Top 24 Things To Do In Chesapeake, Virginia

things to do in chesapeake va
| 12 min read

Who says smaller towns don’t make fun getaway destinations? Putting all such misconceptions to rest is Chesapeake, perched along the Intercoastal Waterway in the heart of Coastal Virginia. Not just a pristine natural landscape, Chesapeake is also an abyss of rich history. Right from cultural events to exciting festivals, humbling natural trails to shining history, zingy food scene to a lively atmosphere, you’ll find it all here. We’ve put together the best of things to do in Chesapeake, Virginia, to make your lives simpler, so start planning your getaway right now! We’re not kidding, you’ll love it there.

1. Learn about the flora and fauna at Chesapeake Arboretum

things to do in chesapeake va | learn about the flora and fauna at chesapeake arboretum
Source: instagram

Start your Chesapeake itinerary with a trip to one of its most beautiful places, the Chesapeake Arboretum. Once a humble farmhouse, the Chesapeake Arboretum picked up popularity as well as expanded in the area. Today, it is rife with the region’s most important flora and fauna systems. It was set up to promote horticultural and ecological awareness, but soon gained popularity for how beautifully it was done up as well. Walkthrough its neatly laid out trails and find yourself engulfed in the many themed gardens there. The Wildlife Trail South Chesapeake Loop and the Virginia Birding trails are where you’ll have luck spotting animal species. This “nature’s classroom”, as the authorities like to call the Chesapeake Arboretum, is a regional treasure trove of natural beauty.

Chesapeake Arboretum

Address: 624 Oak Grove Rd, Chesapeake, VA 23320, USA

Website: Chesapeake Arboretum

Opening hours: 6am - 8pm (daily)

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2. Check out Cavalier Wildlife Management Area's exotic wildlife

Exploring: (hey, what's that damned thing in the lower left?) @ Cavalier Wildlife Management Area off Ballahack Rd. in...

Posted by Brian J. Bodnar on Saturday, 6 July 2019

Chesapeake’s natural beauty is formidable and another one of the testaments to that is the thriving wildlife of the Cavalier Wildlife Management Area, which comprises of the Dismal Swamp tract connected with the Dismal Swamp Canal and the Cavalier tract. Much of the area is covered by rich forestland, so you’ll find neo-tropical songbirds, canebrake rattlesnakes, white-tailed deer, and black bears calling this habitat their home. To protect the wildlife here, authorities have now put a ban on hunting activities and fishing is only allowed with a permit. Otherwise, it is a great place to engulf oneself in the beauty of nature and also indulge in some animal-spotting.

Cavalier Wildlife Management Area

Address: 3853 Ballahack Rd, Chesapeake, VA 23322, USA

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3. Enjoy boating with your partner at Northwest River Park

Give your Virginian getaway a romantic tryst and enjoy a boat ride at the Northwest River Park with your partner. Flowing through dense greenery and calming waters of the river, the ride makes for a perfect blend of recreation as well as exploration. The park is state-owned and is a great space for unwinding amidst quietude and the company of your loved one. If you’re done boating, you can even do some fishing, hiking, or even camping at the park.

Northwest River Park

Address: 1733 Indian Creek Rd, Chesapeake, VA 23322, USA

Website: Northwest River Park

Opening hours: 9am - 7pm (daily)

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4. Visit the Great Bridge Battlefield & Waterways History Foundation

Created to preserve the history of the 1775 Battle of Great Bridge and the Albemarle & Chesapeake Canal and build on its importance, the Great Bridge Battlefield & Waterways History Foundation has set up a park to commemorate one of the most important markers in Chesapeake’s history. Offering educational tours and a great space for seeing the battlefield, the foundation is quite invested in highlighting the importance of a battle that played an important part in American independence. Many tourists now flock here to spend time outdoors as well as learn about the enriching history.

