The Coffeeneuring Challenge kicked off four years ago as a small affair with 12 finishers. Thanks to their efforts, word of mouth, and I’m not even sure what else, coffeeneuring is now an annual event that keeps expanding in popularity.

Some don’t know the history of coffeeneuring, and that’s okay. There are enough of us around to write the Wikipedia entry if and when that time comes, including Vannevar from Pittsburgh, Pennsylvania.

Vannevar, who writes the blog Type 2 Clydesdale Cyclist, has successfully completed the Coffeeneuring Challenge all four years. In today’s guest post, he shares his reflections about about coffeeneuring in Pittsburgh, the overall appeal and growth of this evolving annual fall tradition, and coffeeneuring as a form of bike advocacy. It’s great stuff. Thank you, Vannevar!

1. You were 1 of only 12 people who completed the Coffeeneuring Challenge in its first year. What attracted you to it, and why do you think coffeeneuring has caught on like it has?

Coffeeneuring is naturally attractive to me. Bike, coffee, outside, exploring, writing, maps, tweet-blogging; it perfectly represents the core of my Venn diagram.

I think coffeeneuring has caught on with others for the same reasons– plus it’s social and beginner-friendly so you can invite others.

It’s low-budget, unpretentious, and you customize your own choices. (It would be too hipster to say, you curate your own coffeeneuring path.) The Chasing Mailboxes presence has certainly helped connect far-flung yet like-minded fellow travelers.

Coffeeneuring aligns with localvore, shop-local sensibilities. I notice most people choose indy coffee shops when they’re available over national chains (NTTAWWT) and that’s consistent with my own sense of coffeeneuring.

Tweeting / blogging / Facebooking about cycling in whatever place I find myself is bike advocacy. It’s making the pitch that cyclists are out there, participating in the economy, supporting local businesses. I want them to see me, futzing around outside their stores because there’s no bike parking and then coming in and spending money.

Finally, as a geek I’m also motivated that linking to my fave shops on social media helps their Google presence and their Search Engine Optimization (SEO) goals. If you went to a small business and said, how’d you like to have a handful of local bloggers linking to your website, they’d be ecstatic.

2. What is the coffeeneuring landscape like in Pittsburgh? How has it changed (if at all) since the first year of the Coffeeneuring Challenge in 2011?

The landscape has changed; shops have come and (sadly) gone. The biggest change in Pittsburgh’s coffeeneur-shed is the explosion of cycling.

Local politics reached a tipping-point due to twelve years of BikePgh advocacy– we started seeing bike racks and bike corrals, sharrows and bike lanes, and the number of cyclists has really climbed.

The Great Allegheny Passage (GAP)-C&O trail connection from Pittsburgh to D.C. (350 miles of trail!) was completed and there has been major economic impact. There has also been a lot of positive media bike-buzz. To sum it up: over the last four years, Pittsburgh cycling has gone mainstream.

To me the big thing is 2015 Coffeeneuring, when Pittsburgh sees the initial wave of BikeShare. If I was a coffeeshop owner, I’d want a BikeShare station in front of my shop or nearby on my street.

Imagine hopping a free 30-minute ride from your workplace, docking the bike, and enjoying a coffee. Then pick up a bike and go back to your day. And if a bike shop owner can’t get a BikeShare out front, I’d want a bike corral.

3. Pittsburgh has a fairly large coffeeneuring contingent. What is it about Pittsburgh that makes it a coffeeneuring city?

I think the BikePgh message board played a role in coffeeneuring’s catching on. Another factor is that Pittsburgh has ninety distinct neighborhoods, and coffeeneuring is an opportunity to explore and see new places- who doesn’t love that.

from a “2013 coffeeshop without walls” in Point State Park, terminus of the Great Allegheny Passage

4. What are the ideal ingredients for a good coffeeneuring experience?

• Adventure and Novelty; it should be a shop that’s new to you, or infrequently seen. The distance or terrain really isn’t a factor, because: adventure.
• Bike parking is a big factor, right out front. I have brought my bike into a coffeeshop where parking wasn’t available.
• A noob-friendly coffee shop always wins; show me a sign identifying three unusual coffees and let me choose between fruity/ earthy/ citrus, and I am yours.
• Friendly staff is key, and so is a tolerant customer-base. Because some people think cyclists dress funny. Do I really need to mention WiFi and electrical outlets?
• Let me also say: if you’re doing coffeeneuring right, you’re going to encounter a less-than-perfect coffee shop because you’re exploring and investigating and that’s OK.

5. Do you have an absolute favorite coffee shop? What is it and why?

In a place with 90 neighborhoods, I have these absolute favorite coffee shops:

• Blue Canary, Ambridge. bike friendly, bike parking, the ice for iced coffee is made of frozen coffee, bike friendly, vinyl music, excellent coffee.
• Big Dog Coffee, SouthSide. bike friendly, bike parking, great oatmeal for breakfast, excellent novel coffee.
• Commonplace Coffee, Squirrel Hill. this place is All About Excellent Coffee.
• Tazza D’Oro, Highland Park. so bike friendly, three weekly rides stage out of there. Excellent coffee, great staff, great pastries.

6. You are 1 of only 6 7 people who have completed the Coffeeneuring Challenge every year. What keeps you coming back?

Riding my bike, out in the weather, looking for new places, revisiting faves, drinking coffee, low admin tasks.

The question is, what could keep me away?

7. What did I forget to ask you that I should have?

Two things you possibly forgot to ask: what do I see in the future of coffeeneuring, and you forgot to ask about The Bike!

What do I see in the future of coffeeneuring?

I see coffeeneuring growing and adapting. People’s worlds are changing, and I think the requirement for weekend riding (whenever your weekend is) is becoming anachronistic and a barrier.

In a world of three part-time jobs and Lyft-driving, I anticipate a “twice a week max” Coffeeneuring Challenge policy.

I see coffee shops embracing coffeeneuring as a smart business move. What shop owner wouldn’t want to be attracting cyclists – both for the business, and to enhance the shop’s vibe? A forward-thinking group of coffee shop owners could offer incentives for coffeeneuring at their places.

The bike!

Finally, the bike – Surly Long Haul Trucker, known at times as Precious, also known as Cankles.