Planning a Weekend Road Trip to Litchfield County - Stamford Moms

Looking for a last minute summer staycation weekend in Connecticut that’s fun for the whole family? Consider Litchfield County.  In addition to unique lodging options, fresh and local dining and plenty of fun activities ranging from pick-your-own to hiking to a day at the races at Lime Rock Park to Sunday mornings at the famous Elephant Trunk Flea Market, this quick hour and a half drive to the northwestern side of our great state makes for an easy getaway.


A summer trip north coincides with The Five Senses Festival presenting world-class music and dance concerts, interactive art, family activities, locally-sourced and crafted food and creative conversation in a visually stunning yet intimate natural setting over three summer weekends in Washington, Connecticut.  Created by internationally renowned New York City dance company Pilobolus together with Spring Hill Vineyards, Stephanie and Tim Ingrassia, the event kicks off on Saturday, July 20 with The Pilobolus Five Senses Ball, which, along with the help of donors and supporters, helps support Festival programming being offered free and low-cost to attendees.

Over the following festival weekends (July 21, July 26-July 28 and August 2-August 4), Kids and Family workshops, meant to inspire and invite artists of all ages to participate, include such offerings as:

  • An outdoor studio created to craft awe-inspiring projects with a rotation of artists and concepts (FREE with RSVP).
  • A square dance with the Pilobolus dancers (FREE with RSVP).
  • Capoeira Workshop (FREE with RSVP).
  • A participatory songwriting workshop with Grammy-nominated songwriter Terry Radigan (FREE with RSVP).
  • A weaving workshop where each participant will complete their own nature tapestry to take home (FREE with RSVP).
  • A live visual arts and performance collaboration, featuring artists from the New York Academy of Art sketching, painting and capturing the movements of the Pilobolus dancers (FREE with RSVP).
  • Pilobolus Summer Workshop Student Show (FREE with RSVP).

Free childcare is also offered from 9 a.m. – noon and 4 p.m. – 7 p.m. for parents to enjoy some of the adult-only programming!

The Festival Field at Spring Hill Vineyard (292 Bee Brook Road in Washington, Connecticut) houses a sprawling, grassy field for music, dance, visual art, and children’s workshops, as well as a 250-seat outdoor granite amphitheater designed by artist Mark Mennin using 120 tons of pink Connecticut granite; a silo houses a mirrored grotto raised 60 feet in the air created by Randy Polumbo; a tent housing headlining concerts and lectures; a wine cave; and vintage Airstream serve food and cocktails from Chef Cassandra Purdy, made with ingredients and recipes sourced from local farmers and collaborators.  

Festival events are held rain or shine.  For more information or to obtain tickets, visit


Winvian Farm offers eighteen individually designed cottages, including a Treehouse suspended 35 feet above the forest floor, a spacious barn and silo-like cottage build around a white oak tree, and a full-restored 1968 Sikorsky helicopter. 

The Mayflower Inn and Spa is set on a beautiful 58 acre property, and offers guest rooms and suites evoking a small, traditional, country inn feeling.

The Heritage Hotel offers a modern, full-service resort destination with 163 guestrooms and suites, a golf course, tennis center and kids club.


Award-winning Community Table has reopened with a new Executive Chef and ownership team, offering farm-fresh food in a beautiful setting.

The White Horse is a rustic, neighborhood go-to featuring a pub menu, fireplace and patio seating.

The Bantam Bread Co. makes all of its breads and pastries in-house from scratch – and sells other local goods from the area!

A trip to Litchfield County isn’t complete without a taste of ice cream at Arethusa Farm, made right at the shop’s farm in Bantam.

Join The Stamford Moms Network Community

Stay up-to-date with what is happening in-and-around the Stamford community with local events, community highlights, and exclusive deals.