20 Places To Visit On A Boston to Los Angeles Road Trip

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Road-tripping from Boston to Los Angeles is an epic adventure from America’s northeast corner to the country’s southwestern tip. The 2983-mile (4801 km) journey takes around 44 hours if you drive non-stop, but why would you want to drive through when there’s so much to see along the way?

Explore iconic cities such as New York, Washington D.C., Dallas, St. Louis, San Diego, Philadelphia, and so many more amazing destinations across the United States. It crosses through 17 states and some of the most picturesque landscapes in North America, making it one of the world’s most iconic road journeys. Here are our top picks of the 20 places not to be missed. 

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20 Places To Visit On A Boston to Los Angeles Road Trip

1- Providence, RI

church and houses in downtown providence
The lovely Providence, Rhode Island, is a charming spot to visit on a road trip from Boston to LA.

Providence is the largest city in Rhode Island and is home to several exciting attractions, including Brown University, a world-renowned research institution that’s a member of the prestigious Ivy League.

As the seat of governance in the state, Providence is a hotbed for New England culture and history.

The city is a popular destination among road trippers thanks to its healthy balance of old, new and unique, which includes attractions such as the John Brown House Museum, the annual WaterFire festival, and the charming Federal Hill neighbourhood.

Providence is 51 miles (82 km) and about a 1-hour drive from Boston.

Top tour: Narrated Boat Tours Providence.

2- Hartford, CT

boston to los angeles hartford
The golden domed capitol building in Hartford, Connecticut.

Officially the capital of Connecticut and unofficially the ‘Insurance Capital of the World’, Hartford is a delightful New England city that’s ideally located about halfway between Boston and New York City.

The mid-sized city is home to a surprisingly large number of public parks, historic landmarks and unique cultural institutions for a city of its size.

Hartford has significant landmarks, such as the historic Mark Twain House & Museum, the commanding Connecticut State Capitol and the city’s charming Downtown neighbourhoods.

Hartford is 73 miles (117 km) and about a 1.5-hour drive from Providence.

Top tour: Hartford Scavenger Hunt: The Riches Of Hartford.

3- New York City, NY

New York City skyline view from Little Island
You’ll need days or weeks to explore New York City.

Made up of the five boroughs of Brooklyn, Manhattan, Staten Island, the Bronx and Queens, New York City is one of the world’s cultural and economic capitals.

The vibrant and incredibly diverse city is filled with too many sights and attractions to sample in one lifetime, not to mention world-class shopping and dining options.

While it can be hard to decide what to see and skip when road-tripping through New York City, there are a couple of standout New York landmarks every visit to the Big Apple should feature.

Central Park, the Statue of Liberty, Times Square and the Empire State Building are four iconic NYC landmarks to tick off your to-see list.

Some lesser-known NYC attractions, such as the High Line, Ellis Island and Coney Island, are equally spectacular.

No matter how you spend your time in America’s biggest city, there’s never a dull moment and plenty of things to do in New York city at night.

New York City is 118 miles (190 km) and about 2 hours and 15 minutes drive from Hartford.

Top tickets: The New York Sightseeing Flex Pass: Save Big on 100+ Attractions and Tours!

4- Philadelphia, PA

aerial view of downtown skyline philadelphia
The streets of Philadelphia in Pennsylvania.

Colloquially known as the ‘City of Brotherly Love’, Philadelphia is a city that tells the tale of America’s origins better than any other city. 

Philadelphia is where the Founding Fathers signed the Declaration of Independence in 1776 and where Sylvester Stallone famously jogged up the stairs of the Philadelphia Museum of Art in the film franchise Rocky.

The city served as the country’s first capital from 1775 until 1800 and is the second-largest metro area in the Mid-Atlantic and Northeast regions after New York City.

Philly is home to incredible sights, culture and history, so it’s best to stay for a couple of days to get more out of your road trip and there are lots of places to have fun in Philadelphia at night.

Iconic Philly attractions include the Liberty Bell, Independence Hall, the Philadelphia Museum of Art and the observation deck atop the One Liberty Place building, including any food joint serving up Philly’s most famous culinary item: the Philly cheesesteak.

Philadelphia is 95 miles (153 km) and about 1 hour 50 minutes drive from New York City.

Top tour: Philadelphia Hop-On Hop-Off City Tour.

5- Washington, D.C.

Aerial of landmark Abraham Lincoln Memorial in Washington, D.C. seen from back
One must-do while on a Boston to Los Angeles road trip is to explore Washington DC,

The capital of the United States and home to the world-renowned Smithsonian Institute, Washington D.C. is a city that needs no introduction.

