Rip Van Winkle, “The Eternal Dreamer”

“Unbelievable! Meet Rip Van Winkle, the Man Who Slept for Centuries and Woke Up in a Whole New World!”

• Alias: Rip Van Winkle
• Gender: Male
• Race: Human
• Occupation: None (formerly a laborer)
• Religion: Undefined (Not explicitly mentioned in the story)
• Allies: The villagers of his hometown
• Enemies: None (though he experiences occasional conflicts due to his prolonged absence)
• Abode/Base of Operations: A small village in the Catskill Mountains
• Nationality: American
• Languages: English
• Alignment: Neutral Good
• Affiliation(s): None (Rip is not affiliated with any specific group or organization)
• Significant others: His wife, Dame Van Winkle

Rip Van Winkle is an enigmatic figure caught between the realms of reality and myth. Known for his extraordinary slumber, Rip is a man of humble origins, living in a small village nestled in the picturesque Catskill Mountains. With his disheveled gray hair, unkempt beard, and a weathered face etched with the marks of time, Rip’s appearance mirrors his unconventional life.

Having led a carefree and idle existence, Rip often finds himself escaping the monotony of everyday responsibilities by venturing into the surrounding wilderness. It is during one of these ventures that he stumbles upon an encounter that changes his fate forever. Seeking respite from his nagging wife, he wanders into a secluded glen and succumbs to a deep sleep, enduring a timeless slumber that spans decades.

As Rip awakens, disoriented and disbelieving, he discovers a world transformed. The village he once knew has evolved, and familiar faces have aged or vanished. In this newfound reality, Rip navigates the challenges of adapting to a society that has moved on without him, wrestling with a sense of displacement and yearning for the familiarity of the past.

Driven by an insatiable curiosity and a desire to reconnect with his lost identity, Rip embarks on a quest for self-discovery. He seeks to understand the passage of time, reconcile his place in this changed world, and ultimately find a sense of belonging. Along the way, he encounters both kindness and indifference, weaving his way through the tapestry of life as he seeks solace and purpose.

Rip Van Winkle is a middle-aged man with disheveled gray hair and a thick, unkempt beard. His face bears the wrinkles of age and weariness, hinting at the many years he spent in slumber. He is dressed in tattered clothing, remnants of a bygone era, which further emphasizes his disconnection from the present. Despite his unkempt appearance, there is a glimmer of wisdom and resilience in his eyes, reflecting the depth of his experiences.

Though plagued by moments of nostalgia and a longing for the simpler times of his youth, Rip’s journey becomes a testament to the resilience of the human spirit. He learns to adapt, to appreciate the beauty of life’s fleeting moments, and to embrace the gift of second chances. Through his encounters and experiences, Rip discovers that while the world may change, the essence of humanity remains timeless.

Rip Van Winkle

Medium humanoid (human), neutral

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Armor Class 13 (leather armor)
Hit Points 58 (9d8 + 18)
Speed 30 ft.

STR	DEX	CON	INT	WIS	CHA
10 (+0)	14 (+2)	14 (+2)	12 (+1)	12 (+1)	16 (+3)

Saving Throws Wis +3, Cha +5
Skills History +4, Insight +3, Persuasion +5
Senses passive Perception 11
Languages Common
Challenge 3 (700 XP)

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Actions

Rusty Musket. Ranged Weapon Attack: +4 to hit, range 40/120 ft., one target. Hit: 7 (1d12 + 2) piercing damage. If the target is hit, it must succeed on a DC 13 Constitution saving throw or be incapacitated for 1 minute.

Slumbering Charm (Recharge 5-6). Rip Van Winkle casts a sleep-inducing charm in a 30-foot cone. Each creature in that area must make a DC 13 Wisdom saving throw. On a failed save, a target falls into a deep slumber and is unconscious for 1 minute or until it takes damage or is awakened.

Evasive Step. As a reaction, when Rip Van Winkle is targeted by an attack, he can use his uncanny reflexes to dodge out of harm’s way. He gains a +4 bonus to AC against the triggering attack.

Lair Actions

On initiative count 20 (losing initiative ties), Rip Van Winkle takes a lair action to manipulate the flow of time within a 60-foot radius centered on himself. Rip can choose one of the following effects:

• Temporal Distortion: Rip Van Winkle casts the slow spell on all creatures of his choice within the area. The affected creatures must make a DC 13 Wisdom saving throw or have their speed halved, take a -2 penalty to AC and Dexterity saving throws, and can’t use reactions. On their turn, they can either use an action or a bonus action, not both. They also can’t make more than one melee or ranged attack during their turn.
• Time Slip: Rip Van Winkle teleports up to 30 feet to an unoccupied space he can see within the area. He can then make a single attack or use his Slumbering Charm as a bonus action.

Equipment

• Leather armor
• Rusty musket
• Tattered cloak
• Weathered backpack containing various trinkets and items from a bygone era.

Abilities

Timeless Slumber. Rip Van Winkle has advantage on saving throws against being charmed, frightened, or put to sleep magically. Additionally, magical effects that would age him or alter his physical appearance have no effect.

Lingering Confusion. Rip Van Winkle’s presence and actions often confuse and disorient his opponents. Whenever a creature within 10 feet of him makes an attack against him, it has disadvantage on the attack roll.

Eternal Wanderer. Rip Van Winkle is immune to exhaustion and does not require sleep. He does not age naturally and cannot be magically aged.

Idiosyncrasies

Rip Van Winkle, although initially disoriented and unaware of the passage of time, is a skilled marksman with his rusty musket. His ability to induce slumber reflects the prolonged sleep he experienced in the legends. His lair actions, involving temporal manipulation, represent his connection to the distorted passage of time. He is clad in worn and weathered attire, adorned with a tattered cloak that seems to carry the weight of forgotten years.

CR Level

Rip Van Winkle is assigned a challenge rating of 3 (700 XP), taking into account his combat abilities, the potential impact of his Slumbering Charm, and his evasiveness in battle.

Please note that the above representation is a homebrew adaptation of Rip Van Winkle into the D&D 5th Edition system and may require adjustments based on the specific campaign or setting.

Currently in the World

Rip Van Winkle is a middle-aged man of average height and build. His once-brown hair has now turned gray and falls untidily over his forehead. He sports a thick, unkempt beard that adds to his disheveled appearance. Rip’s face bears the weathered lines and weariness of a life spent outdoors, with a hint of kindness in his weary eyes.

Currently, Rip Van Winkle is lounging beneath the shade of a massive oak tree, surrounded by the picturesque beauty of the Catskill Mountains. The serene atmosphere of the mountain village is enhanced by the soft rustling of leaves and the distant chirping of birds. Rip is dressed in tattered and outdated clothing, reflecting his detachment from the passing of time.

His mood is one of deep contemplation mixed with a touch of confusion. Having recently awakened from a 20-year slumber, Rip finds himself bewildered by the changes that have occurred in his absence. He grapples with a sense of longing for the familiar past and a desire to navigate the unfamiliar present. Rip Van Winkle’s current surroundings serve as a backdrop to his contemplative state, evoking a mixture of nostalgia and curiosity.