U.S. 20 in Massachusetts from Boston to Springfield

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Route U.S. 20 is one of the original trans-national roads, although it was not actually designated as coast to coast until the 1940’s. From east to west, it starts in Boston MA and stretches all of the way to Newport OR, a distance of 3365 miles (5425 Km). Today, U.S. 20 is the longest road in the country.




The eastern terminus of U.S. 20 is Kenmore Square in Boston, at its junction with route MA-2. This area sits in-between the Charles River and the Boston Fens, and it is known for two famous landmarks - Fenway Park and the giant CITGO sign. Fenway Park, home to the Red Sox, was built in 1912, and it is the oldest stadium in use in major league baseball. The Citgo sign was erected in 1940 and is well known by those who watch baseball and those who drive into Boston along I-90.



The back of the Green Monster at Fenway Park


U.S. 20 makes its way west along Commonwealth Ave, passing the length of Boston University. It crosses the Charles River, goes through the suburb of Watertown, and enters Waltham MA. Waltham was founded in 1694, and has a long history as a center of manufacturing and labor organizing. In the early 19th century the Boston Manufacturing Company was founded in in the towns of Waltham and Lowell, and built the first integrated textile mills in the United States. In 1824, workers in those plants carried out the first industrial strike in the United States, over pay and working conditions. The town was also home to the Waltham Watch Company, founded in 1850. Workers here walked off their jobs in 1924 over wage cuts imposed by the company. The Charles River Museum of Industry and Innovation currently has an exhibit on these strikes. When you visit make sure to see the beautiful town commons and the historic buildings that are in the area.


The Waltham Museum

Bristol Lodge

First Parish in Waltham Church

Waltham Music Hall

The Commons in Waltham

Statue of Nathaniel C. Banks

Waltham Centennial Marker on the Commons



We stopped for lunch at an excellent restaurant in the town of Marlborough. Thairrific serves wonderful lunch specials in the style of a bento box, so you get salad, dumplings, and a main course for a reasonable price.

Passing through the town of Charlton we almost missed The Yankee Diner as we sped along the road. This classic diner was originally opened in the I 1950’s. It gained new ownership at the start of 2025, and is open for breakfast and lunch.



Yankee Diner Interior
Former outlet for Charlton Mills


U.S. 20 continues, passing south of Worcester and into the town of Sturbridge. Sturbridge is best known as the home of Old Sturbridge Village, a historic recreation of life in the 19th century. The town’s Main Street is filled with businesses here to serve its residents and visitors. New buildings include restaurants and stores, but there some that date back to the 1800’s. I was walking with my camera and a local gave me a great tip. At the bottom of the lot behind the Sturbridge Marketplace at the Falls is a poorly marked path. It you walk about 40 yards you will get to the mill pond formed by a dam across the Quinebaug River, and the falls over that weir.




Blackington Building


Sturbridge Marketplace At The Falls


The weir on the river

The Mill Pond


Continuing on our drive, we arrived in the town of Palmer. Palmer was incorporated in 1775, and was a woolen mill town for many years. I was intrigued by the architecture of several restaurants on Main Street. The one that stopped us was the Day and Night Diner. Manufactured in 1923, the owners over the years have maintained its original look inside and out.




Down the street we found the Palmer Restaurant, whose facade is decorated as a Miami mainstay. Nearby is the Walnut Street Cafe. This little brick box was built in 1962 and gives the vibe of a working man’s bar.

Palmer Restaurant

The Walnut Street Cafe


From Palmer, U.S. 20 wends its way towards Springfield MA. As it passes through the city’s eastern suburbs (one strip mall after another) it jumps on to I-291, bypassing the city center as it heads west.   

Location: Massachusetts, USA

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