DC is where politics, history and culture combine to create a fascinating city filled with monuments, stunning architecture and plenty of diverse nightlife options.

There are several well-known landmarks in DC, such as the Lincoln Memorial, the US Capitol, the White House, and some less uptight venues, such as the National Cherry Blossom Festival and the Washington Harbour.

There are also several professional sports teams to cheer for in DC, so be sure to add the country’s capital to your list of places to visit between Boston and Los Angeles.

Washington D.C. is 139 miles (224 km) and about a 2.5-hour drive from Philadelphia.

Top tour: Explore Washington DC at night on the Washington DC Monuments by Moonlight Tour by Trolley.

6- Pittsburgh, PA

boston to los angeles pittsburgh
View of downtown Pittsburgh from top of the Duquesne Incline, Mount Washington, in Pittsburgh, Pennsylvania USA.

Pittsburgh’s steep hills, steel bridges and rampant rivers are visually appealing. 

The city is a hotbed for arts, culture and sports in Pennsylvania and has played a pivotal role in the success of artists like Andy Warhol and philanthropic industrialist Andrew Carnegie.

The Steel City features several exciting museums and cultural institutions for road trippers to stop by, including the Andy Warhol Museum and the Carnegie Museum of Art.

The city is also a great venue to explore the outdoors thanks to the scenic Three Rivers Heritage Trail, the National Aviary and Point State Park, making this an all-encompassing modern city with lots of things to do in Pittsburgh at night and during the day.

Pittsburgh is 240 miles (386 km) and about a 4.5-hour drive from Washington D.C.

Top tour: Pittsburgh HOP-ON HOP-OFF All Day Tour Pass.

7- Cincinnati, OH

One of the best cities for foodies in the Midwest, Cincinnati is an incredibly unique and charming Ohio destination filled with indoor, outdoor, historic and cultural sights to take in.

The city lies on the banks of the Ohio River and borders the state of Kentucky to the south, providing Cincinnati with some of the most scenic natural landscapes in the country.

Nicknamed the ‘Queen City’, Cincinnati is home to trendy bars, restaurants, cafes, and several cultural institutions such as the Cincinnati Art Museum and the Cincinnati Music Hall. 

Cincinnati is 289 miles (465 km) and about a 4.5-hour drive from Pittsburgh.

Top tour: Cincinnati Ultimate Queen City Underground Tour.

8- Louisville, KY

downtown skyline in Louisville
The downtown skyline of Louisville in Kentucky.

Steeped in Southern charm and rich sporting culture, Louisville is a gem of a city packed with amazing sights and attractions.

Louisville is home to the world-famous Churchill Downs racecourse, which hosts the annual Kentucky Derby, one of the biggest and most glamorous horse racing events on the racing calendar.

The city is also Muhammad Ali’s birthplace and you can learn more about the boxing legend at the Muhammad Ali Center.

Continue to scratch your sports itch at the Louisville Slugger Museum & Factory, which has been manufacturing the Louisville Slugger baseball bat since 1884 in the heart of Louisville.

Louisville is 100 miles (161 km) and about 1 hour 40 minutes drive from Cincinnati.

Top tour: Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby.

9- Indianapolis, IN

Downtown Indianapolis skyline at twilight
Indianapolis is a cool city to explore on a Boston to LA driving trip.

Indianapolis is by far the largest city in Indiana and one of the largest inland cities in the United States.

It’s packed with world-class attractions to explore and is a favourite road trip destination thanks to its proximity to Chicago, Louisville, Columbus and St. Louis.

The city’s biggest attraction, in terms of visitor numbers and sheer size, is the famous Indianapolis Motor Speedway, a 2.5-mile-long (4 km) racecourse that’s seen some of the biggest races in NASCAR and Indycar history.

Indianapolis also teems with historical significance, which can be uncovered at the Benjamin Harrison Presidential Site, the Indiana State Capitol and the Conner Prairie.

Indianapolis is 114 miles (183 km) and about a 2-hour drive from Louisville.

Top tour: Smartphone-Guided Walking Tour of Downtown Indianapolis Sights & Stories.

10- St. Louis, MO

boston to los angeles st louis
St. Louis downtown city skyline.

Famous for being the home of the Gateway Arch and the enormous Anheuser-Busch Brewery, St. Louis is one of the finest Midwest cities you’re likely to come across.

St. Louis is Missouri’s second-largest metro area after Kansas City and boasts a refreshing mix of old and new architecture, attractions and landmarks to sample.

