These 8 Urban Walking Tours Are Quirky to the Max

June 27, 2016

More interactive than a guidebook and more personal than a hop-on bus tour, walking tours combine entertaining guidance, quirky trivia, a chance to explore like a local…and snacks.

Sold? We’ve picked eight of the best urban walking tours around, where you’ll get to nosh on BBQ, admire public art…even indulge your Hamilton obsession. It doesn’t matter if you’re in town for the long weekend or want to get to know your own city a little better—it only matters that your shoes are comfy. 

NEW YORK: TENEMENTS, TALES, AND TASTES: Fact: New York wouldn't be its vibrant and diverse self without its immigrant communities. To learn more about the city's immigrant traditions, sign on for Urban Adventures's fascinating Tenements, Tales, and Tastes tour. Attendees will get a primer on Lower East Side history while sampling knishes, dumplings, and other delicacies first brought to the city by way of Ellis Island.

Image courtesy of Rachel K. So Photography/Flickr
PHILADELPHIA: MURAL MILE WALKING TOUR: If you haven't already discovered Philadelphia's incredible Mural Arts Program, what's keeping you? (Seriously, just look around—there are more than 3,600 public artworks in town.) If that scale sounds a little tough to tackle solo, though, get started with a guided Mural Mile Walking Tour, which takes attendees past Center City's showstoppers.

Image courtesy of Steve Weinik for the City of Philadelphia Mural Arts Program
SEATTLE: COFFEE TOUR: Yeah, yeah, it might be a cliché that Seattleites are obsessed with their java...but seriously, the coffee is good here, people. For further proof, opt to spend several hours on Seattle By Foot's Coffee Crawl, which tutors caffeine fiends on the local scene, with more than six brewed samples included. (Maybe nosh on a pastry first to avoid any tremors.)
SAN FRANCISCO: RADICAL SF ROUTE: The City by the Bay might be famous these days for its tech and start-up scene, but don't forget that San Francisco has long been a countercultural hub. Wild SF Tours's Radical SF Route winds its way through The Castro and Mission District while tutoring amblers on local civil rights history, political street art, and area activist movements.

Image courtesy of Wild SF Tours
PORTLAND: FLAVOR STREET FOOD CART TOUR: Given that Portland has so many food trucks (over 500, if anyone's counting) that they need to be organized into pods, having guidance on the tastiest eats is a borderline necessity. Thankfully, there's Portland Walking Tours's Food Cart Tour to the rescue. From gelato to Cajun beer chicken chili, Turkish toast to Belgian waffles, attendees are in for a globetrotting eating extravaganza. Maybe wear your loose pants.

Image courtesy of Portland Walking Tours
CHICAGO: PEDWAY TOUR: The Windy City is famous for its architecture-themed riverboat tours. But once you've seen sky-high Chicago, train your sights on the subterranean Pedway Tour, run by Chicago Elevated. Described by the improv-trained guide Margaret Hicks as "the unsung hero of Chicago," The Pedway charts an underground path through (well, mostly below) the Loop and comes with all kinds of quirky lore—and many natives don't even know it's there.

Image courtesy of Chicago Elevated
WASHINGTON DC: HAMILTON'S DC: What's your name, man? Alexander Hamilton is def the Founding Father du jour, thanks to, oh, one of the most successful Broadway musicals of all time. Whether or not you've hit the ticket jackpot, you can also get your Hamilton fill on this DC walking tour, which gives attendees the lowdown on this singular man—and, sticking with the theme, ends at The Hamilton restaurant and bar.

Image courtesy of Washington Walks
AUSTIN: BRUNCH, BEER & BBQ TOUR: There are a few musts for any food lovers spending time in Austin. Breakfast tacos? Check. BBQ? Yup. Craft beer? That too. Desserts? Who wouldn't! You could try to hit all of your stops solo...or you could sign on for a Brunch, Beer & BBQ Tour, which does all of that in one (plus, yes, brunch). 'Cause everything is bigger in Texas—including the urban walking tours.
NEW YORK: TENEMENTS, TALES, AND TASTES: Fact: New York wouldn't be its vibrant and diverse self without its immigrant communities. To learn more about the city's immigrant traditions, sign on for Urban Adventures's fascinating Tenements, Tales, and Tastes tour. Attendees will get a primer on Lower East Side history while sampling knishes, dumplings, and other delicacies first brought to the city by way of Ellis Island.

Image courtesy of Rachel K. So Photography/Flickr
PHILADELPHIA: MURAL MILE WALKING TOUR: If you haven't already discovered Philadelphia's incredible Mural Arts Program, what's keeping you? (Seriously, just look around—there are more than 3,600 public artworks in town.) If that scale sounds a little tough to tackle solo, though, get started with a guided Mural Mile Walking Tour, which takes attendees past Center City's showstoppers.

Image courtesy of Steve Weinik for the City of Philadelphia Mural Arts Program
SEATTLE: COFFEE TOUR: Yeah, yeah, it might be a cliché that Seattleites are obsessed with their java...but seriously, the coffee is good here, people. For further proof, opt to spend several hours on Seattle By Foot's Coffee Crawl, which tutors caffeine fiends on the local scene, with more than six brewed samples included. (Maybe nosh on a pastry first to avoid any tremors.)
SAN FRANCISCO: RADICAL SF ROUTE: The City by the Bay might be famous these days for its tech and start-up scene, but don't forget that San Francisco has long been a countercultural hub. Wild SF Tours's Radical SF Route winds its way through The Castro and Mission District while tutoring amblers on local civil rights history, political street art, and area activist movements.

Image courtesy of Wild SF Tours
PORTLAND: FLAVOR STREET FOOD CART TOUR: Given that Portland has so many food trucks (over 500, if anyone's counting) that they need to be organized into pods, having guidance on the tastiest eats is a borderline necessity. Thankfully, there's Portland Walking Tours's Food Cart Tour to the rescue. From gelato to Cajun beer chicken chili, Turkish toast to Belgian waffles, attendees are in for a globetrotting eating extravaganza. Maybe wear your loose pants.

Image courtesy of Portland Walking Tours
CHICAGO: PEDWAY TOUR: The Windy City is famous for its architecture-themed riverboat tours. But once you've seen sky-high Chicago, train your sights on the subterranean Pedway Tour, run by Chicago Elevated. Described by the improv-trained guide Margaret Hicks as "the unsung hero of Chicago," The Pedway charts an underground path through (well, mostly below) the Loop and comes with all kinds of quirky lore—and many natives don't even know it's there.

Image courtesy of Chicago Elevated
WASHINGTON DC: HAMILTON'S DC: What's your name, man? Alexander Hamilton is def the Founding Father du jour, thanks to, oh, one of the most successful Broadway musicals of all time. Whether or not you've hit the ticket jackpot, you can also get your Hamilton fill on this DC walking tour, which gives attendees the lowdown on this singular man—and, sticking with the theme, ends at The Hamilton restaurant and bar.

Image courtesy of Washington Walks
AUSTIN: BRUNCH, BEER & BBQ TOUR: There are a few musts for any food lovers spending time in Austin. Breakfast tacos? Check. BBQ? Yup. Craft beer? That too. Desserts? Who wouldn't! You could try to hit all of your stops solo...or you could sign on for a Brunch, Beer & BBQ Tour, which does all of that in one (plus, yes, brunch). 'Cause everything is bigger in Texas—including the urban walking tours.