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City Guide: Oakland

City Guide: Oakland

City Guide by Jillian Betterly and Heather MacKinnon, Photography by Jillian Betterly

It’s very common for bikes to bring different communities together out here in Oakland. Even though this is a large urban area, our love of bicycling often unites us, linking those who ride bikes together to give this big city a small town feel. Heather MacKinnon and I crossed paths a few years back due to our similar passions—we met on bikes, and found out later about our joint love for film photography and the arts. Here is our discussion on the town we love, and things that we feel make it special.

How long have you have you been riding  in Oakland?

Heather: Almost 4 years now. My first experience with Oakland was back in 2011 for an FWOD (For Women Only Duh) group ride. They guided about 30+ of us for their holiday co-ed ride and it was a great first experience. I moved here from Boston and although my family calls me bi-coastal, I currently call Oakland home.

Jillian: Also 4 years. I moved here from Colorado, but I’m originally from Upper Michigan. I discovered this Oakland when I biked from Eugene, OR to San Francisco, CA. The coastal route changed my life!. I fell in love with the biking community in the Bay area, and the coastal environment. I went back to Colorado, put my one month notice in and here I am.

What do you wish people knew about cycling in Oakland? What makes it different than other places you’ve cycled in?

Heather: This place is so rich with diversity and culture that it’s only natural to see the cycling community reflect the same, it’s this really nice ‘togetherness’. I hesitate to use the word clique because there isn’t any group of people who ride bikes that are excluded. Kids on tall bikes hanging with roadies hanging with fathers hanging with messengers hanging with scraper bikes. Because of this vast network of individuals riding bikes, it creates this incredible mass of relatability that is so inspiring. How could you not ride a bike here? It just feels really good to be apart of.

Jillian: I was thinking the same as well. I never lived in a place where so many people share one commonality that makes for an awesome Biketopia. I see our community as very progressive in building a better bike future across generations.
Also we have a very welcoming bike community, we are helping and looking out for one another. It makes for a vast support network, which is particularly important in the women’s cycling scene.


Whats the best part about riding in Oakland? What’s the worst part?

Heather: The WEATHER. This is coming from a girl who grew up in a place where snow days are a kids family holiday. I know what it's like to layer 3 pairs of wool socks and two pairs of gloves just to survive the work day (messenger work). So I love Oakland weather. Any local will tell you, we only have 1.5 seasons (mostly a warm fall, and sometimes a hot summer). And yes, this is all year ‘round. Though we are close to San Francisco, the weather patterns do differ. We rarely see the cliche Karl the Fog (

The worst part is bike theft. It’s really, really bad out here. Like, breaking into your backyard kind of bad. If you have to lock outdoors, be very mindful. Use more than one lock. I usually always have my back-up cable with me if I’m headed downtown or out for the night, and I never lock up overnight anywhere.

Jillian: Biking around and looking at the art. Oakland has a strong art scene and puts out some great visual art, from graffiti to murals. We also have many great sculptures and several different architectural periods of houses. You can see commissioned murals and rogue pieces by GATS (Graffiti Against the System). There are some art houses as well. Up in Berkeley there is a house with sculptures made 100% out of beach trash. Riding around the neighborhoods you’ll see Victorians from the 1860’s to craftsman and bungalow style homes. There is just so much to visually take in!

The worst part—some of the roads here look like glitter with glass from broken car windows. The roads out here have hazards just like any place, but there seems to be always so much glass. I ride with tools, spare tube and kevlar lined tires.

What is your favorite long distance route?

Heather: I just discovered riding the Bay Trail up to Point Richmond. You won’t be gaining any Strava KOM points with this one but I promise you’ll enjoy the views. Some of my favorite of the bay area are right along the water and this quiet, paved bike trail follows about 15+ miles of it. Make sure to stop at Seabreeze Cafe for snacks and drinks and a quick ‘gram post. My favorite route begins on the trail in Emeryville and follows north to Point Richmond. And because the trail is flat it's easy for you to decide to take it really chill or turn it into a solid training session with the headwind. Just make sure you have proper lights if you’ll be out there after dark. (route link:

Jillian: I escape to the hills. You can ride up Tunnel Road, and go a few different ways from there. A few years ago, a friend and I built a spin wheel of all the routes, you could stop at the top and spin for a route. One route is my favorite though and shows the best of what Oakland cycling is, Tunnel>Skyline>Pinehurst>Redwood>Oakland. It goes from epic 360 views of the Bay Area to rolling into Redwoods in the canyons and has climbs that give you a run for your endurance. Redwood Road is also the gateway to more routes towards Palomares Dam road, if you want to push your ride in the 60-70 miles range. (link to 30 miles ride: and More Miles:


What is your favorite route for short distance? 

