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23 US Cities Ideal for a Long Weekend

Jessica Spiegel
By 
Jessica Spiegel
Freelance Writer
9 min read
Last updated 
November 12, 2020

With limited vacation time, long weekends are an awesome way to see more while taking minimum time off work. And while you could visit any city for just a few days, some cities are better suited for quick trips for a variety of reasons. For example, if the airport is hours from the city or you can’t do anything fun without renting a car, that’s not ideal for a short getaway. We focused on the following three criteria:

  1. There should be a major airport in town so it doesn’t take two (or more) hours to get there after you land.
  2. You should be able to get around easily without renting a car, using things like public transit or ride sharing.
  3. There’s enough to see and do that you won’t get bored but also not so much that you’ll feel rushed.

There’s something for every travel interest here, in every part of the country. Here are some of the best US cities for long weekend trips.

Note that as the coronavirus pandemic continues, cities are in different stages of reopening (and those stages could change). Check with local news sources before you make plans. 

Nashville

Nashville skyline.

Tennessee’s capital city is almost as well-known by its nickname, “Music City,” as it is by its real name. And while some of the main attractions focus on country music (the Country Music Hall of Fame and the Grand Ole Opry among them), Nashville celebrates all kinds of musical genres with live shows every night in venues all over town—there’s even a free app to help you find live gigs to suit your musical taste. Between shows, check out the full-size replica of Athens’ Parthenon in Centennial Park and fuel up with some local barbecue or Nashville’s beloved “hot chicken.” 

  • Best time to go: April-October
  • Nearest airport: Nashville International Airport (BNA)
  • Day trip with a car: See the world’s longest cave at Mammoth Cave National Park (about 93 miles away)

Sample deals to Nashville: 

Detroit

When people talk about Detroit in recent years, it’s often in terms of resilience—with good reason. The Detroit that’s emerging from its auto-industry-induced slump is a truly exciting one. Industrious Detroiters have created a vibrant maker culture. 

There are exceptional little restaurants in nearly every neighborhood, and shops around town stock locally made goods from Shinola’s famous watches to the unique home decor at City Bird. Several makers get their start at business incubator Ponyride, which welcomes tours (and shoppers). Don’t miss a visit to the Detroit Institute of the Arts, too, to see the enormous Diego Rivera murals.

  • Best time to go: April-June or September-October
  • Nearest airport: Detroit Metropolitan Wayne County Airport (DTW)
  • Day trip with a car: Check out the cute beach town of Lexington (on Lake Huron; about 82 miles away)

Sample deals to Detroit: 

Chicago

Chicago never appears to take its “Second City” nickname as a slight. In fact, one of the best things about Chicago might just be how much big-city entertainment is packed into its relatively small size, including the many fabulous museums (including the Field Museum and Art Institute of Chicago). 

A river cruise is always a good idea in Chicago, especially when it’s an architectural tour, and in nice weather you can join the locals strolling through Millennium Park (snap a photo of your crazy reflection in “The Bean”). And no matter what type of cuisine you’re looking for, Chicago delivers. Dig into classics like Chicago-style hot dogs or deep-dish pizza or dine at award-winning restaurants like Alinea and Girl & the Goat.

  • Best time to go: April-May or September-October
  • Nearest airport: Chicago O’Hare International Airport (ORD)
  • Day trip with a car: Check out the architecture of Frank Lloyd Wright with a tour of his home and studio in in Oak Park (about nine miles away)

Sample deals to Chicago: 

New Orleans

In New Orleans, it seems like there’s always something to celebrate. Parades aren’t just a Mardi Gras event and there’s music in the streets every night. This is where jazz was born, so pay your respects at Preservation Hall or pick any club on Frenchmen Street. Check out the room full of flashy Mardi Gras Indian suits at the Backstreet Cultural Museum in the Tremé neighborhood. Ride the streetcar through the Garden District to see the stately mansions. Or check out the excellent National World War II Museum. 

Local culinary delights include jambalaya, gumbo, po’boy sandwiches, the gargantuan muffaletta, and the famous beignets at Café du Monde—just remember not to wear black or you’ll be just as coated in powdered sugar when you leave as the beignets were when they arrived at your table.

  • Best time to go: February-May or September-December
  • Nearest airport: Louis Armstrong New Orleans International Airport (MSY)
  • Day trip with a car: Tour the bayous and swamps of Barataria Preserve, in Jean Lafitte National Historical Park and Preserve (about 17 miles away)

Sample deals to New Orleans: 

Savannah

Georgia’s oldest city, Savannah is heavy on the history and Southern charm. The historic district is what you probably picture when you think of Savannah, with its famous squares (there are 22 in total) and grand old oak trees. Between that and the Victorian district, visitors can see historic homes that date from the 18th and early 19th centuries—some of which have been turned into museums, art galleries, restaurants, and B&Bs—without walking very far at all. 

