Holly Jolly Light Trail 2025 is Southern Maryland’s biggest and brightest holiday lights tradition—bringing families, neighborhoods, and communities together for a magical seasonal celebration. Hosted by The Southside Group Real Estate, this community event invites participants to decorate their homes and yards for all to enjoy, while visitors drive the official Light Trail Route to vote for their favorite stops. It’s holiday magic, local pride, and community spirit—all wrapped up in one glowing package.
Mark your calendars — the Holly Jolly season is almost here! ✨
⬇️ Click the register button to join this year’s Holly Jolly Light Trail. ⬇️
Keeping your lights on each night through December 30, weather permitting, and spreading holiday cheer across Southern Maryland all season long.
Register your home to be featured on the Holly Jolly Light Trail 2025 map and sign up to be part of the Trail between November 26 – December 7, 2025.
Go all out! Lights, inflatables, music — let your creativity sparkle and make your home one of the brightest on the map.
Send in your best shots by December 12, 2025 to be featured on the official Trail Map and social media.
Starting December 14, the public can tour the Trail and join our Facebook Live Tour Guide Adventures as we visit some of the most festive homes across Southern Maryland!
💡 Don’t forget to cast your votes for your favorite displays before December 28!
On December 30, the community’s top picks will be announced and crowned in multiple categories!
📍 The official 2025 Trail Map and Route will be announced soon!
Families across Southern Maryland enjoy the Holly Jolly Light Trail 2025 each year. Get ready to join the fun — share the excitement with your neighbors and encourage them to participate so we can light up even more homes across the region!
🎅 Tune In & Get Cozy
Grab your cocoa, favorite blanket, and settle in as we take you along the Trail live on Facebook!
💡 Join the Fun in Real Time
Comment during the live streams, cheer on your favorite displays, and share the holiday spirit with others watching! Explore every stop along the Holly Jolly Light Trail 2025.
📸 Be Part of the Magic
Snap a pic or screenshot your favorite stops and tag/mention us on social media: Southern Maryland Holly Jolly Light Trail—you might get featured!
🎁 Don’t Miss a Stop
Follow our Facebook page to stay updated on Live Tour times, featured neighborhoods, and surprise giveaways!
Please keep the Holly Jolly Light Trail fun and safe for everyone:
A big thank you to our amazing sponsors and community partners for helping keep this event bright!
The Southside Group Real Estate, serving Southern Maryland, is the host and sponsor of the 2025 Holly Jolly Light Trail, bringing neighbors together to celebrate holiday spirit and community.
Lighthouse Title, is a Southern Maryland-based title and settlement company committed to guiding clients home with expert, local service.
Neal Tipton, a loan originator at Waterstone Mortgage in Waldorf, Maryland. He’s focused on delivering a seamless and responsive mortgage experience — whether you’re buying your first home or refinancing.
Lakeside Title Company is a trusted local leader in real estate settlement and title services. We’re proud to have them sponsor the 6th Annual Holiday Joy Light Trail, spreading light and holiday cheer across Southern Maryland!
From our Southside family to yours — thank you for bringing the light, laughter, and love that make Southern Maryland’s holidays so special.
Here’s to our 6th year of the Holly Jolly Light Trail — let’s make 2025 the brightest yet! 🎅💡
Need help? The Southside Team is here to sprinkle a little holiday magic — contact us today!
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