key west
Skip Vegas and head to Key West Instead | Darryl Brooks/Shutterstock
Skip Vegas and head to Key West Instead | Darryl Brooks/Shutterstock
Travel

The Best Small Cities in America to Visit for a Weekend

A quick getaway to a glitzy metropolis can be invigorating, but really, you need a full week to truly experience America's biggest and best cities. And while we're all for a relaxing trip to a cute small town, there's only so much leaf-peeping and antiquing you can do before you get bored. So why not split the difference? America's small cities offer the best of both worlds: all the trappings of a small town -- don't worry, there will be many opportunities to use the word "quaint" -- with enough culture, restaurants, breweries, and bustle to keep up with the big boys. Even better, you can easily fly (or drive) in and out and feel like you truly got to know the place. The sweet spot, we figure, is somewhere between 20 and 80 thousand folks -- who we can only assume will welcome you to town and swiftly point you to their favorite neighborhood dive and the bartender to ask for. Feel free to pack light.

Bozeman, Montana
Just out of Bozeman, Chico Hot Springs is basically a natural hot tub under the Big Sky | Chico Hot Springs

Bozeman, Montana

Population: 46,596 
Bozeman has long flown under the radar. Not for much longer -- some say this mountain town is poised to be the next Boulder, Colorado. It's an immediate charmer thanks to its gorgeous mountain setting and delightfully walkable downtown district jam packed with cool bars and restaurants. Home to Montana State University, you’ve got laid-back college town vibes paired Western small-town charm and a touch of big-city culture, like the Museum of the Rockies and an iconic music venue, The Rialto

Did we mention the outdoors? There's skiing, with the locals-heavy Bridger Bowl 30 minutes away and the larger Big Sky resort just an hour from town. There's some of the best fly fishing in the world, most notably in the Paradise Valley region down the road (on the way you’ll pass Livingston, quite possibly the coolest small town in America and an old Bourdain favorite). You’ve got hiking, biking, whitewater rafting, hunting, and anything else you can think of doing outside under the glorious Big Sky. And you’ve also got hot springs, from the in-town Bozeman Hot Springs (where live bands rock the outdoor pools) to the world-famous and awesomely funky old-school Chico Hot Springs further on down from town. 
 
Must eat & drink: Grab some bison tenderloin and cocktails at the upscale Open Range. Then make your way into some of Bozeman’s delightful neon-signed dives like Crystal Bar and the local chapter of the Eagles Club, where it's not uncommon to see a live 13-piece jazz band made up of community members playing to a crowd ranging from hipster poets to military vets. Montana Ale Works and Roost Fried Chicken are additional Bozeman musts, and you’ll definitely want to hit MAP Brewing to take in a pint overlooking the waters edge of the Bozeman Beach
 
Don’t leave without: Taking a trip to Yellowstone. It’s only 90 minutes away. -- Jay Gentile

Ithaca, New York
Taughannock Falls is a waterfall that you should chase | Walter Bibikow/DigitalVision/Getty Images

Ithaca, New York

Population: 30,999 (~60,000 when classes are in session)
Those unfamiliar with Upstate New York might undersell Ithaca as just a college town. It is, after all, home to Cornell University, Ithaca College, and Tompkins-Cortland Community College. And though the vibe of the city is definitely heightened when classes are in session, there's a lot more to it than Andy Bernard would have you believe. 

Ithaca is the perfect retreat for those wanting to escape the big city scene but keep all the perks larger cities have to offer. You can enjoy the bars and farm-to-table restaurants, catch a theatrical performance or a live outdoor concert, and shop to your heart's content without feeling like you've put 30 miles on your legs. But the city also gives you room to breathe. Admire the antique houses in the various historic neighborhoods like East Hill and Cornell Heights, two National Register Historic Districts. Slow your pace as you walk down colorful tree-lined streets through downtown, taking in architecture reminiscent of simpler times. Lazy afternoons can be spent following lush trails and crossing historic bridges leading to gorges and lakeside views not far from the city center. Chase waterfalls -- there are 150+ if them within 10 miles of downtown -- which demand to be photographed before diving in. And yes, those colleges are worth a visit: Cornell and Ithaca each boast more than a century of history and some of the the east coast's most lovely campuses. When you're done, take in the sunset over Cayuga Lake from Stewart Park, where you will inevitably wonder why you didn't come to Ithaca sooner. 

