Fall has arrived in Chesapeake — and Halloween fun is already creeping in! From pumpkin patches and fall festivals to spooky (but family-friendly) events, Chesapeake is packed with can’t-miss celebrations this season. Don’t let your family miss out — keep scrolling for the biggest list of Chesapeake fall and Halloween events happening in 2025!
Last updated: October 10, 2025
🍁 Family-Friendly Chesapeake Fall & Halloween Attractions Open All Season Long
These local farms, corn mazes, and haunted attractions are open multiple weeks during the season, offering the perfect blend of fall fun and Halloween thrills:
Mount Pleasant Farms Fall Festival
2201 Mount Pleasant Road, Chesapeake, VA 23322
Dates: Every Saturday and Sunday through October.
Corn maze Wagon rides U-pick pumpkins Barrel train rides Kids play area which includes the corn pit, hay maze, and petting zoo.
Stop by the Sip & Savor tent for some delicious crafted lemonade.
Tickets/wristbands are sold in the red barn behind the store.
Great Bridge Pumpkin Patch
125 Peaceful Road, Chesapeake VA 23322
Bounce houses and pumpkin patch. Terror Woods available for adults and older kids.
Hours: Monday - Saturday: 9am-8pm Sunday: 9am- 7pm
Pricing:
Pumpkins - pay per pound
Pumpkin Patch Playland - $20/child or $10 for kids under 2 years
Hayride - $4 per person
Playland Season Pass $100
Hickory Ridge Farm
Dates: Every day through the end of October
Pricing: Play area just $7.50….Adults free, 2 and under free!
Or hayride, barrel train and play area for $14.75!
Adult hayride $5.50
Pony rides daily 10-2 PM, 75 lb weight limit $8.50
Attractions: Bounce houses, Corn Pit, Children’s corn maze, Friendly farm animals to feed and pet, Giant hay climb, Sand piles, Play houses, Yard games, How tall this fall sign, Big swings, Picnic tables, Tire climb, Food vendors daily
Face Painter every weekend from 10-3
Bergey's Barnyard
Hours: Mon - Fri 9-6, Closed Sundays
Pricing:
October pricing
*Columbus Day, October 13th, will be Friday activities & pricing*
Monday - Thursday: $12
What's included? Cornmaze, petting zoo & pumpkin patch
Friday: 8 & up - $15
7& under - $10
What's included? Cornmaze, petting zoo, hayride, pumpkin patch & 1 shot on the corn gun
Saturday: 8 & up - $20
7 & under - $12
what's included? Cornmaze, petting zoo, hayride, pumpkin patch & 1 shot on the corn gun
*65 & over are free everyday and one and under are free everyday
Historic Greenbrier Farms Fall Festival
225 Sign Pine Rd, Chesapeake VA 23322
September 14 - October 30 9:00 am - 6:00 pm
Play Area – $8 (Ages 2+, Adults FREE)
• Bounce Houses & Yard Games
• Friendly Barnyard Animals (feed cups available)
• FREE Hayrides
• Sand Piles & Tire Climbs
• Pumpkin Patch Adventures
• Fall Photo Ops all around the farm
Weekend Parking $10
The Haunting happens Fridays & Saturdays 7-10PM
Tickets $20 per person, Parking $10 per car
Some of these events are weather-dependent. Always confirm details before heading out.
🎃 Chesapeake Halloween & Fall Fun Events
Please note: Many Chesapeake fall and Halloween events haven’t been announced yet. We will keep updating this guide as new details come in. Be sure to bookmark this page and check back often for the latest!
💡 Know about a family-friendly fall festival, Halloween event, or trunk-or-treat in Chesapeake that’s not listed? Submit your event here.
Saturday, Oct. 11
Sunday, Oct. 12
Saturday, Oct. 18
Sunday, Oct. 19
- Pumpkin Painting at the Town Square Play Cafe
- Trunk or Treat at the Garage Brewery
👻 Love this guide? Don’t ghost us! Subscribe now (it's FREE!) so you never miss the best Chesapeake family fun.
Thursday, Oct. 23
Friday, Oct. 24
- Pumpkin Barre
- Playgroup: Pumpkin Guts Sensory Bin
- Trick or Treat Through the Corn Maze
- Silly Spooky Kids Night Out
Saturday, Oct. 25
- Public Safety Trunk or Treat
- Sheriff Dave Rosado's Tricks and Treats
- Early Trick or Treating at Greenbrier Mall
- Fall Festival at Great Bridge Baptist Church
- Harvest Festival and Trunk or Treat
Sunday, Oct. 26
- Trunk or Treat at Big Ugly Brewing
- Trunk or Treat at Deep Creek United Methodist Church
- Great Bridge United Methodist Church Trunk or Treat
Monday, Oct. 27
Wednesday, Oct. 29
Thursday, Oct. 30
Friday, Oct. 31
- Playgroup Strides Trick or Treating FIT4MOM Southwest Chesapeake
- Fall Festival and Trunk or Treat at Rivercrest Christian Fellowship
👉 Check back often, as we’re adding more Halloween events and spooky fun happenings in Chesapeake all season long!
Know of a Halloween event in Chesapeake that should be listed? Submit it here.
We make every effort to ensure the accuracy of event information. However, we recommend checking with the venue to make sure an event is not changed or canceled.
Get a FREE kid-friendly calendar full of festivals, activities, and events in the Chesapeake, VA area delivered right to your inbox when you subscribe for free!
By signing up, I agree to receive emails from Macaroni KID. I also agree to the privacy statement and cookie policy.
