Greenwood Trails

390 Winchester Road, Winsted, CT
Capacity: 200 people

About Greenwood Trails

Located on over 100 wooded acres in the beautiful Berkshires, two hours north of New York City and 2 hours south of Boston, Greenwood Trails is the perfect place to host your next event! We are well experienced with a variety of groups, including weddings, corporate events, school groups, and retreats. Groups range from small (30 people) to large (200) and can last one day or up to one or two weeks. We provide a wide range of services to accommodate your group’s individual needs. Our facilities are available for retreats and rentals in May through mid-June, and again from mid-August through October.

Package Pricing

Lunch Menu Starts at
$15 /person
Pricing for all event types
Dinner Menu Starts at
$21 /person
Pricing for all event types
Ovenight Stay Starts at
$49 /person
Pricing for all event types

Event Spaces

Arts And Crafts Building
Basketball Court 1
Basketball Court 2
Basketball Court 3
Dining Hall
Health Care Center
Indoor Basketball
Recreation Hall
Soccer Field
Softball Field
Tennis Court 1
Tennis Court 2
Tennis Court 3
Tennis Court 4
The Den
Venue Types
  • Max Number of People for an Event: 200