Must eat & drink: Grab upscale Italian at Gola Osteria or wood-fired pizza at Ciao!, then prepare to get crisp: With the highest density of craft cideries in New York state -- 10 within a 30-minute radius -- your first move drink should probably come from an apple. Head to Finger Lakes Cider House, and if you're visiting in early fall, you can hit up the annual Cider Week. Meanwhile, you're smack in the middle of Finger Lakes Wine Country, which boasts over 200 wineries, distilleries, and breweries.

Don't leave without: A hike through Taughannock Falls State Park leads to a 215-foot waterfall roaring off cliffs that tower nearly 400 feet above the gorge. -- Carol Cain
MORE: Ithaca is also the birthplace of French bread pizza -- learn more about it here

Key West, Florida
Duval Street -- home of Key West's most divey dive bars | Jeff Greenberg/Universal Images Group/Getty

Key West, Florida

Population: 26,990
Key West is kind of like Florida's Las Vegas. But dirtier. And more historic! Sure, the bars along Duval Street are a factory of regret, but if you want to avoid them altogether the place is still beautiful and rife with history, and believe it or not, there's plenty to do that doesn't involve daiquiris.

Though Smathers Beach isn't much to speak of, spending the day strolling the tropical streets filled with 100-year-old homes is a fascinating way to explore the island. As are the Mel Fisher buried-treasure museum, the Hemingway Home, and the Harry Truman house. And if you went to Florida to get on the water, there are no shortage of dives, including some amazing day trips out to the Dry Tortugas.

Then, of course, there's the nightlife. Going here and trying to hit "local spots" would be like going to New York and eating at bodegas. The touristy spots are the best, and with maybe the exception of Rick's, any bar you hit on Duval will be the laid-back, old-Florida, pseudo-divey experience you’re looking for. The place is packed every weekend with tourists and bachelor/bachelorette parties, and good judgment/inhibition typically gets left somewhere around the Seven Mile Bridge

Must eat & drink: Key lime pie at the Blond Giraffe. Fresh seafood pretty much everywhere.

Don't leave without: Making some terrible decisions. Kidding! Well, not really, but no trip to Key West is complete without a night on Duval Street and its holy triumvirate of bars: Irish Kevin's, Sloppy Joe's, and Captain Tony's. -- Matt Meltzer
MORE: Dive deeper with this guide to the Keys' best beaches

The Shop
Kick back with an oyster or a dozen from The Shop | The Shop

Portland, Maine

Population: 67,000
While there are no delightfully quirky comedies about the East Coast’s Portland (yet), this is a city you need to know and get to -- immediately. Portland, Maine, is rising in the ranks as a go-to for weekenders from cities like New York and Boston. Not just for its historic character (think ivy-draped brick facades and cobblestone lanes) but because Portland is cool. Like, really cool. The walkable downtown boasts dog-friendly breweries, boutique wineries, fancy donuts, industrial-chic restaurants, food trucks that are outposts of those industrial-chic restaurants. Not only that, the sweeping waterfront is peppered with sailboats ready to take you out to one of the hundreds of Calender Islands that scatter Casco Bay. 

Must eat & drink: Duckfat. 100% go to Duckfat. You probably have even heard of Duckfat -- it's one of the OGs of that whole chef-driven sandwich thing, and one of the best sandwich shops in the country. They cook everything in duck fat. The fries are legendary, and the main restaurant has a satellite operation that serves only the fried potatoes. You’re also eating oysters in Portland, so be sure to visit The Shop, which is a raw bar and shellfish market. Portland also has a ridiculous wealth of breweries. If you know your suds then you definitely know Allagash Brewing Company, but you may want to check out the boutique breweries like Rising Tide and Bunker Brewing