The city’s most popular draw is the Gateway Arch, which is 630 feet (193 m) and the largest monument in the United States.

However, the oversized stainless steel arch is not the only thing to see in St. Louis.

The city’s many urban parks and outstanding culinary options make the city a haven for foodies and outdoorsy types.

More than 25 million visitors visit St. Louis annually to explore its charms. And with fascinating places to visit such as the City Museum, Busch Stadium and the St. Louis Union Station, it’s easy to see why.

St. Louis is 242 miles (389 km) and is within a 4-hour drive from Indianapolis.

Top tour: St. Louis Bar Hunt: Saucy St Louis Bar Crawl.

11- Kansas City, MO

boston to los angeles kansas
Kansas City.

Neatly divided into two sections that spill over into two states, Kansas and Missouri, Kansas City is a haven for foodies, artists and sports fanatics.

The city is home to several successful sports teams and is famous for BBQ and fountains.

Not to be outdone by other Midwest dream destinations such as Chicago or St. Louis, Kansas City features many unique attractions and things to do to make road-trippers squeal with delight.

Stop by the American Jazz Museum, the Kauffman Center for the Performing Arts, and rowdy Arrowhead Stadium to maximise your stay in lively Kansas City.

Kansas City is 248 miles (399 km) and about a 4-hour drive from St. Louis.

12- Oklahoma City, OK

Image of Oklahoma City in morning light from above shopping area.
Oklahoma City is a big city to explore while on a Boston to LA driving vacation.

The Sooner State’s capital and largest city, Oklahoma City, known as ‘OKC’, is a vibrant arts and culture hub in the heart of America’s cowboy country.

OKC is most famous for being the home of the NBA’s Oklahoma City Thunder, however, the city features several other attractions that are just as great to experience.

OKC is home to the National Cowboy & Western Heritage Museum, the Oklahoma State Capitol, and many other things to see and do in and around the city.

A large draw to the city is the historic Route 66, which cuts right through Downtown Oklahoma City and played a significant role in the city’s development during the mid-20th century.

A truly modern city with world-class shopping and dining options, a vibrant nightlife scene, and oodles of Wild West character, OKC is a city that you’ll love exploring.  

Oklahoma City is 353 miles (568 km) and about a 5-hour drive from Kansas City.

13- Dallas, TX

road into dallas at twilight
Driving into Dallas at twilight is ok as there’s plenty to do in the city at night.

The Lone Star State’s cultural and spiritual capital is synonymous with cowboy boots, BBQ and football.

Dallas, or the Big D as locals call it, sprawls out across a metroplex that has grown into the fourth-largest city in the United States.

Dallas is a city built on oil but shaped by its art scene, diverse cultures and various passionately supported sports teams.

It grew from a small settlement in 1841 into the cosmopolitan city it is today, with attractions, dining options and entertainment that rival some of the world’s best cities. And you will also find many fun things to do in Dallas at night.

While Dallas may not be Texas’ official state capital but it’s the city that comes to mind when you mention Texas.

Visit the AT&T Stadium, Pioneer Plaza and the annual Texas State Fair.

Dallas is 205 miles (330 km) and about a 3.5-hour drive from Oklahoma City.

14- Amarillo, TX

painted wrecked cars sticking out of the sand
The Cadillac Ranch in Amarillo is a public art installation of old car wrecks.

Amarillo is a vibrant and unique city in the centre of the Texas Panhandle.

The city is a couple of miles from the halfway point along the famous Route 66, which runs from Chicago to LA. 

Amarillo has an eclectic collection of attractions around themes such as cattle farming, large-scale helium production and even nuclear weapons manufacturing.

The largest city in the Lone Star State’s Panhandle and home to rodeos, art festivals and the famous Cadillac Ranch, Amarillo beckons road trippers like an oasis in the dry plains of far north Texas.

Amarillo is 365 miles (587 km) and about a 6-hour drive from Dallas.

15- Albuquerque, NM

The most populous city in New Mexico and a hotbed for Native American and Spanish cultures, Albuquerque is a vibrant and incredibly scenic city that perfectly blends indoor and outdoor living.

Albuquerque treats visitors to adobe structures, magnificent art galleries and unique events, such as the annually-held Albuquerque International Balloon Fiesta.

Tall peaks and scenic canyons dot Downtown Albuquerque’s landscape, beckoning road trippers to ditch the city for a more laid-back time exploring the region’s spectacular natural landmarks.

Albuquerque’s historic neighbourhoods are worth exploring no matter what you’re interested in or who you’re travelling with.  