Heather: Lake Merritt is my favorite short trip considering I live pretty close, but anyone can hop on to the bike lane which runs around the lake at 3.3 miles a lap. It’s pretty difficult to strike out on a place to stop by and have lunch on the water. It’s like Prospect Park in Brooklyn but without the hill climb, or like Golden Gate Park in SF but without the fog. They just added a beautiful new parklet on the west side by the Oakland Museum of California. Make sure you find the taco truck on Foothill, or the bike polo kids at Athol. (route links:

Jillian: Hands down the Mountain View Cemetery. It’s a little elevation gain, but worth it. I take my friends on the cemetery ride when they visit, it’s a route that encapsulates the best of Oakland. I start from downtown Oakland, ride up Broadway to Piedmont, and on the top of Piedmont Ave. is the entrance. Ride your bike thru the cemetery and climb to the top. Views of Oakland and San Francisco, beautiful architecture and gardens of poppies really make this place outstanding. Stop and visit Timeless (link: Coffee, on Peidmont Ave,and have some of the best vegan cheesecake (ever!) and coffee before or after the cemetery. (route link:


What’s the best part of commuting by bikes in Oakland?

Heather: It’s easy, like really easy. Most of the streets are extra wide and leave enough space for you to comfortably ride with traffic. I’ve never felt pushed off the road here. There are tons of bike lanes too. There’s even a FREE map of the cycling in the area, make sure you grab one. Something that’s important to note about commuting here in comparison to other cities I’ve lived in (Boston, NYC, LA) is that cars are aware of cyclists and they’re nice about it. They will stop before you do. It’s a very safe feeling that makes my commute more relaxing.

Jillian: The hard work of our local bike advocacy groups makes cycling in Oakland safer and safer. New bike lanes, teaching people be safer on the streets thru bike education classes, it just gets better day after day for us. I also love seeing friends out and about. Everyday I get to ring my bell or stop and chat with a fellow rider.


What's your favorite bike shop?

Heather: KING KOG! I have to say King Kog because they’re family and we just started a new team after they opened their second location here. Gina pretty much nails it as a strong female bike shop owner with Shawn, a mother of two, and plays in a band. Also, the new shop is absolutely beautiful: fully decked with one of kind NJS frames and even some coffee while you wait for the guys to work on your bike. It’s also nicely tucked away in the newly renovated downtown area, right near Temple Tattoo and Analog. Since December they’ve hosted 3-4 races / events so far, they’re pretty crucial to the community here. 

Jillian: I like Bay Area Bikes, as it has a wide range of cycles and is also female owned. They have three locations, each serving different type of bicyclist. You can rent bikes at the Jack London Square location, grab maps, get a biked worked, it’s a good starting place. They also have a location on Broadway that sells more road, touring and mountain biking gear plus they sell Green Guru upcycled bike gear. Then they have one more location that caters to the cargo families. I love seeing moms rolling with kids everyday, it’s so cute. Glenda has worked very hard to support the cycling community, and she donates regularly to local bike advocacy groups. 


Favorite pre/post ride coffee shop or meet up spot?

Heather and Jillian: Bicycle Coffee and Telegraph Beer Garden. It’s an unanimous vote. We both love these places, both have great welcoming atmospheres.

Heather: Oh without a doubt Bicycle Coffee for the pre-ride, I’ve been coming here since December and I’m treated with consistent radness from these folks every single time. I couldn’t be more excited to talk about this shop being in Oakland after branching from Los Angeles, because they do such an amazing job blending the love of bicycles with the love of coffee.

And the post-ride has to be awarded to Beer Garden, recently renamed Telegraph. They have maybe a dozen benches decked outside and who can say no to awesome bar food (Vegan/ Vegetarian) and a new liquor bar in the back? This place is a great hybrid of a local spot and a friendly place to meet new folks.

Jillian: Bicycle Coffee hosts art shows, free music and they do an early sunday am track bikes ride. I just love sitting outside at Telegraph after a fun ride with friends, good food and great beer selection. Both places are bike friendly, dog friendly, and you’re bound to see a friend or two. One dollar beer cans on Monday nights at Telegraph and free coffee fridays at Bicycle Coffee, what’s not to love about that insider tip!


What’s the most practical insider tip you’d give anyone visiting and cycling in your city?

Heather: If you even dare to take your bicycle on public transit, expect dirty looks. Although bikes are now allowed on BART at all times, most people don’t want to see how much fun you’re having during their morning commute. Going into San Francisco in the morning? Wait until after 10am or so. Coming back into Oakland? Wait until after 7pm or so. Careful though, BART runs on Cinderella hour: last train is around midnight.

Jillian: Back to bike safety, check out Bike East Bay ( for locking tips, how to ride on public transit with your bike and other great information for your visit. Lock your bike and do not leave it in a car. Our bike community is very friendly and always up to helping, they’ll always point you in the right direction.




Rider Profile: Suzie Livingston

Rider Profile: Suzie Livingston

Rapha Women's 100

Rapha Women's 100