Massachusetts Route 27
A Journey Through History and Scenic Beauty

Massachusetts Route 27, commonly known as Route 27, is a vital highway in the heart of Massachusetts, offering not only a convenient way to navigate the state but also a glimpse into its rich history and scenic beauty. 

Stretching from the southern city of Kingston to Chelmsford, via Brockton, Natick and Maynard.

This highway plays a crucial role in connecting 27 communities in 3 counties and providing access to Interstate 95 and Interstate 495, and several other major roads.

Route 27 Details & Description

Length of the Highway: Route 27 covers a total distance of 73.44 miles (118.19 kilometers).

Southern Terminus: Route 27 begins at the intersection with Route 106, in Kingston, just a stone’s throw from Kingston Bay.

Northern Terminus: The highway comes to an end in Chelmsford town center, at the intersection of Routes 4, 110 and 129.

Route 27

Credit: Wikipedia Commons

Major Highways Intersecting with Route 27

Route 27

Credit: Wikipedia Commons

  • Route 123 in Brockton
  • Interstate 95 in Sharon
  • Route 1A in Sharon
  • Interstate 95 in Walpole
  • Route 1 in Walpole
  • Route 109 in Medfield
  • Route 16 in Wellesley
  • Route 9 in Natick
  • Route 30 in Natick
  • Route 135 in Wayland
  • Route 20 in Wayland
  • Route 2 in Sudbury
  • Route 117 in Sudbury
  • Route 62 in Maynard
  • Route 111 in Boxborough
  • Interstate 495 in Boxborough
  • Route 111 in Littleton
  • Route 2A in Acton
  • Route 111 in Acton
  • Route 4 in Bedford
  • Route 225 in Bedford
  • Route 2A in Concord
  • Route 126 in Wayland
  • Route 2 in Concord
  • Route 62 in Concord
  • Route 2 in Lincoln
  • Route 126 in Lincoln
  • Route 2A in Lexington
  • Route 4 in Lexington
  • Route 2 in Lexington
  • Route 2A in Arlington
  • Route 60 in Arlington
  • U.S. Route 3 in Arlington
  • Route 2A in Belmont
  • Route 60 in Belmont
  • Route 2 in Belmont
  • U.S. Route 3 in Cambridge
  • Route 28 in Cambridge
  • Route 3 in Cambridge
  • Route 16 in Cambridge
  • U.S. Route 1 in Boston

Towns and Cities Along Route 27

Route 27 passes through 3 counties:

Plymouth, Norfolk and Middlesex,  and coincidently enough, 27 vibrant communities, including:

  • Kingston
  • Pembroke
  • Hanson
  • Halifax
  • Bridgewater
  • Brockton
  • West Bridgewater
  • Easton
  • Stoughton
  • Sharon
  • Walpole
  • Medfield
  • Sherborn
  • Natick
  • Wayland
  • Sudbury
  • Maynard
  • Acton
  • Boxborough
  • Harvard
  • Littleton
  • Westford
  • Chelmsford
The Isaac Davis Monument in Acton, located along Route 27

The Isaac Davis Monument in Acton, located along Route 27

Credit: Wikipedia Commons

History of Route 27

Route 27 was established in 1927 (another coincidence) as part of the New England road marking system. Its origins date back to the early 19th century when it was primarily a stagecoach route. Over time, it evolved into a modern highway to accommodate the growing transportation needs of the region.

Changes and Improvements Over Time: 

  • The construction of a new bridge over the Charles River in Sherborn in 1998.
  • The reconstruction of the intersection with Route 135 in Natick in 2005.
  • The installation of a roundabout at the intersection with Route 20 in Wayland in 2010.

The redesign of the intersection with Route 2A in Acton in 2013.

Granite road sign in Sudbury. The left side marks Route 27.

Granite road sign in Sudbury. The left side marks Route 27

Credit: Wikipedia Commons

Recent Improvement Plan in Natick

Route 27 Expansion in Natick
Route 27 Expansion in Natick | Credit: BETA Group, Inc.

