Christmas in the Valley

Our valley elevates community fun throughout the year.

Main Street Middletown hosts fundraising opportunities annually in order to continue supporting our area businesses and events. We celebrate our community, history, and culture.

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Christmas in the Valley

December 4, 2021 @ 4:00 pm - 8:30 pm


Join us Saturday, December 4, 2021 and step back in time to this nostalgic-rich holiday event, complete with caroling, holiday music, our town tree lighting and of course a visit from Santa Claus!

4:00pm – 5:30pm & 6:30pm – 8:30pm Visit with Santa outside Town Hall

4:00pm – 7:00pm (every half hour) Story telling with Mrs. Claus on More Ice Cream’s porch

4:00pm – 7:00pm Photo opportunity with Frosty at Middletown Valley Bank

6:00pm Lighting of the Town Tree & Caroling with MHS Chorus

7:00pm Holiday music program at Zion Lutheran Church

Throughout the evening enjoy The Frederick Catactones caroling, donuts at Bobbi Prescott, Remax Results, roasting marshmallows with the Boy Scouts on Main Street, make a reindeer treat at 19 W. Main Street with MHS NAHS!


Bring a toy! Get a Santa Sack!

Bring an unwrapped toy to donate and in return receive a Santa Sack from Main Street Middletown. Visit all of our friendly businesses who will offer goodies to help fill up your sack!


Elf Hunt

Throughout December find the elves in downtown business windows and turn in your ballot to Town Hall before December 31 for a chance to win a prize! Download your entry ballot here.


Write a letter to Santa!

Santa would love to hear from you! Mail your letter to Santa by December 19 in the mailbox located in front of Town Hall. Please include a self addressed stamped envelope to help the elves.


2021 Christmas in the Valley Ornament

This year’s ornament captures The Main Cup’s charming courtyard featuring the Art on Main sculpture. Ornaments may be purchased at Town Hall. $30 each, includes stand and gift box. Ornaments are available for purchase at the Town Hall during normal business hours. All proceeds from ornament sales fund the Christmas in the Valley event on December 4, 2021.


Shop early and local this holiday season!



December 4, 2021
4:00 pm - 8:30 pm


Town of Middletown
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Downtown Middletown, Maryland
31 West Main Street
Middletown, MD 21769 United States
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