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Cheshire
is a quiet valley town located ten miles north of Pittsfield in Berkshire County. Settled in 1766, this town of approximately 3,400 boasts a 500-acre lake, spectacular views from Stafford Hill and one of the most unusual monuments in the country. In 1801, the Elder John Leland presented President Thomas Jefferson with a 1,235-pound cheese made by Cheshire farmers. The huge cheese was four feet in diameter and was drawn by oxen to the Hudson River and shipped to Washington where it was presented to President Jefferson as a "Token of Regard from the Citizens of Cheshire." A replica of the original cheese press now sits in Leland Park. The Pioneer Monument is another Cheshire monument that memorializes the founders of the town and arguably has one of the most beautiful views of the Berkshires from its' spot on Stafford Hill. The town of Cheshire is on Hoosac Lake, which offers picnicking, camping and boating at Horn's Beach. Other attractions in the town include the Solomon Cole House, a former Masonic meeting place replete with an eight panel Christian door that forms the double cross as protection from witchcraft. Beneath the wallpaper in one of the rooms was discovered the beehive, the Royal Arch, the Bible - balance, the square and the compass. Cheshire also offers 225 miles of open slopes and wooded trails for skiers and excellent fishing on the South Branch of the Hoosic, which originates at Hoosac Lake in the town.
Surrounding areas: Lanesborough, Massachusetts (4.5 mi), Adams, Massachusetts (4.9 mi), Dalton, Massachusetts (6.1 mi), Jiminy Peak, Massachusetts (6.4 mi), Savoy, Massachusetts (6.8 mi), Hancock, Massachusetts (8.3 mi), Hinsdale, Massachusetts (8.7 mi)
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Cheshire Vacation Rentals
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Cheshire Hotels and Resorts
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| | | Hotels & Motels |
| Carriage House Motel | US Rt 7 | New Ashford, MA | 4.9 mi. | (413) 458-5359 | | Dublin House Motel Brodie MT | Resort US Rt 7 | New Ashford, MA | 4.9 mi. | (413) 443-4752 | | Kerry House Motel Brodie MT | Resort US Rt 7 | New Ashford, MA | 4.9 mi. | (413) 443-4752 | | The Springs Motor Inn | | New Ashford, MA | 4.9 mi. | (413) 458-5945 | | Travelodge Pittsfield | 16 Cheshire Rd | Pittsfield, MA | 6.8 mi. | (413) 443-5661 | | Crowne Plaza Pittsfield | 1 West St | Pittsfield, MA | 9.1 mi. | (413) 499-2000 | | Howard Johnson Express Inn | 213 Main St | Williamstown, MA | 9.7 mi. | (413) 458-8158 | | Holiday Inn Berkshire | 40 Main St | North Adams, MA | 9.8 mi. | (413) 663-6500 | | The Orchards | 222 Adams Rd | Williamstown, MA | 10.0 mi. | (413) 458-9611 | | Willows Motel | 480 Main St | Williamstown, MA | 10.2 mi. | (413) 458-5768 | | The Williams Inn | 1090 Main St | Williamstown, MA | 10.7 mi. | (413) 458-9371 | | Patriot Suites Hotel | 8 Dan Fox Dr | Pittsfield, MA | 11.6 mi. | (413) 997-3300 | | Comfort Inn | 1055 South St | Pittsfield, MA | 11.9 mi. | (413) 443-4714 | | Howard Johnson | 462 Pittsfield Rd | Lenox, MA | 12.1 mi. | (413) 442-4000 | | Knights Inn | 474 Pittsfield Rd | Lenox, MA | 12.1 mi. | (413) 443-4468 | | Lenox Motel | 525 Pittsfield Lenox Rd | Lenox, MA | 12.1 mi. | (413) 499-0324 | | Econo Lodge | 390 Pittsfield Rd | Lenox, MA | 12.5 mi. | (413) 637-4244 | | Days Inn | 194 Pittsfield Rd | Lenox, MA | 13.4 mi. | (413) 637-3560 | | Sedgwick Inn | 17971 Rt 22 | Berlin, NY | 14.0 mi. | (518) 658-2334 | | Ladd Brook Motor Inn | Rt 7 | Pownal, VT | 14.6 mi. | (802) 823-7341 | | Cornell Inn | 203 Main St | Lenox, MA | 14.9 mi. | (413) 637-0562 | | The Village Inn | 16 Church St | Lenox, MA | 15.5 mi. | (413) 637-0020 | | Best Western Black Swan Inn Inc | 435 Laurel St | Lee, MA | 17.4 mi. | (413) 243-2700 | | Williamsville Inn | 286 Gtbarrington Rd | West Stockbridge, MA | 18.2 mi. | (413) 274-6118 | | Super 8 Motel | 128 Housatonic St | Lee, MA | 18.6 mi. | (800) 800-8000 | | Shaker Mill Inn | 2 Oak St | West Stockbridge, MA | 19.0 mi. | (413) 232-4600 | | The Red Lion Inn | 30 Main St | Stockbridge, MA | 20.8 mi. | (413) 298-5545 | | Southshire Inn | 124 Elm St | Bennington, VT | 21.8 mi. | (802) 447-3839 | | Apple Valley Inn And Cafe | Rt 7 S | Bennington, VT | 21.9 mi. | (
