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A US Cross-Country Road Trip Itinerary From Seattle to Boston

Seattle and Boston merged skyline

20 days. 13 states. An unforgettable road trip itinerary that features some of the best scenery in the country. The journey from Seattle to Boston will take travelers through the incredible glacial landscapes of Montana, past South Dakota's famous Wild West towns and to the Amish countryside villages in Pennsylvania. Measuring more than 1600 miles, this cross-country road trip will be an adventure to remember. 

Rent a car with VroomVroomVroom to start exploring. Use our map below to find fantastic points of interest along the route from Seattle to Boston. If you have any suggestions to add, let us know in the comment section below!

Day One - See the surreal sights of Seattle

Before you head off in your rental car, take some time to explore the Emerald City. Visit the world's first Starbucks at the Pike Place Market, and try some of the delicious food at various stalls. The Museum of Pop Culture is another great Seattle attraction. It celebrates contemporary music, movies, and science fiction. Visitors can even try their hand at learning a musical instrument at the SoundLab!

Finish your day at Seattle's beautiful Gas Works Park, a sought-after destination for local artists and photographers. The abandoned gas plant and fantastic views of the city skyline are well worth the journey.

  • Local Tip: Don't miss the inspiring collection of world-famous glass artist Dave Chihuly at Chihuly Garden and Glass. While you are here, why not pay a visit to the Space Needle? You can purchase a combo ticket and visit both attractions for a lower price!

German architecture in Leavenworth

Day Two: Find a fairytale German town in Washington

You might not expect to find a traditional Bavarian village in the foothills of Washington's Cascade Mountains. In fairytale Leavenworth, just two hours from Seattle, visitors will find just that. Sample some authentic German cuisine and visit the world's largest collection of nutcrackers at the Nutcracker Museum. Catch the Leavenworth Summer Theater performing an outdoor tribute to the Sound of Music, or if you are visiting in winter head to one of the surrounding world-class ski resorts.

With 300 days of sunshine a year, this is the perfect destination for hiking. The great outdoors is at its best here, with the surrounding Alpine Lakes wilderness full of postcard-perfect vistas. Come and see why more than 2.5 million visitors a year descend upon Leavenworth. 

  • Local Tip: The stunning Enchantments hike is a must if you are visiting Leavenworth. The region is home to over 700 miles of scenic hiking trails. 

Day Three - Cruise on beautiful Lake Couer d'Alene

Today you will leave Washington and head into Idaho. Couer d'Alene is the perfect destination to spend the night before continuing on your road trip. Enjoy a day relaxing by the water, or take a cruise on Lake Couer d'Alene. You can also enjoy the lakeside scenery at the Tubbs Hill Nature Trails. The loop trail is just two miles long and offers some fantastic views. If the weather is colder, there is also plenty of shopping to enjoy, as well as a number of golf courses around the lake and local art galleries. 

Day Four - The clear waters of Flathead Lake will blow you away

From one beautiful lake to another, Highway 93 will take you to a unmissable sight hidden away in Montana - the beautiful Flathead Lake. You will find beaches in the town of Polson, and another at West Shore State Park. Many visitors choose to stay in Lakeside, where there are a number of local bed and breakfasts. Wander through the town and visit a number of specialty coffee shops such as Lakeside Coffee Co and Glacier Perks. For a great meal, the Farmhouse and Tamarack Brewing Company serve some delicious food. Relax on the lakeside after your long day's driving. 

  • Local Tip:The beaches at Polson and West Shore State Park offer beautiful views of the lake, but if you are traveling with small children they can be difficult to access. Volunteer Park in Lakeside offers wheelchair accessible sidewalks and a dock, and is a better option for those who may struggle to visit the other beaches. 
Going to the Sun Road in a rental car

Day Five - Drive the Going-to-the-Sun Road

Take the 50 mile Going-to-the-Sun Road to experience one of America's most scenic highways. Crossing the stunning Glacier National Park, visitors will be treated to some incredible impressive views of the surrounding mountain ranges and valleys. There are plenty of places to stop and enjoy the view along the way, such as the popular Avalanche Creek, home to the Trail of the Cedars. Be sure to roll up your windows as you pass the Weeping Wall, which during the spring sprays water onto the road. 

  • Local Tip: Explore Wild Goose Island to enjoy some of the most iconic views in the park. From the lakeside visitors will have fantastic views of the surrounding peaks. 

Day Six - See the remnant's of Butte's mining industry

It will be easy to find Butte. The city lies at the crossroad of Interstate 15 and 90. The town has a colorful mining history, and there are plenty of places Downtown where you can discover the history of the town. Having a rental car means you can explore the quaint neighborhoods, and see all of the sights. Discover Butte's mining past at the Berkeley Pit, the remnants of the mines that were closed in 1982. The Butte Silver Bow County Courthouse, a beautiful example of the architecture unique to the region. Outside of Butte, marking the continental divide, the city is watched over by the Our Lady of the Rockies statue. The impressive statue is over 90 feet tall. 