For a look at another side of Savannah’s history, check out the Pin Point Heritage Museum and learn about the culture and foodways of the Gullah Geechee, descendants of enslaved Africans who worked the rice fields of Georgia and South Carolina.

  • Best time to go: March-July
  • Nearest airport: Savannah/Hilton Head International Airport (SAV)
  • Day trip with a car: Relax on the beaches of Hilton Head Island (about 31 miles away)

Sample deals to Savannah: 

Charleston

charleston street.

Charleston is the biggest city in South Carolina (though it’s still quite small) and routinely shows up on lists of the prettiest cities in the country. Its historic downtown is full of beautiful buildings that date from the mid-1700s, many of which have been converted to museums. Charleston’s coastal location made it an important city during both the American Revolution and the Civil War (don’t miss the Powder Magazine and Fort Sumter, respectively, to learn more about that history), although these days the city’s waterfront setting is part of what attracts visitors. 

All the leisurely strolling Charleston encourages helps you work up an appetite, which is a good thing—the restaurant scene is a delicious mix of traditional Lowcountry comfort food and Michelin-starred cuisine.

  • Best time to go: March-May or September-November
  • Nearest airport: Charleston International Airport (CHS)
  • Day trip with a car: Beaufort (about 70 miles away)

Sample deals to Charleston: 

Denver

Colorado’s “Mile High City,” Denver, boasts some 300 days of sunshine and proximity to some of the best outdoor playgrounds in the country. You don’t have to leave the city limits, however, to get into the Denver spirit of embracing the outdoors. The city’s walkable downtown has plenty of unique shops and restaurants, and it’s not far from the enormous City Park (where you’ll find the Denver Zoo as well as two lakes). 

Exploring on two wheels is easy, too, with more than 80 miles of paved bike trails. There’s a fabulous collection of Native American and Western art at the Denver Art Museum and book lovers won’t want to miss a stop at the city’s beloved Tattered Cover Book Store. And when you’re thirsty, hit the Denver Beer Trail to sample from any of the dozens of breweries in the area—including the eight in downtown Denver alone.

  • Best time to go: April-May or September-October
  • Nearest airport: Denver International Airport (DEN)
  • Day trip with a car: Go for a hike in Rocky Mountain National Park or Estes Park (about 70 miles away)

Sample deals to Denver: 

Portland

Portland doesn’t have what most people might consider “famous attractions.” Instead, Oregon’s biggest city turns its lifestyle into an attraction, inviting visitors to enjoy the same things that locals love. A quirky entrepreneurial spirit has made Portland’s dining scene far more diverse than you’d expect for a city its size (thanks in large part to the thriving food cart culture). Plus there are dozens of craft breweries in Portland. 

Powell’s City of Books is a popular stop (yes, you’ll need a map inside the store)—but if you’d rather explore all the lush outdoor spaces, hit the trails in the enormous Forest Park northwest of downtown or stroll the paved trails on both sides of the Willamette River.

  • Best time to go: June-September
  • Nearest airport: Portland International Airport (PDX)
  • Day trip with a car: Go hiking and waterfall hunting at the Columbia River Gorge (about 30 miles away)

Sample deals to Portland: 

Seattle

Seattle combines big city attractions with the lush Pacific Northwest outdoors, so there’s something for just about everyone. There’s the iconic Space Needle, of course, but while you’re in the Seattle Center area don’t miss a visit to the spectacular Chihuly Garden and Glass Museum or the Museum of Pop Culture. Watching fishmongers toss salmon at Pike Place Market is another Seattle standby, although if you’d rather get out on the water itself you can kayak Portage Bay. 

The city that introduced the world to grunge still has a vibrant music scene—favorite venues include Showbox, The Crocodile, and Tractor Tavern. And every Seattle neighborhood has a variety of world-class eateries, from coffee shops to gastropubs to Michelin-starred restaurants.

  • Best time to go: June-September
  • Nearest airport: Seattle-Tacoma International Airport (SEA)
  • Day trip with a car: Marvel at the beauty of Snoqualmie Falls, which you may recognize from the opening credits of Twin Peaks (about 29 miles away)

Sample deals to Seattle: 

Austin

Unlike many state capitals, Austin doesn’t let its position as the seat of Texas’ government prevent it from simultaneously being an exciting city to visit. Live music thrives in Austin, where Austin City Limits is just the tip of the concert venue iceberg. In addition to country, you can find every musical style from big band jazz to zydeco playing every night around the city. 

