5 Must-Do Bay Area Adventures for 2015

The 7-mile Dipsea Trail takes hikers through stunning wilderness.
The 7-mile Dipsea Trail takes hikers through stunning wilderness. Scott Mattoon
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The start of a new year (Happy 2015, by the way!) usually brings with it plenty of well-intentioned resolutions. But research shows that the vast majority of those fail, making us feel like failures along with them.

So, as 2015 kicks off, why not ditch the resolutions in favor of some bucket-list adventures instead? You'll get some of the same feel-good benefits—training for some of these suggestions means getting in better shape, for example—without any added pressure. Along the way, you'll tick off some must-do bucket-list adventures in the Bay Area.

1. Bring Your Own Big Wheel race

Just another heat at the Bring Your Own Big Wheel race on Easter Sunday.
Just another heat at the Bring Your Own Big Wheel race on Easter Sunday. Blane Bachelor

This don’t-miss event, which takes place on the afternoon of Easter Sunday, is one of the most fantastically zany events SF has to offer—and that’s saying a lot for this notoriously off-the-wall city. Bring Your Own Big Wheel , which involves hundreds of costumed, crazy adults barreling down one of the city’s twistiest, steepest streets—on Big Wheels—was started by some of the same folks behind Burning Man (which speaks volumes for its spirit). The event takes place in Potrero Hill, on Vermont Street, which is Lombard’s lesser-known but equally twisted sister. The event starts at 4 pm with a kid’s race, but the real hilarity starts with the adult heats, which run for a couple of hours. Join in the insanity with your own wheels (and a costume, of course), or just watch from the sidelines (arrive early to get a good viewing spot) and try not to wet your pants from laughing so hard.

Insider Tip: If you’re hoping to join in the insanity, start scouring Craigslist now for used Big Wheels and the like. Only entrants with plastic wheels are allowed, and they sell out both online and in retail stores far in advance. And if you’re planning on bringing an adult beverage, do it discreetly—alcohol is officially banned, and cops have been aggressive about busting folks in recent years.

2. Whale Watching in the Farallon Islands

A whale surfaces at the Farallon Islands, which is chock-full of marine life.
A whale surfaces at the Farallon Islands, which is chock-full of marine life. Flickr/Jay Phillips

Yes, the boat ride out to this group of islands, which lie nearly 27 miles from San Francisco, can be notoriously rough. Yes, the weather can be cold and nasty. And yes, there’s a chance you may never see any whales. Regardless, the adventure should be one to set your sights on for 2015.

Trips with the Oceanic Society, a nonprofit that has been leading whale-watching trips to the Farallons since 1974, run from May through November on the 56-foot Salty Lady, a Coast Guard-certified vessel, on weekends and select Fridays. Even if you never catch a glimpse of the magnificent ocean mammals, you’ll see a breathtaking array of other marine life, including fur seals, elephant seals, and sea lions, as well as a mind-boggling array of seabirds: puffins, guillemots, auklets, cormorants, gulls, pelicans, albatross, and more.

Insider Tip: Unless you're as sea-weathered as Captain Ahab, don’t try to tough this one out without some anti-motion sickness meds. And bring layers, including a waterproof jacket and hat, as unpredictable Bay Area weather can make the trip miserable without the proper gear.

3. ** The Dipsea Race **

The famous Dipsea Trail offers plenty of stairs and views of the Pacific Ocean.
The famous Dipsea Trail offers plenty of stairs and views of the Pacific Ocean. Class V

With spectacular terrain that spans woodlands, coastal canyons, and more than 2,200 feet of actual elevation gain, the 7.4-mile Dipsea Race is not only the oldest trail race in the country, it’s also one of the toughest. The spectacular route goes along the famed Dipsea Trail , from Mill Valley to Stinson Beach in Marin County. But don’t expect the gorgeous landscape, which runs through Muir Woods National Monument and Mount Tamalpais State Park and offers spectacular views of the Pacific, to offset the quad-killing aspects of the race. The brutal start includes three sets of stairs as tall as a 50-story building, followed by hills and trails with names like Dynamite, Insult, and Cardiac before the final set of 688 stairs.

And if that weren't enough, some competitors who really want to punish themselves take on the Double Dipsea, which starts and ends at Stinson Beach, doubling up the route.

Insider Tip: With just 1,500 slots and double the amount of entries, the process to get in is competitive and refreshingly old school: You have to download the form and snail mail it in. But that gives locals an advantage, as the race does include a first-received, first-get-in component. The date that entries open has not yet been released, but last year it was in mid-March.

4. Bay to Breakers

A sampling of the costumes found at Bay to Breakers.
A sampling of the costumes found at Bay to Breakers. Blane Bachelor

There may be no more quintessentially San Franciscan event than this 10K road race/rolling party, which winds its way across the city in a mass of nearly 40,000 runners, many of whom boast quirky, creative costumes. Bay to Breakers , which started in 1912, is the oldest continuously run road race in the country, and it’s a must-do at least once, whether you run or just watch the insanity from the sidelines. Some wacky traditions: a tortilla toss at the starting line, a group of salmon who run the course backwards, and a pink gorilla, “Hape Ashbury,” who kicks the race off with the elites.

Insider Tip: Don’t let the hordes of drunken revelers fool you: Like the Bring Your Own Big Wheel race, alcohol is strictly prohibited, and organizers have cracked down on drinking even more in recent years.

5. Escape from the Rock Duathlon

The swim from Alcatraz is 1.5 miles across the frigid San Francisco Bay.
The swim from Alcatraz is 1.5 miles across the frigid San Francisco Bay. Flickr/Dawn Ellner

This duathlon doesn't have quite the cache on the adventure-sports circuit as its older cousin, the renowned Escape from Alcatraz Triathlon (which is already sold out for 2015). But the Escape from the Rock  does have the same sphincter-puckering swim component: a 1.5-mile swim from Alcatraz, the world's most famous prison, through the frigid, fearsome waters of San Francisco Bay—the same route that claimed plenty of inmates trying to make their own escape from the Rock. Granted, you'll have a wetsuit (though there are a few brave souls who do the swim without one), but you'll still have to contend with current strong enough to suck you out into the Pacific. Once you make it to shore, the seven-mile run to Fort Point and back will feel like a picnic if your legs aren't frozen solid, that is.

Insider Tip:  Forget about keeping perfect form or rhythm during the swim component, and just focus on making it to shore. The strong currents will force you to lift your head up often to sight landmarks.  

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