Day Seven - Experience Montana hospitality in Billings

Located on the banks of the mighty Yellowstone River, Billings is a great place to spend the night and experience the hospitality of Montana. Your fourth day in "Big Sky Country" will not disappoint. The region is great for wildlife-spotting, and there are plenty of unique wonders to discover. Visit the Pictograph Caves, just south of Billings and visit the three caves. Before you leave Billings, remember to visit the site of Custer's Last Stand, the Little Bighorn Battlefield Monument

Day Eight - See America's most famous presidents at Mount Rushmore

Head into South Dakota and stop in at the must-see town of Deadwood for a taste of the Wild West. The outlaw spirit still resonates in Deadwood, and the entire town has been registered as a national historic landmark. In the center of the Black Hills region you will find Rapid City, which is often bustling with tourists intent on exploring the famous Mount Rushmore. The Crazy Horse Memorial and Custer State Park are also  nearby. You'll find plenty of accommodation options in Rapid City. 

Local Tip: There is a variety of shopping and dining in Rapid City. The city's Main Street features life-sized bronze statues of America's Presidents. Be sure to check them out!

Scenery in the Badlands, South Dakota

Day Nine - Head through the Badlands

How many miles to Wall Drug? Find out the answer to the question plastered on so many bumper stickers and signs in South Dakota.  As you leave Rapid City you will soon come across the small town of Wall. The real attraction for tourists here is the large store locally called 'Wall Drug'. Having opened in 1931, the collection of 26 retail stores has become a world-renowned phenomenon. Grab your five cent coffee before you hit the road again. You will then drive through the Badlands National Park. The iconic buttes and canyons, with wildlife such as bison, bighorn sheep, coyotes, prairie dogs and eagles is one of South Dakota's best attractions. On the edge of the park stop at Delta Nine, an underground concrete silo that once held a Minuteman II missile.

On your way past Chamberlain, stop and see the impressive 'Dignity' statue. And just up the road you will find another unique roadside attraction in Mitchell, the Corn Palace, with murals made from different colored corn. Spend the night at Sioux Falls. The city has many attractions such as the waterfalls of Falls Park, the Delbridge Museum of Natural History or the Great Plains Zoo.

Day Ten - See the Twin Cities

Time to see the beautiful Twin Cities! Minneapolis and St Paul are bursting with history and culture. You can visit some of the many local museums and galleries to learn more. For a great view of St Anthony Falls, visit the historic Stone Arch Bridge in Minneapolis and follow the walking path. The Basilica of Saint Mary is also well worth a visit to check out the beautiful architecture. Another great place to visit is the Minneapolis Sculpture Garden, where visitors can see unique works including the famous Spoonbridge and Cherry. 

  • Local Tip: To escape the city and visit a beautiful waterfall, head to Minnehaha Regional Park. It is one of the region's most popular parks. 

Day Eleven - Experience the best of Wisconsin

On your way through Wisconsin, stop in at Green Bay, the home of the legendary Green Bay Packers. Take a tour of Lambeau Field to get a behind the scenes look at the Packers stadium. In the atrium, the Green Bay Packers Hall of Fame displays plenty of sporting memorabilia. For a classic Wisconsin meal, visit 1919 Kitchen & Tap. Try some venison sloppy joes or parmesan-breaded cheese curds. 

Spend the night at Milwaukee. Visit the Milwaukee Art Museum, home to more than 30,000 pieces of art. If you're on a tight schedule, the architecture of the museum is impressive enough alone. The building has a sunscreen that opens at 10am. The city is also home to the world's only Harley-Davidson Museum, displaying 450 bikes. 

  • Local Tip: Visit the Milwaukee Public Market, and try specialty food at this year-round market. The Outdoor Urban Market features more local vendors where visitors can find handmade jewelry, arts and crafts, as well as fresh fruit and vegetables. 
Chicago skyscrapers at night

Day Twelve - Explore Chicago and beyond

You can't stop by Chicago without visiting the city's hub of arts and entertainment. Millennium Park is known worldwide for its unique Cloud Gate sculpture. Not far away, spend some time on Navy Pier and enjoy a ride on the Centennial Wheel. From the pier you can take a cruise on Lake Michigan. Enjoy seeing the sights along the city's riverside walks, or get some retail therapy on the Magnificent Mile, the center of fashion in the city. The area is also home to a number of restaurants.

Chicago is also known for its museums. The Museum of Science and Industry homes mind-blowing exhibits, visitors can even visit a German submarine and learn how they work. The Field Museum is also great to learn more about natural history. If you would prefer to explore gardens, the Chicago Botanic Gardens make for a beautiful day out. 

