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Fall Fun Guide 2024

Your Guide to Family Fun this Fall in Chesapeake VA 2024

By Diana Ditty September 16, 2024

Find Your Family Fun this Fall in and around Chesapeake. All things fall will be listed below: pumpkin patches, hayrides, photo opportunities, and more. This list of family friendly fall events and activities will be updated often, so check back often!


Historic Greenbrier Farms Fall Festival
Free: Bounce Houses, Hayrides, Playground, Barnyard Animals, Yard Games
Paid: Pumpkin Patch, Kids Corn Maze, Pre-Picked Pumpkins, Sunflowers & Wildflowers, Festival Games, Face Painting, Fairy Hair
225 Sign Pine Rd, Chesapeake VA 23322
September 14 - October 30 9:00 am - 6:00 pm
Weekend Parking $10

Hickory Ridge Farm
Various Prices: Hayrides, Barrel Train, Farm Animals, You-pick Pumpkin Patch, Toddler Hay Maze, Bounce Houses, Food Trucks
2928 Battlefield Blvd S, Chesapeake VA 23322
September 14 through October 30  
Mon-Thurs 9AM-8PM, Fri 9AM-9PM Saturday 10AM-9PM, and Sunday 10-7

Great Bridge Pumpkin Patch
900 N Battlefield Blvd, Chesapeake VA 23320
Bounce houses and pumpkin patch
Pumpkin Patch Play Land: Sept- 17th thru Oct- 31th
Monday- Thursday:  9am-8pm  Friday- Saturday: 9am- 9pm, (9am- 7 pm on Sundays)

Mount Pleasant Farms Fall Festival
U-pick pumpkins, a corn maze, wagon rides, pony rides, barrel train rides, and a playground.
2201 Mount Pleasant Rd, Chesapeake VA 23322
Every Sat and Sun in October  10am - 6pm

Bergey's Barnyard
Corn maze, petting farm, pumpkin patch, kiddie mazes, corn gun and hayrides
Prices and availability of each attraction vary by day
September 14 - October 31



If you just love perusing the craft and vendor markets that pop up every fall, you will want to check this list for the scoop on fall fairs or festivals happening in Chesapeake!

Community Fall Festival at Rejuva Med Spa
September 20, 2024 from 2-6PM

Community Fall Festival at Atlantic Shores Christian School
September 21, 2024 from 10AM - 3PM

Grassfield High School PTSA Fall Craft Fair
September 28, 2024 from 9AM - 3PM

Friday Fall Farmers Market
Every Friday from October 4 through November 29 from 11AM-3PM

Fall Vendor Market at The Downtown Patty
October 4 from 10AM-4PM

Fall Festival at Great Bridge Church of Christ
October 5 from 4-6PM

Fall Fest at Jackson Memorial Baptist Church
October 5 from 12-3PM

River Walk Fall Craft Fair
October 12 from 9AM-2PM

Great Bridge High School PTSA Fall Craft Fair
October 12 from 9AM-3PM

MKL Produce Fall Festival
October 12 from 10AM-5PM

Portlock Primary and Carver Intermediate Fall Festival
October 18 from 5:30-730PM

CoVA Collective Realty 7th Annual Fall Fest
October 19 from 10Am-1PM

Kids' Pumpkin Decorating Party 
October 22 from 4-8PM

4th Annual Fall Farm Fair at Equestrian WISH
October 26 from 10:30AM-3PM


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