Your Ultimate Eastern Shore Winter Guide ❄️💙
Winter on the Eastern Shore is filled with twinkling lights, festive events, Santa sightings, cozy moments, and family fun. To make your planning easier (and save you from endless scrolling!), this Ultimate Winter Guide collects all of the season’s best resources in one place.
Use this page as your personal index to quickly jump to whatever you’re looking for—free activities, tree lightings, Santa events, and more. Bookmark it so you can check back as new events are added! ⭐
🍂 Quick Navigation
Free Winter Fun Guide
Budget-friendly fun all season long! Outdoor activities, library programs, festivals, and more—no admission required.
➡️ View the Complete 2025 Free Winter Fun Guide
Tree Lightings and Holiday Happenings Guide
Every tree lighting, parade, holiday market, concert, and festive celebration happening across the region.
➡️ View the Tree Lighting and Holiday Happenings Guide
Local Santa Sightings Guide
Want to meet Santa? Here’s the full list of Santa photo ops, breakfasts, and appearances.
➡️ See the 2025 Eastern Shore Santa Sightings Guide
Pin & Share This Guide so other local parents can join the fun! #shorekidsadventures
❄️ Let the Winter Magic Begin!
Discover all the best local winter fun in one spot—events, Santa sightings, tree lightings, and more to brighten your season.
Our Indoor Activities and Play Places Guide is Here!
Find playful indoor spaces such as hands-on play gyms, family-friendly movie theaters, bowling alleys, indoor pools, escape rooms, cozy bookstores, fitness gyms, gaming stores, candy and ice cream shops, art galleries, local museums, and more!
