The Ultimate Guide to Festivals in Chesapeake

festivals in Chesapeake

Chesapeake, a vibrant city in Virginia, is a hub for an array of exciting festivals that cater to diverse interests. From seafood feasts to cultural celebrations, Chesapeake offers something for everyone throughout the year. Whether you’re a foodie, a wine enthusiast, or an outdoor adventurer, you’ll find a festival that suits your taste in this charming city.

Key Takeaways

  • Chesapeake hosts a variety of festivals throughout the year, catering to different interests and age groups.
  • The Chesapeake Jubilee is a family-friendly event featuring music, entertainment, food, and amusement rides.
  • Seafood lovers should not miss the Blue Crab Festival and The Taste of Chesapeake, both offering a plethora of seafood delicacies.
  • Wine enthusiasts can enjoy tastings and local food pairings at the Chesapeake VA Wine Festival.
  • Outdoor enthusiasts can participate in kayaking tours and nature exploration during KayaXpedition.

Chesapeake Jubilee: A Family Extravaganza

family enjoying a festival in Chesapeake

The Chesapeake Jubilee is back for 2024 and promises to be a family extravaganza like no other. Held from May 14-17 at Chesapeake City Park, this event is packed with music, food, and plenty of amusement park rides for kids of all ages.

The Blue Crab Festival: A Seafood Lover’s Dream

seafood festival in Chesapeake

The Blue Crab Festival is a seafood lover’s dream come true. Held annually, this festival celebrates the rich maritime traditions and seafood cuisine of Chesapeake. It’s a perfect family outing where you can indulge in fresh, local seafood while enjoying scenic views and live entertainment.

Chesapeake VA Wine Festival: Sip and Savor

wine festival in Chesapeake VA

Wine enthusiasts gather each October at the Chesapeake Virginia Wine Festival. Here, you can sip your way from cabernets to zinfandels, trying bites of delicious local treats as you drift from tent to tent.

Chesapeake Restaurant Week: A Culinary Adventure

festive food celebration in Chesapeake

Chesapeake Restaurant Week is the perfect opportunity to explore the city’s vibrant culinary scene. Prix fixe menus are the ideal way to experience all the sweet, savory, and totally satisfying options that Chesapeake has to offer. This yearly week-long celebration of all things edible is a must-visit for any food enthusiast.

Virginia Arts Festival: A Cultural Celebration

cultural festival in Chesapeake Virginia

The Virginia Arts Festival is a vibrant celebration of the state’s rich cultural diversity. This annual event brings together artists and performers from various backgrounds, offering a unique opportunity for cultural exchange and appreciation. It’s a must-visit for anyone looking to immerse themselves in the arts.

Performing Arts

From ballet to contemporary dance, the festival showcases a wide range of performing arts. One of the highlights is the Divine Nine/HBCU Night with Dance Theater of Harlem, which provides a unique opportunity for Virginia Arts Festival attendees to experience the rich traditions of historically black colleges and universities.

Visual Arts

The festival also features stunning visual arts exhibitions. Visitors can explore galleries filled with works from local and international artists. These exhibitions offer a glimpse into the diverse artistic expressions that make up Virginia’s cultural landscape.

Workshops and Classes

For those looking to get hands-on, the festival offers a variety of workshops and classes. These sessions are perfect for both beginners and experienced artists looking to hone their skills. Whether you’re interested in painting, sculpture, or dance, there’s something for everyone.

KayaXpedition: Paddle Your Way to Fun

festival at a waterfront with kayaks and people enjoying water activities

KayaXpedition is one of the most exciting family-friendly activities in Chesapeake, offering a unique way to explore the area’s beautiful waterways. Whether you’re a seasoned paddler or a beginner, there’s something for everyone to enjoy.

Kayaking Tours

Experience the thrill of kayaking through Chesapeake’s scenic routes. The tours are designed to cater to all skill levels, ensuring that everyone has a memorable time on the water. Don’t miss the chance to paddle through the historic Dismal Swamp Canal, a favorite among locals and visitors alike.

Family Activities

KayaXpedition isn’t just about kayaking; it’s a full-day adventure packed with fun for the whole family. From interactive games to educational sessions about local wildlife, there’s plenty to keep everyone entertained. Be sure to check out the Paddle for the Border event, which is a highlight of the festival.

Nature Exploration

Immerse yourself in the natural beauty of Chesapeake as you paddle your way through its waterways. The event offers a unique opportunity to observe local flora and fauna up close. Don’t forget to bring your camera to capture the stunning landscapes and wildlife sightings.

Bergey’s Corn Maze: Fall Fun for Everyone

fall festival at a corn maze in Chesapeake

Bergey’s Corn Maze is the perfect destination for a fun-filled fall day with family and friends. For just over a month each fall, visitors can wind their way through the fields of maize, enjoying the crisp autumn air and beautiful scenery. It’s an experience that captures the essence of the season.

