbrier Mall, Chesapeake, Virginia
© Greenbrier Mall


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


Expert opinion: Where should I go this weekend for fun? Iowa, WI, From New Orleans, ME, FL, Carlsbad, CA, Montauk, FL, Beaches near DC -- You are reading "What to Do in Chesapeake, Virginia this Weekend" Back to Top

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

Things to Do in Chesapeake, Virginia: South Norfolk Jordan Bridge
© James/stock.adobe.com


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


Top Rated: Last minute places for couples: Charleston WV, Pensacola, Baton Rouge, Colorado Springs, Dayton OH, Dauphin Island, Provincetown, New Orleans, Philadelphia, UT, AZ, From NYC, CO -- You are reading "Top Romantic Tourist Attractions in Chesapeake, Virginia" Back to Top

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

Great Bridge Battlefield and Waterways Foundation, Chesapeake, Virginia
© Great Bridge Battlefield and Waterways Foundation

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



Affordable things to see near me, must-visit beaches: East Coast Beaches, SC, Beaches near Orlando, Last Minute, NH, Houston, Palm Springs, Monterey, From Atlanta, GA, Sedona AZ -- You are reading "What is There to Do with Kids in Chesapeake, Virginia" Back to Top

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

Things to Do in Chesapeake, Virginia: Elizabeth River Park
© Aris Suwanmalee/stock.adobe.com

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


In-depth reviews of our favorite places: Best caves in the U.S., SD, Galena IL, Boise, St. Pete, San Jose, Taos, Fayetteville, Steamboat Springs, NH, East Coast, DE, GA, Little Rock

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

Things to Do in Chesapeake, Virginia: Cutlass Grille
© lena_rx7/stock.adobe.com

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, the Cutlass Grille is open for both lunch and dinner. 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


Insider travel recommendations: UT, Indianapolis, From Kansas City, Mackinac Island, Chattanooga, RI, From Chicago, Sacramento, Nantucket, Girls Getaways, Santa Barbara, PA, Michigan beaches -- "Best Things to Do in Chesapeake, Virginia for Locals & Tourists - Restaurants, Hotels" Back to Top

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

Things to Do in Chesapeake, Virginia: The Egg Bistro
© 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


What to do near my location: Carmel, WA, UT, MN, Chicago, NE, NV, NH, NJ, NM, Kirkland, Taos, SoCal Camping, West Palm Beach, LA Beaches, Things to Do in Moab

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

Wicker's Crab Pot Seafood, Chesapeake, Virginia
© Wicker's Crab Pot Seafood

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


Cool places to go near me: Wichita, CT, CA, Corpus Christi, Best aquariums in the US, Hartford, NM, GA, NC, UT resorts, NM, LA, MI, DE, PA lakes -- "New cool stuff to do in Chesapeake, Virginia" Back to Top or Romantic Getaways

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

Things to Do in Chesapeake, Virginia: Abuelo's Mexican Restaurant
© grinchh/stock.adobe.com

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


Free things to do, beaches near me: Leavenworth WA, Day trips from Las Vegas, Norfolk, Treehouse vacations, San Jose, Mexico, Jacksonville Beaches, WV, Woodstock, IL, Tampa Beaches, IN, Calistoga, Glowing Beaches

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

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

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.

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


Top sights: Shenandoah, Virginia wineries, Fredericksburg


12 Best Things to Do in Chesapeake, Virginia



You are reading "12 Best Things to Do in Chesapeake, Virginia " Back to Top