Middletown Holiday Events

Gingerbread house decorating party

EPIK Athletics 20 Dec 2025

Candle Concert 3: Holiday Classics at United Church

United Presbyterian Church 20 Dec 2025

National Lampoon's Christmas Vacation

Paramount Theatre of Middletown 19 Dec 2025

National Lampoon's Christmas Vacation

Paramount Theatre of Middletown 20 Dec 2025

Candle Concert 3🎄🎻🕯️Holiday Classics at United Church

United Presbyterian Church of Middletown 20 Dec 2025

Christmas Party @ The Switch Inn

126 E Main St, Middletown, NY 20 Dec 2025

Bonfire Winter Warmer: Live Music with Shades, Ugly Sweater Party, Cocktails, & More!

4 South Street, Middletown, NY, United States, New York 10940 19 Dec 2025

Customer Appreciation Party @ The Switch Inn

126 E Main St, Middletown, NY 16 Dec 2025

Gingerbread House Holiday Brunch

Oak & Reed Downtown 20 Dec 2025

December 20th Belle Pepper's Bingo Brunch!

Tapped 20 Dec 2025

Christmans Classics on the Lanes at Quinnz Pinz

13 Railroad Ave, Middletown, NY, United States, New York 10940 21 Dec 2025

Santa 🧑‍🎄 & Pizza 🍕

Pecorino's Pizzeria 21 Dec 2025

Urban Air Crystal Run's Cookies with Santa!

1 North Galleria Drive, Middletown, NY 10941 16 Dec 2025