Albuquerque is 288 miles (463 km) and about a 4.5-hour drive from Amarillo.

16- Grand Canyon National Park, AZ

The Grand Canyon National Park is a vast sprawl of protected land that’s most famous for being the home of the Grand Canyon, which is, without a doubt, a must-see landmark during any road trip through the Southwest United States.

Featuring stunning gorges, colourful cliffs, tons of Native American history, and incredibly rich biodiversity, the canyon is also a venue for events and attractions.

From an ultra-marathon to its Grand Canyon Skywalk, the Grand Canyon is among the most significant natural features in the world to explore.

It is always a fun, family-friendly road trip destination worth spending extra time at. 

Grand Canyon National Park is 410 miles (660 km) and about a 6.5-hour drive from Albuquerque.

17- Tucson, AZ

Tucson, Arizona’s second-largest city after Phoenix, is right in the middle of the hot and dry Sonoran Desert.

This lively city is home to the main campus of the University of Arizona, which provides Tucson with a breadth of entertainment options, nightlife and a general youthful spirit.

The city is renowned for its unique Mexican-inspired art and cultural scenes and is home to several scenic urban parks and botanical gardens.

Tucson’s most famous attractions include the Wild West-themed Old Tucson area, the historic Mission San Xavier del Bac and the famous Gaslight Theatre.

Outside of Downtown Tucson, the surrounding Sonoran Desert reveals its stunning natural landmarks such as the Saguaro National Park, the Sabino Canyon and the Tucson Mountain Park, all fantastic outdoor venues to explore whilst spending time in Tucson.

Tucson is 340 miles (547 km) and about a 5-hour drive from Grand Canyon National Park.

18- San Diego, CA

the streets of San Diego with tall palms
On a Boston to Los Angeles road trip, you’ll want to stop by San Diego.

Sun, surf and fantastic nightlife are three things you’ll find in San Diego.

The city is as far south as you can go in California, meaning San Diego’s vibrant culture and history is as much Mexican as American.

Apart from being home to Coronado Beach and Mission Beach, two of the best beaches in the country, San Diego is bursting with world-class attractions everywhere you turn.

Most of San Diego’s landmarks can be found in and around Balboa Park, which makes exploring San Diego super convenient.

A vast trolley system also connects Downtown San Diego with the city’s scenic outskirts, enabling road trippers to ditch their car to uncover every corner of sizzling San Diego before hitting the road again towards Los Angeles.

San Diego is 406 miles (653 km) and about a 6-hour drive from Tucson.

Top tickets: San Diego Zoo 1-Day Pass Ticket.

19- Palm Springs, CA

cars and traffic lights on the Palm Springs highway
Palm Springs is a fabulous place to spend time while journeying from Boston to Los Angeles.

Palm Springs has always been a popular weekend getaway destination for SoCal residents looking to trade the state’s beaches and large cities for the state’s more serene interior desert.

Put on the map by Hollywood A-listers during the 20th century, thanks to its many high-end spa resorts and shopping districts, Palm Springs remains a popular destination that many flock to even today.

The city is home to multiple unique attractions, including the Living Desert Zoo and Gardens, the Palm Springs Aerial Tramway and the annual Indian Wells tennis tournament, which takes place in next-door Indian Wells.

Palm Springs is jam-packed with amazing activities and events for all to enjoy throughout the year.

One of the region’s biggest is the Coachella Valley Music and Arts Festival, which attracts over 250,000 festival-goers annually.

Palm Springs is 139 miles (224 km) and about a 2.5-hour drive from San Diego.

Top tickets: Palm Springs Aerial Tramway Admission Ticket.

20- Anaheim, CA

Situated right on the border of Los Angeles in California’s famous Orange County, Anaheim is a popular destination on the West Coast.

Anaheim is among SoCal’s most exciting places to visit with a fantastic year-round climate, two major sports franchises, and a mosaic of different cultures worldwide.

Of course, its most famous attraction is Disneyland, which has been attracting families since 1955. 

Knott’s Berry Farm is Anaheim’s other major theme park, with dry and wet amusement rides.

But Anaheim is not all about theme parks, no matter what you’re interested in or who you’re travelling with, Anaheim has something for all ages to see, do and experience.

Anaheim is 90 miles (145 km) and is less than a 2-hour drive from Palm Springs. 

Top tickets: LA Dodgers Baseball Game Ticket at Dodger Stadium.

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Jessica Shaw is a storyteller who has lived in four U.S. states - Missouri, Georgia, Ohio and Illinois - and has visited many others. She loves history and nature and is a big fan of road tripping.