The Model 1866 was the gun that started it all for Oliver Winchester’s company, though it went though several variations during its production making them highly collectible. Rock Island Auction Company’s Dec. 6-8 Premier Auction in Bedford, Texas will offer several variations of this legendary Winchester lever action with some of the outstanding examples shown below, noting the differences.

The Model 1866 was the first gun to bear the Winchester name after the New Haven Arms Henry Rifle of the Civil War and the company’s reorganization to reflect Oliver Winchester’s name. The 1866, known as the “Yellowboy” because of the distinct color of its gunmetal frame, was introduced shortly after the war. With about 170,100 Model 1866s produced in rifle, musket and carbine configuration, it saw widespread use in every corner of the United States and beyond. The gunmetal alloy frame proved to be durable in the harsh environments of the American West than iron frame guns.

The company didn’t initially call the rifle the Model 1866 until its successor, the Model 1873 was introduced. Before that, it was commonly referred to as the “Improved Henry,” “Winchester Repeating Rifle,” or the “Sixteen Shooter.”

Winchester 1866 First Model

First off, let’s cover all four models of the quintessential Winchester 1866. We’ll start with this extremely rare, first model Winchester 1866 flatside carbine. Known as a “flatside” thanks to its flat loading gate and its lack of fore end flare or “lip,” these models were the first year production of the first Winchesters even if they did still bear the Henry patent. However, the patent wasn’t the only reminder they carried with them of their former namesake; they also have the telltale “Henry drop” at the rear of the receiver, an additional screw in the upper tang, and no exterior serial number.

This Winchester 1866 has the desirable, early production, flatside receiver and loading gate, and two-line Henry and King’s patent barrel address (very faint). The matching serial number is stamped on the left side of the lower tang, stock inlet, and buttplate. It is fitted with a blade front sight integral to the front barrel band, a two-leaf rear sight, and a saddle ring mounted on the left of the receiver.

A closeup of this early Winchester 1866 shows the flatside loading gate.

Winchester 1866 Second Model

The second model Winchester 1866 rifles are also easy to tell once you know the signs. These models have less of the “Henry drop” in front of the hammer, still bear the Henry patent, and in its early serial number range, the numbers are still placed on the inside of the gun. These guns are also no longer “flatsides” because the loading gate is scalloped and the front end of the receiver is flared to accommodate the fore end. Looking at this gun, it is hard to believe that it is over 100 years old! Look at the high condition of the brass and the crisp factory engraving.

This incredible second model Winchester 1866 features the Henry patent marking on the barrel. The gun is inscribed to Daniel C. Murphy” on the upper left of the frame and “San Francisco 1868” on the upper right. features a Beach combination blade and globe front sight which was then a brand new innovation given it was covered by U.S. patent no. 63690 of April 9, 1867, granted to Edgar B. Beach (1837-1925) of West Meriden, Connecticut, for an “Improvement in Convertible Rifle Sights.” The Beach sight gives the option of a blade, globe, or a post on top of the globe as sighting options.

The factory engraving on this Winchester 1866 is in the early “Samuel Hoggson” style used by Winchester in the 1860s. Similar examples can be seen on page 66 and 67 of “Winchester Engraving” by R.L. Wilson. The engraving on the forend cap, frame, and buttplate primarily consists of scrollwork on beaded backgrounds, and there are also additional floral designs and borders on the frame. In addition to the engraving, this rifle has a gold plated finish on the brass/gunmetal components and a beautifully figured deluxe walnut stock.

Winchester 1866 Third Model

Third Model Winchester 1866 rifles smooth out the “Henry drop” even more and are the first to have a serial number on its exterior. These models had those numbers behind the triggers (with few exceptions) and were the first to lose the Henry patent information. Instead they have the “King’s Improvement” lettering. This particular model was shipped in 1870 when the west was still untamed. Its attractive dark patina and wood show this saddle ring carbine was a working gun.

This third model Winchester 1866 manufactured in 1870 has a frontier-issued appearance.

This third model Winchester 1866’s barrel and magazine tube having an attractive dark patina with slight traces of original blue finish in the protected areas associated with a frontier issued arm. The brass is fine and has a pleasing appearance. The receiver has tight fitting side plates.

Winchester 1866 Fourth Model

The fourth and final stage in the evolution of the Winchester 1866 almost smooths the “Henry drop” out completely and moves the serial number to the rear of the tang, though there are variances to this serial number placement. The font of the serial number also changes from very block like to a more script-like appearance. These, of course, are only the most noticeable changes that took place in these iconic firearms. To list all the changes and to do so accurately, would take an entire book! Thankfully George Madis has provided just such a reference for the motivated collector.