Great Bridge Battlefield & Waterways History Foundation

Address: 1775 Historic Way, Chesapeake, VA 23320, USA

Website: Great Bridge Battlefield & Waterways History Foundation

Opening hours: 24 hours (daily)

Price: Free

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5. Plan a family picnic at Great Bridge Lock Park

Editor's Note: There's no photo available at the time of writing

Perched along the Intracoastal Waterway on a small peninsula surrounded by the water of the Albemarle-Chesapeake Canal on one side and the Elizabeth River on the other is the 7-hectares (19-acres) Great Bridge Lock Park that makes for another one of Chesapeake’s most idyllic outdoor spaces. Chesapeake locals flock there by hordes to enjoy a picnic or one of the other activities, so we suggest you too must try and plan one. There’s a large play area for children, dedicated fishing zones for enthusiasts, foot trails, and manicured gardens to lay and bask in the sun, so you can couple your picnic with other fun stuff to do. There’s something for folks for all age groups, so just put together your picnic basket and head along.

Great Bridge Lock Park

Address: 199 Locks Rd Chesapeake, Virginia 23320

Website: Great Bridge Lock Park

Opening hours: 8am - 7pm (daily)

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6. Buy local items from the Hickory Ridge Farm

#PTA Spirit night Pumpkin Patch Fund raisers are super popular at the farm! We can customize your night and work together to make it what you need!!

Posted by Hickory Ridge Farm on Monday, 22 July 2019

Buy something from the family-run Hickory Ridge Farm and take a bit of Chesapeake back home to relish. Setup to promote local farming, everything at the Hickory Ridge Farm is fresh and straight off the ground. Else, book yourself on one of their Pumpkin or Strawberry Picking Field trips and enjoy your time there. While the Pumpkin Picking Field trips are usually in the Fall, the Strawberry Picking Field trips are hosted over the summer (June-August). Unfortunately, these are subject to change, so it’s best you keep a tab on their website or their Facebook page for the latest schedules and timings to plan your outing accordingly.

Hickory Ridge Farm

Address: 2928 S Battlefield Blvd, Chesapeake, VA 23322, USA

Website: Hickory Ridge Farm

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7. Spend time outdoors at the Chesapeake City Park

Source: Photo by Flickr user Rain0975 used under CC BY-ND 2.0

Sprawled across an area of 36ha (90 acres) is the Chesapeake City Park, a multi-amenity, a city-owned park that makes for one of the best outdoor activity locations in the town. While the Fun Forest (covered later) is a kids’ playground, the horseshoe, volleyball and basketball courts can be accessed by enthusiasts. Else, you can head over to the Skate Park for some rollerblading or just sit in the park and bask in the Virginian sun. There’s also a designated Dog Parks area for your furry buddies to enjoy time outdoors with you and a proper Walking Trail for you to get sweating, doing some jogging, running, or walking. Then there’s the Robert G “Buddy” Bagley Stage within the park premises, which is a popular venue for local events, so keep a tab on the park’s Facebook page if you’d like to attend one.

Chesapeake City Park

Address: 900 City Park Drive, Chesapeake, VA 23320

Website: Chesapeake City Park

Opening hours: 9am - 7:30pm (daily)

Price: Free

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8. Have a fun day with kids at Fun Forest

Take your kids to the Fun Forest and have them let their hair loose, tumbling about and jumping around the swings. Part of the Chesapeake City Park, Fun Forest is city-owned and makes for an ultimate playground for kids to socialize and put some of their energy to good use. The swings of the park have been designed to encourage the development of motor skills in children along with being super fun. There are also some of the simpler swing sets for the smaller children. Else, take them over to the Children’s Fossil Dig to marvel at the pseudo dinosaur bones and fossils or the aquatics area for them to ogle at the water animals.

Fun Forest

Address: 900 City Park Dr, Chesapeake, VA 23320, USA

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9. Observe a moment of silence at the Chesapeake 9/11 Memorial

Posted by Chesapeake 9/11 Memorial on Thursday, 27 October 2016

Only if you’ve been living under a rock or are too young would you not have heard of the devastating 9/11 attacks that happened in USA. To commemorate all those involved with the attacks in some way, a 4.9-tonne (5.5-ton) steel beam from the World Trade Center has been placed on concrete rubble near the main entrance of the Chesapeake City Park. The beam has been fenced off, so visitors are only allowed to look at it from afar. So, if you do land yourself for a walk to the park, do remember to go over and observe a moment’s silence at the memorial. Day of Remembrance ceremony is held annually over here on September 11th, so if you are in Chesapeake during the time, you can make it for that too.

