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  1. Bennington

    Bennington is a town in Southwestern Vermont. Boasting five covered bridges it is a classic Vermont country town, and is also home to Bennington College.

  2. Williamstown (Massachusetts)

    Williamstown is a town in the Berkshire Hills at the northwest corner of Massachusetts. It shares a border with New York and Vermont.

  3. North Adams

    North Adams is a town in the Berkshire Hills of Massachusetts. In the 19th century it was the industrial center of the region.

    People near Bennington

  4. Arlington (Vermont)
  5. Mount Snow

    Mount Snow is in the towns of Wilmington and West Dover, in southern Vermont. It is located off Vermont's famed Route 100 - aka the skiers' highway.

  6. Adams (Massachusetts)

    Adams is a small town in the Berkshire Hills region of Massachusetts. It features the summit of Mt.

  7. Sandgate (Vermont)

    Sandgate is a town in Southern Vermont near the border of New York.

  8. New Ashford

    New Ashford is a small town in the Berkshire Hills region of Massachusetts.

  9. Florida (Massachusetts)

    Florida is a small town in the Berkshire Hills area of Massachusetts.

  10. Cambridge (New York)

    Cambridge is in Washington County in the rural northeast of the Capital District of New York.

  11. Manchester (Vermont)

    Manchester is a town in southernwestern Vermont, nestled at the foot of 3,816-foot Mount Equinox. It has a tranquil old-world atmosphere, and Manchester Center is a shopper's paradise that is completely different from the village with its signs, sights and many shops.

  12. Cheshire (Massachusetts)

    Cheshire is a town in the Berkshire Hills region of Massachusetts.

  13. Wilmington (Vermont)
  14. Stratton

    Stratton is a ski resort in Southern Vermont, located in the New England region of the United States.

  15. Hancock (Massachusetts)

    Hancock is a town in Massachusetts in the Berkshire Hills region.

  16. Lanesborough

    Lanesborough is a small town in the Berkshire Hills region of Massachusetts.

  17. Pittsfield

    Pittsfield is a small city in western Massachusetts. It is the largest city in Berkshire County and home to Berkshire Community College .

  18. Jamaica (Vermont)

    Jamaica is a village in Vermont. It is a great place to stay when going to Stratton ski resort.

  19. Troy (New York)

    Troy is a city in Rensselaer County, New York located northeast of Albany. Its nicknames include "The Collar City" and "Home of Uncle Sam.

  20. Watervliet (New York)
  21. Lenox (Massachusetts)

    Lenox is a town in the Berkshires of Massachusetts, about 3 hours from New York City and 2.5 hours from Boston.

  22. Newfane

    Newfane is a town and county seat of Windham County in Southern Vermont.

  23. Becket

    Becket is a small town in the Berkshires of Western Massachusetts.

  24. Capital District

    New York's Capital District is centered on the state capital of Albany,

  25. Lee (Massachusetts)
  26. Rensselaer (New York)

    Rensselaer is a city in New York on the Hudson river opposite Albany.

  27. Albany (New York)

    Albany is the capital of New York and the county seat of Albany County. It is home to just under 100,000 residents, most of New York State's key government offices, and seven colleges and universities.

  28. Stockbridge

    Stockbridge is a town located in Berkshire County in Western Massachusetts. As of the 2000 census, the town had a total population of 2,276.

  29. Saratoga Springs

    Saratoga Springs is located just south of the Adirondacks in upstate New York. Long a vacation destination for New Yorkers, Saratoga Springs is a pleasant town filled with swanky shops, spas and horse racing.

  30. Clifton Park

    Clifton Park is a city in the Hudson Valley in the Capital District region of New York. It is situated in Saratoga County right between Albany and Saratoga Springs in upstate New York.

  31. Brattleboro

    Brattleboro is a town of 12,000 people in southern Vermont. From points south, it will most likely be the place for travelers to begin their exploration of Vermont.

  32. Ballston Spa

    Ballston Spa is a town in the county seat of Saratoga County in New York. The town is well-known for it's walkable village with hometown restaurants, shops and museums.

