Unearth the dark delights hidden in every nook and cranny of Chesapeake with our all-inclusive Halloween guide, your passport to a night of unforgettable frights and supernatural wonders. Our Halloween handbook decodes Chesapeake's cryptic crosswords for longtime puzzle masters and word-loving werewolves.
Popular Events: Experience the spine-chilling thrills of the Haunted Hunt Club Farm, where eerie attractions and ghostly tales await. Venture into the Chesapeake Halloween Bar Crawl, featuring a variety of themed bars and festive drink specials that will keep the spirits high. And the Great Bridge Pumpkin Patch is something you definitely don't want to miss, offering family-friendly activities like hayrides and pumpkin picking. See more details on these and other fun events and activities below!
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Top Halloween Events In and Around Chesapeake
- Haunted Hunt Club Farm (Virginia Beach)
- Great Bridge Pumpkin Patch
- Chesapeake Halloween Bar Crawl
- Chesapeake Wine Festival
- Monster Fest 20
- Annual Chincoteague Island Oyster Festival (Chincoteague Island)
- Graves’ Mountain Apple Harvest Festival (Syria)
- Fall-O-Ween Festival (Newport News)
- Virginia Wine & Garlic Festival (Amherst)
- Suffolk Peanut Festival (Suffolk)
See these and even more events listed below!
Chesapeake Area Haunted Experiences
Haunted Hunt Club Farm
What to Expect:
A comprehensive scream park featuring various terrifying attractions and live entertainment.
Description:
Haunted Hunt Club Farm offers a thrilling Halloween experience with terrifying haunts, live entertainment, midway concessions, and vendors. Visitors can enjoy unlimited times through all featured haunts, including a haunted hayride, death alley cemetery walk, forbidden fields haunted cornfield maze, and a village of the dead. The event promises spine-tingling terrors and unforgettable nights with its all-new Scream Team and Extreme Halloween features.
Where: Virginia Beach | More Info: Haunted Hunt Club Farm
Family-Friendly Fall Activities Near Chesapeake
Great Bridge Pumpkin Patch
What to Expect:
A combination of traditional fall activities and a thrilling Terror Woods experience.
Description:
The Great Bridge Pumpkin Patch in Chesapeake, VA, offers a variety of family-friendly activities including a pumpkin patch, inflatables, hayrides, and Terror Woods for a spooky experience. Visitors can enjoy the festive atmosphere with pumpkins, mums, and other fall decorations.
Where: Chesapeake | More Info: Great Bridge Pumpkin Patch
Chesapeake Wine Festival
What to Expect:
A charity-driven wine festival featuring over 20 Virginia wineries and live entertainment.
Description:
The Chesapeake Virginia Wine Festival is a 14th annual event celebrating wine and charity. Held on October 12, 2024, at Chesapeake City Park, it features unlimited tastings from over 20 premier Virginia wineries and an extensive selection at the International Wine Village. The festival includes live entertainment, a Craft Beer Garden, and specialty food vendors. Proceeds benefit local community charities, including the Chesapeake Regional Mammogram 3D mobile van and the Boys & Girls Clubs of Hampton Roads.
Where: Chesapeake | More Info: Chesapeake Wine Festival
Graves’ Mountain Apple Harvest Festival
What to Expect:
A comprehensive farm experience with live music, farm activities, and local food vendors.
Description:
The Graves Mountain Apple Harvest Festival is a 55-year-old celebration honoring Blue Ridge farmers and their harvest offerings. The event takes place over three weekends in October, featuring live bluegrass music, a petting zoo, hayrides, horseback trail rides, and a variety of festival foods including apple pies, apple butter donuts, and fresh apple cider. Visitors can also explore the farmyard with goats, chickens, rabbits, pigs, cows, and sheep, and enjoy activities like pick-your-own apples and UTV tours.
Where: Syria | More Info: Graves’ Mountain Apple Harvest Festival
Annual Chincoteague Island Oyster Festival
What to Expect:
The festival offers a unique blend of local seafood and live entertainment, making it a must-visit event for seafood lovers.
Description:
The 51st Annual Chincoteague Oyster Festival is a celebration of the local seafood industry, marking the beginning of oyster season. Enjoy a variety of seafood dishes, including raw, steamed, and fried oysters, as well as clam fritters, clam chowder, shrimp cocktail, and more. The event features live music by "Island Boy" and an Extravaganza Raffle with exciting prizes.
Where: Chincoteague Island | More Info: Annual Chincoteague Island Oyster Festival
Suffolk Peanut Festival
What to Expect:
The event's unique feature is its comprehensive celebration of Suffolk's agricultural roots and community spirit through diverse activities and entertainment.
Description:
The 46th Annual Suffolk Peanut Fest is a family-friendly event celebrating Suffolk's roots and agricultural heritage. It features concerts, amusement rides, contests, a demolition derby, peanut cup race, motorcycle rally, fireworks, and more. The festival includes live music by Easton Corbin, the World’s Only Peanut Butter Sculpting Competition, and various activities like pony rides, petting zoo, and cornhole tournament.
