It’s taken me all summer to make the arrangements and get everything set, but as of today I’m happy to announce my newest travel adventure: The Great American (…and Canada!) Hipster Project.

The search for the coolest cultural things to do in America (…and Canada!)

The project

It’s this 7-week trip I’m currently on in North America. Over the next several weeks I’ve set some goals and made some travel arrangements to make my trip home a bit more exciting and interesting. While hopping back and forth across the continent, I’ll be seeking out the coolest cultural things to do in each city I visit. Whether it’s attending the Toronto International Film Festival, dive bars in Boston or trendy restaurants in California, I’m scoping out some of America’s most interesting cities. I plan to try new things, re-experience some history and explore new cities with new friends.

Everything from flea markets to music festivals, Texas-style sushi rolls to legendary San Francisco burritos, swimming pools and wine trails. This is the Great American (…and Canada!) Hipster Project.

Who/What is a hipster?

Before I hop on my next flight…a few details. You’re probably wondering who or what I consider to be a hipster. I throw the word around a lot and because of this habit, it might be hard to pin down a definition. I’ve tried before but it ended up pretty vague.

I’m an eternal optimist and “hipster” is just about the only label I’m proud to self-apply. But if I must: hipsters are non-gender-specific people that like the most current trends (even when those are kickbacks to older generations). Sometimes they’re obnoxious, sometimes they’re self-involved, sometimes they’re awesome and friendly. Regardless, hipsters tend to seek out the “next big thing” and thus are always on the lookout for the coolest cultural things to do…around the world or in their backyard. And that’s reason enough why I’m proud to label myself as a hipster. Even if no hipster ever would use the word themselves.

But let’s not argue semantics. Let’s see all the cool & trendy cities I plan to visit…

Where I’m headed

Seven weeks in more than seven cities. It won’t be easy and it’s taken months of planning, but here it is—the final itinerary & plan:


Southwest & Midwest

  • Dallas, Texas
  • Austin, Texas
  • Cleveland, Ohio
  • Columbus, Ohio




  • Toronto
  • Montreal




  • San Francisco
  • Sonoma Valley



New England

  • Boston, Massachusetts
  • New York City
  • New Haven, Connecticut


These cities may not be the most intuitive choices for finding the most hipster places in America…but that’s the point. I want to prove that just about any major city with a decent population can be trendy, exciting and yes, even interesting for a hipster. I’ll look out for the most interesting restaurants (or food carts), the most unique hotels and the most unusual events.

In addition to having fun exploring a lot of these cities, I’ve also lined up a few speaking gigs, including at a college in Connecticut (stay tuned!) and at the Boston Meet, Plan, Go event in October. If you haven’t heard of MPG, check out the details for the Boston event—it’s a nation-wide event encouraging career breaks.

How I’m planning to travel

It’s not just the destinations that matter. Half the fun of traveling is the way you travel. To keep myself on my toes, I’ve set some guidelines for myself during the Great American (…and Canada) Hipster Project. And even though I’ve already got a travel manifesto, these travel rules will help set this trip apart from my others.

1. Eat well

That means no fast food. Yes, I’m planning seven weeks of travel around America and I’m planning to not step inside a McDonald’s once. I’ll be embracing the hipster lifestyle head-on. That means healthy organic foods when possible and occasional vegetarian days (though of course not while in Texas). I’ll look for the trendiest gourmet restaurants as well as the hole-in-the wall, dive-y restaurants hidden in gas stations.

2. Look good

I’ve had a hundred different travel styles over the years. Sometimes I’m a backpacker, sometimes not. On this trip I’m a bit of both: couch-crashing & boutique hotels are both on the itinerary. And because I’m also attending weddings, I’ve even got a business suit with me! I’ll be sporting my trendiest t-shirts during most of the trip, though: a hpptster shirt from Kneadle and tees from Out of Print Clothing…not to mention Primark and H&M.

3. Travel smart

What’s the most important accessory for a hipster? The internet. And with a borrowed iPad, a cheap smartphone from Best Buy and a MiFi internet point from Verizon, I’m all gadgeted-up. And to make certain I’m sticking to my own rules, rather than stuffing my gadgets in my backpack’s pockets and throwing my laptop in a hipster bag, I’m traveling in style with my lovely leather laptop bag from Knomo.

4. Live it up

With so many adventures and mini-trips planned during my seven weeks in America, I want to make sure I stay comfortable. And though I’m not expecting much sleep (there are plenty of clubs and bars I’m hoping to check out), I do enjoy the occasional comfort of a king-size bed! Who ever said dirty hipsters had to sleep on park benches in train stations? Give me a hotel room with bath salts and a floor-to-ceiling mirror and maybe I’ll actually wear a quiff (unlikely).

Follow the trip!

If you want the low-down on all the most cool, most hip spots during my travels, be sure to follow my travel adventures. Follow the trip here:

Mad props to my family and friends who are supporting me at home and abroad during the trip. Couldn’t do it without your weddings, couches and home-cooked meals! And thanks to the companies and tourism boards helping with many of these travel arrangements.

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