10/17/2012 11:16 am ET Updated Dec 17, 2012

Biking the Bay: Mount Tam to Pelican Inn

Standing tall in the Marin Hills lies Mount Tamalpais. Peaking at nearly 2,600 feet, it pokes the sky like no other mountain in the Bay Area.

There is confusion over the etymology of the name Tamalpais, but many believe that the meaning is derived from the Coast Miwok Native American people's word for coastal mountain (Tamal Pais). The Coast Miwok inhabited the Marin area, but legend has it that they rarely set foot on Mount Tam because they feared the woods were haunted by an evil witch.

As Halloween approaches, I double dog dare you to try this ride in the evening... As the sun dips into the Pacific, tempt fate and race the Tamalpais Witch out of the hills before night falls!

Distance: 40 miles
Challenge: Two Serious Climbs
Reward: Views and Brews
What to Bring: $8... I guess that's what a beer costs now

Head north leaving San Francisco and the city stressors behind like we always do, but let's change it up as we enter Sausalito. Instead of taking Alexander Avenue, turn left immediately after crossing Golden Gate and circle your way back under the bridge. The hill is not quite as fun, but it's a pleasant alternative, away from traffic and out of harms way. Work your way along Horseshoe Bay, past the Presidio Yacht club on East Road, and soon you'll find yourself in familiar territory cruising down Bridgeway and onto the bike path.

At Bayfront Park, turn left on Sycamore into downtown Mill Valley and mentally prepare for the larger of your two major climbs. The incline begins slowly and fluctuates in difficulty over the twenty minutes it will take to reach the top. If you have successfully done the Headlands climb, you should be plenty prepared for the challenge... But even if your legs feel like jelly or your granny gear is busted I encourage you not to turn back! There is no shame in finishing the ascent on foot, rolling your bike through the tall Redwoods and soaking in the unforgettable coastal views.

Make sure you take a moment to enjoy the beauty on the way up, because you will need 110 percent of your focus on the bumpy road as you plummet down the other side. It is insanely fun but a little intense. There are often no guardrails on the switchbacks and if the Mt. Tam Witch was going to mess with you, this would be the spot... so be careful! On weekdays you can really build up speed, but on weekends traffic around Muir Woods National Park can slow you down considerably. Regardless of the day, downhill's never last long enough. At least at the bottom of this one there is Guinness waiting at the Pelican Inn.

Hopefully, the stop has left you rested and the beer has inflated your confidence. If you find yourself saying things like "that last climb wasn't so bad" or "hills are actually really fun" I'd say you've got enough energy for part 2. Hop back in the saddle and finish the loop taking Highway 1 back to Mill Valley. As difficult as the winding road can get, biking along the edge of the world makes it impossible not to smile through the pain. As you eek your way over the top of the final peak, take joy in your accomplishment and let gravity take care of any lingering stress left in your system.

Keep the rubber side down, SF.

Check out the mapped route.