Texas barbecue is a mainstay on plenty of menus (the lines outside Franklin Barbecue are always long), and Tex-Mex breakfast tacos are a local favorite. Don’t miss a trip to the Lyndon Johnson Presidential Library, which includes a replica of LBJ’s Oval Office. And, if the weather is right, head for the oldest swimming pool in the state, Barton Springs.

  • Best time to go: March-May or September-November
  • Nearest airport: Austin-Bergstrom International Airport (AUS)
  • Day trip with a car: Visit the historic town of Gruene, home to the oldest dance hall in Texas (about 46 miles away)

Sample deals to Austin: 

San Diego

San Diego.

With miles of beautiful beaches and sunny weather nearly all year long, San Diego is understandably appealing. Add in historic neighborhoods, excellent dining, and a waterfront boardwalk and it’s hard to resist. The Victorian-era buildings in the Gaslamp Quarter are now art galleries, restaurants, and boutiques—not to mention some of the city’s most lively nightclubs. 

Dig into local history with a visit to Mission San Diego de Alcalá, one of the first Spanish missions in California. When strolling the boardwalk, it’s impossible to miss the former US Navy aircraft carrier, which is now a museum. You can also hop on a boat to take in the city from the water. San Diego's colorful Little Italy neighborhood is still home to Italian food markets as well as some of the city’s best restaurants. Browse the delicious options at the Little Italy Food Hall, taking advantage of San Diego’s great weather to enjoy the enormous open air dining area.

  • Best time to go: March-May or September-November
  • Nearest airport: San Diego International Airport (SAN)
  • Day trip with a car: Head to San Juan Capistrano to explore a former Spanish mission built in 1776 (about 67 miles away)

Sample deals to San Diego: 

Boston

The Massachusetts capital has historical appeal in abundance. The 2.5-mile Freedom Trail connects Revolutionary War sites, including the home of Paul Revere, a monument to the Battle of Bunker Hill, and the square near the Old State House where the 1770 Boston Massacre took place. Stately Faneuil Hall, once a meeting hall where independence-minded colonists rallied against English rule, is now home to a popular market. The oldest public park in the United States, Boston Common is still a lively gathering place today. 

Learn about more recent history with a stop at the John F. Kennedy Presidential Museum & Library or take a short trip across the Charles River to explore the many museums at Harvard University and MIT. 

  • Best time to go: June-October
  • Nearest airport: Boston Logan International Airport (BOS)
  • Day trip with a car: Explore the lighthouses and seafood shacks of Cape Cod (about 70 miles away)

Sample deals to Boston: 

San Francisco

San Francisco looms large on the American cultural landscape, so it’s easy to forget this hilly city has a fairly small footprint that’s easy to explore in a few days. The waterfront is a great place to start. Popular Pier 39, where sea lions often laze on the docks, is only one small part of the Embarcadero; be sure to make your way to the Ferry Building Marketplace and time your visit so you can take advantage of the wide selection of gourmet grub on offer there.

Explore bustling food markets in Chinatown, vintage shops in Haight Ashbury, Italian cafes in North Beach, and art galleries in the Mission. Snap a photo of the famously twisty Lombard Street (just know that driving the street takes ages because of the queue) and the colorfully painted Victorian houses on Alma Square. Don’t miss a tour of Alcatraz Island—there’s way more to the history than just the prison.

  • Best time to go: September-November
  • Nearest airport: San Francisco International Airport (SFO)
  • Day trip with a car: Spend a day wine tasting among the rolling hills on Napa Valley (about 67 miles away)

Sample deals to San Francisco: 

Louisville

Kentucky’s biggest city is just one stop on the state’s famous Bourbon Trail, but Louisville deserves a few days of your time all by itself. Besides the treasured tipple, Louisville’s claims to fame trend more toward the world of sports—it’s the birthplace of both boxing legend Muhammad Ali and the Louisville Slugger baseball bat. You can learn about Ali’s life at the Muhammad Ali Center or pay your respects at his grave. Baseball fans can tour the Louisville Slugger Museum and Factory. 

If you’re a horse racing fan, check the calendar at Churchill Downs, home of the Kentucky Derby. And even if you never leave the city limits to explore the state’s distilleries, you can sample your way along the “Urban Bourbon Trail.” 

