Top Things to Do Near Chesapeake, Virginia

Chesapeake, Virginia, is a delightful vacation destination that offers a blend of natural beauty and rich history. Whether you’re planning a quick getaway or a longer trip, this city has something for everyone. One of my favorite things to do here is paddle along the tranquil rivers, soaking in the peaceful scenery—it’s the perfect escape from the hustle and bustle. If you prefer land-based fun, explore the top picks for shopping or dive into local events and attractions, each adding its own charm to this vibrant place.

Top Things to Do Near Chesapeake, Virginia

Family Fun for All Ages

Chesapeake is packed with activities that families will love. At Chesapeake City Park, kids can burn energy at the skate park and playground, play basketball or volleyball, and explore scenic trails. When weather doesn’t cooperate, head indoors for bowling at Bowlero Western Branch or get creative with pottery painting at GLäZENFYRE. The Charles H. Taylor Visual Arts Center offers wonderful art exhibitions that inspire young minds.

Step Back in Time

History buffs will appreciate Chesapeake’s long history dating back to European settlement. The African American Heritage Trail offers a powerful self-guided driving tour through important sites. Don’t miss the Great Bridge Battlefield and Waterways Museum, which brings to life the pivotal Battle of Great Bridge during the Revolutionary War.

Shop ‘Til You Drop

From big-name stores at Greenbrier Mall to unique finds at 3 Little Black Birds (think vintage treasures and handcrafted items), Chesapeake is a shopping destination for all tastes. Aimaleigh’s Boutique offers stylish clothing and perfect gifts for everyone on your list.

Indoor Adventures

When you need AC relief, Chesapeake delivers great indoor fun. Let kids run wild at FunVille Indoor Playground or lace up skates at Chilled Ponds Ice Sports Complex. The whole family can get crafty at GLäZENFYRE or enjoy friendly competition at Bowlero Western Branch.

Nature’s Playground

Chesapeake’s parks and nature spots offer endless recreation. Walk the scenic trails at Oak Grove Lake Park, go bird watching at Great Dismal Swamp National Wildlife Refuge, or try fishing at Elizabeth River Park. The Chesapeake Arboretum showcases beautiful tree species and historic Caleb Williamson Farm House.

Year-Round Events

No matter when you visit, exciting events await. Summer brings the Chesapeake Jubilee with fireworks, rides, and shrimp feast. Foodies love Restaurant Week for culinary delights, while the Holiday Craft Show kicks off seasonal shopping with handmade gifts. Don’t miss the magical Pugh Family Christmas Light Show!

Delicious Dining

Seafood lovers rejoice at Pirate’s Cove Restaurant and Black Pelican Seafood Company, both known for fresh catches and great atmosphere. For something different, try Cutlass Grille’s Jamaican flavors or The Butcher’s Son for premium organic steak. Local breweries like Studly Brewing (baseball-themed!) and Big Ugly Brewing (with food trucks) offer craft sips and fun trivia nights.

Easy Day Trips

Expand your adventure with quick trips to:

• Virginia Beach: Famous oceanfront beaches and Virginia Aquarium
• Norfolk: Explore the Virginia Zoo and massive USS Wisconsin BB-64
• Hampton: Discover aviation history at Virginia Air and Space Science Center

Insider Tips

• Beat traffic by visiting attractions early
• Wear comfortable shoes for exploring
• Check weather conditions before outdoor plans
• Try the amazing local seafood
• Ask the visitor center about lesser-known gems
• Stay hydrated during outdoor adventures