100 Ways to Wayward

Wayward is for adventures of all stripes: Hiking, Motorcycles, Biking, Sailing, Equestrian, Small Planes, Road Trips, Off Road trips, Pack rafting, Overlanding, Paddling, Vanlife’ing… you name it.

Looking for some inspiration? Try out one of these:

  1. Drive across the continental United States.

  2. Hike the Appalachian trail.

  3. Organize a car rally.

  4. Follow your favorite band for the entirety of their tour.

  5. Map a year of living in a van.

  6. Drive from Spain to Vietnam.

  7. Bike as far as you can before the sun goes down. Track It!

  8. Retrace Louis and Clark’s route.

  9. Test your Vehicle’s off-road capabilities… for an entire week.

  10. Organize a socially distanced charity ride.

  11. Float down the Mississippi River. All the way.

  12. Map the route to your favorite hot spring.

  13. Hike the Pacific Crest TraIl.

  14. Visit every baseball stadIum. And use posts to rank them.

  15. Visit all the national parks, Track your stays.

  16. Motorbike across Vietnam.

  17. Organize a century ride for your cycling club.

  18. Go on a hike, but go off trail.

  19. Do the Eco-challenge.

  20. Buy a house boat. Live by maritime law and map your time off land.

  21. Abandon society and live in the wild (preferably not Antarctica).

  22. Trace you're ancestry as far back as possIble. Share the route with your grandparents.

  23. Buy a $500 car. Track how far you can drive it before it dies.

  24. Visit all 50 states.

  25. Revisit the States you liked.

  26. Revisit the States you didn’t like.

  27. Race to Mackinac.

  28. Track the Mack Back.

  29. Backpack somewhere you’ve never been before. The place has to start with the same letter as your name.

  30. Visit all seven continents.

  31. Hike to the tallest hill in your town.

  32. Go kayaking or canoeing.

  33. Float on a mattress Into the center of a lake! #parenttrap

  34. Recreate a map of historical events.

  35. R2AK (Race to Alaska)

  36. Complete the “I’ve Been Everywhere” Challenge.

  37. Bike around your city for the day.

  38. Drive Route 66.

  39. Hike the outer loop trail around Chicago.

  40. Take Wayward on a picnic!

  41. Go to Fargo. North Dakota.

  42. Do the Drifty.

  43. Drive to your chIldhood home. While you’re there write a letter to your parents or your future self.

  44. Go whitewater rafting with your phone in a dry bag!

  45. Take a long weekend adventure with Wayward. You deserver it.

  46. Travel to see the Northern Lights.

  47. Hike to the Hollywood sign.

  48. Ride every train line in your city.

  49. Go solo camping. YOU CAN DO IT!

  50. Buy one of those Coleman mini bikes and do something weird.

  51. Horseback ride with Wayward in your saddle bag.

  52. Boat the Great Loop.

  53. Follow around a feral cat for as long as you can. Try to infiltrate the feral cat community.

  54. Blue Ridge Parkway.

  55. Go camp at that one spot your friend won’t shut up about.

  56. Motorcycle through any national park.

  57. Drive the road to Hana in Maui… continue past Hana, all the way around the island.

  58. Take Wayward to the golf course and get an aerial view of your game.

  59. Visit the 7 wonders of the world. Track the voyage along the way.

  60. FInd the 8th wonder of the world.

  61. Take Wayward on a safari.

  62. Finish your bucketlist.

  63. Delete all your social media apps and use only Wayward to let people know you are alive.

  64. Take Wayward with you on the boat for a weekend. BONUS POINTS FOR TUBING.

  65. Drive south. Take 2 Left Turns, Take 1 Right Turn. Go Straight for 36 mIles, turn if necessary. Then take 2-3 left turns. Boom! you’re there.

  66. Do that one trip you’ve been saving for.

  67. Go deeeeep into the boundary waters.

  68. Use Wayward to spell words on a map. Use this to propose, or just to learn how to spell.

  69. Buy a one way plane ticket. Track your adventure with Wayward.

  70. Take Wayward on a hot air balloon!

  71. Get in your car. Call a friend. At every Intersection, they choose the direction you go.

  72. Take Wayward to see the Fall foliage in the Northeast.

  73. Recreate "Homeward Bound" but with humans instead of dogs and a sassy cat.

  74. Go hang gliding with Wayward in your pocket.

  75. Ask someone you love where they want to go. Take them there and track it with Wayward.

  76. El Camino de Santiago

  77. Track moving to a new place with Wayward. TRIPS TO TARGET INCLUDED.

  78. Take Wayward on a camel ride.

  79. Take Wayward hunting.

  80. Walk across the United States.

  81. Wall Drug.

  82. Visit the site of your first kiss. Share the location with the person you kissed. Rekindle the romance. Sell the story to Netflix. Get rich.

  83. Track a walking tour of your city.

  84. Island Hop.

  85. Go to the highest elevation you can.

  86. Travel to a country you can’t pronounce with Wayward.

  87. Organize a single track mountain bike race.

  88. Go wine tasting around Napa with Wayward. Frolic in the vines.

  89. Throw a dart at a Map. Go There.

  90. Circumnavigate Australia.

  91. Do the Mongol Rally.

  92. Motorcycle from Wyoming to Patagonia.

  93. Travel outside your comfort zone. Take Wayward along on the journey.

  94. Use Wayward to have an alibi for a crime you did not commit.

  95. Go on a cross-country search for an old family heirloom. Keep track of where you've already looked.

  96. Drive the “Big Five” parks in utah.

  97. Finally take an Amtrak across the country.

  98. Try something new with Wayward. Skateboard, rollerblade, pogo stick, etc.

  99. Climb to the top of a mountaIn. Then ski down It.

  100. RandoNaut to find adventure near you.

  101. Drive into the sunset. Tell us what you find.