  • Best time to go: April-May or September-October
  • Nearest airport: Louisville International Airport (SDF)
  • Day trip with a car: Watch a horse show at the Kentucky Horse Park outside of Lexington (about 78 miles away)

Sample deal to Louisville: 

Salt Lake City

Utah is a must-visit destination for several beloved ski resorts and National Parks, but urbanites should put Salt Lake City on their list, too. Check out the Natural History Museum of Utah for a history lesson on the American West, and then visit the Church History Museum on Temple Square to learn about the Mormon settlers who arrived in the area in the mid-1800s. 

Salt Lake City’s food scene ranges from award-winning fine dining to a plethora of food trucks, and since Utah is no longer the teetotalling state it once was, SLC is home to a growing slate of craft breweries, wineries, and distilleries—not to mention more than 200 bars in the city in which to sample the local beverages.

  • Best time to go: September-October
  • Nearest airport: Salt Lake City International Airport (SLC)
  • Day trip with a car: Explore the 30,000-acre expanse of the Bonneville Salt Flats (about 100 miles away)

Sample deals to Salt Lake City: 

Boise

Boise at night.

Boise is the kind of city adventure travelers use as a home base for outdoor recreation nearby, but there’s plenty of reason to explore the city itself, too. There’s a vibrant Basque community in Boise, as evidenced by the Basque Museum and Cultural Center (as well as several Basque eateries). Art lovers can check out the Boise Art Museum or the enormous outdoor mural at Freak Alley. And foodies can expect a lot more from the restaurant scene than the potatoes Idaho is famous for. When you want to enjoy the great outdoors without leaving town, hop on a bike and ride the 25 paved miles in River Greenbelt park.

  • Best time to go: April-June or September
  • Nearest airport: Boise Airport (BOI)
  • Day trip with a car: Marvel at the lunar-like landscape at Craters of the Moon National Monument (about 170 miles away)

Sample deal to Boise: 

Miami

Miami is arguably one of the most colorful cities you’ll ever visit. There’s the aquamarine water that laps at the sandy beaches, of course, but that’s not all—from the marvelous Miami Beach architecture to the vibrant Little Havana neighborhood, this is a place that feeds all the senses. 

Art lovers can admire the Art Deco buildings along Ocean Drive and then pick from a host of art experiences in the city, including contemporary art at The Bass Museum of Art and the Pérez Art Museum Miami, and the murals and street art on display at Wynwood Walls. Little Havana’s buzzing Calle Ocho (8th Street) offers visitors an international experience without a passport. Feast on Cuban sandwiches and then dance the night away at one of the area’s salsa clubs.

  • Best time to go: March-May
  • Nearest airport: Miami International Airport (MIA)
  • Day trip with a car: Hop in an airboat for a tour of Everglades National Park (about 41 miles away)

Sample deals to Miami: 

Cleveland

Maybe everyone has heard that “Cleveland Rocks” since the late 1970s, but it never hurts to have an updated reminder. Music has long been a big deal in Cleveland (the term “rock and roll” was coined by a local DJ), and visitors have flocked to the Rock and Roll Hall of Fame since it opened in 1995. Fine art is also on display in Cleveland, with excellent collections at both the Cleveland Museum of Art and Museum of Contemporary Art. 

The historical influence of Polish immigrants shows up on restaurant menus (kielbasa and pierogies are local favorites) and there’s a growing number of breweries in the area. If you need to work up an appetite, take a stroll along Lake Erie and wave to Canada on the other shore.

  • Best time to go: April-May or September-October
  • Nearest airport: Cleveland Hopkins International Airport (CLE)
  • Day trip with a car: Learn about Amish life or shop for art and handicrafts in Amish Country (about 78 miles away)

Sample deals to Cleveland: 

Kansas City

Missouri’s biggest city holds appeal for a variety of visitors, from music lovers to foodies to sports fanatics. As jazz moved through the United States from New Orleans, it established a foothold in Kansas City that hasn’t faltered. Explore the city’s musical history at the American Jazz Museum and then head to the 18th and Vine Jazz District for a show in one of the clubs.

Not only did Kansas City stamp its own flavor on jazz, it did the same to barbecue. KC-style is a must in this city of more than 100 barbecue joints—Bryant’s and Gates are two favorites. There’s a local sports team for every season, from the Chiefs to the Royals to Sporting KC, but don’t miss the Negro Leagues Baseball Museum for some historical perspective.

  • Best time to go: May-September
  • Nearest airport: Kansas City International Airport (MCI)
  • Day trip with a car: Explore the unique geology—including springs, caves, and sinkholes—of Ha Ha Tonka State Park (about 158 miles away)

Sample deal to Kansas City: 

Philadelphia

Philadephia.