Don’t leave without: Taking a sailing trip to one of the many Calendar Islands. Maine Sailing Adventures takes people out on a variety of sails; check out the day sail aboard the 74-foot British design gaff rigged cutter (if that means something to you, you belong in Portland). They also have a yoga sail (if you're into that), but more importantly they have a wine sail. For $65 you get to learn about (um, drink) wine on a boat with pairable snacks. -- Meagan Drillinger
MORE: You're also gonna need a lobster roll: Here are the best in Maine and beyond

Santa Fe, New Mexico
Into earth tones? Then get into Santa Fe. | Andriy Blokhin/Shutterstock

Santa Fe, New Mexico

Population: 83,776
Easily the biggest city on this list of small cities, Santa Fe has emerged like a desert mirage as an oasis for great food, incredible art, and its stunning natural Southwestern beauty. This earth-colored city serves as a thriving art hub, as the trippy installations at Meow Wolf and litany of galleries on Canyon Road can attest. You are very likely going to consider owning a turquoise belt buckle at some point, but resist the urge. Instead, put in some quality hot-tub time at the Japanese-inspired Ten Thousand Waves

And be prepared to eat. A lot. Santa Fe is one of the best places to eat in America, period, and it's not all red and green chiles. But it's also a lot of red and green chiles, served lovingly atop world-class Tex-Mex fare at classic joints like Tia Sophia’s, Palacio Café, and the Pink Adobe, where slow-braised meats, fire-roasted peppers, and, yes, love find their way into pretty much everything. And, of course, don't skimp on the booze. This is, some say, the birthplace of the margarita as we know it. Hit up Maria's New Mexican Kitchen, which boasts a 60-year legacy and more than 200 varietals on its binder-like menu. So yeah, maybe buy that belt after you've gone up a few notches.

Must eat & drink: Along with the classics, grab a green chile cheeseburger at Santa Fe Bite: it's a 10-ounce sirloin patty with roasted Hatch chiles and an easy blend of Swiss & American cheese on a house-made brioche bun.

Don't leave without: You've come to the desert to escape from something, and there's no better place to do just that than the hiking trails through the Atalaya Mountains. The year-round gorgeous views of the vast expanse are what inspired Georgia O'Keeffe's most famous non-flower works. -- Sean Cooley
MORE: Plan a trip around the best things to do in Santa Fe this fall

South Lake Tahoe, California
Emerald Bay is great for swimming... in the summer. Explore by boat instead when it's cold | vernonwiley/E+/Getty Images

South Lake Tahoe, California 

Population: 22,036
Tahoe isn't a bachelor-party default for Northern Californians because it's close than Las Vegas. It's because the casinos here are really just the late-night icing on the weekend-long cake of fun on the Cal-Neva border. People have a Vegas mentality without the Vegas douchebaggery. And your hangover goes away a lot quicker when you're standing next to one of America's most spectacular mountain lakes. For snow sports, Heavenly is one of the best party mountains in the world, and even has a bar where you can drink in two states at once. And there isn't much of a falloff in the summer, with golf in nearby Village, mountain biking, hiking, or just being lazy on a boat in the middle of the lake. The Fourth of July fireworks are among the best around, and even non-holiday weekends are packed all summer long.

Must eat & drink: It's not all casino buffets, though there are plenty of those. Get the Beaver Burger at the Lucky Beaver. The flame-broiled Pat LaFrieda meats make this the perfect meal after a hard day on the slopes, and it good enough to make you forget all the bad puns.

Don't leave without: Cruising through Emerald Bay. In the summer, this is best done by renting a boat (or, better, knowing somebody who owns one) and getting in some waterskiing along the way. But even in the winter, taking a boat cruise is worth the few cold hours on the water to see one of the most photographed places in California. -- Matt Meltzer

Passenger Coffee
Those who wander... probably find themselves in Lancaster | MarisaAlbrecht.co

Lancaster, Pennsylvania

Population: 59,322
We’ve previously highlighted this Pennsylvania town for its secretly great food scene, owing to its farm-to-table restaurants and bevy of eclectic dining choices. But Lancaster, a two-hour drive from Philadelphia, has far more to offer than just good eats. 