) - | | Comfort Inn | 19 Allen St | Rutland City, VT | 22.1 mi. | (
) - | | Elsie K. Powell House Inc. Pitt Hall | 524 Pitt Hall Rd | Old Chatham, NY | 22.8 mi. | (518) 794-8811 | | Best Western New Englander Motor Inn | 200 Northside Dr | Bennington, VT | 23.4 mi. | (802) 442-6311 | | Hampton Inn Bennington | 51 Hannaford Sq | Bennington, VT | 24.1 mi. | (802) 440-9862 | | Holiday Inn Express Hotel And Suites | 415 Stockbridge Rd | Great Barrington, MA | 25.8 mi. | (413) 528-1810 | | Averill Stand | Rt 100 | Wilmington, VT | 25.8 mi. | (
) - | | Crafts Inn Alonzo's | 26 Ginstell Ln | Wilmington, VT | 25.8 mi. | (
) - | | Horizon Inn | | Wilmington, VT | 25.8 mi. | (802) 464-2131 | | Misty Mountain Lodge | Stowe HL Rd | Wilmington, VT | 25.8 mi. | (
) - | | Nutmeg Inn | Rt 9 W | Wilmington, VT | 25.8 mi. | (
) - | | The White House Of Wilmington | 178 Rt 9 S | Wilmington, VT | 25.8 mi. | (802) 464-2135 |
| | | Bed & Breakfast |
| Bull Frog Bed & Breakfast | Conway Rd | Ashfield, MA | 19.2 mi. | (413) 628-4493 | | Historic Merrell Inn | 1565 Pleasant St | South Lee, MA | 20.6 mi. | (413) 243-1794 | | Trail's End A Country Inn | 5 Trl End Ln | Wilmington, VT | 25.8 mi. | (802) 464-2727 |
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Cheshire Weather & Climate
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Western New York, including The Berkshires, has a moderate four-season climate. The first significant snowfall usually occurs in December, but it varies from year to year. Some years there is no snow or ice until after the first of the new year, and the temperatures near The Hudson River stay quite mild. March is the month to look for the first signs of spring, although cool temps can linger throughout the month. Summers are hazy, warm and humid. September can be mixed with either clear, cool Canadian air or humid, warm air with intense downpours. October is possibly the most beautiful month in the Berkshires with warm, sunny days and cool, crisp nights. Perfect weather for enjoying the foliage. Typically, colors peak the first three weeks of October.
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| Month |
High Temp |
Low Temp |
Rainfall |
Ocean Temp |
| January |
28°F |
11°F |
4.34 in. |
- |
| February |
31°F |
13°F |
3.14 in. |
- |
| March |
40°F |
21°F |
4.26 in. |
- |
| April |
52°F |
32°F |
4.18 in. |
- |
| May |
64°F |
44°F |
3.69 in. |
- |
| June |
72°F |
52°F |
3.69 in. |
- |
| July |
77°F |
57°F |
3.73 in. |
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| August |
75°F |
55°F |
3.92 in. |
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| September |
67°F |
47°F |
3.99 in. |
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| October |
57°F |
37°F |
4.16 in. |
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| November |
45°F |
28°F |
4.29 in. |
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| December |
33°F |
17°F |
4.02 in. |
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Cheshire Map & Transportation
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| Click each thumbnail image to enlarge. |
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The closest airports in the area are the Albany International airport (ALB) located about 34 miles northwest of Cheshire in Albany, New York, the Barnes Municipal airport (BAF) located approximately 36 miles southeast of Cheshire in Westfield, Massachusetts, the Schenectady County airport (SCH) located roughly 43 miles northwest of Cheshire in Schenectady, New York, the Bradley International airport (BDL) located around 49 miles south of Cheshire in Windsor Locks, Connecticut, and finally the Worcester Regional airport (ORH) located about 68 miles southeast of Cheshire in Worcester, Massachusetts.
