This is a list of turnpike roads, built and operated by nonprofit turnpike trusts or private companies in exchange for the privilege of collecting a toll, in the U.S. state of Massachusetts, mainly in the 19th century. While most of the roads are now maintained as free public roads, some have been abandoned.

Background In the late 18th century and early 19th century, turnpikes, as opposed to ordinary roads of the same time, were roads where gates barred travelers from continuing and at which payments were demanded for the use of the road. The word "turnpike" itself comes from the fact that these gates, called "pikes," were "turned" once the toll was paid. The privilege of building and operating turnpikes was conferred by the state legislature to "turnpike corporations". Turnpikes were constructed using private capital, were privately owned, and were operated for revenue from toll collection. The turnpike era in Massachusetts began in 1796, when the first act of incorporation for a turnpike was passed. By 1850, most turnpike corporations had either been dissolved or had stopped collecting tolls. In all, 118 acts of incorporation were passed (ten of these were in the territory that later became the state of Maine). Typical toll rates were twenty-five cents for every coach with additional charges of four cents for every man and horse.

List of turnpikes The following 19th century turnpikes were chartered and built in Massachusetts: Turnpike nameRouting or locationDates of operationModern designationFirst Massachusetts TurnpikeNorth Wilbraham–Palmer–Warren1796–1819US 20–Old Warren Road–Route 67Second Massachusetts TurnpikeNorth Adams–Drury–Charlemont1797–1833Route 2Third Massachusetts TurnpikeNew York state line near Lebanon Springs,Pittsfield,Worthington,Northampton1797–1829Lebanon Springs Road (abandoned)-West Street, Pittsfield resumed on east side of Pittsfield at Grange Hall Road-Robinson Road–Route 143–East Street/Chesterfield RoadWilliamstown TurnpikeNew York state line–Williamstown–North AdamsBerlin Road-Bee Hill Road-Route 2 The portion between Berlin Road and Bee Hill Road survives as a hiking trail.Fifth Massachusetts TurnpikeGreenfield–Athol–Leominster(with branch from Athol to Northfield)1799–1832Route 2Sixth Massachusetts TurnpikeAmherst–Greenwich–Oakham–Shrewsbury1799–1829Local roads west of Rutland and east of Holden; Route 122A (Rutland–Holden). Pelham–Greenwich is now under the Quabbin Reservoir.Eighth Massachusetts TurnpikeBecket–Chester–Russell1800–1844US 20Ninth Massachusetts TurnpikeDouglas–Mendon–Bellingham1800–1833Southwest Main Street–Hartford Avenue (old Middle Post Road)Tenth Massachusetts TurnpikeNew York line–Lenox–Becket–Sandisfield–Connecticut line1800–1855Route 8 / US 20–local streets north of LenoxThird New Hampshire TurnpikeNew Hampshire line–Townsend1801–1826Old Turnpike Road (connects to NH 124)Twelfth Massachusetts TurnpikeEgremont–Sheffield—Connecticut line1801–1857US 7–Egremont Road–Route 23Salem TurnpikeBoston–Lynn–Salem1802–1868Broadway–Route 107Norfolk and Bristol TurnpikeDedhamWashington Street–US 1 / Route 1AQuincy Turnpike Quincy Fourteenth Massachusetts Turnpike Shelburne Camden Turnpike Camden, Maine First Cumberland Turnpike Cumberland, Maine Belchertown and Greenwich Turnpike Belchertown Fifteenth Massachusetts Turnpike Great Barrington Wiscasset and Augusta Turnpike Augusta, Maine Medford Turnpike Somerville Braintree and Weymouth Turnpike Weymouth Chester Turnpike Middlefield Cambridge and Concord Turnpike Concord Newburyport Turnpike Danvers Becket Turnpike Becket Essex Turnpike Middleton Route 114Wiscasset and Woolwich Turnpike Maine North Branch Turnpike Winchendon New Bedford and Bridgewater Turnpike Weymouth Petersham and Monson Turnpike Athol Union Turnpike (Massachusetts) Concord–Leominster 1804–1830 Taunton and New Bedford Turnpike Not marked Blue Hill Turnpike Milton Hartford and Dedham Turnpike Millis Dorchester Turnpike Dorchester Bath or Governor King's Turnpike Maine Brush Hill Turnpike Milton Andover and Medford Turnpike Reading Middlesex Turnpike Cambridge to Tyngsboro Parallel to US 3; portions survive as present Broadway and Massachusetts Avenue in Cambridge, Massachusetts Avenue and Lowell Street in Arlington, Lowell Street in Lexington, Middlesex Turnpike in Burlington, Bedford, and Billerica, Old Middlesex Turnpike and a segment of River Street in Billierica, Turnpike Road, North Road, a segment of Princeton Street, Tyngsboro Road in Chelmsford, and Middlesex Road in Tyngsboro.Worcester and Fitzwilliam Turnpike Winchendon Ashby Turnpike Ashby Route 119Worcester and Stafford Turnpike Holland Plum Island Turnpike Newbury Worcester Turnpike Boston to Worcester Route 9Housatonic River Turnpike West Stockbridge Alford and Egremont Turnpike Egremont Lancaster and Bolton Turnpike Bolton Wrentham and Walpole Turnpike Walpole Stoughton Turnpike Stoughton Taunton and South Boston Turnpike Randolph Hingham and Quincy Turnpike Hingham Hudson Turnpike West Stockbridge Douglas, Sutton and Oxford Turnpike Douglas Great Barrington and Alford Turnpike Egremont Mill Dam Boston Barre Turnpike Barre–Princeton Route 62Chester Turnpike Chester Watertown Turnpike Watertown Central Turnpike Framingham Turnpike from Cambridge to Watertown Watertown Gore Turnpike Douglas Pontoosac Turnpike Chester Taunton and Providence Turnpike Taunton Hampden and Berkshire Turnpike Otis Granite Turnpike

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