By: Matt Meltzer
Sure, our national parks are beautiful, beach camping is a blast, and taking a road trip is a fun way to spend a few days, but sometimes you want to explore a totally new city. And for that, we've got you covered.
At Thrillist, we've been in the "have fun in the city" game for over a decade now, and our resources run DEEP. Which is why we tapped our crack staff of writers and editors across the country to whittle down 300-plus American cities (with populations over 90k) to the absolute 25 best for spending three days. From bars and restaurants, iconic foods, and live tunes, to museums, outdoor activities, and cheap Airbnbs (not to mention beaches, parks, and ease of getting around), we took into consideration everything that makes for a great weekend.
It wasn't easy, but, in the end, we came up with a bucket list we think stands up to the test. And one we think you'll want to start working your way through right away -- 'cause, you know, there are only a couple dozen weekends left in the year!
25. Sioux Falls, SD
Must-eat/drink: Smoked pheasant, or some other wild game cooked only as South Dakotans can do it, at Parker's Bistro
Don't leave without: Walking around the entire city. The great thing about Sioux Falls is that you can literally walk through Downtown (and the sculpture walk) to the serene Falls Park, and then back through East Bank, in an afternoon. The city is impeccably clean and its cutting-edge restaurants (like CH Patisserie, one of the 21 best bakeries in America) and breweries can hold their own against any from a city 10 times the size. Hit Monks House of Ale Repute on the right weekend, and it'll be sampling beers from all over the Midwest in the courtyard.
Weekend highlights: It's South Dakota, so maybe going in February isn't really the move. But in the summer, you can have a great weekend there for a fraction of what you would spend in a larger town, and the walkability, cleanliness, and proximity to wilderness (Palisades State Park is only about 30 minutes away) make it a great city to try for a few days. Plus, the local hockey and basketball teams not only sell out their games, but play in two of the cooler arenas in all of minor-league sports: the Denny Sanford Premier Center and the Sanford Pentagon.
24. Kansas City, MO
Must-eat/drink: Ribs at Joe's Kansas City Bar-B-Que
Don't leave without: Touring Boulevard Brewing and drinking something you can't get elsewhere at the tap room
Weekend highlights: Look, if you're in Kansas City, you're clearly going to want to OD on barbecue at some point, and a pilgrimage to (no longer Oklahoma!) Joe's is a must for any fan of meat and happiness (though don't sleep on the burnt-end game at LC's). But it's not all about barbecue. It's also a legendary steak town! Skip the chains and snag a butchered-to-order bone-in filet at Anton's. A trip through brewing powerhouse Boulevard (and a few hours in its massive taproom) is a no-doubter for any beer lover, and seeing some famous bass player jump into an impromptu jazz set at the Green Lady Lounge is a can't-miss for any music lover.
Take some time out to amble around singular museum experiences like the National World War I Museum and the Negro Leagues Baseball Museum, but also set aside an evening to eat and drink your way through Westport, down next-level candlelit cocktails at Julep, devour a house-smoked brisket burger at Char Bar (it had been a few hours since you had smoked meat, you were starting to twitch), and get down on some Beard Award-winning fine dining at Bluestem, whose fried chicken-slinging farm-to-table offshoot, Rye, will leave your taste buds forever changed. To review: definitely eat all the barbecue you possibly can, but leave room for more, because Kansas City's doing too many other things well right now to ignore them. It isn't one of the country's seven most underrated food towns for nothing.
23. Providence, RI
Must-eat/drink: Pizza at Al Forno
Don't leave without: Checking out Rhode Island School of Design's Museum of Art, with over 84,000 objects housed on six floors. If you're into history (or architecture), the Rhode Island State House is a definite visit. It has the fourth-largest self-supporting dome in the entire world, and once past security, you're free to roam the halls or sign up for a tour. If you're more of a shopper, head Downtown to Westminster St, an Etsy-like emporium of stores peddling tons of locally made finds. Or, if you plan ahead, reserve a spot in one of Johnson & Wales' three-hour cooking courses -- you'll learn how to prepare everything from pastries to Indian cuisine. And finally, if your getaway is in a warmer month, do not miss Providence's WaterFire, when they set the river ablaze (but not in a Cleveland-in-the-'60s kind of way).
