Woodstock Theater Tickets

Woodstock Theater Schedule

Find the Best Theater Events in Woodstock for 2026

Woodstock is a hub for exciting live entertainment. We've analyzed our sales data to bring you the most popular theater events so you can easily plan your next outing.

Top Theater Events in Woodstock This Weekend

Planning your weekend? There are 5 theater events happening around Woodstock this weekend! Here are the most popular theater events happening in Woodstock from Thursday to Sunday. Don't miss out on the action!

Event Name	Date	Venue	Lowest Price
The Outsiders	May 22	Proctors Theatre	$224
The Outsiders	May 23	Proctors Theatre	$90
An Enchanted Evening Celebrating Magic Tree House	May 23	Colonial Theatre - Pittsfield	$235
The Outsiders	May 23	Proctors Theatre	$189
The Outsiders	May 24	Proctors Theatre	$222

Top 2026 Summer Theater Events in Woodstock

Summer is the perfect time for live events in Woodstock! Check out this list of the top theater events happening from May through September.

Event Name	Date	Venue	Lowest Price
The Outsiders	May 23	Proctors Theatre	$90
The Outsiders	May 23	Proctors Theatre	$189
Moulin Rouge - The Musical	Jun 2	Proctors Theatre	$118
Moulin Rouge - The Musical	Jun 5	Proctors Theatre	$138
Connecticut Ballet: Giselle	Jun 13	Stamford Center For The Arts - Palace Theatre	$93
Bluey's Big Play	Jul 23	Stamford Center For The Arts - Palace Theatre	$66
Annie	Jul 25	The Milford Theater	$80
Derek Hough	Jul 28	Palace Theatre Albany	$99
Hugh Jackman With The Boston Pops	Aug 11	Tanglewood	$89
Cynthia Erivo	Aug 21	Tanglewood	$69

Cheap Things to Do in Woodstock This Weekend (Under $100)

Looking for fun in Woodstock that won't break the bank? You've come to the right place. This list features the best-selling theater events this weekend with tickets under $100.