small gatherings

Built in 1792, Weatherhead Hollow is a historic farmstead, thoughtfully restored and set against rolling fields and mountain views of the hollow, located just 10 minutes from Brattleboro, Vermont.

For small gatherings, celebrations are held late May through mid-October within our restored Bank Barn — a rare New England design built directly into the hillside. The Barn’s timber frame structure and central event hall, accented by chandeliers and twinkling lights, create a striking yet grounded setting for milestone birthdays, dinner parties, anniversary celebrations, showers, creative events, and community gatherings.

The event space comfortably accommodates up to 50 guests for a seated gathering, with the option to expand capacity to 60. Outdoor lawn games in the barnyard are popular, and guests often gather near the fire pit as the evening winds down.

Small Gatherings are intentionally structured as single-day events, offering full-day access with ample time to prepare, host, and conclude your celebration with ease. For catered events, the Barn includes a kitchen prep area, and you’ll find our suggested vendors – including private chefs and popular drop-off services – on our Vendor page. To learn more about the area from a local’s perspective, visit our Guide to the Area page.

Lodging at the Farmhouse and Carriage Barn for up to 12 guests may be available in conjunction with a Barn event and must be reserved directly through Weatherhead Hollow. Third-party bookings are not eligible for event use.

Weatherhead Hollow is approximately two hours from Albany, New York, two and a half hours from Boston, and three and a half hours from New York City. Bradley International Airport in Connecticut is about a 1 hour and 15 minute drive.

Looking for more detail?

To better understand how Small Gatherings work — including planning logistics, vendor guidelines, enhancements, and policies — we invite you to review our Small Gatherings Frequently Asked Questions packet.

To check availability, pricing or begin the booking process, please reach out through our Book Now page.