  33. Greenfield (Massachusetts)

    Greenfield is in Franklin County, Massachusetts. It is home to Greenfield Community College.

  34. Kinderhook

    Kinderhook is the name of both a village and a township in Columbia County in the state of New York.

  35. Deerfield (Massachusetts)

    Deerfield is a small town in Franklin county in western Massachusetts. It is home to Deerfield Academy prep school.

  36. West Chesterfield

    West Chesterfield is a city in the Monadnock Region of New Hampshire.

  37. Otis (Massachusetts)
  38. Berkshire Hills

    The Berkshire Hills are in Berkshire County at the western end of Massachusetts. They are actually three separate mountain ranges, separated by the valleys of the Housatonic River in the south and the Hoosic River in the north.

  39. Monterey (Massachusetts)

    Monterey is a small town in the Berkshire Hills region of Massachusetts.

  40. Great Barrington

    Great Barrington is a pleasant town in the Berkshire Hills region of Massachusetts.

  41. Ludlow (Vermont)

    Ludlow is in Southern Vermont and great place to visit any time of the year. Ludlow is a small village surrounded by wooded hills.

  42. Schenectady

    Schenectady once called the city that lights and hauls the world, is located in the Hudson Valley region of New York. Approximately 20 minutes from New York's capital of Albany, Schenectady is best known as the birthplace of General Electric and for Proctor's Theater.

  43. Blandford
  44. Rutland (Vermont)

    Rutland is a city of about 17,000 people in Southern Vermont. It is the third largest city in the state.

  45. Columbia County (New York)
  46. Northampton (Massachusetts)

    Northampton is a city in the Pioneer Valley of Massachusetts with a picturesque and vibrant downtown, consisting of numerous art galleries, restaurants and quirky shops sprinkled among coffee shops and performing arts venues. It is home to prestigious Smith College and the Clarke School for the Deaf.

  47. Sheffield (Massachusetts)

    Sheffield is in the Berkshires of Western Massachusetts, just north of the border with Connecticut.

  48. Bellows Falls

    Bellows Falls is an incorporated village of 3,000 people in the town of Rockingham in southeastern Vermont. It has enjoyed a renaissance in two main areas since the turn of the millennium.

  49. Plymouth (Vermont)
  50. Hadley

    Hadley is a small town of 4,200, located in the Pioneer Valley, in Western Massachusetts. Despite its small population, it has a reasonable commercial strip that harbors a few malls, providing a more mainstream shopping experience than its larger neighbors, Amherst and Northampton.

  51. Lake George

    Nestled in the pristine Adirondacks, Lake George is a year-round tourist destination. Just 45 minutes (36 miles) outside of Saratoga Springs and 1 hour (60 miles) north of Albany it is worth the effort it takes to get there.

  52. Amherst (Massachusetts)

    Amherst is a town in the Pioneer Valley of Western Massachusetts. Amherst is home to about 35,000 residents as well as the campuses of the University of Massachusetts, Amherst College, and Hampshire College.

  53. Hudson (New York)
  54. Mount Washington (Massachusetts)

    Mount Washington is a tiny town in the Berkshire Hills region of Massachusetts. It is at the southwest corner of the state, the only Massachusetts town to border both New York and Connecticut.

  55. Westfield (Massachusetts)

    Westfield is a city in Hampden County, in the Pioneer Valley region of Massachusetts. It includes the village of Wyben.

  56. Granville (Massachusetts)

    Granville is a town in Hampden County in the Pioneer Valley region of Massachusetts.

  57. South Hadley

    South Hadley is a city in the Pioneer Valley area of Massachusetts. It is home to Mount Holyoke College.

  58. Killington

    Killington is a town in Southern Vermont. It is home to Killington Ski Resort.

  59. Holyoke
  60. Norfolk (Connecticut)

    Norfolk is a town in the Litchfield Hills of northwestern Connecticut.

  61. Chittenden
  62. Swanzey
  63. Keene (New Hampshire)
  64. Salisbury (Connecticut)

    Salisbury is a city in Connecticut. It includes the village of Lakeville, home to Lime Rock Park raceway.

