Distance: 4.2 miles
Venture to Windansea Beach tucked between La Jolla and Pacific Beach, and you’ll think you’ve dreamt and woken up in a tropical location straight out of a destination magazine. The road and sidewalk trail sits up on the cliff overlooking the shoreline, giving the route a postcard-worthy perspective. With the picture-esque rocks, curving coastline, engagement photo shoots, and surfers catching a break far off-shore, you truly have discovered a gem of a route. Begin at Windansea (queue in the noteworthy “Shack” - exactly how it sounds: an islander beach shack with straw roof that surfers post up beneath in between surf sets) to run north for a climbing route of elevation through neighborhoods, sidewalk, and optional sand to arrive at La Jolla Cove. Complete with tidepools, seals, and surfers hopping over rocks to catch their wave, the beauty of this run will distract you just enough to realize the challenge you embark on with the occasional hill climbs and gradual ascent north.