The Skylark Guild originally came into existence during the age of the Larkhall hotels, and was first based in a small room in the Skylark Hotel. Both the guild and the hotel were created by apavey1 (now Alias) in December of 2012. The Skylark Hotel was first constructed on December 23 in the Northeast corner of Larkhall. The hotel saw excellent business and soaring popularity, and it was this that prompted apavey to create a guild with the same name as the hotel. Thus, the Skylark Guild.

     The first member of the new Skylark Guild was andrewwang360 (now DaMorlock), who was a resident of the hotel at the time. From there, the guild soon outgrew the small hotel room it was housed in, and the first Skylark Guild HQ was built just west of the hotel. While the guild was based there, the Skylark Hotel fell into ruin and was subsequently demolished. The Skylark Guild, however, lived on. It soon grew to include 21 members and 3 outposts in various worlds, including Carlow, Stockport, and Shefford. In the middle of January of 2013, the Skylark Guild merged with the Red Army (now the RSU) to form the Larkhall Republic. However, the massive Republic proved too hard to manage, and it fell apart in the beginning of February of the same year.

     With the introduction of Guild Obelisks and official guilds, Skylark soon became official in March of 2013 and moved its HQ to a new, larger building, though still in Larkhall. However, soon after the move, apavey retired as leader of Skylark and leadership was handed over to Andrew, the oldest active guild member. After the RSU (then the Red Army) moved out of Larkhall to New Moscow, Andrew decided to move Skylark to Hallasholm (formerly Lowestoft Place), thus ending the golden era of the Larkhall guilds.

     Skylark membership soon dwindled down to two: Tots and superspyrospam, with all of the others having abandoned the guild when apavey stepped down. Tots soon appeared to stop playing Deepworld, and spyro and Morlock were the only active members of the guild. Although Guardofthedragon joined the guild, Skylark seemed to fade away for several months, and many people forgot that it existed. Near the end of 2013, however, Skylark played a major role in the creation of the United Deepworld Guild Association (UDGA). As the UDGA faded away and more new guilds were created, Skylark began to fade into obscurity once again. The guild is now building a new HQ in The Lark Nest and is attempting to recruit new members to the guild.