Where: Suffolk | More Info: Suffolk Peanut Festival
Virginia Wine & Garlic Festival
What to Expect:
The festival offers a unique blend of wine tastings, live music, and family-friendly activities in a festive agricultural setting.
Description:
The Virginia Wine & Garlic Festival is a fun-filled weekend event at Rebec Vineyards. It features live bands on four stages, wine tastings by local guest wineries, over 150 arts, crafts, and garlicky foods, and activities like a bounce house, KidZone Fun Station, face painting, balloon artists, and magic shows. The festival is family-friendly and offers a variety of entertainment for all ages.
Where: Amherst | More Info: Virginia Wine & Garlic Festival
Fall-O-Ween Festival
What to Expect:
A variety of Halloween-themed activities and attractions in a family-friendly setting.
Description:
The Fall-O-Ween Festival at Newport News Park is a two-day, family-friendly event that offers a variety of spooky and fun activities. Enjoy traditional marketplace crafters and exhibitors, Halloween-themed vendors, wagon rides, live pumpkin carvers, ax throwing, a corn maze, eerie escape rooms, fortune tellers, a huge pumpkin patch, and a mechanical pumpkin ride. The festival also features live stage entertainment, seasonal beer gardens, costumed characters, photo ops, and kid’s activities.
Where: Newport News | More Info: Fall-O-Ween Festival
Apple Dumpling Festival
What to Expect:
The festival offers a variety of activities, including music, crafts, and delicious apple dumplings, all set against the scenic backdrop of downtown Stuart and the Mayo River Rail Trail.
Description:
The Apple Dumpling Festival in downtown Stuart, Virginia, is a delightful fall celebration. On October 19, 2024, from 10:00 AM to 4:00 PM, the festival will feature music, crafts, games, and delicious apple dumplings. The event will also include activities along the Mayo River Rail Trail, making it a perfect day for families and food enthusiasts alike. The vibrant atmosphere and community spirit make this festival a must-attend event in the Blue Ridge region.
Where: Stuart | More Info: Apple Dumpling Festival
Escape Room Virginia Beach
What to Expect:
Thrilling escape rooms with a variety of game themes designed for immersive entertainment.
Description:
Experience immersive entertainment with friends and family at Breakout Games in Virginia Beach. Each escape room offers unique challenges and thrilling adventures, perfect for birthday parties, team-building, or a couples night out. Explore an island, find the kidnapper, restore ancient relics, and more.
Where: Virginia Beach | More Info: Escape Room Virginia Beach
Shockley Farms Corn Maze and Pumpkin Patch
What to Expect:
The event features a variety of seasonal produce and a corn maze suitable for kids.
Description:
Shockley Farms Corn Maze and Pumpkin Patch in Cape Charles, VA, offers a festive fall experience with a corn maze, pumpkin patch, and a variety of seasonal produce like pumpkins, gourds, eggplant, squash, and tomatoes. The attraction is open throughout the entire fall season, providing a fun and family-friendly environment for visitors.
Where: Cape Charles | More Info: Shockley Farms Corn Maze and Pumpkin Patch
Belmont Pumpkin Farm
What to Expect:
Offers a variety of fall activities including pumpkin picking, hayrides, and farm food.
Description:
Belmont Pumpkin Farm is a family-friendly destination celebrating 40 years of fall fun. The farm is open weekends starting September 21, offering activities like hayrides, pumpkin picking, treasure hunts, and scarecrow-making. Visitors can explore the corn maze and sunflower trail while enjoying farm-smoked pulled pork BBQ, street tacos, and pumpkin desserts. The farm also hosts wreath-making workshops and other fun activities, making it a perfect spot for a family outing.
Where: North | More Info: Belmont Pumpkin Farm
Pumpkinville Pumpkin Patch
What to Expect:
Offers a variety of free activities including a hayride and cornfield maze.
Description:
Pumpkinville Pumpkin Patch in Toano, VA, is a fun and seasonal treasure owned by a small family farm in nearby Barhamsville. Visitors can pick their own pumpkins from the patch and choose from a large selection of yard decorations. The patch offers various free activities like a hayride, cornfield maze, bean bag toss, and ring toss, making it enjoyable for both children and adults. It is also a great place to get all your Halloween goodies, including pumpkins, gourds, winter squash, flowers, wooden cut-outs, arts and crafts, and fall decorations.
Where: Toano | More Info: Pumpkinville Pumpkin Patch
Halloween Food, Drink, and Parties Near Chesapeake
Chesapeake Halloween Bar Crawl
What to Expect:
A journey through the city's spookiest bars with exclusive privileges to low drink and food specials.
Description:
Join Chesapeake for a spooktacular Halloween Bar Crawl on October 26, 2024. This event promises an evening of supernatural excitement as you explore the city's spookiest bars. Enjoy generously low drink specials, holiday-themed drinks, and select food specials. The crawl includes free entry into the best bars, a free after-party, and a detailed custom digital pub crawl map. Don't miss the social media costume contest and live music and DJs at certain venues.