Chesapeake 9/11 Memorial

Address: 900 City Park Drive, Chesapeake, VA 23320

Website: Chesapeake 9/11 Memorial

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10. Take your kids to explore the universe at the Chesapeake Planetarium

Does your little one seem interested in all things starry and beyond the clouds? Take them to the superb weekly show at the Chesapeake Planetarium, funded and run by the Chesapeake Public School System. Flaunting state-of-the-art equipment and amenities, the planetarium showcases some of the most special shows that not only leave children starry-eyed but adults as well. And, not just mere show watching, the planetarium also engages its audience in pop quizzes periodically and also welcomes them to indulge in telescope observations after the show, making the whole experience quite hands-on. However, do note that it’s best to reserve seats well in time, since the show is free of cost and there is limited seating available at the planetarium, You can do that by calling up the Chesapeake Public Schools anytime between 8am to 4pm.

Chesapeake Planetarium

Address: 310 Shea Dr, Chesapeake, VA 23322, USA

Website: Chesapeake Planetarium

Opening hours: Thu: 8pm - 9pm (closed from Fri - Wed)

Price: Free

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11. Enjoy the views at Lake Drummond

Frozen Lake Drummond (5355472930)
Source: Photo by Wikimedia Commons user U.S. Fish and Wil... used under CC BY 2.0

Another one of Chesapeake’s beautiful areas is the Lake Drummond, surrounded by forestland and swamps. You can hitch canoe or boat rides across the lake and enjoy being engulfed in the tranquillity of the area. Else, you can also indulge in some fishing. The lake is known to breed species of chain pickerel, crappie, yellow perch, and bullhead catfish among a few others. However, you might need to acquire a permit for doing so. Boat rides on the lake are one of the few must-do things about Chesapeake, so why don’t you also think about trying it.

Lake Drummond

Address: Chesapeake, VA 23320, USA

Website: Lake Drummond

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12. Take a walk down the Dismal Swamp Canal Trail

There’s no dearth of nature trails in Chesapeake and among the best ones remains the Dismal Swamp Canal Trail, which runs adjacent to the Dismal Swamp Canal in Chesapeake. There are designated trails for cycling, hiking, boating, kayaking, and also horseback riding. Else, you can also have a picnic amidst sprawling greenery and a myriad species of wildlife. The trail is flat and easy to access, so it’s great for folks of all age groups. The Dismal Swamp Canal Trail makes for one of the best spots to spend time outdoors, so do remember to go there at least once.

Dismal Swamp Canal Trail

Address: 1200 Dismal Swamp Canal Trail, Chesapeake, VA 23322

Website: Dismal Swamp Canal Trail

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13. Pay your respects at the River Oak Church

With its first worship in 1999, River Oak Church made for one of the prominent centres of worship in the Oak Grove area of Chesapeake and remains so till date. The church’s weekly Sunday services attract many locals from the area and afar. These services are some of the liveliest across churches you’d have seen – there’s singing, dancing, merry-making, and happy faces all around. The staff is extremely friendly and welcoming, so you’ll never feel out of place.

River Oak Church

Address: 255 Great Bridge Blvd, Chesapeake, VA 23320, USA

Website: River Oak Church

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14. Take one of the paint-it-yourself classes at Glazenfyre

Posted by GLaZENFYRE: A Paint-It-Yourself Pottery Studio on Monday, 25 March 2019

One of the best recreational places in Chesapeake where activities are satisfying as well as fun – Glazenfyre. Offering sessions in pottery painting, canvas painting, and glass fusing, the studio attracts kids and adults who’d like to try their hand at painting. They let you pick your piece or design, gather the essentials, and make whatever design you like. If you’re going in for pottery painting or glass fusing, the studio takes care of the messy steps, like firing, glazing, and hanger placement. As for canvas painting, there’s a professional instructor available for help at any time. Once done with your masterpiece, you can also take it home with you as well! Keep a tab on their monthly special events via their website or Facebook page and see if they’re hosting one around your time of travel – they’re quite creative and super fun!