Weekend highlights: The academic and artistic talents of Providence's community run deep, largely due to the presence of an outstanding art school (RISD), an Ivy League university (Brown), and one of the nation's top culinary schools (Johnson & Wales). Providence is an oft-overlooked mecca of cultural offerings and intelligent, interesting people. Pedestrian-friendly streets and amazing architecture make this city a perfect place to stroll aimlessly. The state's access to the freshest seafood and local produce makes the culinary offerings second to none, and there is always something happening, from hockey games at the Dunkin' Donuts Center to art gallery openings and exhibits. Rhode Island may be the smallest state, but Providence proves that bigger isn't always better.
Credit: Flickr/Jay Reed
22. Philadelphia, PA
Must-eat/drink: Cheesesteak, duh. Get one at Pat's. Or Geno's. Or Pat's. Wait, Geno's. Aw, screw it, get one at one of these places.
Don't leave without: While pics near the Rocky statue after you run up the art museum's steps or at Pat's and Geno's in South Philly (aka "cheesesteak Vegas") will probably generate the most interest on your social media feeds, if you want to quietly take in Philly's cobblestone charm, snap up a sundae from Old City's Franklin Fountain and stroll around the historic district. Or, head to Rittenhouse Square and read that book you've been meaning to finish while the city hums in the background.
Weekend highlights: Philly is more than Wing Bowl insanity, Rocky nostalgia, and gooey cheesesteaks; it's a vibrant, unpretentious, blue-collar town and a perfect three-day destination. Between the world-class museums -- the Barnes Foundation is a must-see -- the gorgeous parks, peaceful walking trails, rockin' live-music scene, and excellent food and drink, you will have a blast (even on a tight budget). In fact, with a little insider knowledge, you can find all kind of fun on the cheap. If you like a little culture mixed in with friendly comfort, Philly is the perfect place to visit.
21. Pittsburgh, PA
Must-eat/drink: The Pitts-burger at Primanti Brothers (it's a cliche for a reason, people) and Iron City Beer -- preferably at the same time
Don't leave without: Going out in Shadyside on Friday night, and curing your hangover with a trip to the Strip District the next morning
Weekend highlights: To many, Pittsburgh is the new crown jewel of the Rust Belt. An ex-steel town that's evolved into a hotbed for medical, financial, and film professionals, it's one of the most prosperous cities for young folks in the country. And you know what young people like to do? As Andrew W.K. would say, "Party." It's the quintessential big-ish, small-ish city, where you will almost definitely run into people you know on a night out -- but as long as you're not on the frat-tastic Southside, you probably won't mind.
Pittsburgh may be known as a sports-crazy town, and crap -- it really is. While the six-ring Steelers have a stranglehold on the hearts of 'Burgh fans, you'd be remiss not to visit the jaw-droppingly beautiful PNC Park, with its panoramic view of the city and ball team that can actually play for once in two decades. And the city's art scene is surprisingly vibrant, the main attraction being hometown boy Andy Warhol's palatial museum, complete with its very own balloon room.
For drinks and eats in a distinct setting, it's hard to find a better joint than Church Brew Works -- a brewpub forged out of an abandoned church in the city's Strip District. Cap the night off with a drive up Mount Washington (suckers take the incline) and a nighttime view of the city of three rivers. And seriously, don't talk crap about the Stillers if you value your front teeth.
Credit: Flickr/Erik Drost
20. Cleveland, OH
Must-eat/drink: Burning River, Great Lakes Brewing
Don't leave without: Figuring out that Cleveland actually does rock (and no, you won't run into Drew Carey). It's the Midwestern city at the butt of 80% of fictitious origin-story jokes, but it doesn't really give a crap that it's misunderstood -- because while you were snickering, it was building up a bevy of culture without running up costs like larger cities. It has the Rock and Roll Hall of Fame (fun tip: if you're in a band, bring a physical copy of your music -- you'll get in for free), a stunning new art museum, and a world-renowned orchestra. Walk pockets of town -- Lakeview, Ohio City, Tremont, and, perhaps the most literal and longstanding example, Coventry -- exploding with new energy and old charm in tandem.
