The holiday season in Chesapeake is pure magic — twinkling lights, cozy cocoa, and family traditions that make memories to last all year. Macaroni KID Chesapeake is your go-to guide for everything merry and bright — from festive events and dazzling light displays to Santa visits and local holiday fun. Explore our list below and make this a season your family will never forget.
Bookmark this guide and check back often — we’ll keep adding new events and activities all season long!
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Must-See Holiday Attractions in Chesapeake
Discover the best holiday attractions and light displays that make Chesapeake shine this season. See the full list and map of the most festive 2025 light displays in Chesapeake.
Woodland Christmas Wonderland
📍 Location: 4028 Woodland Dr, Chesapeake, VA 23321
🎁 What Makes It Special: Known as the biggest and best Christmas light display in all of Hampton Roads, according to Christmas in Hampton Roads. This walk-through holiday light display is must-go!
Join their Facebook Group: https://www.facebook.com/groups/113087258864373
Fa La La Land
📍 Location: 306 Cedar Rd, Chesapeake, VA 23322
🕒 Hours: December 13 & 20 from 4-8PM
💵 Cost: FREE
🎁 What Makes It Special: This annual outdoor event at Chesapeake City Hall features Christmas lights and so much more: live performances, roaming holiday characters, food trucks and Santa!
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Upcoming Holiday Events and Santa Visits in Chesapeake
Looking for parades, tree lightings, Santa photo ops, and holiday markets? We’ve got you covered! These family-friendly holiday events in Chesapeake are the perfect way to celebrate the season.
Christmas Parades
- Chick-fil-A Christmas Parade at Chesapeake Square December 6
- 2025 Chesapeake Rotary Christmas Parade December 6
Santa Sightings
We do our best to verify event details, but always double-check before heading out as organizers may change plans without notifying us.
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More Holiday and Winter Fun in Chesapeake
There’s so much happening this winter! Explore even more ways to make the season special:
- Enter the Hampton Roads 12 Days of Christmas Giveaways
- Free Personalized Santa Letter
- Hampton Roads Local Holiday Gift Guide
- Best Holiday Light Displays Near Chesapeake
- Where to Donate or Volunteer This Holiday Season
Share the Holiday Spirit
Hosting a family-friendly holiday event in Chesapeake? Submit it to our calendar so we can share it with local families!
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