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Cheshire Attractions
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| | | Amusement and Theme Parks |
| Jeepers | Albany | NY | 30.8 mi. | | | Hoffman's Playland | Latham | NY | 32.9 mi. | | | Six Flags New England | Agawam | MA | 44.1 mi. | | | High Hopes Orchard | Westmoreland | NH | 46.3 mi. | | | Lake Compounce | Bristol | CT | 62.5 mi. | | | Great Escape | Lake George | NY | 65.9 mi. | | | Magic Forest Park | Lake George | NY | 65.9 mi. | | | Quassy Amusement Park | Middlebury | CT | 71.5 mi. | | | Whalom Park | Lunenburg | MA | 71.8 mi. | | | Sherman's Amusement Park | Caroga Lake | NY | 79.0 mi. | | | Funworld Game Center | Nashua | NH | 87.3 mi. | |
| | | Water Parks |
| Zoom Flume Water Park | Durham | NY | 52.7 mi. | | | Water Slide World | Lake George | NY | 65.9 mi. | | | Splash Down Park | Fishkill | NY | 80.4 mi. | | | Maple Breeze Park | Pawcatuck | CT | 106.6 mi. | | | Water Wizz | Westerly | RI | 106.8 mi. | | | Yawgoo Valley Ski Area and Waterpark | Exeter | RI | 107.6 mi. | | | Splish Splash Water Park | Riverhead | NY | 116.6 mi. | |
| | | Golf Courses |
| Forest Park Country Club | Adams | MA | 4.4 mi. | | | Skyline Country Club | Lanesboro | MA | 5.3 mi. | | | Wahconah Country Club | Dalton | MA | 6.4 mi. | | | General Electric Athletic Club | Pittsfield | MA | 8.7 mi. | | | BasRidge Golf Course | Hinsdale | MA | 9.4 mi. | | | Taconic Golf Club | Williamstown | MA | 10.4 mi. | | | Waubeeka Golf Links | Williamstown | MA | 10.4 mi. | | | North Adams Country Club | Clarksburg | MA | 11.8 mi. | | | Stamford Valley Golf Course | Stamford | VT | 14.0 mi. | | | Greenock Country Club | Lee | MA | 18.6 mi. | | | Edge Hill Golf Course | Ashfield | MA | 19.7 mi. | | | Burden Lake Country Club | Averill Park | NY | 20.2 mi. | | | Mt Anthony Country Club | Bennington | VT | 21.3 mi. | | | Brunswick Greens | Brunswick | NY | 23.3 mi. | | | Hoosick Falls Country Club | Hoosick Falls | NY | 24.9 mi. | | | Haystack Golf Club | Wilmington | VT | 25.4 mi. | | | Sitzmark Lodge | Wilmington | VT | 25.4 mi. | | | Beaver Brook Golf Club | Haydenville | MA | 27.1 mi. | | | Egremont Country Club | Great Barrington | MA | 27.6 mi. | | | Northampton Country Club | Leeds | MA | 28.1 mi. | | | Winding Brook Country Club | Valatie | NY | 28.1 mi. | | | Meadowgreens Golf Course | Ghent | NY | 28.2 mi. | | | Country Club of Greenfield | Greenfield | MA | 28.7 mi. | | | Meadows Golf Course | Greenfield | MA | 28.7 mi. | |
| | | Ski Areas |
| Brodie Mountain | New Ashford | MA | 4.9 mi. | | | Berkshire East | Charlemont | MA | 15.6 mi. | | | Otis Ridge | Otis | MA | 25.8 mi. | | | Butternut Ski Area | Great Barrington | MA | 27.3 mi. | | | Catamount | Hillsdale | NY | 32.3 mi. | | | Mount Snow | Brattleboro | VT | 36.9 mi. | | | Haystack at Mount Snow | Brattleboro | VT | 36.9 mi. | | | Mount Tom | Holyoke | MA | 37.3 mi. | | | Willard Mountain | Greenwich | NY | 40.3 mi. | | | Stratton | Stratton Mountain | VT | 40.5 mi. | | | Bromley | Manchester Center | VT | 42.8 mi. | | | Mohawk Mountain | Cornwall | CT | 50.4 mi. | | | West Mountain | Glens Falls | NY | 57.1 mi. | | | Ski Windham | Windham | NY | 58.3 mi. | | | Hunter Mountain | Hunter | NY | 59.0 mi. | | | Okemo Mountain Resort | Ludlow | VT | 62.2 mi. | | | Temple Mountain | Peterborough | NH | 65.1 mi. | | | Wachusett Mountain | Princeton | MA | 65.9 mi. | | | Mount Southington | Southington | CT | 68.3 mi. | | | Woodbury | Woodbury | CT | 70.4 mi. | |
