Discover Entertainment and Recreation in Chesapeake

Every day promises a new adventure

Ready to join us in celebrating the rich, lively spirit of Chesapeake? Prepare to be delighted by the plethora of activities and spots that make our city truly special. Enjoy the annual excitement of the Chesapeake Wine Fest, Chesapeake Jubilee, and a handful of family friendly foodie events around the city.

Delve into the vibrant local culture, enjoy our array of sports and recreation options, and download a free visitor’s guide to start planning your Chesapeake adventures today.

Savor the Flavors of Chesapeake: A Culinary Journey

Chesapeake’s dining scene is a vibrant celebration of flavors, offering everything from fresh-caught seafood and decadent desserts to hearty breakfasts and upscale dinners. Mark your calendars and join us for Chesapeake Restaurant Week, where locals and visitors can savor exclusive prix fixe menus starting at $15, showcasing the city’s culinary excellence. Year-round, Chesapeake delivers memorable dining experiences with options like fluffy pancakes at cozy breakfast spots, sushi and scallops for lunch or dinner, and deep-dish pizzas or authentic Italian pasta dishes for any occasion. Don’t forget to explore local bars and tasting rooms, where craft beers, fine wines, and signature cocktails perfectly complement your meal. Whether you’re exploring top-rated restaurants in Chesapeake, Virginia, enjoying family-friendly dining, or discovering hidden gems, the city offers unforgettable culinary experiences year-round that showcase the city’s rich food culture and fresh, locally-sourced ingredients.

Want to apply for Chesapeake Restaurant Week? Reach out to Valencia Moore, Sales Manager, Parks Rec and Tourism at valenciamoore@cityofchesapeake.net.

From Farm Fresh to Your Plate

Our city’s commitment to freshness and local produce is echoed beyond the beloved Bergey’s. Places like Cutlass Grille offer a taste of the Caribbean with their authentically smoked meats and vibrant sides. The Butcher’s Son takes this a step further, merging a classic steakhouse vibe with a dedication to ethically sourced and hormone-free meats, demonstrating Chesapeake’s culinary standards and commitments. The Hive Farm Bar and Grill takes the farm-to-table experience to a new level where you can dine at the Historic Greenbrier Farms.

A Melting Pot of Flavors

Chesapeake’s dining scene is a global village on a plate. From the rustic charm and Italian delights of Ynot Italian to the spicy and savory essence of Mexican cuisine at El Puente Mexican Grill, there’s a world of tastes to explore. For those who cherish the bounty of the sea, Wicker’s Crab Pot Seafood offers a dive into local seafood traditions with their family recipes that have been passed down through four generations of Chesapeake Bay watermen.

Scenic Meals and Memorable Moments

Many dining destinations in Chesapeake not only serve delectable dishes but also provide scenic backdrops that make every meal special. Imagine dining al fresco with the natural beauty of Chesapeake as your setting, from waterfront views that capture the heart at Amber Lantern to the cozy, picturesque settings at The Egg Bistro, where brunch turns into a scenic affair.

The Butcher's Son Chop House

Wasserhund

Wicker's Crab Pot Seafood

Union Taco

The Hive Farm Bar and Grill

Cutlass Grille

YNot Italian

Surf Rider Restaurants

Cork & Bull Chophouse

El Puente Mexican Grill

Amber Lantern

Chesapeake Pizza

Festivals & Events: Experience Chesapeake’s Vibrant Community Spirit

Chesapeake celebrates diversity and community through a myriad of vibrant festivals and events throughout the year. Each event not only showcases the unique charm and spirit of Chesapeake but also brings together locals and visitors in celebration and enjoyment. Here’s a closer look at some of the standout events that define the cultural landscape of this dynamic city.

Chesapeake Jubilee

One of the most anticipated events in the city, the Chesapeake Jubilee makes the spring sparkle with exhilaration. Hosted annually at the Chesapeake City Park, this four-day festival each Spring encapsulates the essence of community celebration with stunning fireworks, family entertainment, a BBQ cook-off, and live music performances. The Chesapeake Jubilee is a perfect reflection of the city’s warmth and vibrancy, attracting thousands each year to partake in the festivities.

