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United States: Northeast covers the northeastern twelve US subdivisions: Maryland, DC, New York, Delaware, New Jersey, Pennsylvania and the New England states.

Connecticut

The shield of arms on the current flag of Connecticut shows three grapevines on a white field. These redesigns instead use thirteen hexagonally arranged purple circles, resembling a cluster of grapes; the number of grapes is a reference to the original thirteen states, of which Connecticut was one.

I think I chose a vertical triband in the original blue version of my proposal for the central white stripe to resemble a scroll of paper, representing the Constitution State. The vertical blue stripe on the second flag represents the state's namesake river, which flows vertically through the state. The third is a version of the first using the purple color from the grapes for the background.

Note that I made the first two proposals long before I first saw AlternateUniverseDesigns' proposal, which uses a similar thirteen-grape emblem.

This fourth proposal combines the grapes with an oak, symbolizing the other (arguably older) popular symbol of Connecticut, the Charter Oak. The inclusion of the oak in a canton is based on several other proposals seen on the Connecticut article. A second version similarly uses three oak leaves, harking back in number to the current grapevines (which represent the Connecticut Colony's first three towns); a third and fourth are essentially inverted versions of the second.

Delaware

Like several other of my first few US state flag proposals (e.g. Pennsylvania and New York below) I used the colors from the coat of arms as background design, in this case blue, white and green. In the center is the buff diamond from the current flag. Earlier non-included versions use the exact blue-white-green horizontal tricolor from the coat of arms.

A newer proposal is based on the national flag, consisting of thirteen stripes in the state colors of buff and (colonial) blue. In the center is a white diamond, with inside it a blue lone star, representing Delaware arguably being the first state.

This set of proposals combines several symbols: the buff and blue and the diamond from the current flag; the blue and yellow Nordic cross from the flag of Sweden, representing the New Sweden colony; and the coat of arms of De La Warr, after which the state was indirectly named (inspired by BigRed618's proposal).

Proposals 3 through 5 are unevenly quartered reminiscently of a Nordic cross; #4 uses zigzag stripe divisions in reference to the West part of the De La Warr arms, while #5 uses the colors from the entire arms. #6 and #7 contain twelve diamonds surrounding a large one (representing Delaware as one of the Thirteen Colonies), bordered by the zigzag stripes. #8 uses a horizontal stripe in a black and white vair pattern with thirteen undivided pieces. All include the single star.

I've since figured that the arms of the specific baron of De La Warr whose name was given to the state, Thomas West, would probably not have included the red-yellow-vair Sackville part of the coat of arms, since the first Sackville to become Earl De La Warr did so more than two centuries after West. These proposals, based on proposal #2 above, therefore only use the zigzag from the West arms.

Maine

These redesigns for Maine were inspired by that by VulcanTrekkie45, many of whose flags are banners of the coats of arms of each state's founder, in this case Ferdinando Gorges's (Lozengy Or and Azure, a chevron Gules). My versions combine it with the previous state flag: a star and pine tree on a buff background.

Massachusetts

My first Massachusetts flag keeps the white background from the current flag, and adds a blue stripe at the fly, representing the namesake Massachusetts Bay to the east of the state. The downward-pointing arrow in the center of the white field and the star in the canton are from the shield of arms.

A newer proposal uses the state colors of cranberry, green and blue in a white-fimbriated vertical tricolor (somewhat similar to the red-green-blue flag of Mars). A pine tree, symbol of the New England region and used on the current Massachusetts naval ensign, is in the center. A third flag combines a rotated version of the tricolor with the arrow and star.

New Hampshire

For New Hampshire I decided to use the flag of the state's namesake, the county of Hampshire in the UK, as base design: a red and yellow bicolor. The rising sun on my proposal is taken from the current flag; its nine rays symbolize NH being the ninth state to ratify the constitution (a fact represented on the current flag by the nine stars around the seal).

These flags are also based on the Hampshire bicolor, but switch its colors, like several other flags of "New" states/provinces that use inverted versions of elements from their namesake's flag (particularly Nova Scotia and proposals for New Brunswick and New York).

The second proposal is charged with the blue-red gyronny from the canton of one`of two flags of the 2nd New Hampshire Regiment (the other consists of red and yellow Union Jack-like crosses on blue). The third is the least radical, and uses a simplified version of the state seal as charge.

Some more variations on the Hampshire colors, the seal and both regiment flags.

New Jersey

Much like the ones for New Hampshire, I based most of my proposals for New Jersey on the flag of the place it was named after: the British crown dependency of Jersey. The flag of Jersey has a red saltire (diagonal cross) on a white background; my New Jersey flags hence also use a saltire, though in the state colors of blue and buff.

The first two of the proposals above incorporate a red triangle, which was intended to allude to the Phrygian cap as well as the cornucopia, the items held by the supporters of the current arms, representing the state motto, "Liberty and prosperity". The third, of which the later seventh proposal is an inversion, is charged with a blue-and-white version of the shield of arms, which consists of three ploughs on a blue field.

