Seasons

The Seasons of Woodstock

Woodstock does four things properly: the color in October, Halloween on the street, the menorah on the Green, and the holiday open house in December. Each one has a page that stays put year to year and fills in as the dates come round.

Fall 2026On nowSeptember 20 through November 109 listingsThe busiest month in the Catskills, and the hardest to get a room in. Peak color, the drive up Meads Mountain Road, and the fire tower at the top of it.Halloween 2026On nowOctober 15 through November 212 listingsA costume parade through the hamlet to the Village Green, judging on arrival, and merchants handing out candy. The shows are the second half of it.Christmas 2026Coming upDecember 1 through December 2712 listingsA hamlet-wide open house in early December: tree lighting on the Green, a window-decorating contest, music in the shops. Rooms are easier than in October.Hanukkah 2026Coming upDecember 4 through December 121 listingA public menorah on the Village Green with latkes, cider and a gelt drop from the fire department. The dates move by weeks, so they are listed in full.

The shape of the year here

Summer is the busy season for music and the quiet season for the village itself: the big rooms and the road-trip venues carry it, and the town is full of people passing through. September turns, and by early October the mountains are the reason anyone comes. October is the single busiest month in this part of the Catskills and the hardest one to find a room in. Halloween closes it out on the street rather than indoors. Then it goes quiet, properly quiet, until the open house and the menorah bring the Green back to life in December. January through March the calendar thins out to the rooms that stay open through the winter, which is its own kind of good if you like a bar with a fire and twelve people in it.

If you are planning a trip rather than a night out, the visit guide is the place to start, with lodging, dining and things to do split out, and the Woodstock town guide for the village itself. For a specific night, the full calendar is the real tool.

A season we are missing? Tell us.