The holidays are always fun and festive in Delaware. The Sussex area has no shortage of holiday revelry for your family to enjoy, from craft fairs to light shows to historical mansions. Here are a few of our favorite ways to celebrate this season.
Winterfest of Lights — November 20 to December 31
Wander down the park’s twinkling pathways and take in a wonderland of glowing lights, animated scenes, and charming photo backdrops. The highlight is a magnificent 50-foot Christmas tree that comes to life in a spectacular light show.
Santa Houses Galore
If you want to visit Santa this holiday season, take your pick. Delaware offers plenty of festive stops where families can meet the big man himself.
Rehoboth Santa House
Get ready to share your holiday wishes with Santa at his cozy Rehoboth Beach Boardwalk house. He will be in town to spread cheer on Friday, November 28th from 4 to 6:30 PM, as well as Saturday, November 29th and Sunday, November 30th from 1 to 3 PM. The fun continues the following weekend on Saturday, December 6th and Sunday, December 7th, both from 1 to 3 PM.
You can also visit Santa on Saturday, December 13th and Sunday, December 14th from 1 to 3 PM, and then again for his final weekend appearances on Saturday, December 20th, Sunday, December 21st, Monday, December 22nd, and Tuesday, December 23rd, all from 1 to 3 PM.
Lewes Santa House
The magic continues in downtown Lewes, where Santa will be greeting visitors at his charming seaside house throughout the season. His first appearance kicks off on Small Business Saturday, November 30th, from 1 to 3 PM.
You can also catch Santa during Hospitality Night on Thursday, December 5th, from 5 to 6:30 PM, and right after the Lewes Christmas Parade on Saturday, December 7th. Additional opportunities to visit include Thursday, December 12th from 5 to 7 PM, Saturday, December 14th from 1 to 3 PM, Thursday, December 19th from 5 to 7 PM, Saturday, December 21st from 1 to 3 PM, and a final special visit on Monday, December 23rd from 5 to 7 PM before he heads back to the North Pole.
Canal Cruise with Santa
Experience the magic of the season aboard the Canal Cruise with Santa on Anglers Road. Gather the family and set sail for a festive journey along the canal, where sparkling lights and waterfront views create the perfect holiday backdrop. Enjoy time with Santa as you share smiles, stories, and Christmas cheer. It is a one-of-a-kind way to celebrate the holidays in Lewes that is filled with laughter, joy, and lasting memories.
Milton’s Annual Holly Festival — December 13, 2025
Celebrate the season at Milton’s Annual Holly Festival, a day full of small-town holiday charm. Shop local artisans at downtown locations, the Milton Public Library, and both elementary schools. Enjoy fresh greens and wreaths from the Milton Garden Club, art and jewelry from the Milton Arts Guild, festive carolers, and a visit to the Santa House. The celebration wraps up with the Women’s Club of Milton Holiday House Tour at 2:30 PM.
Celebrate the Holidays the Insight Homes Way
From festive light shows to cozy Santa visits, the holidays in Sussex County capture everything that makes Delaware a special place to call home. At Insight Homes, we build energy-efficient homes designed for comfort, joy, and connection throughout the year. Our homes are built to Zero Energy Ready Home standards, placing them among the most efficient in the nation. With high-performance insulation, advanced air sealing, and efficient heating and cooling, you enjoy even temperatures, quieter rooms, and lower utility costs during every season.
If you are exploring new communities or planning a move to coastal Delaware, discover how an Insight Home can make every season brighter and more comfortable for your family.
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