Trip Ideas outdoor tree road green neighbourhood house Town street residential area urban area sidewalk wall alley human settlement Courtyard estate grass home Garden yard flower suburb infrastructure Village way facade lawn stone curb
Trip Ideas

America’s Coolest Streets

Let us preface this by saying: any list that claims to know the "best" streets in an entire country is, shall we say, debatable. But for our vacay money, these are certainly worth a slot on your bucket list, thanks to buzzy restaurants, historic sights, and shopping experiences you'll never find on the interwebs. Tell your Uber driver we sent you.

See recent posts by Kathryn O'Shea-Evans

Trip Ideas plate food dish bowl meal breakfast cuisine meat produce curry vegetarian food vegetable containing
Trip Ideas indoor Drink alcoholic beverage cocktail distilled beverage Bar dish
Trip Ideas indoor table floor Kitchen room restaurant ceiling Bar café interior design cafeteria Design meal area dining table

Top left and bottom middle courtesy of Emmer & Rye


Rainey Street, Austin TX

Bourbon Street is getting a run for its booze money on Rainey, a collection of century-old bungalows-turned-bars. Prep for a night of debauchery with a locavore dinner at new restaurant Emmer & Rye (order the lamb leg with wasabi arugula), then head to Blackheart--the whiskey list is longer than a small town phonebook (18 year Yamazaki, anybody?)--and Lucille’s, where hammocks and a gin-slinging outdoor bar await.

Book Hotels in Austin
Trip Ideas table wooden food meal bakery dish dessert breakfast brunch hamburger baking sense sweetness restaurant lunch flavor produce
Trip Ideas color red light Christmas mid autumn festival arranged
Trip Ideas sky outdoor metropolitan area skyscraper transport landmark City cityscape urban area metropolis overpass Architecture bridge skyline public transport tower block Downtown skyway platform tower

Clockwise from top left: courtesy of Noah Fecks, New Museum/Lena Huber, and Carl Mikoy


Prince Street, NYC

Of all the hipper-than-thou streets in Gotham, Prince is our favorite—it stretches from the New Museum (where Swiss artist Pipilotti Rist is on view) to Andrew Carmellini’s restaurant The Dutch. Plenty of points in between are must-sees, including bibliophile mecca McNally Jackson Books and St. Patrick’s Old Cathedral, a gothic revival 1809 church where part of _The Godfather _was filmed.

RELATED: 10 Stylish (and Affordable) NYC Stays

Book Hotels in NYC
Trip Ideas indoor floor ceiling building Lobby room interior design Design tourist attraction real estate estate wood empty
Budget Trip Ideas table indoor wine alcoholic beverage Bar Drink restaurant lighting cocktail
Trip Ideas sky road outdoor street lane City pedestrian crossing urban area asphalt road surface neighbourhood residential area human settlement walkway infrastructure Downtown suburb pedestrian shape day

Top left and bottom middle courtesy of the Woody Guthrie Center


Brady Street, Tulsa, OK

Here’s why Brady Street is more than OK (get it?): As the center of the Brady Arts District, it’s home to the Woody Guthrie Center, where you can read the artists journals, see his hand-written original lyrics to This Land is Your Land, and check out his pal Kris Kristofferson’s Joplin and Cash-signed Martin guitar. After, head to The Tavern for chicken and dumplings with a side of duck fat brussel sprouts, and Chimera for a Sarsparilla Old Fashioned cocktail.

Book Hotels in Arizona
Trip Ideas sky outdoor grass tower building landmark structure monument column obelisk horizon clouds day
Trip Ideas sky outdoor grass structure landmark building Architecture City estate residential area way road stone
Trip Ideas road outdoor sky building landmark structure Architecture classical architecture street government building Downtown facade plaza palace City opera house courthouse estate colonnade day

Top right courtesy of Alan Karchmer/NMAAHC


Constitution Avenue, Washington, D.C.

A street with more free museums and eye-popping sights than we can count—including the 555 foot-tall Washington Monument, the National Archives (home to some documents we’re hoping a few news-making politicians make time to re-read), and the brand-spanking new National Museum of African American History? It's basically an IRL version of American History 101.

