Some antique guns need no introduction. This is especially true for Winchester Model 1866 rifles, because they WERE the introduction! With a deep-rooted American heritage, this antique gun led an entire industry for nearly a century. This guide will help to identify the Winchester Model 1866 and provide insight about value if you decide it’s time to sell your gun. Let’s look at the Winchester Model 1866 and learn exactly how to identify one of the best antique guns on the market.

Two 66 Winchester long guns, a rifle (top) and a carbine (bottom.)

First of all, the Winchester 1866 and every model thereafter, came in all sorts of special order varieties, so if yours doesn’t fit an exact definition found here, that’s OK. Take it with a grain of salt and start investigating your specific rifle. These antique guns may have differing variations from the factory, a period modification, or a modern change. Variations from the factory are numerous and affected everything: front sights, rear sights, grooves in the rifling, end caps, markings, screws, side plates, loading gates, sling loops, buttplates, and so on. These often changed several times throughout the 1867 – 1898 production run.  Most other features could be custom ordered (wood type, barrel length, shotgun butt, plating, engraving, etc).

The “standard” features of the antique guns are listed in their respective areas, most frequently covering barrel length, magazine length, and the stock. However, one feature that can be found in nearly all Winchester 1866 models is the caliber: .44 Henry rimfire. A few late production Winchester 1866 rifles were configured to fire .44 Henry centerfire, and period conversions may have been performed to fire .44 Henry CF or other .44 caliber cartridges available at the time. Long story short, if your 1866 isn’t in .44 Henry RF, you have some investigating to do.

The unique yellow tint of the gunmetal alloy gave Winchester’s first lever action rifle its distinct look and "Yellowboy" nickname.

Identifying Winchester 1866 Antique Guns

Confused what you have? Let’s narrow down what it’s not. In the picture below is a Winchester 1866 with another rifle it is often confused with: the New Haven Arms Henry Rifle.

Early Winchester rifles helped shape the country and tame the frontier. Their predecessors helped push firearm design and even served in the American Civil War. If you've ever wanted one to call your own, RIAC's Sporting & Collector Auctions are the place to go.

People often see the yellow “brass” receiver (which is actually a bronze alloy called “gun metal”) and may quickly jump to a conclusion depending on which model they’re more familiar with. However, inspecting the two side-by-side quickly reveals significant differences in both appearance and design. First, one will notice that the right side of the receiver possesses a loading gate, where the Henry rifle does not.

A Henry rifle (top) compared to a First Model 66 Winchester "Flatside" rifle (bottom.) The Henry pictured here is a U.S. martially inspected second contract rifle inscribed for Archibald McAlister of Co. E of the Pennsylvania Regiment Volunteer Corps and the 3rd Regiment of Veteran Volunteers.

The Henry must be loaded via the magazine tube near the muzzle and because of this has an external follower that must be manually depressed prior to loading. It is the absence of this exposed follower that allows the Winchester 1866 to have a fully enclosed magazine and a wooden fore end under the barrel. This keeps dirt out of the magazine, protects the hollow metal tube magazine, and allows for better handling of the antique gun. Other changes are internal as are some of the barrel markings as the company transitioned from the New Haven Arms Company into Winchester Repeating Arms.

The rifle that came after the Winchester 1866 is the Winchester Model 1873. Let’s take a look at a few of their differences.

The most visually defining distinction, of course, is the color of the receiver. Model 1873 rifles were originally created with forged iron, but in 1884 switched to forged steel; available either blued or case-hardened. Next, notice, the raised sideplates on each side of the receiver of the 1873. The “Gun the Won the West” also incorporated a dust cover over the ejection port in the top of the receiver, though this went through many changes. Not visible to the naked eye, the frame for the 1873 was made much stronger than that of the Winchester 1866; allowing this antique gun to take advantage of the recent advances in cartridge technology and fire more powerful rounds. Once the switch to steel was made, the rifles were also lighter and cheaper to produce. The 1873 also incorporated a trigger block, which prevented the gun from firing if the gun were not completely in battery. This is not a key identifying feature, but is worth mentioning here as the rifles’ differences are detailed.

Lengths of Winchester 1866 Antique Guns

That said, the Winchester 1866 came in three different styles: rifle, carbine, and musket.

66 Winchester Rifle

The standard configuration for the rifle is a 24-inch  octagon barrel, crescent buttplate, and a full-length magazine. More could be written about standard markings and features, but as mentioned earlier, they changed so frequently throughout their production that listing the changes requires a thorough reference work. Rifles were the second-highest produced Winchester 1866, trailing far behind the ubiquitous carbines.

66 Winchester Carbine

Often referred to “Saddle Ring Carbines” or abbreviated as “SRC” these were smaller than the Winchester 1866 antique guns. This can be seen in the shorter barrel and forearm, as well as the lack of a forend cap.

From top to bottom, the Winchester Model 1866 musket, the Winchester Model 1866 rifle, and the Winchester Model 1866 carbine.

As the nickname implies, a mounting loop and ring were affixed to the left read side of the receiver so that the firearm could be secured while a riding a horse, either being tied to the saddle or worn by the rider via a carbine sling. Also note the presence of a barrel band in lieu of the fore end cap. Their standard configuration is a 20-inch round barrel and a full-length magazine. The butt stock will vary with the crescent butt stock (shown here) or carbine butt stock (as shown on the musket below).