Weekend highlights: Downtown is better than it's ever been, and the strip that is East 4th St, forever partitioned for pedestrians, is the only block you need for a Saturday night: eat at one of Zack Bruell or Jonathon Sawyer's restaurants, catch a show at the mid-sized House of Blues, and hit the new Horseshoe Casino (inside the old Higbee's, where Ralphie saw the bottom of Santa's boot in A Christmas Story) for a nightcap and roll of the dice. Go to the nearby Hofbrauhaus during brunch for a full-fledged liter-beer-drinking romp and latkes, soundtracked with live polka. This is as Ohio as it gets, and you will love it.
19. Washington, DC
Must-eat/drink: DC has arguably the best Ethiopian restaurants in the country. The go-to spot is Dukem, located on popular U St -- order a combo sampler and throw some tibs on there for good measure.
Don't leave without: Visiting the pandas at the National Zoo -- the cub, Bei Bei, just made his debut this January
Weekend highlights: Visitors to DC can have an amazing time without spending a lot of cash. There are a ton of super-cheap places to eat and a slew of fantastic, totally free things to do, like visiting world-class museums, monuments, memorials, botanical gardens, the aforementioned zoo, and the roof of the Kennedy Center -- which offers breathtaking views. It's also a great biking city: ride down the Mount Vernon Trail, pedal from Nats Park to Kingman Island, or make a beeline for killer local brewery DC Brau.
After all this exercise and thriftiness, you can blow some ducats on a meal at any of José Andrés' small-plate joints (worth it), and catch a show at Rock & Roll Hotel, U Street Music Hall, the 9:30 Club, or the Black Cat -- you might not think of DC as a place that throws down, but these spots will change your mind fast.
18. Madison, WI
Must-eat/drink: The Scrambler from Mickies Dairy Bar
Don't leave without: Drinking a beer, looking at boats, and listening to live tunes, all while sitting waterside at the Memorial Union Terrace
Weekend highlights: Madison is a college town, of course, and it's almost impossible to visit without realizing that; the school has gobbled up the bulk of one side of the constantly visible capitol building. Said campus is worth a walk: Bascom Hill provides the finest view in the city, the famed chairs at the lakeside Memorial Union Terrace are one of the best places I've ever consumed a pitcher of German beer, and Camp Randall Stadium is Football Saturday incarnate. But there's more! Obviously food, including campus stuff like Mickies Dairy Bar, but also, notably, Ella's Deli's acid trip of a Reuben joint, and grinning culinary assassin Tory Miller's tremendous L'Etoile.
Drinking? Yes, they drink here. Constantly! And happily. Keep that in check and you can walk basically anywhere if you really want to. There are parks galore, the zoo is actually pretty impressive, don't forget the lake that Otis Redding's goddamn plane crashed into (great for waterskiing!), and of course, it's all finished off with a healthy coat or two of good old-fashioned Midwest Nice.
17. Santa Rosa, CA
Must-eat/drink: Pliny the Younger at Russian River Brewing Company. One of the world's highest-rated beers, this IPA draws lines around the block when it is released.
Don't leave without: Cycling. Because Santa Rosa is the big city in Sonoma wine country, your best bet for seeing it all is hopping on a bike and touring the wineries and breweries; or, hell, just cycle to take in the views. The same landscapes that make for an exemplary range of wines make for a tremendous variety of vistas, from valley vineyards to gentle mountain terrain to the coast at Bodega Bay. The roads and trails are all super bike-friendly, and you can ride them whether you're an expert cyclist or just lost your training wheels.
Weekend highlights: Santa Rosa has been a popular getaway for people in the Bay Area for decades (it's only an hour and a half from San Francisco) but flying there is easier than you think -- there are nonstop flights from seven West oast cities. And even though there are over 400 wineries in the Sonoma region to visit, you'd be remiss if you didn't spend some time in Santa Rosa. The Downtown -- with its restaurants, antique shops, and historic buildings -- is especially walkable and a nice break in between trips to the vineyards. Added bonus: Santa Rosa feels more like a small town than a wine destination and still boasts that laid-back Northern California vibe seemingly lost in some other area spots.