The included factory letter lists this fourth model Winchester 1866 as a carbine when received at the warehouse on 13 December 1879, that was changed to a 24-inch octagon barrel on Feb. 23, 1880, and that it was shipped two days later.

This fourth model Winchester 1866 features an iron buttplate instead of brass, a serial number stamped in script, and an even less pronounced drop at the top rear of the frame as compared to proceeding models. These fourth models are found starting in the 149000 serial number range and carried on until the end of production c. 1898.

Ulrich Engraved Winchester 1866

The evolution of the Winchester 1866 variations is only one facet of the exciting class of Winchester 1866 rifles present at this sale and the next gun is a clear indicator of that fact. Behold the ultra-rare, C.F. Ulrich engraved and signed, nickel plated Winchester model 1866 musket with its bayonet. Start with a Winchester 1866, which is a collectible in and of itself, now make sure it’s an extremely rare musket version, next make it even more rare with a special nickel finish, then make sure it’s downright scarce on account of its factory engraving, and complete this exercise in rarity by having those engravings be the work of Master Engraver C.F. Ulrich who happened to sign this remarkable firearm! Not to mention the matching bayonet. There’s not even a Ulrich signed or engraved Winchester 1866 musket shown in R.L. Wilson’s “The Book of Winchester Engraving” nor in Madis’ authoritative work.

This ultra rare, exhibition grade Winchester 1866 musket has a nickel finish and engraving by Master Engraver C.F. Ulrich. Ulrich’s signature can be seen to the right of the serial number as shown. It has a distinctive 27-inch round barrel with 24-inch magazine and long (17-inch) forearm, three barrel bands and block-mounted front sight that serves as a lug for a socket bayonet.

This brilliant Winchester 1866 musket was engraved by Master Engraver C.F. Ulrich with American style scrollwork on a punch-dot background. A face is partially hidden in the scrollwork of the left side of the receiver in a style more typical of Gustave Young. Both sides of the receiver are decorated with stylish open panels and shields. The scrollwork panels are separated by elaborate engraved borders.

The previous gun is amazing in its own right, but this 1866 carbine model has nickel plating on its barrel bands, receiver, hammer, lever, and carbine buttplate. It too exhibits a full grade coverage of Germanic scrollwork on a punch dot background with scalloped borders. The gun even has the distinct honor of also being signed by this C.F. Ulrich, but the true “Wow factor,” as if those reasons weren’t enough, comes from this gun being consecutively serial numbered to the first!

This nickel-plated Winchester 1866 carbine is consecutively serial numbered with the previously mentioned musket and also features engraving by Master Engraver C.F. Ulrich who signed it next to the serial number.

The outstanding engraving by Master Engraver C.F. Ulrich pops off the nickel-plated finish of this winchester 1866 carbine. The top, sides and bottom of the receiver (including the upper and lower tangs) and the buttplate heel are decorated with full grade coverage Germanic scrollwork on a punch-dot background with scalloped borders. There are open panels on both sides of the receiver and both side plates as well as a open scroll on the upper tang.

These guns are as close as it gets to looking like they just left the factory floor. To have two of such superior quality, let alone two that are consecutively serial numbered, after the many years since their production, is almost unfathomable.

But consecutive serial numbers isn’t all our Winchester 1866 models have to offer. There will be special finishes, muskets, saddle ring carbines, sporting rifles, and signed Ulrich engraved pieces, and supremely high condition examples. If you love early Winchesters, you’ll be hard pressed to ever find more variety and better condition than at our May Premiere Firearms Auction.

A parting shot of this brilliant pair of consecutively numbered, nickel-plated and C.F. Ulrich-engraved Winchester 1866s, one a musket, the other a carbine.

Henry Rifles

These Winchester 1866 examples are also offered alongside an outstanding selection of Henry rifles that preceded the Model 1866. In fact, some of the 1866s on offer offer bear the Henry patent marking. Among the Henry rifles, collectors will find an extremely rare iron frame example as well as several with Civil War connections.

An extremely rare iron frame New Haven Arms Co. Henry rifle. The Henry rifle was the Winchester 1866’s predecessor.

Winchester Model 1866 Rifles, Carbines and Musket for Sale

While the auction features a fantastic selection of Winchesters — from lever guns to slide action rifles to shotguns to sporting rifles – the December Premier Auction features an amazing slate of highly collectible arms from Colt revolvers to modern guns to Class III guns.

Keep in mind, these Model 1866s are only a few selections of a single model from a sole manufacturer but they serve as an indicator of the quality and quantity of first-class collector and investment grade firearms that permeate this entire sale. To see more of what is appearing in this auction, please visit the Dec. 6-8 Premier Auction online catalog.

• This blog was originally posted April 9, 2014. Updated November 2024.