A Winchester Model 1866 lever action saddle ring carbine manufactured in 1869 and later converted to .44-40 WCF centerfire.

66 Winchester Musket

Often confusing to those unfamiliar, the Winchester 1866 musket is not a muzzle loading longarm. “Musket” is merely a term given to to longer antique guns to differentiate them from other lengths of the same model. However, this term is relatively modern. In 1866, “musket” meant a large bore, long, and clumsy firearm, so Winchester instead termed it the “Infantry rifle.” Very much earning this moniker by looking a lot like a traditional musket, one immediately notices the longer fore end and the additional barrel band. Muskets are far and away the rarest of the Winchester 1866 family, but in the current collecting climate, often do not bring the prices of their more numerous brethren. Standard features of a model 1866 musket are a 27-inch round barrel, 24-inch magazine, 17-inch length fore end, and a flat buttplate with a trapdoor.

Models of Winchester 1866 Antique Guns

There are four different models of the Winchester 1866 rifle, and the differences are slight, but numerous. In fact, subsequent models of Winchester would not go through near so many production changes as the 1866. Later on, Winchester Repeating Arms would run like a finely oiled machine, but in the early years, many changes were incorporated during the production, so the information documenting this model is vast by necessity. Again, this article will attempt to serve as a rudimentary guide and leave the fine detail work to the already well-established resources on the topic.

1st Model

The good news is that 1st Model Winchester 1866 rifles are pretty easy to tell from the rest. They’re often called “flatside” models because the front of the receiver doesn’t flare out to meet the fore end. Some collectors think it’s because the loading gate is flat, instead of with the scallop (a.k.a: recess or cartridge channel) we’re all familiar with, but some 1866 models do possess a scalloped or recessed loading gate. The other telltale feature of a 1st model Winchester 1866 is what is known as the “Henry drop,” even though it was even more distinct in the Henry’s predecessors. This feature is the downward curve of the receiver, forward of the rifle’s hammer. This becomes less pronounced in each subsequent model. 1st models also have an additional screw (two total) in the upper tang and no externally visible serial number. It is stamped on the side of the tang, so the stock must be removed in order to see it. Also not readily identifiable by looking at the outside are the beveled front and back of the sideplates, just like on a Henry rifle. Later models would only be beveled at the front and depend on a long mounting screw to secure the rear. All first model rifles and carbines possess saddle rings, but ensuing models would only see the saddle rings on the carbines. No first models should have a half-cock position for the hammer.

2nd Model

Second model Winchester 1866 rifles are extremely similar to First Models, but when you know what to look for, the differences become readily apparent. First off, the “Henry drop” begins to smooth out in the Second Model, and we also see the introduction of a flared front end of the receiver to meet the fore end. Serial numbers remain hidden until around SN 21000, after which they appear on the lower tang between the trigger and main-spring adjusting screw. Second Models appear in approximately the 15,500 – 25,000 serial number range, and were only available in rifle and carbine styles. Also, half-cock positions began after SN 23,000, so most will not have this feature.

3rd Model

Even less of a “Henry drop” here. This model has the serial number externally stamped in block numerals behind the trigger (with a few exceptions regarding the location). Most have the Henry and King’s patent barrel markings, though the Henry name was eventually dropped, listing only the date in the barrel address. Serial numbers are around 25,000 – 149,000, making it far and away the highest produced of the four models. By the third model, Winchester had worked out many of the early design changes, so in addition to their drastic increase in production, they also began to produce excellent, custom pieces more frequently as well as stunning exhibition works.

4th Model

Here the Henry drop is all but gone and the serial numbers have switched from block letters to a more script-like font located further rearward – between the lever latch and the tang screw. Third and fourth models are so similar, this is often the easiest way to tell them apart. Barrel markings remained the same as the third models. Full magazines and trapdoors in the carbine style buttplate were standard features. Serial numbers range from 149,000 – 170,101.

Hopefully, this article has been of some assistance to those not already familiar with all things Winchester. As you can see, by memorizing a few key characteristics one can quickly become versed in Winchester 1866 rifles far beyond the layperson and even ahead of many other collectors. We look to extend this series with other models of the Winchester rifles. If you have suggestions of other manufacturers and models, we’d love to hear from you in the comments. Thanks for reading and remember to check back every week for more content about about antique guns geared toward collectors at every level of expertise.

The Yellowboy was purchased throughout Central and South America as well, becoming an especially popular firearm of the wealthy elite. This solid silver Winchester Model 1866 rifle, commissioned by President Jose Balta of Peru for presentation to President Mariano Melgarejo of Bolivia, sold for $977,500 in RIAC's December 2021 Premier Auction.

Remember, if you’re interested in shopping for a Winchester 1866 or need help identifying your antique guns, Rock Island Auction can help you find just what you’re looking for to add to your antique gun collection.

The best Winchester lever action rifles for fine arms collectors are available at Rock Island Auction Company.

Sources:

Madis, George. The Winchester Book. Brownsboro, TX: Art and Reference House, 1985. Print.

McDowell, R. Bruce. Evolution of the Winchester. Tacoma, WA: Armory Publications, 1985. Print.

Wilson, R. L. Winchester: An American Legend. Edison: Chartwell, 1991. Print.