Ever the land of delightful contradictions, Lancaster is an urban trendsetter smack in the middle of rolling Amish farmlands; a city with a pulsing nightlife under peaceful, quiet starry skies; a cultural center known for its contemporary art, yet woven with Pennsylvanian history and Amish culture. Whether you’re a planner or a wanderer, downtown Lancaster’s walkable streets are lined with fun spots. Explore the offerings from dozens of local vendors at Lancaster Central Market, America’s oldest continuously operating farmers market. Poke around Lancaster’s events calendar while planning your trip, because there’s sure to be something that suits your particular brand of whimsy, from covered bridge tours to Amish farm experiences to royal merriment at the Pennsylvania Renaissance Faire.

Must eat and drink: Check out "urban cookery" Maison, the pinnacle of slow food, or the charming café On Orange, where you can feast on Swedish pancakes on your first morning in town.

Don’t leave without: Experiencing Lancaster’s First Friday arts extravaganzas on, well, the first Friday of every month. From 5-9pm, the town lights up with art exhibitions, musical performances, and much more from its passionate, deeply talented, and enriching arts community. -- Sammy Nickalls
MORE: Discover other must-visit small towns in Pennsylvania

McMinnville, Oregon
McMinnville's Evergreen Aviation Museum even has its own wine label, because of course it does | Png Studio Photography/Shutterstock

McMinnville, Oregon

Population: 34,617 
A relatively uneventful hour's drive from Portland into the heart of Oregon wine country and you'll happen upon McMinnville, a charming city with a world-class food scene, an actually incredible air museum, and 500 wineries in close proximity.

Start your McMinnville immersion with a walk along downtown’s Rockwellian 3rd Street to peruse the book stores, quirky art galleries, and quaint cafes. You’ll find a sweet little movie theater tucked inside of a pizza shop, and the cash-only Blue Moon Lounge that serves up shuffleboard and a mean prime rib special. Head a few blocks over and you’ll find yourself in the Granary District, where Flag & Wire Coffee is a favorite along with Grain Station Brew Works. Back on the main drag, Atticus Hotel opened last year, offering up luxury bunkhouses, fireplaces in every room, and locally sourced artwork, managing a modern-chic vibe amid the city's charming, time-warp aesthetic.

Must eat & drink: Start with handmade pasta and killer crab lasagna at James Beard America's Classics-certified red-sauce joint Nicks Italian Café. Follow that with a trip to Thistle, a cozy gastropub with a focus on locally sourced ingredients and hard-to-find wine. For late night libations, head over to Cellar Bar, a speakeasy in Hotel Oregon that serves up solid selection of whisky cocktails and ales. 

Don't leave without: December through February is when truffles have reached peak perfection and truffle hunts, festivals and fetes are in full effect. May is a great time to visit for the three-day UFO Fest, though if you’re into flying objects and not of the extra-terrestrial variety, another great stop just outside of town is the Evergreen Aviation & Space Museum, home to Howard Hughes’ wooden Spruce Goose. -- Michelle Gross

Burlington, Vermont
Church Street is the hub of Burlington's low-key great nightlife | Education Images/Universal Images Group/Getty

Burlington, Vermont

Population: 42,899
While virtually a metropolis in one of America's most spread-out states, Burlington still has all the small-town vibes you expect from Vermont: outdoorsy style, beautiful brick streets, and an ultra-chill way of life to go along with its eco-friendly approach to… well, everything. An eating itinerary should include simple crepes from The Skinny Pancake (skipping on the pure maple syrup would be uncouth), pizza with maple-fennel pork sausage from American Flatbread, and maple creemee from almost anywhere. Should you worry about ingesting this much maple? Nah, you'll want to burn calories paddleboarding near Leddy Park, biking the beautiful lakefront path end-to-end, visiting Jeffersonville to ski Smugglers' Notch in winter, or, for the truly crunchy, throwing Frisbee golf in the summer.

A considerable beer haven, Burlington happens to reside in the state with the most craft breweries per capita. Be on the lookout for tap handles pouring the vaunted Hill Farmstead, having risen from college homebrew club to a world-renowned must-drink. A proper brewery crawl should run from Fiddlehead to Magic Hat to Switchback and end at Citizen Cider.

Must eat & drink: A can of Heady Topper at the The Farmhouse Tap & Grill: It's the legendary double IPA brewed in Stowe that launched the hazy/New England IPA craze, and still remains one of the most sought-after beers in America. It has a 100 score on BeerAdvocate. You'll get beer geeks to agree on nothing else, ever.