The biggest city in Pennsylvania is at once historic and cosmopolitan. The city is home to several important sites from the Revolutionary War, many of which are contained in the approximately four blocks of Independence National Park—including Independence Hall (where both the Declaration of Independence and US Constitution were born) and the famous crack in the Liberty Bell. 

Art lovers, set aside some time for the enormous collection at the Philadelphia Museum of Art (don’t miss the “Rocky” statue on the steps) and keep an eye out for the thousands of street art murals around the city. Locals fiercely debate which has the best cheesesteak, Pat’s or Geno’s, but since they’re right across the street from each other it’s easy to sample both before you decide.

  • Best time to go: March-May
  • Nearest airport: Philadelphia International Airport (PHL)
  • Day trip with a car: Stroll the Ivy League campus and visit the Princeton Battlefield State Park in Princeton, New Jersey (about 45 miles away)

Sample deals to Philadelphia: 

Fargo

Even if Fargo is best known as the name of a quirky cult favorite film, the locals don’t seem to mind. In fact, they’ve got a rather good sense of humor about the whole thing—they even have the original wood chipper from the movie on display

Fargo sits on the far eastern edge of North Dakota, just across the border from the Minnesota city of Moorhead (the two are considered one metro area). One of the main attractions, The Hjemkomst Center, is actually in Moorhead. There, you can learn about the area’s Scandinavian roots, and see a replica of a gorgeous Hopperstad Stave Church and a full-scale replica of a Viking ship. In Fargo itself, local historians have been relocating original buildings from elsewhere in the county to the Bonanzaville pioneer village, including the first log cabin built in Fargo in 1869. Keep an eye out for menu items referencing the “Fargo” movie (the word “woodchipper” appears a lot) and be sure to get a selfie with the statue of “Wood Chip Marge” inside the historic Fargo Theatre.

  • Best time to go: June-September
  • Nearest airport: Hector International Airport (FAR)
  • Day trip with a car: Go hiking, birding, or horseback riding in the sprawling Sheyenne National Grassland (about 60 miles away)

Atlanta 

Although Atlanta is Georgia’s biggest city, there’s still Southern hospitality and charm in abundance. Downtown, you’ll find big-ticket attractions like the World of Coca-Cola and the Georgia Aquarium, but leave plenty of time to explore the historic Sweet Auburn neighborhood to the east to visit the Martin Luther King Jr. National Historical Park. Among the sights, you can see the home where he was born, the church where he preached, and the tomb where he’s buried. Atlanta’s restaurants run the gamut from old-school Southern favorites (The Varsity drive-in is a local institution) to fine dining and music festivals of all genres fill the city’s calendar.

  • Best time to go: March-May
  • Nearest airport: Hartsfield-Jackson Atlanta International Airport (ATL)
  • Day trip with a car: See Georgia’s “Little Grand Canyon” in Providence Canyon State Park (about 147 miles away)

Sample deals to Atlanta:

Juneau

Alaska’s little capital city is packed with history and surrounded by dramatic natural beauty. The collection of artifacts at the wonderfully designed Alaska State Museum chronicles the area’s history, from Native Peoples through the Russian colonial period and incorporation into the United States. The Sealaska Heritage Center downtown has historic exhibits on Alaskan Natives—and it also showcases contemporary Native artwork you can bring home as a souvenir. Since it’s a cruise port, Juneau has dozens of organized tour options for day trips to go whale watching or take in the scenery of Tracy Arm Fjord. And even if you’re not visiting for a fishing trip of your own, you can indulge in fresh seafood all over town—just be sure to save some room for a visit to Tracy’s King Crab Shack before you leave.

Note that getting to Juneau from many parts of the United States takes long enough that it’s not a great option for a long weekend. From Seattle, however, the flight is around 2.5 hours; from other major west coast airports it can take as little as 5-6 hours to get to Juneau, plus with an early morning flight you’ll land before noon local time so you can enjoy most of a long weekend in the city.

  • Best time to go: May-August
  • Nearest airport: Juneau International Airport (JNU)
  • Day trip with a car: Spot massive ice chunks calving into the water off Mendenhall Glacier (about 12 miles away) 

Sample deals to Juneau: 

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Last Updated 
November 6, 2020
23 US Cities Ideal for a Long Weekend
Jessica Spiegel
Freelance Writer

Jessica Spiegel is a freelance writer and editor based in Portland, Oregon. She's an obsessive knitter and loves Italy, pho, Sazeracs, the Portland Timbers, and altruism.

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