Tips & Guide

15 Awesome Winter Workout Challenges – That Anyone Can Do

Nothing makes fitness more fun than a good challenge!

Are you working out for the first time (or for the first time in a while)? Or looking to walk or run your first race? Or are you just looking for a way to add a little pizazz to your workouts?

No matter what your fitness level – beginner, weekend warrior, or conditioned athlete – there’s a challenge that’s right for you!

For me, I just like to change things up a bit. Especially in the winter months.

Up here in Connecticut, January means winter. Brrrrr! So the challenge is getting motivated to go outside – whether that means going for a walk or run or hike. Or even just heading to the gym. It gets real cold outside – we’re talking 20-30 degrees most days. And that’s the warm part of the day. Then there’s the wind.

Double brrrrr(x2) on windy days…

How To Ramp Up Your Winter Workouts

So how can you push yourself no matter what the weather?

A challenge, of course!

They can short-term just to change up your routine. Something you can do in 30 days or less.

These can be a lot of fun. Give you a boost. And let you feel the accomplishment of reaching a goal quickly.

Then there’s the longer-term challenges

  • The “get my body ready for the beach in the summer” type of challenge
  • Or the “run my first race this year before I turn ___ (fill in your milestone age, like 30, 40, or 50).
  • And for those who are already in shape the “I want to run ___ miles or do a marathon or triathlon” type of challenge.

Do one of those sound like you?

Usually I’m in the third category. The one where I start training for a half-marathon or an obstacle race like the Warrior Dash (if you haven’t done some type of obstacle race or fun run, you’re missing out on a great experience!).

I’ve been dealing with a lot of injuries in the past 2 years (I’ll write a post on that at some point, I’ve learned quite a few helpful lessons about rehab!) so now I’m in the “I want to get my body healthy so I can move normally without pain” category.

Whatever your goal, these challenges can help you get in shape AND have fun doing it.

A few years ago my family followed the 100 pushup challenge. I don’t think any of us actually got to 100 pushups in a row without stopping … but we still talk about how much fun it was pushing each other to do our best!

So you don’t need to think of these challenges as competition. Or you can join one where you compete against other people (most of the ones below don’t involve others – they’re just you vs you challenges.

You’re just challenging yourself to do your very best. On that note, if you’ve never watched the scene from the movie Facing The Giants about “giving your very best” (and even if you’ve seen in a dozen times it’s still worth watching at least one more time) it is one of the best inspirational videos of all time!

Awesome video, isn’t it? Gets me fired up every time, wow!

So are you ready now? Pumped for your own challenge? Here are a few of the best fitness challenges I could think of. If you deice to do one, let us know which one you chose and what it means to you.

And if you come across any other cool challenges, let me know below.

Time to get started – pick your challenge!

New to exercise? Start with a mile a day for 30 days:
30 day mile a day challenge

Here’s a fun challenge using the most basic exercise – pushups (and one of my favorites)!
100 pushup

Add this to the one above for a full body workout:
200 squats

Then add your abs:
200 situps

And for a little more of a challenge:
30 day plank challenge and 25 pullups

Get your abs in shape in only 2 weeks!
2-Week Crunch Challenge

Want to lose a few pounds? Combine exercise & healthy eating!
30 day weight loss challenge

Here’s a great beginner running challenge
Run 30 Miles in 30 Days

If you’ve never run a 5k (3.1 mile) race, this is a great training plan to help you get started, and includes both walking & running.
Couch to 5k running program

If running an obstacle race is your challenge, this training plan will help get you into shape!
The 10-Week Obstacle Race Training Plan

Have trouble getting motivated to work out in the morning? Anyone can do it for 7 days!
7 day morning workout challenge

Are you a runner looking to ramp up your mileage? Try this 1,000 miles in 1 year challenge!
1 year 1000 miles running challenge

If you’re not a runner – but want to become one – here’s a great 30 day challenge.
Running: 30-Day Quick Start Guide for Beginners

If you’re not a runner – and want to give it a try – here’s a basic 7 day challenge.
7 Day Learn To Run Challenge

The name says it all – learn how to run your first or fastest mile!
30-Day Running Challenge: Run Your First or Fastest Mile



I’m a writer, new mom and foodie. I love sharing what I know while making others feel beautiful. On this blog, I share my healthy lifestyle, simple meals, fitness tips and experiences.

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Kara Bout It