Address: 501 Kempsville Rd, Chesapeake, VA 23320, USA

Website: Glazenfyre

Opening hours: Tue - Thu & Sat: 11am - 7pm; Fri: 11am - 9pm; Sun: 12pm - 6pm (closed on Mon)

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15. Browse through Greenbrier Mall's branded stores

Posted by Greenbrier Mall on Monday, 16 February 2015

Shopping sure can be therapeutic, so head over to Chesapeake’s Greenbrier Mall and pick yourself up stuff from the many branded store outlets there. There’s all the showrooms you can think of – Victoria’s Secret, H&M, JC Penney, Bath & Body Works, and several others. You can spend an entire day here without getting bored.

Greenbrier Mall

Address: 1401 Greenbrier Pkwy, Chesapeake, VA 23320, USA

Website: Greenbrier Mall

Opening hours: Mon - Sat: 10am - 9pm; Sun: 12pm - 5:30pm

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16. Play a round of ice hockey at Chilled Ponds Ice Sports Complex

Add a touch of fast-paced fun to your holiday and head over to the Chilled Ponds Ice Sports Complex for a session of ice skating, figure skating, or ice hockey. Fret not if you’re amongst the uninitiated, they offer learn-to-skate lessons as well and their instructors are some of the best you’ll find in the region! So, enrol yourselves in one of them and return home with a new skill set to flaunt! This one’s ideal for all age groups, so don’t let boredom take over your time and just head over to the Chilled Ponds Ice Sports Complex.

Chilled Ponds Ice Sports Complex

Address: 1416 Stephanie Way, Chesapeake, VA 23320, USA

Website: Chilled Ponds Ice Sports Complex

Price: 12 - 14 USD

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17. Gain new skills at the Norfolk County Rifle Range

Source: Pexels

Ranging from archery to rifle-, pistol-, and shotgun-shooting, there are quite a few activities at the Norfolk County Rifle Range to hone your target skills. Although originally established as a private shooting club, it is now open to non-members as well. All they need to do is separate a separate fee and they can not only use the club’s facilities but also participate in the seasonal events or the competitions and training sessions hosted there. The trainers at the facility are certified and offer all support and coaching to the guests, as required. Don’t worry if you’re a newbie, just ask them for help and return from Chesapeake with a new skill learnt!

Norfolk County Rifle Range

Address: 4321 S Military Hwy, Chesapeake, VA 23321, USA

Website: Norfolk County Rifle Range

Opening hours: 24 hours (daily)

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18. Practice golf techniques at Chesapeake Golf Club

The Forecaddie: Make the last at Evian one to remember

Posted by Chesapeake Golf Club on Wednesday, 17 January 2018

Having broken ground in 1986 and attracting hordes of enthusiasts ever since is the Chesapeake Golf Club, a premier golf course facility in the city. Even though the club has changed ownership quite a few times, its popularity and great maintenance remain top-notch and a hit among users. You can either be a member of the club or avail its services at an a-la-carte payout system. You can even go in for one of their one-on-one or group golfing lessons if you don’t know how to play already. And, not just for adults, this one is for the little ones too. The club offers some yearly junior golf camps as well, so check out their website for latest details and see if you’d like to enrol your little one in this while you’re in Chesapeake.

Chesapeake Golf Club

Address: 1201 Club House Dr, Chesapeake, VA 23322, USA

Website: Chesapeake Golf Club

Opening hours: 7am - 5pm (daily)

Price: 15 - 40 USD

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19. Plan a bowling night with friends at AMF Chesapeake Lanes

Offering some 40 bowling lanes, several billiards/pool tables, a gaming arcade, a sports bar, and a pro shop on-site is the AMF Chesapeake Lanes where gaming is taken pretty seriously and a party mood is a prerequisite. You can hit up any one of their many attractions and make it a grand gaming night for your group. Plus, they keep hosting competition nights as well. You can also head there to catch a live screening of a sport, or just to lounge around. They have all the makings of a super place, so don’t forget a trip down AMF Chesapeake Lanes.

