Travel Guide for the ‘Great American Hipster Project’

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I spent this past September and October traveling around the USA and Canada—visiting friends, family and squeezing in plenty of visits to new cities and destinations. Here’s the final lowdown on my Great American Hipster Project.

Guaca-rolly sushi

Guaca-rolly sushi at the Roll on Sushi Diner in Austin

Texas

In early September, I visited both Dallas and Austin, Texas (in addition to my hometown). I went to friend’s wedding (congrats Allison!) and caught up with friends and family I hadn’t seen in years.

Dallas hipster highlights

  • Dinner at The Cedars Social — modern comfort food and handcrafted cocktails
  • One night of luxury in downtown Dallas at The Joule hotel — rooftop swimming and free drinks at the bar!
  • Eating Empanadas at a hole-in-the-wall restaurant

Austin hipster highlights

Cleveland museum

Inside the Cleveland Museum of Art

Ohio

Ohio was on my itinerary because I wanted to visit my family in Columbus, but I also added a stopover in Cleveland to visit a city I knew very little about. Besides wanting to visit the Rock & Roll Hall of Fame, I wanted to see if Ohio could beat my low expectations. Spoiler alert: it did.

Cleveland hipster highlights

  • The Rock & Roll Museum & Hall of Fame wasn’t just for old music nerds, but just as interesting for me as a twenty-something who listens to indie bands and won’t attend concerts in stadiums
  • Visiting a new brewery in Ohio City, Cleveland’s beer brewin’ district — Nano Brew
  • Rock & Roll themed cocktails at the Ritz Carlton
  • Dinner at the Prosperity Social Club in the Tremont neighborhood — pierogies, empañadas and nachos!

Columbus hipster highlights

  • Walking along the Short North where I spotted lots of cool graffiti
  • Night out in downtown Columbus with tapas and cocktails at Barcelona
  • Ice cream at Jeni’s — awesome flavors even if it was a bit pricey
  • Getting lost in the book stacks at The Book Loft
  • Roast beef sandwich at Katzinger’s Deli — traditional Jewish food

At the Kensington Market in Toronto — thrift clothes

Canada

My trip to Canada was put together by the Explore Canada team so that I could visit the Toronto International Film Festival and a pop music festival in Montreal called, fittingly, Pop Montreal! It was my first visit to Toronto, and, in a word—it was AWESOME.

Toronto hipster highlights

  • Cocktails at the “Cocktail Bar” part of The Black Hoof. We may have had to wait over an hour for a table, and nearly 20 minutes to get each cocktail, but it was worth it
  • Late-night pizza in Toronto’s gayborhood. The other guys and girls in line were social and offered up plenty of nightlife tips for the rest of my weekend
  • Attending TIFF. Jared Leto’s film was particularly good
  • Bar hopping with @NearAfar and @Ayngelina in Toronto’s hipster neighborhood: Ossington Street
  • Lunch in Chinatown with a local, followed by churros near Kensington Market
  • CN Tower Edgewalk — OMG. Cannot believe I survived this
  • Food tour through Queen Street West with @chowbellaTO

Montreal hipster highlights

  • Cocktails at La Distillerie, drinking out of jars and playing Korean drinking games
  • Fresh, Montreal-style bagels — surprisingly different from the NYC-style I’m used to (both are good)
  • Dancing all-night at a nearly empty gay bar (fun!), followed by the requisite poutine (gross!)
  • Realizing I don’t really like the band Deerhoof during the opening night of Pop Montreal
  • Drinks at Casa del Popolo — a hipster bar in Montreal’s Mile End district famous for its connection to the band Arcade Fire (they used to play gigs here before they made it big)
sonoma winery

Wine-tasting at Ram’s Gate in Sonoma

California

After my detour up north into Canada, I headed to San Francisco and the Sonoma region. It’d been years since I had last been to San Francisco and I was determined to have some fun! 

San Francisco hipster highlights

  • Doing the typical touristic things: riding a trolley car, helicopter tour, walking around Pier 39
  • Beers at San Francisco’s legendary Zeitgeist beer garden — very cool atmosphere even if it was cold outside, but I didn’t like that no photos were allowed and you were barred from using phones if sitting at the bar
  • Coffee in the Mission district at the beard-heavy Fourbarrel Coffee
  • A burrito tasting tour through the Mission
  • Cocktail bar crawl with some of the @gogobot crew
  • Visiting the Castro and seeing the Harvey Milk memorial plaque

Sonoma Valley hipster highlights

  • Breakfast with @MarkVogler from Out in the Vineyard — full-on American style breakfast with lots of coffee and apple-flavored sausage!
  • Wine tasting at the modern Ram’s Gate winery — beautiful scenery and excellent wines
  • Lunch at the El Dorado Restaurant in their garden — the truffle fries were amazing!

 

Boston

Sign inside the Boston MBTA subway

USA East Coast

The final weeks of my trip around America saw me back on the East Coast—my old stomping grounds. I spent a weekend in New York City and two more in my old ‘hood of Boston. Besides visiting a million friends who I desperately wanted to catch up with, I still managed to fit in some sightseeing.

New York City hipster highlights

  • Exploring the food in NYC’s Chinatown and Little Italy on a food tour — the eggrolls were amazing!
  • House party in Brooklyn — woot!
  • Running around NYC with @adventurousness including a visit to the Shake Shack
  • Late-night food in Koreatown

Boston hipster highlights

  • Dancing at the table at Soulelujah — one of Boston’s best club nights, every Saturday at ZuZu
  • Gay-dancing at some of Boston’s most popular gay club nights
  • Cocktails and burgers at the new jm Curley bar — try the hushpuppies!
  • Seeing Grizzly Bear live at the Orpheum Theater
  • Brunch at the Highland Kitchen with one of my bestest friends!

Blogs published by Adam Groffman • Please note some posts do make me some money, but I never sacrifice my integrity in exchange for a favorable review. Read the full disclosure policy.

6 total comments on this postSubmit yours
  1. Sounds like fun! Holler if you want hipster recommendations down south :). I can think of a handful in Asheville, Charleston and Atlanta at the very least.

    • Thanks Caroline! I’ve heard good things bout Asheville, actually. Never been myself to either of those cities though.

  2. Neat blog! I totally agree with the Chinatown foodtour in NYC. Num!!

    • NOM indeed! Thanks for the compliment – did you take the same tour in Chinatown?

  3. As a Bostonian I approve of your Hipster activities in my city! Mmm, jm curley is divine, as is Zuzu and Highland Kitchen!

    • JM Curley was one of the highlights in Boston — such an awesome bar! Thanks for your feedback Lillie :)

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