Events.

There is always something to do Downtown!

Check out our signature events and community calendar below!
Downtown has everything you are looking for! From crafts to concerts, BINGO to trivia nights, plays and even parades! Contact organizing business for more details on each event!

You don’t want to miss a weekend downtown!

DMI Signature Events

Community Calendar


South Main Haunted Walking Tour
Nov
1

South Main Haunted Walking Tour

Join us as we delve into the rich tapestry of the city's past, exploring 28 iconic homes that have witnessed the rise and fall of generations, some rumored to be haunted, while all steeped in the captivating history of Middletown's most influential figures.
As twilight descends upon South Main Street, our expert guides will lead you on a captivating adventure through time, where the lines between history and the supernatural blur. With each step, you'll uncover tales of intrigue, tragedy, and the unexplained, as we explore the lives and legacies of the movers and shakers who once called these storied homes their own.

Whether you're a skeptic or a believer, the South Main Haunted Walking Tour offers an unforgettable experience for all who dare to explore its shadowy corridors. So, gather your courage and join us as we embark on a captivating journey through the haunted history of Middletown's South Main Street, where the past and present converge in an unforgettable evening of discovery and intrigue.
A portion of the ticket sales supports the preservation of The Windamere.

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Ghost and Ghouls- Carnival of Curiosities Halloween Party
Oct
31
to Nov 1

Ghost and Ghouls- Carnival of Curiosities Halloween Party

Ghosts & Ghouls: Carnival of Curiosities

The carnival has returned… for one night only.

This Halloween, step beyond the midway and into a mysterious 1930s traveling carnival where the lights still glow, the music still plays…and not everything is quite what it seems.

On Saturday, October 31, The Windamere transforms into the Carnival of Curiosities for our annual Ghosts & Ghouls Halloween Party!

Dance the night away with Party Punch, try your luck along the midway, encounter curious characters, sip spirited concoctions and come dressed to impress for our Halloween costume contest.

But remember…once you enter the carnival, you never know what—or who—you might encounter.

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1891 Halloween Edition
Oct
29

1891 Halloween Edition

Start your Halloween weekend at the historic, rumor-haunted Sorg Opera House! Enjoy a curated mix of spooky, chilling, and fun music.

Join us for a music experience like no other — an evening of curated, spooky, chilling, heart‑stopping and fun music to usher in your Halloween weekend. This collection of tunes by their original artist will be spinning throughout the night. Come and let the shadows of the historic, rumor‑haunted SORG Opera House wrap around you. It’s the perfect place to unwind with friends… and perhaps a few lingering spirits.

This evening of spooktacular fun includes two mind‑numbing cocktails(several varieties to choose from) and ghoulishly delicious snacks. Additional assorted beverages (alcoholic and non-alcoholic) and goodies available for purchase. All proceeds are going to benefit the SORG Opera House.

Additionally, there will be spine-tingling opportunities to win tickets to upcoming Sorg events.

Doors open at 5:30pm with the monster mix of tunes beginning at 6pm. Last call is 7:30pm with the entire evening ending at 8pm. A limited number of tickets are available so purchase yours today. Tickets are limited.

TICKET OPTIONS

GENERAL ADMISSION - $30 – Have a seat or stand and chat at one of several locations throughout the lobby and theatre for your listening enjoyment. Each ticket purchase includes 2 beverages of your choice

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South Main Haunted Walking Tour
Oct
28

South Main Haunted Walking Tour

Join us as we delve into the rich tapestry of the city's past, exploring 28 iconic homes that have witnessed the rise and fall of generations, some rumored to be haunted, while all steeped in the captivating history of Middletown's most influential figures.
As twilight descends upon South Main Street, our expert guides will lead you on a captivating adventure through time, where the lines between history and the supernatural blur. With each step, you'll uncover tales of intrigue, tragedy, and the unexplained, as we explore the lives and legacies of the movers and shakers who once called these storied homes their own.

Whether you're a skeptic or a believer, the South Main Haunted Walking Tour offers an unforgettable experience for all who dare to explore its shadowy corridors. So, gather your courage and join us as we embark on a captivating journey through the haunted history of Middletown's South Main Street, where the past and present converge in an unforgettable evening of discovery and intrigue.
A portion of the ticket sales supports the preservation of The Windamere.

View Event →
Bucktoberfest 2026 with Crooked Dog Comics
Oct
25

Bucktoberfest 2026 with Crooked Dog Comics

  • 3907 Central Avenue Middletown, Ohio, 45044 United States (map)
  • Google Calendar ICS

Join us for our Third Annual Bucktoberfest! This year will be even bigger! Same location, with more vendors! All vendors will be selling items for $1 on Saturday, October 24 and $.50 on Sunday, October 25.

FREE Admission, FREE parking, Food Trucks, Families Welcome!

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Bucktoberfest 2026 with Crooked Dog Comics
Oct
24

Bucktoberfest 2026 with Crooked Dog Comics

  • 3907 Central Avenue Middletown, Ohio, 45044 United States (map)
  • Google Calendar ICS

Join us for our Third Annual Bucktoberfest! This year will be even bigger! Same location, with more vendors! All vendors will be selling items for $1 on Saturday, October 24 and $.50 on Sunday, October 25.

FREE Admission, FREE parking, Food Trucks, Families Welcome!

View Event →
South Main Haunted Walking Tour
Oct
15

South Main Haunted Walking Tour

Join us as we delve into the rich tapestry of the city's past, exploring 28 iconic homes that have witnessed the rise and fall of generations, some rumored to be haunted, while all steeped in the captivating history of Middletown's most influential figures.
As twilight descends upon South Main Street, our expert guides will lead you on a captivating adventure through time, where the lines between history and the supernatural blur. With each step, you'll uncover tales of intrigue, tragedy, and the unexplained, as we explore the lives and legacies of the movers and shakers who once called these storied homes their own.

Whether you're a skeptic or a believer, the South Main Haunted Walking Tour offers an unforgettable experience for all who dare to explore its shadowy corridors. So, gather your courage and join us as we embark on a captivating journey through the haunted history of Middletown's South Main Street, where the past and present converge in an unforgettable evening of discovery and intrigue.
A portion of the ticket sales supports the preservation of The Windamere.

View Event →
South Main Haunted Walking Tour
Sep
25

South Main Haunted Walking Tour

Join us as we delve into the rich tapestry of the city's past, exploring 28 iconic homes that have witnessed the rise and fall of generations, some rumored to be haunted, while all steeped in the captivating history of Middletown's most influential figures.
As twilight descends upon South Main Street, our expert guides will lead you on a captivating adventure through time, where the lines between history and the supernatural blur. With each step, you'll uncover tales of intrigue, tragedy, and the unexplained, as we explore the lives and legacies of the movers and shakers who once called these storied homes their own.

Whether you're a skeptic or a believer, the South Main Haunted Walking Tour offers an unforgettable experience for all who dare to explore its shadowy corridors. So, gather your courage and join us as we embark on a captivating journey through the haunted history of Middletown's South Main Street, where the past and present converge in an unforgettable evening of discovery and intrigue.
A portion of the ticket sales supports the preservation of The Windamere.

View Event →