This flag combines the saltire with an orthogonal cross formed by thirteen red lozenges, representing the thirteen colonies. The lozenges are based on the state's military crest, in turn based on the arms of George Carteret (who owned and named New Jersey), as found by Leonardo Piccioni at the Flags Forum.

These are combinations of the saltire with the interlaced diamonds from a 2012 proposal by Literally Hyperbole and/or Aryq. The diamonds in that flag represent "the general shape of the state and (...) the distinct but connected regions of North Jersey and South Jersey. (...) The white is also a symbol of the urban, modern New Jersey, the yellow a symbol of rural, agrarian New Jersey."

New York

My initial proposal is based directly on the coat of arms: a blue stripe for the sky, a green stripe for the mountains and land, and a somewhat simplified thirteen-rayed rising sun. I made some versions using the blue-white-orange colors from the former Dutch flag, symbolizing the region's Dutch rule in the seventeenth century, after seeing this wiki's New York page and the many existing proposals incorporating these colors.

Many proposals for New York use the White Rose of York as a reference to the state name. These proposals instead represent the state's direct namesake, James, Duke of York (who would later become king of England and Scotland), using the ermine differencing from his pre-monarchical coat of arms.

Based on BigRed618's proposal, a crescent symbolizes the Halve Maen (Half Moon), the Dutch ship with which English captain Henry Hudson (additionally represented in the sixth proposal by the fleurs-de-lis from his arms) sailed to the region in 1609.

I've seen several designers argue against the use of orange, white and blue for an NY state flag, due to their use by New York City (whether because of perceived Downstate-centrism or just risk of confusion) or overemphasis on the state's Dutch/European history, and instead use the state colors of blue and gold. Despite NY sharing these colors with at least six other states and not having adopted them officially, I do think it has a claim to them in terms of what I think might work on the state flag.

The first two of these desings consist of a gold voided cross on blue. #7 takes the current flag's eagle holding a globe (the crest of the state coat of arms), a somewhat pompous yet possibly suitable emblem for the Empire State. #8 and #9 use the aforementioned rose, which in addition to being a symbol of (old) York is also the NY state flower. #8 surrounds the rose by a string of wampum, which is traditional symbolic beadwork of the Iroquois and other local native tribes that was used as currency for trading in the colonial time. Wampum beads were also depicted on the seal of the New Netherland colony, and a treaty between the Iroquois and Dutch was named after a wampum pattern of white and purple stripes, which is depicted in #9.

Pennsylvania

Like many others I think Pennsylvania's keystone would be a great emblem for a new state flag. I used a horizontal tricolor in the blue, yellow and green colors from the coat of arms as background design for my original proposals, with a keystone in either the canton or the center.

I also made some flags based on existing proposals. The third displayed proposal modifies Philip Tibbetts' proposal, which is a banner of the arms of William Penn with a green background (together referring to Pennsylvania's etymology as "Penn's woods") and a key in the central disc (referring to the keystone). I simplified his flag by removed the key, and modified the dimensions.

Lastly, the third "own" proposal combines Tibbetts' green background with the keystone bearing Penn's arms from BigRed618's proposal. I made a version without the white stripe as well, though that turned out to be effectively identical to a proposal by Peregrine.

Also using the keystone-with-Penn-arms, these two flags use the blue-white-yellow color scheme from the state's license plates.

Rhode Island

The first of my proposed flags of Rhode Island is a greatly simplified version of the current flag, keeping only the yellow anchor as charge. I replaced the yellow fringe with narrow yellow horizontal stripes on either side of the white field. Several later proposals use as main emblem thirteen stars arranged in the shape of an anchor.

For these flags, I represented the two parts of the state by two vertical stripes: white for the Providence Plantations (which was founded as a place of religious liberty, as reflected in its name), and red for Rhode (Aquidneck) Island (the most popular etymology for which is the old Dutch translation of “red island”). The blue central stripe symbolizes the bays that separate them, as well as the state’s nickname, the Ocean State.

Proposals 6 and 7 are variations on Philip Tibbetts' proposal, which similarly to some of mine combines symbolism of the state's two parts. One difference with my fourth and fifth proposals is that it represents the Providence Plantations by a chevron, in reference to the triangle of the Eye of Providence. #6 uses a white triangle and diamond that touch the fly side of the flag, and a red anchor; #7 omits the diamond and charges the chevron with a red anchor.

Vermont

My December 2013 proposal for Vermont contains a white triangle with the top side of the flag as its base, alluding to the letter "V" as well as the shape of the state. It incorporates a silhouette of the pine tree from the coat of arms.

I created two additional proposals in December 2014. Both have fields quartered per saltire, keeping the downward-pointing triangle but adding a green upward-pointing triangle which refers to the state name (mont vert = green mountain), inspired by one of Voron Xarya's proposals. The first uses the colors from my earlier proposal; the second uses the officially proposed state colors of green and gold.

Two more flags using triangles, these are horizontal bicolors of gold and green with two counterchanged triangles sharing their bases. The counterchanged rectangle in proposal 4 and the green gem-shaped pentagon in proposal 5 help the green triangle resemble a pine tree and the gold triangle resemble a "V".

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