Greater Middletown · weekend of September 25, 2026
Wine Fest, tree walks, and 37 candles
It's a weekend for wandering, whether that's through wine glasses at The 1851 or under the canopy at Indian Hill Cemetery. Buttonwood Tree turns 37 and wants you at the party. Let's get into it.
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🍷 Wine Fest pours all afternoon at The 1851
🌲 An arborist leads a tree ID walk through Indian Hill Cemetery
🎉 The Buttonwood Tree marks 37 years with a fundraiser
🎸 Brian Dolzani opens the Music on Main fall series
Plus storytime on the Green, a kids' collage workshop, and a pub mixtape night, all below.
All Weekend Long
🎉 Celebrating 37 Years The Buttonwood Tree Performing Arts Center on Pleasant Street throws itself a birthday party this weekend, marking 37 years as a fixture for local arts. It's a fundraiser, so showing up counts as a gift.
Friday
🎸 Trinity Stage Presents Brian Dolzani
Brian Dolzani opens the Music on Main fall concert series at Church of the Holy Trinity, mixing his own songs with a Neil Young tribute set billed as 'The Loner.'
Church of the Holy Trinity · Friday, September 25 · 7:00 PM
🌲 Tree Identification Walk with Arborist John Kehoe
Arborist John Kehoe leads a walk through Indian Hill Cemetery, pointing out what's growing among the historic stones and how to tell one tree from another.
Indian Hill Cemetery · Saturday, September 26 · 10:00 AM
🚧 ROADS:Public Works Updates New signs with QR codes are going up next to active Public Works sites so you can scan for the latest on each project. Next time you hit a cone near a dug-up street, your phone can tell you what's actually going on.
🍃 GOOD NEWS:Free Tobacco Cessation Classes The Middletown Health Department is offering eight sessions of free classes for anyone looking to quit. If you've been meaning to quit, someone in town just made it easier and free.