AMF Chesapeake Lanes

Address: 112 Medical Pkwy E, Chesapeake, VA 23320, USA

Website: AMF Chesapeake Lanes

Opening hours: Mon: 12pm - 12am; Tue - Thu & Sun: 12pm - 11pm; Fri: 12pm - 1am; Sat: 10am - 1am

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20. Relish on American cuisine at Ddeb's- A Taste of Home

Ddeb’s-A-Taste-Of-Home 105 Old Dr. Chesapeake, VA

Posted by The Wes Strong Foundation on Wednesday, 17 October 2018

Bringing the best of homestyle American fare and giving it a restaurant-style twist is Chesapeake’s much-loved Ddeb’s- A Taste of Home restaurant. Although homely in its vibe and flavours, Ddeb’s dishes add the zinginess to the usual home-cooked meals. Plus, their service, presentation, and the portions are amazing! Just give their linguine with carbonara sauce and chicken, crab artichoke dip, everyone’s fav mac and cheese, or the creme brûlée a try, and believe the deliciousness for yourself. Be aware: you’ll want to stop eating, but won’t be able to!

Ddeb's- A Taste of Home

Address: 05 Old Dr, Chesapeake, VA 23322, USA

Website: Ddeb’s- A Taste of Home

Opening hours: Tue - Thu: 11am - 8pm; Fri - Sat: 11am - 9pm (closed on Sun & Mon)

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21. Gulp down punchy drinks at Riff House Pub

Source: Pexels

Bringing the best of music, madness, vibe, and potent drinks under one roof is Chesapeake’s Riff House Pub. What’s even better is that you don’t need to shell out a bomb for the drinks – their rates are quite throwaway! The pub alternatively hosts karaoke and DJ nights along with band performances and concerts. You can trust them to make it a fun-filled night for you, so remember to head there at least once.

Riff House Pub

Address: 2002 Bainbridge Blvd, Chesapeake, VA 23324, USA

Website: Riff House Pub

Opening hours: 11am - 2am (daily)

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22. Dance to the DJ's beats at Upscale Restaurant & Lounge

things to do in chesapeake va | dance to the dj's beats at upscale restaurant & lounge
Source: instagram

Looking to head out after the night is dark? Upscale Restaurant & Lounge is the place for you. Hosting some of the jazziest nights at a stunning location, this restaurant-cum-lounge is quite a hit with the customers. It is highly recommended that you either reach the place early or make prior reservations to catch hold of a good table, else it’s quite likely that you won’t get one or will have to wait obnoxiously long. Also, the place is quite particular about dress codes, so remember to bring your A-game on while dressing up.

Upscale Restaurant & Lounge

Address: 6505 College Park Square, Virginia Beach, VA 23464, USA

Website: Upscale Restaurant & Lounge

Opening hours: Thu - Fri: 7pm - 2am; Sat: 9pm - 2am (closed from Sun - Wed)

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23. Pamper yourself at Natural Elements Spa & Salon

If you’re done with everything else, dive in for some tender love and care at the Natural Elements Spa & Salon. Offering some of the best deals and services for massages, manicures, facials, and other salon services, the team at Natural Elements Spa & Salon is professionally trained and strive to provide the best treatments to customers. You can walk-in or book yourself an appointment.

Natural Elements Spa & Salon

Address: 717 Eden Way N #612, Chesapeake, VA 23320, USA

Website: Natural Elements Spa & Salon

Opening hours: Tue - Fri: 9am - 9pm; Sat: 9am - 8pm; Sun: 11am - 5pm (closed on Mon)

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24. Catch a movie at the Cinemark Chesapeake Square & XD

If nothing else, just sit back and enjoy watching a movie at the Cinemark Chesapeake Square & XD. The place is all about large movie screens, super comfortable seating, and delicious snacks at the snack bar, so you’re guaranteed to enjoy a satisfying movie-watching experience. Movie mine-up changes every week, so check out their website and book tickets to your favourite flick!

Cinemark Chesapeake Square & XD

Address: 2413 Chesapeake Square Ring Rd, Chesapeake, VA 23321, USA

Website: Cinemark Chesapeake Square & XD

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Small but loaded Chesapeake

By now, you’d have gauged that there’s quite a bit to do in this otherwise ‘small’ town – truly, there’s something for everyone here. Not only does the usual, more popular stuff about Chesapeake attract many thousands of tourists in-bound, but also its warm community. These things to do in Chesapeake, Virginia will definitely add the 'yay’ in your 'yaycation’, so hurry along and start planning.

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Priyanjali, a writer and traveler, identifies as a self-proclaimed aesthete dedicated to achieving fulfillment in her personal and professional life. Her skill lies in transforming intangible...Read more

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