Chesapeake’s Christmas Bird Count: A Holiday Tradition

festive holiday birdwatching in Chesapeake

Bird Watching Tips

Held annually by the National Audubon Society, Chesapeake’s Christmas Bird Count is the ideal way to see some of the over 200 species of birds flying south for the winter. Bring binoculars and a field guide to help identify the various species. Dress warmly and wear comfortable shoes for a day of birding.

Community Involvement

This event is not just for bird enthusiasts; it’s a community affair. Volunteers of all ages are welcome to participate. The data collected helps in the conservation efforts and provides valuable insights into bird populations.

Holiday Spirit

The Christmas Bird Count is a festive way to enjoy the holiday season while contributing to a good cause. Participants often share hot cocoa and holiday treats, making it a joyous occasion for everyone involved.

The Taste of Chesapeake: A Seafood Extravaganza

seafood festival in Chesapeake

The Taste of Chesapeake is a family-friendly seafood festival with a hometown feel, set in Historic Chesapeake City. Hosted in partnership with the Chesapeake City Volunteer Fire Department, this event is a must-visit for seafood lovers. You’ll get your fill of Maryland seafood, sip local beers and wines, and take home a souvenir.

OysterFest at Chesapeake Bay Maritime Museum

oyster festival at Chesapeake Bay with maritime museum in the background

The OysterFest at the Chesapeake Bay Maritime Museum is a celebration of the Chesapeake Bay’s most renowned delicacy, the oyster. Visitors can indulge in raw, grilled, or fried oysters while enjoying the waterfront view. This annual festival features oysters served a variety of ways, along with other local fare, craft beer, and spirits, plus live music on two stages.

Oyster Shucking Contest

The festival’s oyster shucking contest is extremely competitive, with the audience given the chore of eating all the oysters as they are opened by the contestants. It’s a fun and engaging event that showcases the skill and speed of the shuckers.

Local Craft Beers

Pair your oyster dishes with local Virginia wine tastings, or head to the micro-brewery garden for some local craft beers. The selection is vast, ensuring there’s something for every palate.

Waterfront Views

Held at the Chesapeake Bay Maritime Museum, take a break from the festivities to explore the exhibits or take a boat ride. The scenic waterfront views provide a perfect backdrop for this delightful festival.

The Great American Food Fest: October Feast

food festival in Chesapeake during autumn

Succulent Ribs

Prepare your taste buds for a mouth-watering experience with the most succulent ribs you’ll ever taste. These ribs are slow-cooked to perfection, ensuring that every bite is tender and flavorful. The festival’s rib contest is one of the highlights, where local chefs compete to showcase their best recipes.

Classic Clam Chowder

Dive into a bowl of classic clam chowder that will warm your soul. This creamy, hearty dish is a staple at the festival, made with fresh clams and a blend of spices that create a symphony of flavors. Don’t miss the chowder cook-off, where you can sample different versions and vote for your favorite.

Live Entertainment

Enjoy a day filled with live entertainment that adds to the festive atmosphere. From local bands playing your favorite tunes to exciting food festival pageants and contests, there’s something for everyone. The entertainment schedule is packed with performances that will keep you engaged and entertained throughout the day.

The Great American Food Fest is not just about food; it’s a celebration of community spirit and culinary excellence. Join us for a day of fun, food, and festivities!


Chesapeake is a vibrant region brimming with a diverse array of festivals that cater to all tastes and interests. Whether you’re a foodie eager to indulge in the Chesapeake VA Wine Festival or a seafood lover looking forward to the Maryland Seafood Festival, there’s something for everyone. Don’t miss out on the unique experiences offered by events like the Chesapeake Jubilee or the OysterFest at the Chesapeake Bay Maritime Museum. With so many exciting activities, delicious food, and rich cultural experiences, Chesapeake’s festivals are a must-visit. So mark your calendars, gather your friends and family, and get ready to create unforgettable memories in Chesapeake!

Frequently Asked Questions

When is the Chesapeake Jubilee held?

The Chesapeake Jubilee is usually held in mid-May at Chesapeake City Park.

What can I expect at the Blue Crab Festival?

At the Blue Crab Festival, you can enjoy all-you-can-eat steamed crabs, BBQ pork, and a variety of beverages.

What activities are available at the Chesapeake VA Wine Festival?

The Chesapeake VA Wine Festival features wine tastings, local food pairings, and live music.

Which restaurants participate in Chesapeake Restaurant Week?

Top restaurants in Chesapeake participate in Restaurant Week, offering a wide variety of diverse cuisines and special deals.

What types of arts are showcased at the Virginia Arts Festival?

The Virginia Arts Festival showcases performing arts, visual arts, and offers workshops and classes.

What can families do at KayaXpedition?

Families can enjoy kayaking tours, family activities, and nature exploration at KayaXpedition.

What attractions are available at Bergey’s Corn Maze?

Bergey’s Corn Maze offers maze activities, a pumpkin patch, and family games.

How can I participate in Chesapeake’s Christmas Bird Count?

You can participate in Chesapeake’s Christmas Bird Count by joining community groups, following bird-watching tips, and embracing the holiday spirit.

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