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Best Summer Ever Challenge (with free printables)

250 Summer Activities

By Brittany Joyner May 25, 2026

In an effort to have the most fun 90's inspired summer ever, I made this challenge for our friend group! You can make a group chat or Drive folder where everyone can put their pictures and videos. Having them all in one spot makes tallying points easy and then you have an awesome collection of memories from the summer! Put them on a slideshow or in a scrapbook that you can look through at your end of summer celebration.

๐ŸŽฏ Goal

Complete as many fun, wholesome, summer-themed tasks as you can from the challenge list before the final date! Earn points for each completed task and compete to be crowned the Best Summer Ever Champion!

๐Ÿงฉ How It Works
  • Download or print your checklist (250 items total, divided by point value: 1, 2, or 3 points).
  • Each family completes tasks and takes a photo as proof of each one (send to the challenge group chat)
  • Tasks can only be counted once per team
  • At the end of the summer, tally up your total points!
๐Ÿง  Scoring
  • โœ… 1-Point Tasks: Quick fun, simple, silly moments
  • โญ 2-Point Tasks: More effort, creative activities
  • ๐ŸŒŸ 3-Point Tasks: Community exploration, full experiences

You can track your progress on a digital form, printable sheet, or photo album — just make sure each completed item has a photo or short video for proof!

๐Ÿ“… Timeline
  • Challenge Begins: June 1
  • Challenge Ends: August 31
๐Ÿ† How to Win
  • The person or family with the highest total point count wins the grand title of “Best Summer Ever” Champion!
  • You can also award bonus titles like:
    • ๐Ÿงบ Picnic Pro (most food-related tasks)
    • ๐Ÿธ Nature Nerd (most outdoor adventures)
    • ๐Ÿ“ธ Memory Maker (best photo album)
    • ๐Ÿงญ Community Explorer (most 3-point tasks)
๐ŸŽ Prize Ideas

Choose one (or mix & match):

  • Custom Trophy or Certificate ("Best Summer Ever Champ 2026")
  • Family Movie Night Kit (popcorn, candy, board game, etc)
  • Bragging rights
  • A “winner’s choice day” — they plan one family fun day for the group to celebrate the end of summer
  • Handmade prize: decorated T-shirt, painted rock trophy, crown, etc