🎸 Caravan of Thieves at Music on Main
Dark cabaret band Caravan of Thieves brings songs about ghosts and the afterlife to the church the night before Halloween itself.
Church of the Holy Trinity · Friday, October 30 · 7:00 PM
Details →between the river and Route 9
Greater Middletown · weekend of October 30, 2026
Halloween weekend takes over Lyman Orchards
Halloween lands on a Saturday this year, which means the whole weekend gets to stretch out around it. Lyman Orchards is basically running its own festival with a haunted house, a pie run, a brew maze, and a fall fest all in one stretch. Downtown's got its own quieter corners too, from storytime at RJ Julia to a cabaret band haunting the Church of the Holy Trinity.
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All Weekend Long
🎨 Sue Zola's Glitter Monsters at Klekolo Sue Zola's glittered monsters are still staring down from the walls at Klekolo World Coffee all weekend long. Grab a coffee on Court Street and let them keep you company while you sit with the paper.
Friday
👻 The Orchard Trials: Haunted House
Lyman Orchards turns its grounds into a haunted house attraction, the kind of scare that's better with a friend walking next to you.
Lyman Orchards · Friday, October 30 · 7:00 PM
Details →👨👩👧👦 Books Are Treats
City Hall hosts a Halloween-themed book event, a gentler way to get the kids in costume mode before the actual trick-or-treating starts.
Middletown City Hall · Friday, October 30 · 11:00 AM
Details →📚 Books Are Treats: free books for kids
Altrusa of Central CT is giving away free books to kids at City Hall. Come meet their Bookworm and pick one to take home.
Middletown City Hall, 245 deKoven Dr · Friday, October 30 · 11:00 AM to 3:00 PM
Cost: Free
Details →Saturday
🏃 Lyman Orchards Pie Run
A running event at Lyman Orchards gets Halloween morning moving, a nice excuse to earn your candy before the sun's even all the way up.
Lyman Orchards Apple Barrel Farm Market · Saturday, October 31 · 7:00 AM
Details →🎀 Pick For Pink
Lyman Orchards turns pumpkin picking into a fundraiser for the Middlesex Health breast center, so your pumpkin haul does double duty.
Lyman Orchards Pick Your Own · Saturday, October 31 · 9:00 AM
Details →🎵 Halloween Music Spooktacular
Singer-songwriters Emmy Brockman and Sarah Lou Richards team up for a Halloween music program in the Hubbard Room, costumes very much encouraged.
Hubbard Room at Russell Library · Saturday, October 31 · 10:30am
Details →🍺 Halloween Brew Maze
The corn maze gets a Halloween twist with a brew-themed evening event, maze navigating made a little more interesting by the dark.
Lyman Orchards Corn Maze · Saturday, October 31 · 6:30 PM
Details →Sunday
🍂 AutumnFest
Lyman Orchards closes out Halloween weekend with a fall festival, a soft landing after a weekend full of scares and candy.
Lyman Orchards Apple Barrel Farm Market · Sunday, November 1 · 10:00 AM
Details →🎻 Kitchen Céilí and Friends
Kitchen Céilí plays traditional music of Ireland, Scotland, and New England at Wesleyan, with Stan Scott and Dorothea Hast among the performers.
Wesleyan University · Sunday, November 1
Details →📚 Storytime at RJ Julia
RJ Julia mixes new picture books with classic tales for morning storytime, a calm little ritual to close out a loud weekend.
RJ Julia bookstore · Sunday, November 1 · 12:00 PM
Details →In Case You Missed It
🏗️ DEVELOPMENT: a Middletown developer A developer is appealing the city's denial of two housing proposals on Washington Street. If you live near Washington Street, this fight over what gets built there isn't over yet.
🏛️ HEADS UP: the Nov. 2 Common Council meeting Next Monday's Common Council meeting will be fully remote since the Chamber space is needed for the general election. Plan to watch from home instead of heading downtown for this one.
🏈 SPORTS: the local scoreboard Friday night football results are in for Middletown and Xavier, and Xavier's soccer team is still unbeaten. Good timing if you're trying to decide which Friday night game to catch next.