Chesapeake Wine Festival

Experience the elegance of fine wines at the Chesapeake Wine Festival. This sophisticated event features unlimited tastings from Virginia’s premier wineries, accompanied by delightful entertainment. Whether you are a connoisseur or a casual enthusiast, the Chesapeake Wine Festival offers a refined gathering to sip, savor, and enjoy the company of fellow wine lovers.

KayaXpedition

Dive into adventure at Chesapeake’s KayaXpedition each June at Oak Grove Lake Park! A paradise for kayakers, canoeists, and SUP fans, this event offers equipment rentals, tranquil waters perfect for all skill levels, and a side of music and food truck fare. Celebrate summer by exploring our beautiful waterways and enjoying all the outdoor fun Chesapeake has to offer!

Chesapeake Rotary Christmas Parade

A staple of Chesapeake’s holiday season, the Chesapeake Rotary Christmas Parade brings festive cheer to the streets. Organized by the Chesapeake Rotary Club, this event features beautifully decorated floats, marching bands, and an appearance from Santa Claus himself. It’s a delightful event that unites the community in the spirit of the holiday season.

Explore More Chesapeake Events

Sports & Recreation: Unleash Your Adventurous Spirit in Chesapeake

Chesapeake, Virginia, is a playground for sports enthusiasts and outdoor adventurers. With eight sprawling outdoor recreation parks, numerous baseball and soccer fields, and an impressive network of more than 22 miles of navigable waterways, the city is a haven for anyone looking to engage in athletics or simply enjoy the great outdoors. Whether on land or water, Chesapeake delivers an unmatched array of recreational opportunities that cater to all ages and interests.

Natural Sanctuaries & Recreational Parks

Chesapeake’s bounty of outdoor spaces serves as a prime setting for walks, bike rides, climbs, and paddles. Discover an abundant array of flora and fauna along the Dismal Swamp Canal or spot various bird species on the Virginia Birding and Wildlife Trail South Chesapeake Loop. For a curated nature experience, the Chesapeake Arboretum’s Camellia Cove invites peaceful exploration. Craving active outdoor adventures? Cycle the Dismal Swamp Canal Trail, engage in a tennis match at Greenbrier Sports Park, or let the kids loose in the expansive Fun Forest at Chesapeake City Park.

Sports Fields Galore

For those who relish team sports, Chesapeake’s well-maintained baseball and soccer fields are a dream come true. Chesapeake’s numerous sports facilities host a variety of youth and adult leagues, tournaments, and casual games throughout the year. They serve as a community hub, fostering camaraderie and healthy competition among residents and visitors alike. And for golfers, both the Battlefield Golf Club and the Chesapeake Golf Club have 18-hole courses with plenty of challenges for newbies and more experienced players.

Waterways Well Worth Exploring

Chesapeake’s waterways offer more than just breathtaking views; they are a haven for a diverse range of water activities including kayaking, canoeing, and stand-up paddleboarding. Whether you’re an experienced paddler or a beginner, the tranquil rivers and canals of Chesapeake provide a serene escape from everyday stress. For those enthusiastic about fishing, Chesapeake’s waterways offer abundant opportunities. Anglers can enjoy both freshwater and saltwater fishing across various locations. The city boasts kayak fishing adventures, urban trout fishing, and easy access to pier fishing spots, ensuring a comprehensive fishing experience whether you are casting from the shore or navigating the waters by boat. Adventure seekers and nature lovers alike will find Chesapeake’s waterways a perfect blend of recreational activities and natural beauty, tailor-made for creating memorable experiences on the water.

Request A Visitor’s Guide

Ready to embark on an unforgettable adventure in the diverse city of Chesapeake, VA, nestled in the vibrant heart of Coastal Virginia. Overflowing with activities, our visitor’s guide is your essential companion to explore everything from sunny family outings to delightful indoor attractions.