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Journey back in time to Windsor, Massachusetts, USA

Explore Windsor, Massachusetts, USA! Uncover its rich history and discover the stories of the people who once called it home. Dive into old newspaper articles, vintage pictures, postcards, and genealogy to learn more about this fascinating town.

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Windsor, Massachusetts, USA - Windsor, Massachusetts, USA - Top of Berkshire Trail, Windsor, Mass.

Windsor, Berkshire, MA

The Town of Windsor, formerly Gageborough, was founded July 4, 1771. Best known for its scenic vistas and pristine wilderness, it has a rich history of early American mills, logging, farming and hearty pioneer settlers. windsormass.com



Explore even more about Windsor, Massachusetts, USA. Keep reading!



Windsor Nostalgia: Vintage Photos, Ads, and Postcards

Windsor, Massachusetts, USA - Top of Berkshire Trail, Windsor, Mass.
Windsor, Massachusetts, USA

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Top of Berkshire Trail, Windsor, Mass.
Windsor, Massachusetts, USA - Greetings from Windsor, Mass.
Windsor, Massachusetts, USA

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Greetings from Windsor, Mass.
Windsor, Massachusetts, USA - Crane Community School, Windsor, Mass.
Windsor, Massachusetts, USA

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Crane Community School, Windsor, Mass.

Discover Unique Gift Ideas and Genealogy Resources From or Related to WINDSOR

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MASSACHUSETTS Gift t shirt Made in MASS, Got Wicked Class Unisex Softstyle T-Shirt

Are you looking for a t-shirt that's as comfortable as it is stylish? Look no further! Our Unisex Softstyle T-Shirt is the perfect blend of comfort, quality, and Massachusetts pride. Whether you're a lifelong Massachusetts resident or just passing through, you'll appreciate the "wicked class" that this shirt exudes.

MASSACHUSETTS Gifts - Cranberries, Baked Beans and Fluffernutter - I Love Massachusetts! - Ceramic Mug MA

Our Ceramic Mug, Cranberries, Baked Beans, and Fluffernutter - I Love Massachusetts! is more than just a beverage holder; it's a piece of art that celebrates the flavors and traditions of the Bay State. So whether you're sipping your morning coffee, evening tea, or a comforting cup of hot cocoa, you can do it with style and a dash of Massachusetts charm. Plus, it's a fantastic conversation starter. Imagine sharing stories about your favorite Massachusetts memories while enjoying a drink from this delightful mug.

MASSACHUSETTS Roots Genealogy Coffee Mug - Celebrate Your Bay State Heritage!

Show off your deep-rooted connection to the Bay State with our Massachusetts Roots Genealogy Coffee Mug! Perfect for sipping your favorite brew while tracing family history, this ceramic mug is a tribute to the rich heritage of Massachusetts.

MASSACHUSETTS Pride Coffee Cup - Made in Mass “Got Wicked Class” Mug

Show off your Massachusetts pride with a sip of sass! The Made in Mass “Got Wicked Class” Mug delivers local humor and hometown swagger in every cup. Perfect for coffee, tea, or hot cocoa, this high-quality ceramic mug comes in 11 oz or 15 oz and is dishwasher & microwave safe. Ideal for early commutes, porch mornings, or late-night study sessions, it’s a bold, fun reminder of where you’re from—and the attitude that goes with it. A must-have gift for anyone who loves Massachusetts, humor, and a wicked good cup of coffee!

Discover Windsor: History, News, Travel, and Stories

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1839 - Windsor
Windsor, Massachusetts
Berkshire county. This town is situated on the ridge of high lands which divides the waters of the Housatonick and Connecticut. Branches of the Housatonick and Westfield rivers rise here. There are some good fish ponds in the town, but no important streams. The surface of the town is much broken, but the soil is warm and finely adapted for grazing. There are some excellent farmers in Windsor, and the productions of the dairy and of cattle are considerable. In 1837 there were 7,157 sheep in the town, principally of the Saxony and Merino breeds. Their wool weighed 21,387 lbs., and sold for $10,521. This town is remarkable for the longevity of its inhabitants; which is doubtless owing to the purity of its air and water.