  • Local Tip: If you want to extend your stay in Chicago, why not explore surrounding destinations like Rockford, where you will find one of the highest quality Japanese gardens in North America. Or if you would prefer to see the best main street in the Midwest, head to the heritage village of Galena. 

Day Thirteen: See unique buildings and sample great food in Toledo

Pass through Indiana toward Ohio. Your cross-state journey ends in the northern town of Toledo. Take the time to explore some of the attractions of the town. In the Old West End neighborhood you will find the Toledo Museum of Art and its Glass Pavilion. The unique architecture of the pavilion took two years to construct. While traveling through Minnesota, Illinois, Indiana and Ohio you will have seen why the area is known for its Great Lakes. In Toledo you can visit the National Museum of the Great Lakes, and learn about the incredible history and international importance of the lakes.

  • Local Tip: Before you leave town, it is a local tradition that you stop in at Tony Packo's for a meal. Try one of the famous Hungarian hot dogs. 

Day Fourteen: Stopover in Pittsburgh

Once you cross the Pennsylvania border, you will come to the city of Pittsburgh. You will find no shortage of museums in the city, but one of the more popular is the Andy Warhol Museum. While admiring the collections of his artworks, you can also try your hand at some of Warhol's classic techniques at the museum. It will be an unforgettable, immersive experience. To see some great gardens, visit the Phipps Conservatory. 

Amish countryside near Lancaster

Day Fifteen - Experience Amish culture in Lancaster

Today's drive will take you deep into Amish country. When you arrive in historic Lancaster, take a trip on the Strasburg Rail Road. It is America's oldest short-line rail road. You can also visit an Amish village and experience the unique lifestyle, and learn more with an authentic Amish lesson taught by a local school teacher. 

Day Sixteen - See the sights of Staten Island

You can't drive past the Big Apple. If you're nervous about hitting the streets of Manhattan in your car, a great place to stay and check out the sights is Staten Island. You will arrive on the island via the Outerbridge Crossing from New Jersey. Stop by at Conference House Park, where you can introduce yourself to Staten Island by exploring the waterfront trails. Spend some time exploring the Conference House historic museum, the site of the 1776 peace conference to end the Revolutionary War. For any war buffs, this is a must-see attraction. 

Just 20 minutes away, find the Historic Richmond Town, New York's only historic village. Explore landmarked buildings such as a blacksmith shop, courthouse and schoolhouse. Nearby, the Jacques Marchais Museum of Tibetan Art holds Tai Chi and Meditation classes. Traveling with kids? The Staten Island Zoo is the place to go. It features a petting zoo, reptile room and a carousel!

  • Local Tip: If you are visiting Staten Island, you need to make time to visit the Snug Harbor Cultural Center and Botanical Gardens. This is an important historical site with multiple museums, art galleries, as well as a stunning botanic garden. 

Day Seventeen - Get lost in New York City

Today it is time to visit another famous New York borough: Manhattan. Take the Staten Island Ferry over to the city, and start your whirlwind day of taking in the sights of New York. Start at the One World Trade Center to get a great view of the city from the observation deck. The tallest building in the Western Hemisphere offers a great view. While you are in the area, visit the 9/11 memorial on the site of the Twin Towers. 

If you like shopping, the impressive Westfield World Trade Center is also nearby. There is plenty more to see in New York such as the Brooklyn Bridge, Broadway, Times Square, Central Park and Rockefeller Plaza. Stop in at the many famous museums and art galleries while you are in town.

Day Eighteen - Travel the coast of Connecticut

People travel from far and wide to see the idyllic coastline of Connecticut. Experience the small town charm of Essex, one of the popular villages along the coast as you head toward Boston. Enjoy the view of the river from the Town Dock, and visit the nearby Connecticut River Museum to learn more about the area. The colonial main street of the town is very photogenic. 

Day Nineteen - Follow the story of the American Revolution in Boston

For your last full day exploring, make the most of your time in Massachusetts' largest city. The historic city played a major role in the American Revolution. Follow the Freedom Trail to learn more. See the Old South Meeting House where the speeches were made from members of the Boston Tea Party, or visit the site of the Boston massacre, the Old State House. The start of the trail is at Boston Common, where you can take a ride on one of the famous Swan Boats. 

Day Twenty - Start planning your next American road trip!

Seattle to Boston is just one of the fantastic routes that will take you across the United States. If you're looking to explore more areas in depth, check out some of our favorite drives here. Prefer to travel to the wintry north? Find out some of the great sights you can see on a road trip through Alaska.

Do you have any suggestions to add to our Seattle to Boston itinerary? Let us know in the comment section.

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