Pencilvania — Historical Trivia Drawing Game
A Historical Trivia Drawing Game

Pencilvania

Travel across American history one drawing at a time!

Object of the Game

Pencilvania is a team-based historical trivia drawing game that turns American history into a race across famous American trails and routes.

Each turn, one player becomes the Artist. The Artist secretly sees a historical answer and must help their teammates identify it by drawing clues. The challenge is that every card includes Restricted Clues—the most obvious things the Artist would normally want to draw.

Solve the answer early and your team earns more Exploration Markers to advance along that card's color-coded Trail.

Over six rounds, teams explore America, complete trails, collect badges, reach landmarks, and compete to build the longest connected trail. At the end of the sixth round, the team with the most points wins.

Pencilvania board game box and components spread on a table

How to Play

Each round, your team draws 3 cards, each showing a historical category and a color-coded Trail. Choose 1 card to play and discard the other 2.

One player becomes the Artist and secretly looks at the answer, a short History Snapshot, and three Restricted Clues.

Each card contains:

  • Historical Category
  • Answer
  • History Snapshot
  • Restricted Clues
  • Color-coded Trail

The Artist secretly looks at the answer, a short History Snapshot, and three Restricted Clues.

The team begins knowing only the historical category.

How the Game Works

Pencilvania turns American history into a race across the map. Each turn, your team draws 3 cards, looks at the category and color-coded Trail on each, and chooses 1 card to play. One player becomes the Artist and secretly sees the historical answer, a short History Snapshot, and three Restricted Clues. The team then has up to three chances to solve the answer:

First Attempt60 seconds3 Exploration Markers

60 seconds with no Restricted Clues — earn 3 Exploration Markers

Second Attempt45 seconds2 Exploration Markers

45 seconds after unlocking one Restricted Clue — earn 2 Exploration Markers

Final Attempt30 seconds1 Exploration Marker

30 seconds after unlocking a second Restricted Clue — earn 1 Exploration Marker

Every marker moves your team farther along that card's Trail on the U.S. map.

Make Your Mark on History

Every correct answer earns your team Exploration Markers to place on the color-coded Trail shown on that card. The faster your team solves the clue, the farther you travel—earning 3 markers on the first attempt, 2 markers on the second, or 1 marker on the final attempt. As the game unfolds, the map becomes a visual race across America, with each team building connected paths along famous historic routes.

Complete the Trails

Pencilvania features 11 color-coded Trails and Routes, including the Appalachian Trail, Oregon Trail, Santa Fe Trail, California Trail, Lewis & Clark Trail, Trail of Tears, Underground Railroad, Route 66, Transcontinental Railroad, Sea Trail, and Air Trail. Fill every space on a Trail to complete it and earn a Trail Completion Badge. The first team to finish that Trail earns 10 points, followed by 7, 5, and 3 points for later finishers.

Build the Longest Trail

Longer connected routes can be just as important as finishing quickly. The first team to build a connected trail of at least three markers claims the Longest Trail award, and another team must build an even longer trail to take it away. The team holding Longest Trail at the end of the game earns a major bonus. Some Trails also lead to iconic American landmarks—completing those routes adds landmarks to your team's collection and can help you earn the Landmark Collector bonus. Teams are also rewarded for completing the most different Trails, so there's more than one path to victory.

Appalachian TrailOregon TrailSanta Fe TrailCalifornia TrailLewis & Clark TrailTrail of TearsUnderground RailroadRoute 66Transcontinental RailroadSea TrailAir Trail

How to Win

After 6 rounds, every team adds up the points they earned while exploring the map.

Trail Completion BadgesFinish a Trail 1st, 2nd, 3rd, or 4th to earn 10, 7, 5, or 3 points
Longest TrailThe team with the longest connected Trail earns 10 bonus points
TrailblazerComplete the most different Trails for 5 bonus points
Landmark CollectorCollect the most Landmark destinations for 5 bonus points
Unfinished TrailsEvery 2 Exploration Markers on an incomplete Trail are worth 1 point

The team with the most points wins Pencilvania.

Completed Trails do not also score individual marker points—their Trail Badge replaces them. That means there's no single path to victory. You can race to finish short Trails, build a long route, collect Landmarks, or spread your exploration across the map. At the end of Round 6, add everything together.

Why You'll Love It

History becomes something you play, not just something you know.Pencilvania mixes trivia, drawing, deduction, and geography into a game where every round feels different.
Everyone has a way to contribute.You don't have to be a history expert or a great artist. Clever drawings, wild guesses, teamwork, and quick thinking can all lead to the right answer.
The clues create great tension.Draw without any Restricted Clues for 3 Exploration Markers, unlock one for 2, or fight through the final clue for 1. Every round gives your team another chance.

Choose your route. Build your trail. Make your mark across American history.

The Pencilvania Experience

Draw. Guess. Explore. Repeat.

Six rounds. Countless moments.

One team wins America.

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