Windsor contains beds of serpentine and soapstone. It is 117 miles W. by N. from Boston, 18 N.N.E. from Lenox, and 12 E.N.E. from Pittsfield. Incorporated in 1771. Population, 1837, 887.
The New England Gazetteer containing descriptions of all the states, counties and towns in New England: also descriptions of the principal mountains, rivers lakes, capes, bays, harbors, islands and fashionable resorts within that territory. By John Hayward, author of the Columbian Traveller, Religious Creeds, &c. &c. Boston: John Hayward. Boyd & White, Concord, N.H. 1839
1845 - WINDSOR. [Pop. 897. Inc. 1771.]
This town was at first called Gageborough, in honor of the last British Governor of the Province; but, just after the Revolution commenced, the name was changed to Windsor.

Windsor originally contained a part of Cheshire,

Branches of the Housatonic and Westfield River rise within a few rods of each other. On the Housatonic, is a beautiful fall of water.

The soil is various, but is best adapted to grazing. Distance from Lenox, 18 miles ; from Boston, 120.
An Elementary Geography for Massachusetts Children by William Bentley Fowle and Asa Fitz, 1845
Windsor Massachusetts, 1890
Windsor is situated in the northeastern part of Berkshire County, about 150 miles from Boston, and 12 miles from Pittsfield and 7 from Dalton by highway. The last two afford the nearest railway stations. The villages are Windsor Hill (Windsor P.O.) at the centre, and East Windsor (P.O.), or Jordanville, in the extreme southeast.

Savoy bounds this town on the north; Plainfield and Cummington, on the east; Peru and Hinsdale, on the south; and Dalton and Cheshire on the west. The farms are reported in the State census as containing 23,204 acres, of which 7,306 acres were woodland. The assessed area is 21,795 acres. The township is about seven miles in length and five in breadth. The geological structure is calcareous gneiss and the Quebec group, in which abound the minerals, zoisite, actinolite and rutile. The general surface is not greatly varied in altitude, yet there are several considerable elevations, of which the most prominent is Windsor Hill, near the centre, which bears a... Read MORE...

1895 - Windsor
Windsor, or Windsor Hill, a post-hamlet in Windsor township, Berkshire co., Mass., on an elevated site, about 13 miles E.N.E. of Pittsfield. It has a church. Pop. of the township, 624.
Lippincott's Gazetteer of the World: A Complete Pronouncing Gazetteer Or Geographical Dictionary of the World Containing Notices of Over One Hundred and Twenty-five Thousand Places ... Joseph Thomas January 1, 1895 J.B. Lippincott
Windsor has something for everyone. Here's a list to get you started:
Windsor Jambs State Park:

Start your visit with a trip to Windsor Jambs State Park. It's a scenic park with hiking trails, picnic areas, and a beautiful waterfall. The park offers an excellent opportunity for hiking, bird watching, and photography.

Notchview Reservation:

This reservation is part of The Trustees of Reservations network and offers a fantastic setting for cross-country skiing and snowshoeing during the winter months. In the summer, it's a great place for hiking and exploring the rolling hills and meadows.

Savoy Mountain State Forest:

Located nearby in Savoy, this state forest features miles of hiking trails, a pristine lake for swimming and boating, and a variety of camping options. It's an ideal spot for a day of outdoor adventure.

Hawley Bog Preserve:

Nature enthusiasts will love the Hawley Bog Preserve, a unique ecosystem home to diverse wildlife, including beavers, otters, and rare bird species. The boardwalk trail offers an up-close look at this ... Read MORE...

Discover YOUR Roots: Windsor Ancestry

Ancestors Who Were Born or Died in Windsor, Massachusetts, USA

We currently have information about 24 ancestors who were born or died in Windsor.

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Updated: 10/7/2023 9:29:14 AM