Hiking Cowles Mountain & Some Sentimentality

If you have time in San Diego…

Make it over to the highest point in the city, Cowles Mountain! It’s an easy enough hike, 3 miles round trip and provides the highest panoramic views of the city. The best part? It’s dog friendly. Oh and they have bathrooms at the bottom of the trail ☺️

Because I am a complete and utter prepare for the worst type of gal, I brought my camelbak, pumpkin seeds, a granola bar, and sunscreen. The only thing that was really needed was the camelbak which the three of us shared.

If you go after 3:30 or so, be sure to bring a light coat! It gets very windy at the top and chilly when the sun starts to set. You’ll see in the pictures when temperatures started to drop by our clothing.

Although it doesn’t start getting green till about 3/4 of a mile up, the scenery is gorgeous with orange clay and desert flowers.

cowels mountain trail #sandiego

Oh, they are also in a nature restoration project so there are little baby cactuses planted everywhere! Next time I’ll put my hand next to them so you can see how tiny they are 😊 you live and you learn.

Smokey, who is a medium to high energy dog (think lab, not husky) was loving every second of it and we finally just let him explore around dragging his little purple leash behind him.


*please note if you are bringing a dog to check the weather! Only a month ago someone’s poor doggy got heat stroke and passed away. Better safe than sorry!*

We must have gone at the perfect interval time (3:30-5:30 pm) because a ton of people were coming down when we went up and even more came up when we were going down. I would say if you enjoy your solitude to avoid to trail at dusk.

Cowels Mountain Trail #sandiego || a tipsy gypsy life #explore

It is definitely a great spot to do a personal workout, walk with a friend, or take your pooch for a walk.. I even saw one amazing mom with 4 kids under 10 and a dog! #superhero.

The view from the top was life-changing for me and way too sentimental.

This was the last time I went hiking at Camelback in 2011. I was 19, and unconsciously still mending my heart from a loss I dealt with two years earlier. I was happy for the week and ecstatic in the moment; I was fit, working hard, and with my best friend in her hometown. I thought I had finally made it. Silly girl, little did I know about the wild roller coaster ride I was about to put myself on.

Hiking Cowles trail in #sandiego | a tipsy gypsy life #travel

Yesterday, almost three years later to the date, I stood upon the highest peak looking over my new home with the loves of my life, loving life. How did I get so lucky?

Don’t demand happiness from yourself before you are ready because believe me, your heart will find a way to fill whatever hole you have.


I’m going to repeat and reword that because I didn’t come up with that, a very very smart person told me this and changed my friggin life.

Whatever you are missing, you will find a way to fill it.

It’s like when you’re craving a food like chocolate. Your body is telling you it needs something, so you grab the first thing that looks right (the chocolates) when your body really wants magnesium (nuts, seeds, leafy greens). Being aware is the first step to a healthy, happy life! Follow your natural urges, your soul tends to know what’s best.

  • Gosh, how beautiful is this? I’ve got friends that are in love with San Diego but I have never been. When I make my way out West, this will easily be at the top of my to-do list! Also, I really needed your sentiment today. So perfect timing. 🙂

    • Lauren @ atipsygypsylife.com

      So glad to hear that 🙂 Hope you can definitely make it out soon! Weather is perfect year round hehe.

  • I just love San Diego! So beautiful!

    xo, mikéla / simplydavelyn.com

    • Lauren @ atipsygypsylife.com

      Ah me too! Thanks for reading!

  • Why hello! I am sorry it took quite some time for me to respond to your comment on my “Bad Weather” post. I enjoyed the irony in your comment of your boyfriend jinxing the trip! That’s always how it seems to go.

    We are in San Diego every year and I have never heard of nor experienced Cowles Mountain! I will actually be out there early 2016 and will make sure this gets put on my list!

    Thank you for sharing your travels and awesome photos 🙂

  • Love these photos! It looks like a beautiful hike, something I need to do more of and have a huge desire to do so! Your dog looks wonderfully happy as well, I love it! 🙂

    Kyah – http://www.weekendtempo.com

    • Lauren @ atipsygypsylife.com

      Thank you! It was absolutely lovely, can’t wait to go back… Love your blog BTW!