The Obvious Answer
Crew Trips
The "Good", The "Great", and The "Best"
The "Bad", The "Worse", and The "Worst*"
Same, Same, Same, Same, Similar
100

A creature known for its flying ability. 

Fly

100
Labor Day Annual Adventure

Waterfall Trip

100

Olivia Rodrigo 2021 Hit.

Good 4 U

100

Taylor Swift 2015 Hit ft. Kendrick Lamar

"Bad Blood"

100

(n.) - a Meteor.

Fireball.

200

A prevalent demographic in Russia.

Russians

200

Dream Denying Terror Trail

Haunted Forest

200

H.O.M.E.S. is adequate acronym for these Northern Border Boating Bodies.

Great Lakes

200

The King of Pop's seventh Studio Album. Released on August 31, 1987

BAD

200

A Wizards favorite action.

Fireball (*8d6 fire damage in a 20ft radius*)

300

A puzzling way to depict art or photographs.

Puzzle

300

Damascas Downhill Derby

Virginia Creeper Bike Trip

300

(v.) - To present as a gift or honor. 

Bestow

300

Idiom meaning "tired or in bad condition".

Worse for Wear

300

Cannons do this...

Fire Balls

400

Major cause of dirty clothes.

Dirt

400

Misty Mountain Cold Cruise

Bryson City Tubing 

400

Central Cattle Country on the North American Continent

Great Plains

400

Bavarian Bun Buddy "mit etwas Sauerkraut"

Bratwurst

400

Adam Ball is caught imbezzling funds....what do we do?

Fire Ball?

500

A specially crafted use of the letters in the English alphabet to slowly deliver information...stamps required. 

Letters

500

Boneyard Beach Bash

Edisto 

500

Fibrous Fire-Retardant Cancer-Causing Crystals. (masks recommended when removing it)

Asbestous

500

Animalia - Chordata - Mammalia - Carnivora - Caniformia - Musteloidea - Mustelidae - Melinae

The European ones (Meles Meles) are arguably cuter.

Badger

500

Jerry Lee Lewis Hit!!!

Great Balls of Fire