Last updated: November 11, 2024
Welcome to the perfect holiday guide for Middletown! Find all the top festive events and attractions right here. From residents to tourists, this guide is your passport to Middletown's festive experiences.
This season, the Wilmington Jaycees Christmas Parade brings the community together with floats, marching bands, and a visit from Santa himself, creating a festive atmosphere for all. The Holiday on Main Street showcases local artisans and food vendors while celebrating the joy of the season. And the Holiday Lights Express is something you definitely don't want to miss, offering a delightful train ride through beautifully decorated neighborhoods. See more details on these and other fun events and activities below!
Have suggestions or corrections? Contact us!
Middletown Holiday Light Displays
Holiday Lights Express
- What to Expect
- Historic first-generation diesel locomotive powers the festive train ride.
- Description
- Ride aboard festively decorated, 100-year-old heated coaches covered in thousands of holiday lights through the Red Clay Valley. Enjoy the holiday decorations of trackside neighbors during this 1-hour evening trip.
- Where
- Wilmington | More Info : Holiday Lights Express
Middletown Holiday Markets and Shopping
Shop 'til You Drop Christmas Extravaganza Vendor Fair & Small Business Saturday
- What to Expect
- Community-driven holiday shopping event with local vendors.
- Description
- Shop 'til You Drop Christmas Extravaganza Vendor Fair & Small Business Saturday offers a bustling marketplace where local vendors and small businesses showcase their holiday wares, making it a great place to find unique gifts and support the community.
- Where
- Middletown | More Info : Shop 'til You Drop Christmas Extravaganza Vendor Fair & Small Business Saturday
Middletown Holiday Shows and Entertainment
Wilmington Jaycees Christmas Parade
- What to Expect
- Local celebrities and dignitaries participating in a festive parade.
- Description
- The Wilmington Jaycees Christmas Parade features local celebrities, marching and string bands, community organizations, floats, and cartoon characters. Santa Claus is the star of the show, and elves will accept Christmas wish lists from children.
- Where
- Wilmington | More Info : Wilmington Jaycees Christmas Parade
Magic of Middletown Tree Lighting Ceremony
- What to Expect
- A celebratory tree lighting with local performances and community spirit.
- Description
- This annual event features the illumination of a grand tree, accompanied by community performances, seasonal music, and family-friendly activities. Local vendors provide refreshments, while attendees gather to celebrate the arrival of the holiday season in a vibrant atmosphere.
- Where
- Middletown | More Info : Magic of Middletown Tree Lighting Ceremony
Middletown Other Holiday Activities
Holiday on Main Street
- What to Expect
- Family-friendly holiday activities with free horse and wagon rides and Santa Claus visits.
- Description
- Holiday on Main Street in Downtown Middletown offers a variety of family-friendly activities, including tree lighting ceremonies, vendor fairs, reindeer games, and decorated vehicle parades. Enjoy free horse and wagon rides, Santa Claus visits, and a festive atmosphere that has been a tradition for over 30 years.
- Where
- Middletown | More Info : Holiday on Main Street
Annual Reindeer Games
- What to Expect
- Family-friendly holiday games and activities.
- Description
- The Annual Reindeer Games feature fun activities and games for all ages, including festive events and holiday cheer.
- Where
- Middletown | More Info : Annual Reindeer Games
Santa Claus Express
- What to Expect
- Santa visits aboard historic locomotives.
- Description
- Ride the Santa Claus Express on the Wilmington & Western Railroad, where Santa greets everyone on board and gives children a special treat. The event features historic locomotives and offers a unique experience for families.
- Where
- Wilmington | More Info : Santa Claus Express
Christmas in Odessa
- What to Expect
- Historic home and public building holiday decorations.
- Description
- Christmas in Odessa is a self-guided walking tour of historic homes and public buildings, many dating from the 18th and 19th centuries, decorated for the holidays. The event includes special events like Santa visits, tea and cookies, and holiday concerts.
- Where
- Odessa | More Info : Christmas in Odessa