In 2023, MassDOT announced a plan to replace the existing structurally deficient Route 27 bridge over Route 9 in Natick and reconfigure the interchange to increase safety, improve mobility and ease congestion

The plan includes:

  • Replacing the existing Route 27 bridge over Route 9 with three independent bridge structures: one for each direction of vehicular traffic and one for a shared use path facility.
  • Replacing the existing partial cloverleaf interchange with a modified diverging diamond configuration that will reduce conflict points and improve traffic flow.
  • Providing four transit stops with corresponding bus shelters for the MetroWest Regional Transit Authority (MWRTA).
  • Providing a shared-use path along the south side of Route 9 that will connect the interchange area with the Cochituate Rail Trail and the MathWorks campus.
  • Providing a new sidewalk along the north side of Route 9 within the project limits.
  • Providing pedestrian-actuated warning systems at multiple crosswalk locations to increase driver awareness and yielding of crossing activity.
  • Providing two new traffic signals along Route 27 to accommodate the crossing traffic associated with the function of the modified diverging diamond.
  • Reconfiguring and improving access between Lakeshore Road and Route 27.
  • Reconfiguring the traffic signal at Route 27 at the Exchange Driveway.
  • Reconfiguring the Route 9 on/off ramps to provide increased deceleration and acceleration lengths.
  • Upgrading and/or replacing existing drainage infrastructure along both Route 27 and Route 9 within the project limits.
  • Replacing the existing median barrier along Route 9.
  • Other ancillary items including low maintenance landscaping, stormwater improvements, retaining walls, guardrail, pedestrian fencing, new signage and new pavement markings.

The project is being considered for the Design-Build Project delivery method, where one team handles both the design and construction. This reduces the time needed to complete the project and promotes collaboration among the engineers, contractor, and MassDOT staff.

Interesting Facts

Unique Features of the Highway: While Route 27 may not be the longest highway in Massachusetts, it boasts a diverse range of landscapes, from coastal areas to picturesque New England towns, making it a popular route for both locals and tourists.

Historical Landmarks Along the Route: Travelers on Route 27 can explore various historical landmarks, such as the Lexington Battle Green, where the first shots of the American Revolutionary War were fired, and the historic towns of Concord and Cambridge, rich in colonial history.

Additional examples:

  • In Kingston, the route passes by the Isaac Winslow House, which is one of the oldest surviving houses in New England and was once owned by a descendant of Mayflower passenger Edward Winslow.
  • In Hanson, the route passes by Camp Kiwanee, which is a historic campsite that was used by Native Americans, colonists, soldiers, and scouts. It also features a rustic lodge that was built by the Civilian Conservation Corps in the 1930s.
Antique road signs in a well in Acton

Antique road signs in a well in Acton

Credit: Wikipedia Commons

  • In Brockton, the route passes by the Rocky Marciano Stadium, which is named after the legendary boxer who was born and raised in the city. It also hosts the annual Brockton High School vs. Bridgewater-Raynham Regional High School football game on Thanksgiving Day.
  • In Walpole, the route passes by the Francis William Bird Park, which is a scenic park that was donated by a wealthy industrialist in 1925. It has over three miles of trails, ponds, bridges, and sculptures.
  • In Natick, the route passes by the Bacon Free Library, which is a historic library that was built in 1880 with funds from a local philanthropist. It has a collection of over 28,000 books and hosts various cultural events.
  • In Sudbury, the route passes by the Wayside Inn, which is a historic inn that was built in 1716 and is reputed to be the oldest operating inn in America. It was immortalized by Henry Wadsworth Longfellow in his poem “Tales of a Wayside Inn”.
  • In Acton, the route passes by the Isaac Davis Trail, which is a historic trail that marks the route of the minutemen who marched from Acton to Concord on April 19, 1775, to fight in the first battle of the American Revolution.
  • In Chelmsford, the route passes by the Old Chelmsford Garrison House, which is a historic house that was built in 1691 and served as a garrison for soldiers during King Philip’s War and Queen Anne’s War.

Driving Through Route 27

Driving on Route 27 can be challenging and risky at times, especially during peak hours, bad weather, or construction.

Maintenance and Upkeep of the Highway

Massachusetts Department of Transportation (MassDOT) is responsible for maintaining Route 27. They regularly inspect and repair the road to ensure it remains safe and functional for all travelers.

MassDOT welcomes any feedback or suggestions from the public regarding the route’s safety and maintenance. You can contact MassDOT by phone at 857-368-4636 or by email at


Massachusetts Route 27 is more than just a highway; it’s a journey through time and nature. As you navigate its winding path, you’ll experience the charm of New England towns, the significance of historical landmarks, and the beauty of the Massachusetts landscape. So, whether you’re a local commuter or an adventurous traveler, Route 27 offers a scenic and historic route worth exploring. Drive safely and enjoy the ride!