Don't leave without: Taking in an evening of charming debauchery on Church Street, the city's main vein of nightlife bridging the neighborhood dive bars of the old north end and the burgeoning arts district on the south end. The circuit will go something like college bar, dive bar, college bar, Retronome dance party, Kountry Kart Deli. -- Sean Cooley
MORE:Learn how the hazy New England IPA took over craft beer

Muskegon, Michigan
There's no way you're not taking a picture in front of a lighthouse | Photography by Deb Snelson/Getty Images

Muskegon, Michigan

Population: 37,287
Muskegon is one of the best beach towns in the Great Lakes state, which puts it in the running for one of the best beach towns in the country. But it stands out from the myriad charming, timeless, sand-dusted hamlets that dot Michigan coastline simply by having, well, people. Lots of them, relatively speaking. A short drive from Detroit, even shorter from Grand Rapids, and a damn-lovely day trip away from Chicago, Muskegon has all the trappings of a great beach town while also serving as a cultural hub. And unlike other, smaller beach towns (Traverse City being a notable exception), this place just hums with art, music, and a great food and drink scene. No wonder everybody's calling it Michigan's next "it" destination. 
 
Still, none of that would matter without the beaches. That's why you're here, and trust that they are magnificent. The crown jewel here is Pere Marquette Beach, one of the Great Lakes' best maintained patches whose white sands and azure waters look almost Caribbean (except, of course, when they're frozen) The requisite beach activities are all here -- sailing, fishing, swimming in a giant body of water without worrying about sharks. Oh, and Muskegon has an amusement park! Michigan's Adventure is smaller scale than, say, Cedar Point, but the very fact that there are good coasters and a big-ass water park in this lake town is astounding. 
 
Must eat & drink: Get your requisite lake perch on the waterfront at the old-school Lake House, gastropub-style cocktail/food pairings at Se4sons, and your Michigan beer fix at Pints & Quarts. During summer, The Deck, right on Pere Marquette beach, combines great drinks and live music to claim status among America's best beach bars

Don't leave without: It's not like you're not gonna take a photo of the South Pierhead and South Breakwater lighthouses, so might as well take a tour too. -- Andy Kryza
MORE: Get a closer look at the other best beach towns in Michigan

Stagecoach Festival
Adventure about a half hour outside of Palm Springs and hit up Stagecoach Festival | Stagecoach Festival

Palm Springs, California

Population: 48,142
Aside from the weather -- basically in the 70s and 80s and dry for most of the year -- and the gorgeous desert vistas, one of the great things about Palm Springs is the sheer range of things you can get up to. Golf weekend? Check. Spa weekend? Check. Outdoor hiking adventure? Check. Bachelor/bachelorette party blowout? Check check. Festival wildness? Oh, super-check: of course, Coachella and its related activities are Palm Springs adjacent, but the success of this fest also means that nearly every weekend there’s a rager there or somewhere nearby, from the EDM-centric Splash House to the country hootenanny Stagecoach to the twice-yearly psych-y Joshua Tree Music Fest

If you’re staying in Palm Springs proper, there’s no need to leave Highway 111, which has tons of bars and restaurants in walking (or free trolley) distance from your hotel and its party-hearty pool. If you’re in one of the neighboring cities, you’re probably there for relaxation, but if you do decide to hit the town, ride shares are abundant and cheap.

Must eat & drink: Workshop Kitchen + Bar has become the go-to new-American spot, but the best restaurant in town is probably Rooster & The Pig, a Vietnamese-fusion hole-in-the-wall that doesn’t take reservations, so be prepared for a looooong wait. Brunch is killer all over the city; Cheeky’s is known for its bacon flights (yes, they’re a thing), while King’s Highway at the Ace has insanely great chilaquiles. If you’re looking for amazing places to drink, you’re also in the right place: Bootlegger Tiki has your crazy-sweet, ultra-legit rum drinks; the craft beer scene is blowing up, with Desert Beer Company the most recent notch in that belt; and Skip’s Little Bar is the newest local-fave, owned by a former Goldenvoice dude, and laced with ticket stubs from his time as a promoter.