Book Hotels in Washington DC
Trip Ideas building outdoor store urban area Shop bookselling street shopping facade retail restaurant
chowder Dining Eat food Food + Drink Seafood soup Trip Ideas indoor dish meal breakfast produce cuisine meat
Trip Ideas Weekend Getaways outdoor plaza neighbourhood Town City shopping mall retail Downtown pedestrian shopping outlet store sign

Pike Place, Seattle

You bet it's touristy. But it's touristy for a reason. Start with a caffeine jolt at the original Starbucks—well, a recreated version of the 1971 flagship—where tabletops were salvaged from a nearby farm and wall tapestries are actually burlap coffee bags. Then hit the 1907 Pike Place Market, where you can sit where Tom Hanks did during filming of _Sleepless in Seattle _while you tuck into New England clam chowder in a sourdough bread bowl at the Athenian.

RELATED: 10 Hottest Spots in Seattle Now

Book Hotels in Seattle
Trip Ideas sky outdoor Beach shore Sea body of water Ocean Coast vacation caribbean Resort Island bay vehicle arecales sandy sand tropics day
Trip Ideas plate table food cake dish plant dessert piece breakfast slice produce meal fruit land plant citrus cheesecake flavor flowering plant chocolate dairy product sliced arranged cream
Trip Ideas outdoor road building sky bus Town street neighbourhood City human settlement vacation residential area plaza Downtown shopping mall tourism parked cityscape walkway retail past tour traveling van

Ocean Drive, Miami Beach

Art Deco-era architecture fiends traverse the globe to study the clean-lined hotels lining Ocean Drive, including Clark Gable’s old hangout, the Park Central Hotel, and the Colony Hotel, a 1935 stunner with an iconic blue neon sign. After perusing the grand dames (and taking a dip in the adjacent turquoise ocean), head straight to the 24-hour News Cafe (a favorite of Gianni Versace) for the best key lime pie you’ll ever taste.

RELATED: Miami's Hottest New Hotels

Book Hotels in Miami
Trip Ideas person table food indoor plate meal dinner brunch supper Party lunch dish sense Family
Trip Ideas food table dish berry plate indoor produce plant fruit dessert crumble land plant baked goods breakfast cranberry cherry pie flowering plant meal blueberry
Trip Ideas tree outdoor property Town building house neighbourhood estate tourism home mansion Village palace monastery Courtyard hacienda old walkway

Bull Street, Savannah

We’d like to petition the city of Savannah to rename this Carb-oholic Avenue, because our favorite things to do on Bull Street involve eating entire plum raspberry pies at Back in the Day Bakery and slurping down tagliatelli all carbonara at Hugh Acheson’s restaurant, The Florence. Afterwards, there’s shopping: don’t miss perusing the expertly curated graphic clothes and housewares at Nola Jane.

RELATED: America's Coolest Southern Towns

Book Hotels in Savannah
Trip Ideas food dish plate indoor salad fruit greek salad produce hors d oeuvre vegetable land plant cuisine flowering plant radish meal square fresh arranged piece de resistance
Trip Ideas plate food piece dish dessert meal slice breakfast rugelach baked goods cuisine produce flavor fork baking
Trip Ideas plate food table indoor dish white meal cuisine breakfast produce vegetable
Trip Ideas indoor floor Living ceiling room Lobby interior design retail wood furniture Boutique Design tourist attraction decorated

Top left and middle courtesy of Rioja, top right and bottom middle courtesy of Bistro Vendome


Larimer Street, Denver

This street in the Mile High City is beloved for its foodie offerings: as the old expression goes, you can throw a pot brownie and hit a restaurant you’d like to try here. Some of the best: Rioja, a James Beard semifinalist with dishes like octopus flatbread and bourbon braised lamb shank, and Bistro Vendome, where the bouillabaisse is so good you could squint and think you’re in Paris.

Book Hotels in Denver
Trip Ideas wine bottle indoor Bar Drink shelf counter distilled beverage tavern alcohol several
Trip Ideas table indoor dish plant food produce land plant cloth flowering plant vegetable flower fruit
Trip Ideas water sky outdoor scene reflection cityscape City body of water River Harbor horizon urban area Sea marina dock human settlement cloud morning dusk skyline evening waterway vehicle bay several day

Thames Street, Baltimore

Edgar Allen Poe was actually here. That’s the feeling you get at The Horse You Came In On Saloon, because he was—this 1775 bar is purportedly the last one Poe visited before his death. Indeed, this part of Baltimore, known as Fell’s Point, teems with American history and lore. Stop by Frederick Douglass-Isaac Myers Maritime Park Museum to explore the docks where the famous abolitionist lived and worked, before stopping in at Thames Street Oyster House for note-perfect Maryland Crab soup.

Book Hotels in Baltimore

Want More?



All products are independently selected by our writers and editors. If you buy something through our links, Jetsetter may earn an affiliate commission.