  65. Chicopee
  66. West Springfield (Massachusetts)

    West Springfield is a city (known as a town) in Hampden County in the Pioneer Valley region of Massachusetts. Often referred to as West Side, West Springfield is just west of Springfield (Massachusetts), divided by the Connecticut River.

  67. Claremont (New Hampshire)
  68. Springfield (Massachusetts)

    Springfield is the largest city on the Connecticut River, in the Pioneer Valley of Massachusetts, USA. It sits 24 miles (40 km) north of Hartford, Connecticut, and 5 miles(8 km) north of the Connecticut state line.

  69. Cairo (New York)

    Cairo is a town in Greene County in New York. It is located next to East Durham (home of one of the largest Irish festivals in New York.

  70. Agawam

    Agawam is a town in the Hampden County part of the Pioneer Valley region of Massachusetts. It includes the village of Feeding Hills.

  71. Woodstock (Vermont)

    Woodstock is a quaint little town in the state of Vermont in New England. The town has two police cars in its town arsenal, and is known for its old town buildings.

  72. Windsor (Vermont)

    Windsor is in Southern Vermont. Windsor has a small population of 3,800 people and sits on the banks of the Connecticut River.

  73. Ticonderoga

    Ticonderoga is a town in the Adirondacks that borders both Lake George and Lake Champlain.

  74. Cornish (New Hampshire)

    thumb|300px|Cornish-Windsor Bridge - longest covered bridge in the US

  75. Ludlow (Massachusetts)

    Ludlow is a town in central Massachusetts, about a 15- to 20-minute drive to downtown Springfield.

  76. Chester (New York)

    The Town of Chester is made of several communities in the Adirondacks around the small hamlet of Chestertown. Other hamlets within the town boundaries include Pottersville, Friends Lake, Loon Lake, and Schroon Lake.

  77. Longmeadow

    Longmeadow is an affluent, postcard-perfect looking town in Hampden County, Massachusetts, located between the City of Springfield and the Connecticut border.

  78. Sharon (Connecticut)
  79. Cornwall (Connecticut)

    Cornwall is a town in Connecticut. It is comprised of many small parts from yesteryear, but today is generally divided into three parts, Cornwall Bridge, West Cornwall, and Cornwall Village.

  80. Greene County (New York)
  81. Rochester (Vermont)

    Rochester is a small town in Vermont. It is known as "The Heart of the Green Mountains" as it is nestled in the White River Valley in the shadow of the Green Mountains.

  82. Petersham

    Petersham is a small quintessential New England town located in the North Quabbin region of central Massachusetts.

  83. Windsor Locks
  84. Enfield (Connecticut)
  85. Simsbury
  86. Amenia (New York)

    Amenia is a township in Dutchess County, New York. This page also covers the village of Wassaic, 6 miles south of downtown Amenia.

  87. Quechee

    Quechee is a small town centered around Quechee Gorge in Southern Vermont. Although the gorge was the original attraction, a small resort town has now popped up around it.

  88. Crown Point (New York)

    Crown Point is a town on the New York side of the Champlain Valley in the Adirondacks.

  89. Saugerties
  90. Red Hook

    Red Hook is the name of both a village and a township in Dutchess County, New York. The town encompasses the villages of Red Hook and Tivoli as well as the hamlets of Annandale-on-Hudson, Barrytown and Upper Red Hook.

  91. Harwinton

    Harwinton is a small town in the Litchfield Hills region of Connecticut that was founded in 1737.

  92. Avon (Connecticut)

    Avon, Connecticut is a little town just outside of the capital, Hartford.

  93. East Windsor (Connecticut)
  94. Windsor (Connecticut)
  95. Somers (Connecticut)
  96. White River Junction

    White River Junction is a village on the Connecticut River in eastern Vermont. It is in the town of Hartford.

  97. Kent (Connecticut)
  98. Rhinebeck

    Rhinebeck is a township in Dutchess County, New York. The township encompasses the village of Rhinebeck as well as the hamlet of Rhinecliff.

  99. Rindge
  100. Windham (New York)

    Windham is a township in New York state's Catskill mountains. In winter the town is a popular ski destination for the New York City metro area; in other seasons there is golf, hiking, mountain biking, and fishing.