When is the best time to stretch?

I agree with Dr. Salt and for most clients I find that it is just easier for most people to knock it out at one time while they are in the gym.  A great warm up is to do foam rolling on tender areas, static stretch the same tight areas and a 5-10 minute walk the person generally is good to go.

I also find it very relaxing and effective to do foam rolling or trigger point release first thing in the morning and/or right before bed.  I personally find it to be a tension releaser (literally) and something very relaxing.  I like to do it late at night while watching TV to unwind and work out tender and tight areas throughout my body.

The key in any form of flexibility strategies is to just be consistent.  Stretching or foam rolling once or twice a week does not get it done.  It is always better to do 4-5 sessions of 5 minutes in length of flexibility work than 1 session per week of 30 minutes.  If you are consistently working on your flexibility, range of motion then over time it will greatly improve.  I generally find that relaxing environments are the best time to do do this, it is why I recommend this right before sleeping or waking up.  The body is more relaxed and will respond nicely to whatever flexibility you choose.

The key is just to be consistent, if you find that it is easiest to be consistent around workout times then that will work just fine.

William B. Salt II., MD
It's a good idea to stretch before you exercise. Do light stretching as part of your warm-up, but wait until after your warm-up or for your cool-down period to do more aggressive stretching. Research shows that holding a stretch for at least 30 seconds provides the most lasting benefits.
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Stretching (flexibility) can be performed at any time throughout the day, but it is a critical part of a proper warm-up before exercise. Using an overhead squat assessment and observing your posture throughout the day will help you to determine which muscles are tight and need to be stretched. 

Just like with resistance training, an integrated approach should be used with flexibility. To begin, use self-myofascial release and static stretching.  This is known as corrective flexibility and the focus is to improve muscle imbalances, for example protracted (forward) shoulders. 

Another great time to perform flexibility training is as a cool-down to your workout. Here self-myofascial release and static stretching should be used.    

The best time to stretch is early in the morning before you start your day. This sets the length of the muscle for the remainder of the day, allowing you to move more freely without restriction or pain. Perform dynamic stretches in the morning. These consist of bodyweight exercises such as prisoner squats, lunges, push-ups with a rotation, etc. In the evening, perform static stretching for the muscles you stretched in the morning. Hold each stretch for 30 seconds.
Most doctors suggest stretching at the end of your activity, when your muscles are warm. A five-minute slow walk or jog to warm up before each exercise session is recommended. The warm-up will raise your heart rate and core body temperature, as well as pump blood into the large muscle groups, getting them ready to work.

The cool-down phase of your activity is especially important in protecting you from exercise injury. Spend five minutes slowing your movements down to a gentle walk. This lowers your heart rate. Then take 10 minutes for a post-cool-down stretch. It's this step that many people skip but which can increase flexibility and help you injury-proof yourself.

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Important: This content reflects information from various individuals and organizations and may offer alternative or opposing points of view. It should not be used for medical advice, diagnosis or treatment. As always, you should consult with your healthcare provider about your specific health needs.