Stonybrook Golf is a 9-hole public course with a golf shop and the new and popular Clubhouse Provisions restaurant. The course offers a challenging , picturesque layout with rolling hills, uneven lies, and elevation changes, white the restaurant provides a hip, modern dining experience with panoramic views of the course.

White Memorial has 4,000 acres of preserves and 40 miles of trails. The most popular is the Little Pond Boardwalk Trail, an elevated 1.2 mile boardwalk around Little Pond. White Memorial's conservation center and nature museum are just about 10 minutes from the Winvian.

Mt. Tom State Park, located off Route 202 on the southwest edge of Litchfield, is a summer haven with a beach, swimming area, boat launch, and picnic tables. There's a great all-season hike up to a stone tower with panoramic western views. It's about 15 minutes from the Winvian.

Topsmead State Forest is a 510-acre gem 15 minutes away with hiking trail through open meadows and woodlands. The property was once the summer home of Edith Morton Chase. Visitors may picnic informally on the grounds, residence lawns included.

Covered Bridge Electric Bikes in West Cornwall (where there's a historic red covered bridge) offers E-bike rentals for scenic rides along the Housatonic River.

Explore Litchfield's history through engaging exhibits, diverse programs, and an extensive collection. The Society includes the Litchfield History Museum, Helga J. Ingraham Memorials Library, Tapping Reeve House, Litchfield Law School, and Tapping Reeve Meadow.

Litchfield Distillery makes award-winning premium spirits, including Straight Bourbon Whiskey, flavored bourbons, Gin, Vodka, flavored vodkas, and more. Visit the distillery for the popular tours and tastings.

The Ripley Waterfowl Conservancy is a non-profit wildlife refuge dedicated to preserving rare and endangered waterfowl through captive breeding, research, and education, with over 250 acres of meadows, wetlands, and forests open to the public on weekends. Visitors can see a diverse collection of birds, including cranes, swans, and geese, and explore the grounds, which feature aviaries, ponds, and walking trails. The conservancy, founded on the collection of ornithologist S. Dillon Ripley, offers a unique experience for families and nature lovers.