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Meadows, Canyons + Oaks…Oh My!

FUN SAN DIEGO DATE IDEA: Hollenbeck Canyon Hike | DateOxygen.com

It’s hard to believe that every majestic oak tree started out as a couple of nuts who decided to stand their ground. Before hiking those grounds, stop off at the local deli and produce market to pack up a picnic lunch to be relished underneath the royal offspring of said nuts. Savor the natural beauty of one of San Diego’s most beautiful wilderness areas as you follow the trail through meadows, over hills, and along a canyon. Feeling energetic and romantic? Follow the trail up the mountain to a viewpoint that will take your breaths away. Sit back and relax…THIS is what life’s about. If you need a refuel, stop off at a local brewery for some burgers and brew.

  • WHERE: East County (Jamul)
  • VIBE: Active, Eat & Drink, Romantic
  • INVESTMENT: $, $$
  • WHEN: Morning, Afternoon, Evening
  • HOW LONG: 4-6 hours, 6+ hours, All Day
  • MEAL: Lunch, Dinner
  • DRESS: Sporty


    1. Pack up your picnic on the way to Hollenbeck Canyon at…
      Bravo Café & Yogurt
      12887 Campo Road, Spring Valley, CA 91978
Steele Canyon Produce
12869 Campo Road, Spring Valley, CA 91977
  1. Drive to the trailhead, park and set off to…
    Hollenbeck Canyon
    Honey Springs Road, Jamul, CA 91935
  2. If you need a refuel, stop off for a burger and craft beer at…
    Jamul Town Brewery and Tap
    13881 Campo Road B1, Jamul, CA 91935


Allow some extra time for relaxing on the hike…maybe on a blanket in the shade of a towering oak or kicking back on that mountaintop rock with a view. Surprise your date and whip out a mini-bottle of champagne and two plastic flutes to toast to the beauty surrounding you.


  • Don’t forget the basic picnic and hiking accessories…including WATER.
  • Turn left on Honey Springs Road to get to the Hollenbeck parking lot. If you hit Otay Lakes Road (on your right), you’ve gone too far!
  • Check out the map in the parking lot and familiarize yourselves with your route before setting off. Better yet, study & print the map before you ever leave home.
  • Not including breaks, allow about 3-4 hours for the hike and some chill time.
  • Suggested route: Once you set out from the trailhead, always stay to the right. About middway (1-1/2 hours), you’ll reach a small creek (roughly 5 feet wide). The way home is just BEFORE the creek to the right. BUT, if you cross the creek, head straight up the hill, and go through the break in the fence on the right (just before the trail turns to the left), you’ll reach a highpoint with rocks just begging you to sit on them and soak up the stellar views. This is where you should break out the bubbly. When you’re ready to continue, head back to the other side of the creek, and take an immediate left. This will return you right where you started.


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