Tramp

The highways of the Sword Coast—though little more than dirt ruts in prairie grass and mountain rock—are home to many outcasts of the world. Among the loose-knit communities of these outcasts is a wanderer-warrior tradition called the Tramps.

Comfortable in a life of homelessness, Tramps are often former soldiers and heroes who have found that their lives are most complete when walking the well-beaten paths of Faerun. Some are the leaders of groups of highwaymen, extorting the traveling folk for money. But just as many are open-hearted defenders of the weak and ill and see the roadways as their sacred ground and the travelers through them as pilgrims needing protection through the cruel beauty of the Coast’s roads.

Survival is difficult every day, and the monsters of the wilds often encroach on the lands close to the roads. The Tramps fight back against these evils with a mixture of luck, cunning, and a unique approach to the sword-and-shield that focuses on studying opponents’ weaknesses and dealing pin-point-accurate and deadly attacks (in contrast to most shield traditions which focus on defense). Knowledge of this fighting technique is passed down through generations of oral storytelling, tramp to tramp. It is this knowledge and the accompanying appreciation for the houseless spaces between the cities that has made from outcasts and beggars an incredible tradition of scruffy fighters.

Wanderer's Instincts

When you choose this archetype at 3rd level, you gain proficiency in one of the following skills of your choice: Athletics, Perception, or Survival. Furthermore, you may add your Intelligence modifier to Initiative rolls.

Iron and Wood

Starting at 3rd level, when you score a critical hit with a short sword, longsword, or shield (see below), you may re-roll the damage result up to 2 times (but must choose when to "stop" and take that result). The number of re-rolls increases when you reach certain levels in this class, increasing to 3 at 5th level, 4 at 10th level, and 5 at 15th level.

Furthermore, for you shields count as martial offhand weapons (1d4 base). As such, when wielding a sword and shield, you may make a Shield Bash attack as a bonus action: 1d4+proficiency+STR+(weapon modifiers/other).

The Knowledge of Grasses

Starting at 7th level, your wanderlust has made your mind keen. You possess incredible attention to detail in your surroundings and company. You may add your Intelligence modifier to Wisdom (Insight) and Wisdom (Perception) checks. Also, gain knowledge of one of the following languages: Halfling, Dwarven, Elven, or Goblin.

The Highway Way

Starting at 10th level, when you use Iron and Wood to reroll critical damage you add your intelligence modifier to the total.

In addition, you gain proficiency in Wisdom saving throws (if already possessed, gain proficiency in Constitution or Intelligence.)

Smarter than Death

Starting at 15th level, when wearing a shield and wielding a short or longsword, you add your intelligence modifier to damage rolls with these weapons (this stacks w/damage granted from The Highway Way).

Last Road Home

Starting at 18th level, once per long rest, you may add your Intelligence score to your damage roll on a successful melee attack. Following this attack, you take damage equal to half your current total and disadvantage on all rolls for the remainder of the encounter.