🍺 Twilight Hard Cider Maze
Lyman Orchards' corn maze goes after dark with six hard ciders to sample along the way. A fall night walk with a little bite.
Lyman Orchards Corn Maze · Friday, October 16 · 5:00 PM
Details →between the river and Route 9
Greater Middletown · weekend of October 16, 2026
Trick or treat downtown, plus a fall fundraiser
Main Street fills with costumes this weekend for Downtown Trick or Treat. A glitter monster or two is still watching you at Klekolo, and Lyman Orchards gives its corn maze a cider-soaked twist Friday night if you want your scares after dark.
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All Weekend Long
🎨 Sue Zola's Glitter Monsters at Klekolo Sue Zola's glitter monsters are still grinning down from the walls at Klekolo World Coffee all weekend long. Grab a coffee and let them stare back at you for a while.
Friday
🏃 Middlesex Monster Dash 5K
A 5K run at CT State Community College Middlesex gets a monster theme, good for burning off some energy before the weekend's candy haul.
CT State Community College Middlesex · Friday, October 16 · 5:30 PM
Details →Saturday
🎃 Downtown Trick or Treat
Two weeks before Halloween, downtown gets its own trick-or-treat day. Dig out a costume and make the rounds.
Main Street · Saturday, October 17 · 11:00 AM
Details →🎨 Earth and Art for All in the North End
The North End hosts a free community gathering mixing art and the outdoors, open to the whole neighborhood.
185 Johnson Street · Saturday, October 17 · 2:00 PM
Cost: Free
Details →🎀 Pick For Pink
Lyman Orchards' pumpkin fields turn into a fundraiser for Middlesex Health's breast center, so you can pick your pumpkin for a good cause.
Lyman Orchards Pick Your Own · Saturday, October 17 · 9:00 AM
Details →🎨 Glow-in-the-Dark Rock Painting
Kids turn plain rocks into glowing little creations in the library's activity room, paint and imagination doing all the work.
Activity Room at Russell Library · Saturday, October 17 · 2:00 PM
Details →Sunday
🎶 Mixtape Match
1741 Pub & Grill closes out the weekend with a sing-along game night run by a DJ, and it's free to play. Grab a table.
1741 Pub and Grill · Sunday, October 18 · 6:00 PM
Details →🌟 Connecticut Bridal & Wedding Expo
Vale Fieldhouse fills with vendors and ideas for anyone planning a wedding, one stop to compare notes under one roof.
Vale Fieldhouse · Sunday, October 18 · 11:00 AM
Details →In Case You Missed It
🏗️ DEVELOPMENT: rezoning requests and an Arcade update Middletown's Planning & Zoning Commission took up rezoning requests for Randolph Road and South Main Street, while a council panel got an update on the Arcade redevelopment. Two corners of town could look different before long, and the Arcade project keeps inching forward downtown.