Don’t leave without: Ordering a martini and people watching in the piano bar at Melvyns, a classic steakhouse frequented by the Rat Pack, whose side room is now a singles bar for charming octogenarians. -- Jeff Miller

Twin Falls, Idaho
Shoshone Falls is 45 feet higher than Niagra Falls... and probably Instagrammed just as much. | Png Studio Photography/Shutterstock

Twin Falls, Idaho

Population: 50,000
Southern Idaho’s most stunning Snake River town is home to the roaring Shoshone Falls  and best-of-the-West locals who are more than ready to share what they love about their city. A high-desert hub for outdoorsy types, Twin Falls has more than 30 waterfalls and endless options for hiking, biking, rock climbing, and water sports. Centennial Waterfront Park gives access to the Snake River for kayaking. Iconic Shoshone Falls, the "Niagara of the West," is 212 feet high -- 45 feet higher than Niagara -- and flows over a 1,000-foot-wide rim. Downriver is the canyon hotspot where legendary stunt man Evel Knievel would ultimately embrace his daredevil ways by trying to rocket across the expanse -- something you can do much more safely via a tandem leap off a 486' tall bridge with a professional BASE Jumper. 
 
The downtown area has the requisite boutique motels like the Blue Lakes Inn, a likable turnpike-side inn, alongside classic modern hotels and a wealth of Mexican restaurants. The very recently revitalized and walker-friendly downtown area is drawing people together with a variety of new businesses and free concerts in the town square. This resurrected Main Street rises above others with historic charm and ultra-affordable restaurants, like Slice. Seldom does an adventure-seeker get to experience such a robust city life without straying away from the natural landscapes they came to the area for in the first place. 
 
Must eat & drink:Elevation 486 is fine dining with epic scenery 486-feet above the 1,400-foot-wide Snake River Canyon (try the Idaho trout that’s raised in spring-fed farms). O’Dunkens Draught House is a classic “everyone knows your name” joint to meet local movers and shakers, like staff from the Times News (est. 1905), which unlike what we’re seeing at papers countrywide, still employs and rewards talent.
 
Don't leave without:Kayaking the Snake River from Banbury Hot Springs to 1,000 Springs -- indeed, this is a land of endless natural hot tubs -- where a highlight is a stopover at Blue Heart Springs, an idyllic cove with crystal-clear water and monument-status rock formations. -- Bruce Northam

MASS MoCA
Contemporary art and a scenic drive of fall foliage -- what more could you ask for? | MASS MoCA

Northampton, Massachusetts

Population: 28,593
Northampton is less quaint Western Mass town and more edgy urban oasis/cultural center, with all the bars, galleries, and hipsters to prove it. A get-yourself-acquainted stroll is worth it just to take in the town's quirks… and to get a lay of the land before the eventual revelry comes to fruition. Your obligatory night-out bar crawl should touch The Green Room, The Dirty Truth, and McLadden's, which pours 105 draft beers and 160 whiskeys. Depending on your age/intentions, you might end at Tunnel Bar, a hip lounge/martini den built into -- you guessed it -- an old tunnel under the railroad tracks. Northampton's also a hotbed of live tunes, with a solid ensemble of venues -- the Calvin Theatre, Iron Horse Music Hall, Academy of Music) -- making the city a magnet for touring acts.

But you don't come to Western Mass to sit inside, so spend a day exploring the surrounding area. Hike/drive up to the Summit House on Mount Holyoke; appreciate the farms (corn! Asparagus! Dairy!) as you drive along the Route 47 Scenic Byway toward South Hadley (just be sure to grab a coffee at the Thirsty Mind when you get there); or, if you're up for venturing a little further from home, visit the insanely popular Tree House Brewing Co. in Monson or hop on the Mohawk Trail (Route 2) out to the Berkshires and North Adams, Mount Greylock, and MASS MoCA (Massachusetts Museum of Contemporary Art). There is no more gorgeous drive to peep the fall foliage in all of the country.

Must eat & drink: Along with the stuff above: Pizza at Joe's, seafood at Eastside, and burgers -- from tzatziki-covered veggie patties to Juicy Lucys -- at Local Burger.

