Western Connecticut & Massachusets

Our route begins and ends at Lover's Leap State Park (see below) just south of New Milford, CT but just begin your scenic loop wherever it's convenient.


Left map - The 95 mile northbound leg follows US Hwy 7, and mostly follows the Housatonic River through small towns and rural western Connecticut & Massachusets. View larger map with directions. 


Right map - The 112 mile southbound leg follows State Hwy 8 to Torrington, CT and returns to New Milford on US 202. View larger map with directions.


Lovers Leap State Park, 3 miles south of New Milford, CT east of the Housatonic River, on Grove Street.


"Trails through the park will lead the walker through centuries of land-use history. Heading northeast from the parking lot the trail utilizes the 1895 Berlin Iron Bridge, one of five remaining in Connecticut, to cross the Housatonic River. Across the bridge the Lovers Leap Trail heads southeast 1,200 feet to the rock formation that gives the park its name. From here, tradition has it, that the Pootatuck Indian Chief Waramaug’s daughter, Princess Lillinonah, and her lover plunged to their deaths. The Chief himself died in 1735."

Kent Falls - Wikipedia photo
Kent Falls - Wikipedia photo

"Kent Falls, located in the northeastern section of the town of Kent, is a series of waterfalls on a mountain stream known as Falls Brook. The stream begins in the town of Warren, draining an area of six or seven square miles. It then flows west to the big fall where it plunges approximately 70 feet in a dramatic cascade. From here the stream descends in a series of lesser falls and cascades to the valley, where it enters the Housatonic River some 200 feet below the brink of the big fall only a quarter mile away."

The West Cornwall Covered Bridge crosses the Housatonic River on CT Hwy 128.

Wikipedia photo
Wikipedia photo


In the town of Great Barrington, MA we turn right and US7 crosses the river before once again heading north. The river leaves us temporarily, diverting west of Monument Mountain, before making it's final appearance in Stockbridge, MA once home to Norman Rockwell and now featuring the museum with the "worlds largest collection of original Norman Rockwell art". More info on Rockwell and other artists can be found at www.atrsy.net

Squaw Peak on Monument Mountain in western Massachusets - Wikipedia photo
Squaw Peak on Monument Mountain in western Massachusets - Wikipedia photo


In downtown Pittsfield, US7 jogs right 3 blocks before heading north on 1st Street for the final 15 miles toward Williamstown near the northwest corner of Massachusets.


Famous Residents of Pittsfield, MA 

Robin Williams, actor who maintains a summer home in Pittsfield.


Henry Wadsworth Longfellow, poet, educator, linguist owned a home on East Street now site of Pittsfield High School.


Herman Melville, author, resided at Arrowhead in Pittsfield, MA where he wrote his most famous novel, Moby Dick. Herman Melville lived in Pittsfield from 1850 to 1863, during which time he wrote Moby-DickPierre: or, The AmbiguitiesThe Confidence-Man: His Masquerade, and The Piazza Tales. His home, Arrowhead, is maintained as a museum by the Berkshire Historical Society.