16. Boulder, CO
Must-eat/drink: Any "tap room rarity" at Avery Brewing
Don't leave without: To truly take advantage of all Boulder has to offer, grab a pressed juice at Pearl St's Wonder Press, and then transfer that juice to your CamelBak, because it's time to go hiking at Chautauqua. Or biking. Or trail running. Or rock climbing. The numerous outdoor options are one of Boulder's many draws. Weather is another one -- the sun practically never stops shining (it also requires you to wear sunscreen, as the sun's gonna burn you pretty good when you hang out at 5,400ft). Even in the winter!
Weekend highlights: For one of the smaller towns on this list, Boulder holds its own in terms of outdoor activities, food, beer, weather, and general beauty. Sure, it's not exactly dirt-cheap to hang out here, which costs it a few points in the ranking. But the outdoor stuff is free. Oh, and there's legal weed. Some people visit for the weekend solely for the bud, but when the weekend smokers travel back to their home states, there's no chance that cannabis is the only reason they want to come back.
Credit: Flickr/Visit St. Pete/Clearwater
15. St. Petersburg, FL
Must-eat/drink: The Crank IPA at Cycle Brewing, one of the 10 best breweries in Florida
Don't leave without: Checking out Jannus Live, not so much just to catch a show but because it's the centerpiece of the main stretch of bars on Central Ave (located in a courtyard in the middle of the block). The restaurants in the area are part of an exploding food scene that few outside of Florida know exists, but you can easily fill a weekend trying places like The Mill and Birch & Vine. Then heading for craft cocktails at Cask & Ale or Mandarin Hide, or beers at Cycle Brewing or 3 Daughters.
Weekend highlights: St. Petersburg is quickly becoming the East Coast's answer to San Diego: a place once known for its impeccable beaches that's now the cool, smaller city with great beer, innovative food, and far fewer people to share it with than its larger neighbors. Not only that, but there's also Fort De Soto Park with one of the best beaches in Florida, Clearwater or Siesta Key and MORE beaches, the Rays, and even a Dali Museum.
14. Asheville, NC
Must-eat/drink: Pulled whole-hog BBQ at Buxton Hall
Don't leave without: Hiking. Or biking. Or doing SOMETHING outdoors. Yeah, Asheville's got one of the best beer scenes in America but going to the Blue Ridge Mountains without getting ON the mountains is like going to New York and not eating pizza. There're literally 2,000 miles of hiking and mountain-biking trails here, plus a 60ft natural water slide in Pisgah National Forest. And the Biltmore -- the most beautiful place in North Carolina -- is here too!
Weekend highlights: If you're into beer, and the outdoors, and live on the East Coast, Asheville is like your Portland or Denver (without, ya know). But it's a far more affordable destination than either of those, and boasts a lot more in a smaller area. Sierra Nevada just opened its only East Coast outpost here, and Asheville has more breweries per capita than any city in the US. Getting there can be tricky (the airport only serves seven cities and has four airlines), but it's not a bad drive from much of the Mid-Atlantic. And once you're there, the city is incredibly walkable -- so even if you ignore our advice and shirk the mountains, you can burn off all that beer and barbecue just strolling from one place to another.
13. Chicago, IL
Must-eat/drink: A burger at Au Cheval
Don't leave without: An architecture boat tour, closing down a 4am bar, catching some comedy, getting out of Downtown
Weekend highlights: If you've never been to Chicago, it's understandable that there are certain obligatory boxes you're going to want to check, which is fine. Get that selfie in front of the Bean before hitting a museum or the aquarium if you must. Take an architecture boat tour (actually a fantastic intro to Downtown and the lakefront). Hit Second City or iO for some world-class comedy, and (obviously) consume the local holy trinity of deep dish, Chicago-style dogs, and Italian beef.
But you're doing yourself a serious disservice if you spend your whole weekend tethered to the Downtown area, because the neighborhoods are where you find the city's true pulse. Head north to Wrigleyville if sports are your thing, or to Lincoln Square for some Half Acre beer and incredible pie if they aren't. Head west and walk the 606, a repurposed discontinued train line linking four of the city's most vibrant (and delicious) neighborhoods. Head south to Bridgeport for the White Sox, yes, but also for Maria's, a hybrid beer bar/bottle shop some call a "slashie" that you won't want to leave. Just don't spend your whole weekend within a couple of blocks of Michigan Ave, because you're better than that.
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