Don't leave without: Hiking to the top of Mount Tom or Mount Holyoke for stunning views of the Pioneer Valley, and seeing a show at the historic Calvin Theatre (opened 1924) -- Dave Baldwin
MORE: Peep this list of the best New England spots for leaf-peeping

Biloxi, Mississippi
Did you really visit Biloxi if you didn't go on the pier? | Donovan Reese/Photodisc/Getty

Biloxi, Mississippi

Population: 45,968
Folks wrongly assume Biloxi's nothing more than a bunch of casinos sitting on the shores of the Gulf of Mexico. And, yes, the city's skyline is dominated by the IP, Beau Rivage, Hard Rock, and others. But beyond the gambling, this small city is easily the best tourist destination in Mississippi. While it's not typically considered part of the American paradise that is the Redneck Riviera, the beaches here boast the same white sand and calm waters as their Florida and Alabama neighbors, with a fraction of the people. But just swimming in the ocean only nets you half of the experience; an afternoon spent on a shrimping boat or an oyster schooner is the best way to ensure you bring fresh fish to one of the dozens of area restaurants that'll cook it up for you.

During the summer, hit the Hard Rock for an afternoon pool party. It's not going to be like Rehab in Vegas, but that’s part of the charm. Coming to Biloxi is seeing the real South... and the young professionals and party people who visit for the weekend make this as much of a cultural experience as a vacation. You'll find the same when you go out at night, where casual bars like Adventures and The Ole Biloxi Fillin' Station are filled with friendly Mississippians happy to tell you all about life on the delta.

Must eat & drink: Gumbo at Mary Mahoney's Old French House, a Bloody Mary at Ole Biloxi Fillin' Station, a fried shrimp po-boy at Rosetti's Café in Quality Poultry and Seafood

Don't leave without: Going out on a shrimping boat. Or, if you'd rather not work so much, just take a Biloxi oyster schooner at sunset. -- Matt Meltzer
MORE:Discover why the "Redneck Riviera" is an American treasure

Portsmouth, New Hampshire
Portsmouth is about as Gilmore Girls as you can get without fast-talking | Sean Pavone/Shutterstock

Portsmouth, New Hampshire 

Population: 21,796
Settled inconspicuously on the southeast side of New Hampshire in 1630, Portsmouth is a city rich in history and rife with the kinds of colonial houses and cobblestone alleyways you always see on postcards or Gilmore Girls. Quaint doesn’t even begin to explain Portsmouth’s, well, quaintness, but that’s what you get when a small space (just under 17 square miles) is taken over by hipsters. Of course, you’ll find a cobblestone main street lined with boutiques, record stores, and a place literally named G. Willikers! Books & Toys
 
Breathtaking foliage paired with twee breakfast spots make Portsmouth particularly well-suited for an autumn weekend. If you want to get twee-er than twee, make a point to stop inside Portsmouth Book & Bar. It’s a bookstore and a bar. (If getting toasty with your nose in a book is wrong, I don’t wanna be right.) Go fishing on Four Tree Island, mill around Prescott Park, or make the 10-minute journey into Kittery, Maine, for the sole purpose of bragging about walking from one state to the other. 
 
Must eat & drink: Stop at Cure for an intimate dinner with an insanely nice patio and even better patio view. Get the clam strip roll at The Beach Plum and savor the authentic New England seafood experience. Kaffee Vonsolln offers some of the best high-quality, ethically sourced, and small-batch roasted coffee, including their signature Kick Blend, which is “a mix of Central American and Indonesian coffee” made to put hair on your chest. Their words, not ours. 
 
Don't leave without: Making a stop at The Friendly Toast: These guys are known for their stellar breakfast, but their barbacoa ramen is absolutely insane. If you’re a record collector or even record appreciator, definitely stop at Bull Moose Records for a superb choice of vinyl and cassettes. -- Jeremy Glass
MORE: Expand your itinerary with the coolest things to do in New Hampshire

Sign up here for our daily Thrillist email, get Next Flight Out for more travel coverage, and subscribe here for our YouTube channel to get your fix of the best in food/drink/fun.