It's Small Business Saturday! Remember to shop local this holiday season! Visit our downtown for some great shopping, dining, and entertainment! Our downtown has it all! Visit for a full list of our local businesses to find what you are looking for this holiday season! #middletownnybid #holidays2019 #shoplocalshop local

Pictures from the 2019 Annual Christmas Tree Lighting Parade & Ceremony! From Friday, November 29th 2019. Thank you to all who made this parade so amazing! 

2019 Annual Christmas Tree Lighting Parade & Ceremony

Get those letters in! 



Christmas Tree Arrival

Date: Tuesday, November 19, 2019

Location: Festival Square (35-37 West Main Street)

Tuesday, November 19, 2019 marks the arrival of the City of Middletown Christmas Tree. The tree has been donated by the Donovan Family, and will be cut from their home in the Town of Wallkill. The tree is estimated to be around 45 f.t. tall and was planted by the house’s original owners in 1977.

Aspen Landscaping and Tree Service, the City’s Department of Public Works and Park’s Department will cut the tree beginning at 8 a.m. and erect it in Festival Square at approximately 9:30 a.m. The Middletown Police Department and the Town of Wallkill Police Department will escort Regional Trucking as they transport the tree from the Town of Wallkill to Downtown Middletown.

Harry Rotolo & Sons, Inc., members of The International Brotherhood of Electrical Workers (IBE Local 363), will decorate the Tree with lights on Saturday, November 23, 2019.

The City of Middletown and the Downtown Business Improvement District thanks Aspen Landscaping and Tree Service, Regional Trucking and Harry Rotolo & Sons, Inc. for donating their services and the Donovan Family for donating the tree to make this event possible.

Tree Arrival

Our holiday wreaths are going up downtown in preparation for all our Festivities! Who's ready for all our events taking place downtown this year? Mark those calendars for our Tree Arrival, Our Middletown Merry Mailboxes rolling out, Our 2019 Tree Lighting Parade & Ceremony, Small Business Saturday & The Quick Stop Santa Stop! Big shout out to the Middletown BID & The Middletown DPW for all their help in preparing and placing our wreaths.

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Tree lighting


Are you a local business or non profit located in Middletown NY & looking to participate in our Parade? Feel free to stop by our document center and download our Partipcation Form & Guidelines 

Orange County Executive Steven M. Neuhaus and City of Middletown Mayor Joseph M. DeStefano participated in a ceremonial groundbreaking with other dignitaries on Tuesday to celebrate the start of construction to extend the Heritage Trail an additional 4.2 miles from Hartley Road in the Town of Goshen to East Main Street in the City of Middletown.

Ceremonial Groundbreaking from the Heritage Trail