Middletown Christmas Events & Things to Do 2025

Experience the charm of Christmas in Odessa, a self-guided walking tour showcasing historic homes and buildings adorned for the holidays. This cherished event features Santa and Mrs. Claus, a gingerbread house decorating contest, live Christmas concerts, and a fresh greens sale. Conclude the day with the heartwarming Odessa Tree Lighting...

Experience the enchanting magic of the holiday season with a tour of Newark, Delaware's most spectacular Christmas light displays. From dazzling synchronized light shows to charming neighborhood decorations, these festive displays transform the area into a winter wonderland. It's a perfect, family-friendly adventure to create lasting holiday memories.

Immerse yourself in the enchanting holiday spirit with Havre de Grace's dazzling light displays. Wander through the town as it transforms into a winter wonderland, adorned with festive illuminations. This event offers a charming and magical experience for all ages, perfect for creating lasting holiday memories.

Experience the magic of the holidays at Hagley Museum's "Holiday Nights." This special event offers a rare opportunity to tour the first du Pont family home, Eleutherian Mills, beautifully decorated and illuminated for the season. Discover the "Our Storied Past" theme, which brings beloved holiday tales and traditions to life....

Experience the magic of Yuletide at Winterthur, where classic literature and holiday charm intertwine. Wander through the historic mansion, transformed by artful displays inspired by beloved stories, and marvel at dazzling outdoor lights. Discover a giant gingerbread creation, a miniature 18-room dollhouse, and a festive model train display. Special evening...

Step into a breathtaking holiday spectacle at A Longwood Christmas, where the Gardens are transformed into a radiant jewel box. Explore enchanting displays of vibrant colors, twinkling lights, and stunning floral arrangements. Witness magical fountain shows set to holiday music and wander through illuminated tunnels for an unforgettable festive experience.

Experience the magic of the season at the Glasgow Holiday Celebration & Market. This festive event features a variety of gift and specialty food vendors, live music, and engaging performances. Children can enjoy a holiday train ride, a craft station, and photos with Santa and costumed characters. Don't miss the...

Immerse yourself in the holiday spirit at the 24th annual Spirit of Christmas Celebration in Historic New Castle. This beloved event blends community festivity with the town's rich colonial history. While tickets grant access to a special historic house tour, most of the day's programming, including browsing market vendors and...

Discover the festive spirit at the Havre de Grace Farmers Market, offering a special holiday selection from May through December. Browse a diverse array of local produce, artisanal foods, handmade crafts, and unique gifts. It's the perfect place to find seasonal treats and support local vendors.

Step back in time to experience a Victorian holiday extravaganza in historic Chestertown, Maryland. This two-day event transports visitors to 1840s London with a festive atmosphere, complete with entertainment, home tours, artisan markets, and delicious food. Don't miss the chance to visit Santa, enjoy carriage rides, and perhaps even participate...

Prepare for a magical holiday evening as Chris Pinnella, a platinum-selling artist, returns with his 12-piece orchestra to perform beloved Christmas classics and all-time hits. The STAR Centre will be transformed with thousands of candles, creating an unforgettable, intimate concert experience. This all-ages show promises to fill you with holiday...

Delaware's professional ballet company presents its enchanting production of The Nutcracker. Follow Marie on a magical holiday dream through a swirling snowstorm to the Land of Sweets, featuring Tchaikovsky's iconic score and a lavish production. This beloved holiday tradition promises a captivating experience for all ages.

Step into a heartwarming holiday celebration at The Candlelight Theatre with 'Christmas by Candlelight 2025.' This acclaimed musical production, voted Best Musical by subscribers, features beloved seasonal and sacred tunes, along with delightful new surprises. Experience the magic of the yuletide season in an intimate setting, perfect for creating lasting...

Celebrate New Year's Eve with a vibrant deck party at Chesapeake Inn. Enjoy music, drinks, and a festive atmosphere as you welcome the new year. This event offers a lively setting with scenic views, perfect for ringing in 2025 with friends and fellow party-goers.

Get ready for Middletown's dazzling Holiday Spectacular Parade! This beloved event brings the community together for a festive celebration featuring creative floats, marching bands, and holiday cheer. It's the perfect way to usher in the holiday season with family and friends.

Experience the magic of the holiday season as Middletown Elves collect letters and deliver them straight to the North Pole. Children can write their wishes and drop them in special mailboxes located at various town spots. In return, Santa will send a personalized letter back to your child, creating a...

Experience the magic of the holiday season at Dover's annual Capital Holiday Tree Lighting Ceremony. This festive event brings the community together for an evening of joy, featuring enchanting musical and dance performances, a special photo opportunity with Santa Claus, and delightful grab-and-go crafts for children. The highlight is the...