Close this search box.

Plan a Self-Guided Scenic Drive in Connecticut!


Plan a self-guided scenic drive in pretty Connecticut; this state is famous for its beautiful small towns and farms and country drives. And lots of fall color still happening! 

Litchfield/Northwest Region 

New Milford, Kent, and Mount Tom State Park drive loop — 46 miles 

This drive will take travelers past the Housatonic River, famous for fly fishing and white water rafting; near two covered bridges; and through Kent and its many art galleries, historic homes and churches. 

Points of Interest: 

Two covered bridges in the area are Bull’s Bridge in Kent and Kent Falls Bridge in Kent Falls State Park. 

Morrison Gallery on Old Barn Road in Kent. See interesting changing exhibits of modern art, photography, sculpture and more. Also, check out Heron American Craft Gallery on Main Street in Kent. Great for gift buying: art, household decor, ceramics, clothing and jewelry, greeting cards. 

The House of Books on Main Street in Kent is packed with high-quality literature; a whole rooms of children’s books; cards, music and gifts 

Side Trips: 

Travel a few miles north on Route 7 beyond Calhoun Corners, through Housatonic Meadows State Park, and into Cornwall to see the West Cornwall covered bridge. This area is famous for its great fall foliage. 

Mount Tom State Park in Litchfield. Swimming and boating in the lake, hiking to a fire tower 1,325 feet above sea level. 


Kent Coffee and Chocolate Co. on Main Street in Kent. The cure for low energy, before or after a glorious hike in the Litchfield countryside. Come enjoy and take home gourmet chocolates and handmade desserts and truffles. 

Haight Brown Vineyard, Chestnut Hill Road in Litchfield. Set on 10 acres of pristine farmland, this hospitable vineyard offers winery tours, self-guided vineyard walks, wine tasting, classes, and lots of seasonal special events.

Torrington to Norfolk Through People’s State Forest — 58 miles 

This drive passes through many lovely small towns and the adjacent Peoples State Forest and American Legion State Forest. Also near this drive is Lake McDonough, a scenic, unspoiled public recreation area. 

Points of Interest: 

People’s State Forest & American Legion State Forest, Barkhamsted. These two adjacent state forests are located along the west branch of the Farmington River. There are lots of places for picnicking. Check out the forests’ trail map and take a walk. 


Thorncrest Farm & Milk House Chocolates in Goshen is on the state’s Chocolate Trail. Calling itself The Home of Single Cow Origin Chocolates, Thorncrest serves chocolate in all the divine ways we have come to know and love. 

Jerram Winery in New Hartford is on Connecticut Wine Trail of wineries and vineyards that open their doors to tours and tastings. 

Waterbury Area Loop — 42 miles 

This loop is good for people with limited time to spend. With only short stops for viewing the scenery, the trip should take less than two hours. Black Rock Park offers excellent hiking, scenic views, and Indian legends. People with more time to spend should visit Waterbury’s Mattatuck Museum, with exhibits chronicling the industrial and cultural history of the Naugatuck Valley. 

Nearby Points of Interest: 

Mattatuck Museum, 144 W. Main Street, Waterbury (203-753-0381) 

Black Rock State Park, Route 6, Watertown (860-283-8088) 

Southford Falls, Route 188, Oxford (203-264-5169) 


Leave a Reply

Your email address will not be published. Required fields are marked *

Related Articles

Keep Exploring!

Sign up for our newsletter to get the latest news about all things New England.

All Things New England

Sign up for our newsletter to get the latest news about all things New England.