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Holiday Fun in Chesapeake: Your 2025 Family Guide

Santa sightings, craft fairs, seasonal attractions, and more!

By Diana Ditty December 4, 2025

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!


Tim Mossholder | Canva

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!


 Raven GS | Canva

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

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.


Jill Wellington | Canva

More Holiday and Winter Fun in Chesapeake

There’s so much happening this winter! Explore even more ways to make the season special:

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!

Never miss local events, giveaways, or guides — subscribe to Macaroni KID Chesapeake (it’s free!).

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