| | | State Parks |
| Wahconah Falls State Park | | MA | 6.3 mi. | | | Balance Rock State Park | | MA | 6.9 mi. | | | Windsor James State Park | | MA | 8.8 mi. | | | Natural Bridge State Park | | MA | 10.2 mi. | | | Taconic Trail State Park | | MA | 11.4 mi. | | | Clarksburg State Park | | MA | 13.0 mi. | | | Bates Memorial State Park | | MA | 14.0 mi. | | | Woodford State Park | | VT | 22.5 mi. | | | Woodford State Park | | VT | 22.8 mi. | | | Gardner State Park | | MA | 25.4 mi. | | | Sweet Pond State Park | | VT | 30.0 mi. | | | Peebles Island State Park | | NY | 30.3 mi. | | | Shaftsburg State Park | | VT | 31.0 mi. | | | Shaftsbury State Park | | VT | 31.7 mi. | | | Elwell State Park | | MA | 32.0 mi. | | | Skinner State Park | | MA | 34.8 mi. | | | Fort Dummer State Park | | VT | 35.1 mi. | | | Campbell Falls State Park | | CT | 36.2 mi. | | | Hampton Ponds State Park | | MA | 36.3 mi. | | | Holyoke Heritage State Park | | MA | 38.1 mi. | |
| | | Museums |
| Hancock Shaker Village | Pittsfield | MA | 8.8 mi. | (History) | | Sterling and Francine Clark Art Institute | Williamstown | MA | 10.6 mi. | (Art) | | Hidden Hills Historical Museums | Chesterfield | MA | 20.2 mi. | (History) | | Norman Rockwell Museum at Stockbridge | Stockbridge | MA | 20.6 mi. | (Art) | | Historic Deerfield | Deerfield | MA | 28.4 mi. | (History) | | Rensselaer County Historical Society at the Hart-Cluett Mansion | Troy | NY | 29.3 mi. | (History) | | Troy's RiverSpark Visitor Center | Troy | NY | 29.3 mi. | (History) | | Irish American Heritage Museum | Albany | NY | 30.8 mi. | (History) | | Albany Institute of History & Art | Albany | NY | 30.8 mi. | (Multidisciplinary) | | New York State Museum | Albany | NY | 30.8 mi. | (Science) | | University Art Museum | Albany | NY | 30.8 mi. | (Art) | | Smith College Museum of Art | Northampton | MA | 31.2 mi. | (Art) | | Eric Carle Museum of Picture Book Art | Amherst | MA | 34.9 mi. | (Art) | | Mead Art Museum | Amherst | MA | 34.9 mi. | (Art) | | Wistariahurst Museum | Holyoke | MA | 37.3 mi. | (History) | | Hildene | Manchester | VT | 41.8 mi. | (History) | | Springfield Museums | Springfield | MA | 43.2 mi. | (Multidisciplinary) | | Springfield Science Museum | Springfield | MA | 43.2 mi. | (Science) | | George Walter Vincent Smith Art Museum | Springfield | MA | 43.2 mi. | (Art) | | Springfield Museum of Fine Arts | Springfield | MA | 43.2 mi. | (Art) |
| | | Zoos and Aquariums |
| Trevor Zoo | Millbrook | NY | 60.2 mi. | | | Beardsley Zoological Gardens | Bridgeport | CT | 96.4 mi. | | | Roger Williams Park Zoo | Providence | RI | 103.1 mi. | | | Mystic Aquarium | Mystic | CT | 103.6 mi. | | | New England Aquarium | Boston | MA | 108.1 mi. | | | Franklin Park Zoo | Boston | MA | 108.1 mi. | | | Utica Zoo | Utica | NY | 111.3 mi. | |
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