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The Brattleboro Union High School marching band needed to raise money to get to Washington, D.C. They had been invited to perform in a big parade and looked at creative ways to raise the necessary funds for transportation, food, and lodging.
The parade was the Cherry Blossom parade and the year was 1986.

One of the ways they tried to make some money was publishing a game called “Brattleboro Trivia.” It came with a playing board, plastic playing pieces (one looks like a UFO), dice, a bank's worth of play money, and a set of trivia books with questions and answers about Brattleboro.
The object of the game was simple: be the first to “score $150.”
Each player got a trivia booklet. The questions and answers were contributed by the general public and divided into the categories of History, Sports, Music and Art, General Questions, and Business.
Pieces were moved around a monopoly-esque game board that featured the names of businesses who had helped sponsor the game/trip to D.C., as well as a question category on each square. Land on a square, look at the category, and the player to the left would ask a trivia question.
Correct answers earned a player $10. If they landed on “Community Knowledge” or “Adult Education” they would have to go to that special area of the board and the rules changed a bit - $20 for a correct answer, but a $5 penalty for a wrong one.
There were other special squares. Going to jail meant losing a turn, or paying a fine.
The first to get $150 would win.
Artwork for the trivia booklets was done by Meegan McCaffrey, a member of the band at the time. There are illustrations of band members playing their instruments in each of the five booklets. One of them contains a reprint of the letter accepting them into the 1986 National Cherry Blossom Parade, too. A check for $150 was required along with a written acceptance of the invitation.
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Ready to try a few questions? Good. From the Music & Art category:
- What annual concert is performed in the BUHS gym?
- What was the BUHS musical in 1980?
- What year was “Carnival” the BUHS musical?
- Who founded the Brattleboro Book Club in 1849?
- What was the overture played at the 1936 BHS graduation?
- Who was the director of the BUHS Band that marched in the Macy’s Parade in NYC?
- Who painted the picture of the “Colonel” on the BUHS gym floor?
Hanging in there? Let’s try a few from the “General” category:
- Who was the editor of the Brattleboro Reformer in 1960?
- How many days did it take to move the Episcopal Church?
- When was the completion of the Canal Street road project - a 4-lane highway - on Hospital Hill?
- Who was the chairman of the 1984 Brattleboro Town School Board?
- What was one of the first fast food chains to come to Brattleboro?
How did you do with the sample questions? (I’ll give the answers later on in the week.)
Brattleboro Trivia was not only a fundraising tool, but has become a snapshot of Brattleboro from "way back then" in the 1980's. Some businesses that supported the project are still familiar names in town, like Lyon Travel, Lawton Dry Cleaners, and Cerosimo Lumber Co.,. Others have faded into memories, like Ames on Putney Road and the Flat Street Nightclub
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Hmm, South Pacific I think. Followed by "Oklahoma!" the next year and "How to Succeed in Business Without Really Trying" the next. I was in all three pit orchestras - trumpet.
- Who was the director of the BUHS Band that marched in the Macy’s Parade in NYC?
Bob Simonds.
- Who painted the picture of the “Colonel” on the BUHS gym floor?
I always thought that Simonds was responsible for the sign in the gym, but maybe not the floor. He was always huge on "the South" and was really into the "Pride of the South" thing.
- What was one of the first fast food chains to come to Brattleboro?
Burger King or maybe Burger Chef?